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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 10:27:48 UTC

Update Date

2022-07-14 23:24:51 UTC

HMDB ID

HMDB0004080

Secondary Accession Numbers

HMDB04080

Metabolite Identification

Common Name

Anandamide

Description

Anandamide, also known as arachidonoylethanolamide (AEA), is a highly potent endogenous agonist of the cannabinoid CB1 and CB2 receptors. CB1 receptors are predominantly found in the central nervous system (CNS) where they mainly mediate the psychotropic effects of tetrahydrocannabinol (THC) and endocannabinoids, whereas the expression of the CB2 receptor is thought to be restricted to cells of the immune system. It was suggested that AEA might inhibit tumour cell proliferation or induce apoptosis independently of CB1 and CB2 receptors, via interaction with the type 1 vanilloid receptor (VR1). VR1 is an ion channel expressed almost exclusively by sensory neurons, activated by pH, noxious heat (> 48-degree centigrade), and plant toxins and is thought to play an important role in nociception. Cervical cancer cells are sensitive to AEA-induced apoptosis via VR1 that is aberrantly expressed in vitro and in vivo while CB1 and CB2 receptors play a protective role. (PMID: 15047233 ). Novel prostaglandins (prostaglandin glycerol esters and prostaglandin ethanolamides) are COX-2 oxidative metabolites of endogenous cannabinoids (such as anandamide). Recent evidence suggests that these new types of prostaglandins are likely novel signalling mediators involved in synaptic transmission and plasticity (PMID: 16957004 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0004080
     RDKit          3D
Anandamide
 62 61  0  0  0  0  0  0  0  0999 V2000
   10.6557    1.0929    1.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6299    0.2547    0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6754   -0.3757    1.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6187   -1.2312    0.6733 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7282   -0.4376   -0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0809    0.6666    0.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7908    0.8067    0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8475   -0.1750   -0.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9505    0.4203   -1.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6646    0.4325   -0.9521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9725   -0.1629    0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1860    0.9698    0.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1180    0.9740    0.9569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9387   -0.1927    0.5021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851   -0.7907    1.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9771   -0.8862    1.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8388   -0.4184    0.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6543   -1.5988   -0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5534   -1.2048   -1.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5969   -0.2239   -0.8011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7476    0.1582    0.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4700    0.3260   -1.7905 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4905    1.2792   -1.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5103    0.7451   -0.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1525   -0.3869   -0.9918 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0269    0.4672    1.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1479    2.0185    1.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4428    1.3716    0.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1889    0.9642   -0.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2202   -0.4809   -0.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3013   -1.0506    1.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2817    0.3920    1.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1056   -2.0291    0.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0458   -1.7132    1.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1732   -1.0916   -0.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5070    0.0393   -0.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7720    1.4200    0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3891    1.6846    1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3788   -1.0445   -0.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3687   -0.6832    0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3920    0.8792   -1.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0040    0.8897   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3556   -0.9706   -0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6379   -0.4792    1.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7649    1.8219    1.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5714    1.8490    1.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6240    0.2745   -0.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4135   -0.9633   -0.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0782   -1.1676    2.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5115   -1.3451    2.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6123    0.2672    1.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4099    0.0622   -0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9274   -2.3361   -0.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3064   -2.0188    0.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9078   -0.7011   -1.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0722   -2.0867   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3528    0.0118   -2.7893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0349    2.2140   -1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0114    1.5827   -2.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3179    1.5021   -0.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0275    0.5944    0.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3928   -0.1859   -1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 22 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 25 62  1  0
M  END

  Mrv1652303262018252D          

 25 24  0  0  0  0            999 V2000
 9995.8523 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5668 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1377 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2816 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.4231 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1067 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.7084 9999.3866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9994.423110000.6233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8213 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9938 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5381 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.2792 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3636 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.5646 9999.7989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0769 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7923 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.6170 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.3324 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.0477 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.8724 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.5857 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.3011 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.0165 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.7299 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.4453 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  2  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  2  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004080

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO

> <INCHI_IDENTIFIER>
InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15-

> <INCHI_KEY>
LGEQQWMQCRIYKG-DOFZRALJSA-N

> <FORMULA>
C22H37NO2

> <MOLECULAR_WEIGHT>
347.5347

> <EXACT_MASS>
347.282429433

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
43.92950925412751

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide

> <ALOGPS_LOGP>
5.98

> <JCHEM_LOGP>
5.313802251

> <ALOGPS_LOGS>
-5.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.375825066096787

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.435299736387627

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3152897074754692

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
112.96520000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.70e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
anandamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004080
     RDKit          3D
Anandamide
 62 61  0  0  0  0  0  0  0  0999 V2000
   10.6557    1.0929    1.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6299    0.2547    0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6754   -0.3757    1.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6187   -1.2312    0.6733 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7282   -0.4376   -0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0809    0.6666    0.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7908    0.8067    0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8475   -0.1750   -0.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9505    0.4203   -1.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6646    0.4325   -0.9521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9725   -0.1629    0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1860    0.9698    0.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1180    0.9740    0.9569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9387   -0.1927    0.5021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851   -0.7907    1.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9771   -0.8862    1.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8388   -0.4184    0.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6543   -1.5988   -0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5534   -1.2048   -1.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5969   -0.2239   -0.8011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7476    0.1582    0.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4700    0.3260   -1.7905 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4905    1.2792   -1.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5103    0.7451   -0.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1525   -0.3869   -0.9918 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0269    0.4672    1.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1479    2.0185    1.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4428    1.3716    0.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1889    0.9642   -0.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2202   -0.4809   -0.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3013   -1.0506    1.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2817    0.3920    1.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1056   -2.0291    0.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0458   -1.7132    1.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1732   -1.0916   -0.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5070    0.0393   -0.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7720    1.4200    0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3891    1.6846    1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3788   -1.0445   -0.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3687   -0.6832    0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3920    0.8792   -1.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0040    0.8897   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3556   -0.9706   -0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6379   -0.4792    1.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7649    1.8219    1.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5714    1.8490    1.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6240    0.2745   -0.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4135   -0.9633   -0.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0782   -1.1676    2.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5115   -1.3451    2.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6123    0.2672    1.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4099    0.0622   -0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9274   -2.3361   -0.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3064   -2.0188    0.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9078   -0.7011   -1.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0722   -2.0867   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3528    0.0118   -2.7893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0349    2.2140   -1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0114    1.5827   -2.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3179    1.5021   -0.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0275    0.5944    0.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3928   -0.1859   -1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 22 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 25 62  1  0
M  END

HEADER    PROTEIN                                 26-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAR-20         0                                  
HETATM    1  C   UNK     0    8658.9248666.291   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.2588665.522   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8657.5908665.522   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8661.5928666.291   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8656.2568666.291   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8663.1338666.291   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    8654.9228665.522   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0    8656.2568667.830   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8664.4668665.522   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8653.5888666.291   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8665.8048666.291   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8652.2558665.522   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8667.3458666.291   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8650.9218666.291   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    8668.6778665.522   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8670.0128666.291   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8671.5528666.291   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8672.8878665.522   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8674.2228666.291   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8675.7628666.291   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8677.0938665.522   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8678.4298666.291   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8679.7648665.522   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8681.0968666.291   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8682.4318665.522   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7    8                                                  
CONECT    6    4    9                                                       
CONECT    7    5   10                                                       
CONECT    8    5                                                            
CONECT    9    6   11                                                       
CONECT   10    7   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

COMPND    HMDB0004080
HETATM    1  C1  UNL     1      10.656   1.093   1.086  1.00  0.00           C  
HETATM    2  C2  UNL     1       9.630   0.255   0.305  1.00  0.00           C  
HETATM    3  C3  UNL     1       8.675  -0.376   1.266  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.619  -1.231   0.673  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.728  -0.438  -0.294  1.00  0.00           C  
HETATM    6  C6  UNL     1       6.081   0.667   0.391  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.791   0.807   0.502  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.847  -0.175  -0.075  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.950   0.420  -1.067  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.665   0.432  -0.952  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.973  -0.163   0.214  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.186   0.970   0.820  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.118   0.974   0.957  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.939  -0.193   0.502  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.685  -0.791   1.619  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.977  -0.886   1.631  1.00  0.00           C  
HETATM   17  C17 UNL     1      -4.839  -0.418   0.550  1.00  0.00           C  
HETATM   18  C18 UNL     1      -5.654  -1.599  -0.015  1.00  0.00           C  
HETATM   19  C19 UNL     1      -6.553  -1.205  -1.137  1.00  0.00           C  
HETATM   20  C20 UNL     1      -7.597  -0.224  -0.801  1.00  0.00           C  
HETATM   21  O1  UNL     1      -7.748   0.158   0.375  1.00  0.00           O  
HETATM   22  N1  UNL     1      -8.470   0.326  -1.791  1.00  0.00           N  
HETATM   23  C21 UNL     1      -9.491   1.279  -1.486  1.00  0.00           C  
HETATM   24  C22 UNL     1     -10.510   0.745  -0.501  1.00  0.00           C  
HETATM   25  O2  UNL     1     -11.152  -0.387  -0.992  1.00  0.00           O  
HETATM   26  H1  UNL     1      11.027   0.467   1.904  1.00  0.00           H  
HETATM   27  H2  UNL     1      10.148   2.018   1.429  1.00  0.00           H  
HETATM   28  H3  UNL     1      11.443   1.372   0.358  1.00  0.00           H  
HETATM   29  H4  UNL     1       9.189   0.964  -0.410  1.00  0.00           H  
HETATM   30  H5  UNL     1      10.220  -0.481  -0.258  1.00  0.00           H  
HETATM   31  H6  UNL     1       9.301  -1.051   1.922  1.00  0.00           H  
HETATM   32  H7  UNL     1       8.282   0.392   1.969  1.00  0.00           H  
HETATM   33  H8  UNL     1       8.106  -2.029   0.078  1.00  0.00           H  
HETATM   34  H9  UNL     1       7.046  -1.713   1.464  1.00  0.00           H  
HETATM   35  H10 UNL     1       6.173  -1.092  -0.936  1.00  0.00           H  
HETATM   36  H11 UNL     1       7.507   0.039  -0.993  1.00  0.00           H  
HETATM   37  H12 UNL     1       6.772   1.420   0.836  1.00  0.00           H  
HETATM   38  H13 UNL     1       4.389   1.685   1.043  1.00  0.00           H  
HETATM   39  H14 UNL     1       4.379  -1.044  -0.585  1.00  0.00           H  
HETATM   40  H15 UNL     1       3.369  -0.683   0.786  1.00  0.00           H  
HETATM   41  H16 UNL     1       3.392   0.879  -1.952  1.00  0.00           H  
HETATM   42  H17 UNL     1       1.004   0.890  -1.720  1.00  0.00           H  
HETATM   43  H18 UNL     1       0.356  -0.971  -0.156  1.00  0.00           H  
HETATM   44  H19 UNL     1       1.638  -0.479   1.046  1.00  0.00           H  
HETATM   45  H20 UNL     1       0.765   1.822   1.154  1.00  0.00           H  
HETATM   46  H21 UNL     1      -1.571   1.849   1.408  1.00  0.00           H  
HETATM   47  H22 UNL     1      -2.624   0.274  -0.269  1.00  0.00           H  
HETATM   48  H23 UNL     1      -1.414  -0.963  -0.035  1.00  0.00           H  
HETATM   49  H24 UNL     1      -2.078  -1.168   2.475  1.00  0.00           H  
HETATM   50  H25 UNL     1      -4.511  -1.345   2.497  1.00  0.00           H  
HETATM   51  H26 UNL     1      -5.612   0.267   1.040  1.00  0.00           H  
HETATM   52  H27 UNL     1      -4.410   0.062  -0.310  1.00  0.00           H  
HETATM   53  H28 UNL     1      -4.927  -2.336  -0.380  1.00  0.00           H  
HETATM   54  H29 UNL     1      -6.306  -2.019   0.800  1.00  0.00           H  
HETATM   55  H30 UNL     1      -5.908  -0.701  -1.918  1.00  0.00           H  
HETATM   56  H31 UNL     1      -7.072  -2.087  -1.594  1.00  0.00           H  
HETATM   57  H32 UNL     1      -8.353   0.012  -2.789  1.00  0.00           H  
HETATM   58  H33 UNL     1      -9.035   2.214  -1.083  1.00  0.00           H  
HETATM   59  H34 UNL     1     -10.011   1.583  -2.414  1.00  0.00           H  
HETATM   60  H35 UNL     1     -11.318   1.502  -0.321  1.00  0.00           H  
HETATM   61  H36 UNL     1     -10.028   0.594   0.476  1.00  0.00           H  
HETATM   62  H37 UNL     1     -11.393  -0.186  -1.935  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6   35   36
CONECT    6    7    7   37
CONECT    7    8   38
CONECT    8    9   39   40
CONECT    9   10   10   41
CONECT   10   11   42
CONECT   11   12   43   44
CONECT   12   13   13   45
CONECT   13   14   46
CONECT   14   15   47   48
CONECT   15   16   16   49
CONECT   16   17   50
CONECT   17   18   51   52
CONECT   18   19   53   54
CONECT   19   20   55   56
CONECT   20   21   21   22
CONECT   22   23   57
CONECT   23   24   58   59
CONECT   24   25   60   61
CONECT   25   62
END

HMDB0004080
     RDKit          3D
Anandamide
 62 61  0  0  0  0  0  0  0  0999 V2000
   10.6557    1.0929    1.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6299    0.2547    0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6754   -0.3757    1.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6187   -1.2312    0.6733 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7282   -0.4376   -0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0809    0.6666    0.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7908    0.8067    0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8475   -0.1750   -0.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9505    0.4203   -1.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6646    0.4325   -0.9521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9725   -0.1629    0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1860    0.9698    0.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1180    0.9740    0.9569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9387   -0.1927    0.5021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851   -0.7907    1.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9771   -0.8862    1.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8388   -0.4184    0.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6543   -1.5988   -0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5534   -1.2048   -1.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5969   -0.2239   -0.8011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7476    0.1582    0.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4700    0.3260   -1.7905 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4905    1.2792   -1.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5103    0.7451   -0.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1525   -0.3869   -0.9918 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0269    0.4672    1.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1479    2.0185    1.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4428    1.3716    0.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1889    0.9642   -0.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2202   -0.4809   -0.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3013   -1.0506    1.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2817    0.3920    1.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1056   -2.0291    0.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0458   -1.7132    1.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1732   -1.0916   -0.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5070    0.0393   -0.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7720    1.4200    0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3891    1.6846    1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3788   -1.0445   -0.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3687   -0.6832    0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3920    0.8792   -1.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0040    0.8897   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3556   -0.9706   -0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6379   -0.4792    1.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7649    1.8219    1.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5714    1.8490    1.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6240    0.2745   -0.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4135   -0.9633   -0.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0782   -1.1676    2.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5115   -1.3451    2.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6123    0.2672    1.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4099    0.0622   -0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9274   -2.3361   -0.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3064   -2.0188    0.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9078   -0.7011   -1.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0722   -2.0867   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3528    0.0118   -2.7893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0349    2.2140   -1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0114    1.5827   -2.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3179    1.5021   -0.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0275    0.5944    0.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3928   -0.1859   -1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 22 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 25 62  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z,8Z,11Z,14Z)-N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamide	ChEBI
(all-Z)-N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamide	ChEBI
AEA	ChEBI
Anandamide (20.4, N-6)	ChEBI
Anandamide(20:4, N-6)	ChEBI
Arachidonic acid N-(hydroxyethyl)amide	ChEBI
Arachidonoyl ethanolamide	ChEBI
Arachidonylethanolamide	ChEBI
N-(2-Hydroxyethyl)anachidonamide	ChEBI
N-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-ethanolamine	ChEBI
N-(5Z,8Z,11Z,14Z-Icosatetraenoyl)-ethanolamide	ChEBI
N-Arachidonoyl ethanolamine	ChEBI
N-Arachidonoyl-2-hydroxyethylamide	ChEBI
N-Arachidonoylethanolamine	ChEBI
Arachidonate N-(hydroxyethyl)amide	Generator
N-(5Z,8Z,11Z,14Z-Eicosatetraenoyl) ethanolamine	HMDB
5,8,11,14-Eicosatetraenoylethanolamide	HMDB
N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamide (all-Z)	HMDB
N-(2-Hydroxyethyl)arachidonamide	HMDB
Anandamide (20.4,N-6)	HMDB
Arachidonoylethanolamide	HMDB
N-Arachidonoylethanolamide	HMDB
Anandamide	MeSH
N-(2-Hydroxyethyl)arachidonylamide	HMDB
N-Arachidonylethanolamide	HMDB
N-Arachidonylethanolamine	HMDB
AEA(22:6)	HMDB
Acylethanolamine 22:6	HMDB

Chemical Formula

C₂₂H₃₇NO₂

Average Molecular Weight

347.5347

Monoisotopic Molecular Weight

347.282429433

IUPAC Name

(5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide

Traditional Name

anandamide

CAS Registry Number

94421-68-8

SMILES

CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO

InChI Identifier

InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15-

InChI Key

LGEQQWMQCRIYKG-DOFZRALJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

N-acylethanolamines

Alternative Parents

Substituents

N-acylethanolamine
Fatty amide
N-acyl-amine
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Alcohol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

fatty amide (CHEBI:2700 )
N-(polyunsaturated fatty acyl)ethanolamine (CHEBI:2700 )
N-(long-chain-acyl)ethanolamine (CHEBI:2700 )
endocannabinoid (CHEBI:2700 )
N-acyl ethanolamides (endocannabinoids) (C11695 )
N-acyl ethanolamines (endocannabinoids) (LMFA08040001 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16118355)
Cerebrospinal Fluid (CSF) (PMID: 19817812)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

Extracellular (HMDB: HMDB0004080)
Membrane (HMDB: HMDB0004080)

Source

Exogenous

Exogenous (HMDB: HMDB0004080)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0004080)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Epilepsy (MarkerDB: MDB00000439)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00047 g/L	ALOGPS
logP	5.98	ALOGPS
logP	5.31	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	15.44	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	112.97 m³·mol⁻¹	ChemAxon
Polarizability	43.93 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	196.515	31661259
DarkChem	[M-H]-	196.335	31661259
DeepCCS	[M+H]+	191.624	30932474
DeepCCS	[M-H]-	189.266	30932474
DeepCCS	[M-2H]-	222.311	30932474
DeepCCS	[M+Na]+	197.756	30932474
AllCCS	[M+H]+	193.8	32859911
AllCCS	[M+H-H2O]+	191.2	32859911
AllCCS	[M+NH4]+	196.2	32859911
AllCCS	[M+Na]+	196.9	32859911
AllCCS	[M-H]-	192.2	32859911
AllCCS	[M+Na-2H]-	194.4	32859911
AllCCS	[M+HCOO]-	197.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Anandamide	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO	3375.1	Standard polar	33892256
Anandamide	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO	2576.9	Standard non polar	33892256
Anandamide	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO	2849.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Anandamide,1TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO[Si](C)(C)C	2863.5	Semi standard non polar	33892256
Anandamide,1TMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO)[Si](C)(C)C	2799.1	Semi standard non polar	33892256
Anandamide,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2853.6	Semi standard non polar	33892256
Anandamide,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2908.6	Standard non polar	33892256
Anandamide,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2886.9	Standard polar	33892256
Anandamide,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO[Si](C)(C)C(C)(C)C	3111.6	Semi standard non polar	33892256
Anandamide,1TBDMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C	3049.8	Semi standard non polar	33892256
Anandamide,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3350.0	Semi standard non polar	33892256
Anandamide,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3257.3	Standard non polar	33892256
Anandamide,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2940.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Anandamide GC-EI-TOF (Non-derivatized)	splash10-0gb9-1910000000-79c55260280d43c9a900	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Anandamide GC-EI-TOF (Non-derivatized)	splash10-0fs7-5900000000-75831770c51e1d2f739d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Anandamide GC-EI-TOF (Non-derivatized)	splash10-0gb9-1910000000-79c55260280d43c9a900	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Anandamide GC-EI-TOF (Non-derivatized)	splash10-0fs7-5900000000-75831770c51e1d2f739d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Anandamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-02a5-7493000000-c585906fb5c6d8aa4ff3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Anandamide GC-MS (1 TMS) - 70eV, Positive	splash10-0fki-9353100000-6c635dea7003727f3b83	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Anandamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Anandamide 10V, Positive-QTOF	splash10-0002-1029000000-acb4551dcc9e3f6e05dd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Anandamide 40V, Positive-QTOF	splash10-03xr-9000000000-45148e922a9fd54fabf5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Anandamide 20V, Positive-QTOF	splash10-03di-9230000000-c1ae6b0473246ef09b54	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Anandamide 40V, Positive-QTOF	splash10-03xr-9000000000-100fb9f29334308faa9d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anandamide 10V, Positive-QTOF	splash10-01ot-5149000000-76b6af47eca436d3e5ec	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anandamide 20V, Positive-QTOF	splash10-03dl-9131000000-069d65af4be10e925d42	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anandamide 40V, Positive-QTOF	splash10-03dl-9230000000-3590307e1cf3aab76689	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anandamide 10V, Negative-QTOF	splash10-0002-0009000000-004521084d25577be5fe	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anandamide 20V, Negative-QTOF	splash10-01r2-5019000000-1c63bb1751f58bf91f0c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anandamide 40V, Negative-QTOF	splash10-0006-9010000000-161a34c3d66caea4a293	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anandamide 10V, Positive-QTOF	splash10-01ot-9328000000-b4562c25b6933ac7a7ba	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anandamide 20V, Positive-QTOF	splash10-03dl-9000000000-4d45bc23e3d763bd083b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anandamide 40V, Positive-QTOF	splash10-03dl-9100000000-ed96624588d13e15a5bf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anandamide 10V, Negative-QTOF	splash10-0002-0009000000-a3f88dce43caba26e0b0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anandamide 20V, Negative-QTOF	splash10-0002-5129000000-5f007c24785520e490c5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anandamide 40V, Negative-QTOF	splash10-052f-9010000000-868cfda7283947a9fbc4	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.008 +/- 0.016 uM	Adult (>18 years old)	Both	Normal	16118355	details
Blood	Detected and Quantified	2.99 +/- 5.39 uM	Adult (>18 years old)	Both	Normal	16118355	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	3.12 +/- 1.2 uM	Adult (>18 years old)	Both	Normal	21359215	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.01165 +/- 0.00753 uM	Adult (>18 years old)	Both	Normal	19817812	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00255 +/- 0.00178 uM	Adult (>18 years old)	Both	Epilepsy	19817812	details

Associated Disorders and Diseases

Disease References

Epilepsy
Romigi A, Bari M, Placidi F, Marciani MG, Malaponti M, Torelli F, Izzi F, Prosperetti C, Zannino S, Corte F, Chiaramonte C, Maccarrone M: Cerebrospinal fluid levels of the endocannabinoid anandamide are reduced in patients with untreated newly diagnosed temporal lobe epilepsy. Epilepsia. 2010 May;51(5):768-72. doi: 10.1111/j.1528-1167.2009.02334.x. Epub 2009 Oct 8. [PubMed:19817812 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023303

KNApSAcK ID

Not Available

Chemspider ID

4445241

KEGG Compound ID

C11695

BioCyc ID

CPD-7598

BiGG ID

Not Available

Wikipedia Link

Anandamide

METLIN ID

Not Available

PubChem Compound

5281969

PDB ID

Not Available

ChEBI ID

2700

Food Biomarker Ontology

Not Available

VMH ID

C11695

MarkerDB ID

MDB00000439

Good Scents ID

Not Available

References

Synthesis Reference

Qi, Longwu; Meijler, Michael M.; Lee, Sang-Hyeup; Sun, Chengzao; Janda, Kim D. Solid-Phase Synthesis of Anandamide Analogues. Organic Letters (2004), 6(10), 1673-1675.

Material Safety Data Sheet (MSDS)

Not Available

General References

Felder CC, Nielsen A, Briley EM, Palkovits M, Priller J, Axelrod J, Nguyen DN, Richardson JM, Riggin RM, Koppel GA, Paul SM, Becker GW: Isolation and measurement of the endogenous cannabinoid receptor agonist, anandamide, in brain and peripheral tissues of human and rat. FEBS Lett. 1996 Sep 16;393(2-3):231-5. [PubMed:8814296 ]
Contassot E, Tenan M, Schnuriger V, Pelte MF, Dietrich PY: Arachidonyl ethanolamide induces apoptosis of uterine cervix cancer cells via aberrantly expressed vanilloid receptor-1. Gynecol Oncol. 2004 Apr;93(1):182-8. [PubMed:15047233 ]
Sang N, Chen C: Lipid signaling and synaptic plasticity. Neuroscientist. 2006 Oct;12(5):425-34. [PubMed:16957004 ]
Anton M, Rodriguez-Gonzalez A, Rodriguez-Rojo IC, Pastor A, Correas A, Serrano A, Ballesta A, Alen F, Gomez de Heras R, de la Torre R, Rodriguez de Fonseca F, Orio L: Increased plasma oleoylethanolamide and palmitoleoylethanolamide levels correlate with inflammatory changes in alcohol binge drinkers: the case of HMGB1 in women. Addict Biol. 2018 Nov;23(6):1242-1250. doi: 10.1111/adb.12580. Epub 2017 Nov 27. [PubMed:29178411 ]

Enzymes

Enzyme Details

1. Fatty-acid amide hydrolase 1

General function:: Involved in carbon-nitrogen ligase activity, with glutamine as amido-N-donor
Specific function:: Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of these molecules. Hydrolyzes polyunsaturated substrate anandamide preferentially as compared to monounsaturated substrates.
Gene Name:: FAAH
Uniprot ID:: O00519
Molecular weight:: 63065.28

Reactions

Anandamide + Water → Arachidonic acid + Ethanolamine	details

Enzyme Details

2. Abhydrolase domain-containing protein 4

General function:: Involved in hydrolase activity
Specific function:: Lysophospholipase selective for N-acyl phosphatidylethanolamine (NAPE). Contributes to the biosynthesis of N-acyl ethanolamines, including the endocannabinoid anandamide by hydrolyzing the sn-1 and sn-2 acyl chains from N-acyl phosphatidylethanolamine (NAPE) generating glycerophospho-N-acyl ethanolamine (GP-NAE), an intermediate for N-acyl ethanolamine biosynthesis. Hydrolyzes substrates bearing saturated, monounsaturated, polyunsaturated N-acyl chains. Shows no significant activity towards other lysophospholipids, including lysophosphatidylcholine, lysophosphatidylethanolamine and lysophosphatidylserine
Gene Name:: ABHD4
Uniprot ID:: Q8TB40
Molecular weight:: 38794.1

Enzyme Details

3. N-acyl-phosphatidylethanolamine-hydrolyzing phospholipase D

General function:: Involved in metal ion binding
Specific function:: Hydrolyzes N-acyl-phosphatidylethanolamines (NAPEs) to produce N-acylethanolamines (NAEs) and phosphatidic acid. Responsible for the generation of anandamide (N-arachidonoylethanolamine), the ligand of cannabinoid and vanilloid receptors (By similarity).
Gene Name:: NAPEPLD
Uniprot ID:: Q6IQ20
Molecular weight:: 45595.15

Enzyme Details

4. Fatty-acid amide hydrolase 2

General function:: Involved in carbon-nitrogen ligase activity, with glutamine as amido-N-donor
Specific function:: Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of these molecules. Hydrolyzes monounsaturated substrate anandamide preferentially as compared to polyunsaturated substrates.
Gene Name:: FAAH2
Uniprot ID:: Q6GMR7
Molecular weight:: 58303.115

Reactions

Anandamide + Water → Arachidonic acid + Ethanolamine	details

Enzyme Details

5. Cannabinoid receptor 1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Involved in cannabinoid-induced CNS effects. Acts by inhibiting adenylate cyclase. Could be a receptor for anandamide. Inhibits L-type Ca(2+) channel current. Isoform 2 and isoform 3 have altered ligand binding
Gene Name:: CNR1
Uniprot ID:: P21554
Molecular weight:: 52857.4

Showing metabocard for Anandamide (HMDB0004080)

MOL for HMDB0004080 (Anandamide)

3D MOL for HMDB0004080 (Anandamide)

3D SDF for HMDB0004080 (Anandamide)

3D-SDF for HMDB0004080 (Anandamide)

PDB for HMDB0004080 (Anandamide)

3D PDB for HMDB0004080 (Anandamide)

SMILES for HMDB0004080 (Anandamide)

INCHI for HMDB0004080 (Anandamide)

Structure for HMDB0004080 (Anandamide)

3D Structure for HMDB0004080 (Anandamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions