anandamide (CHEBI:2700)

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CHEBI:2700 - anandamide

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ChEBI Name	anandamide

ChEBI ID	CHEBI:2700

Definition	An N-acylethanolamine 20:4 resulting from the formal condensation of carboxy group of arachidonic acid with the amino group of ethanolamine.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Bijay

Secondary ChEBI IDs	CHEBI:88116

Supplier Information	ZINC000002528042

Download	Molfile XML SDF

more structures >>

Molfile

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The Resolver thinks Mol

E7Y - Ideal conformer

Mrv1927 06032115113D

starting HoverWatcher_5

Time for openFile(E7Y - Ideal conformer

Mrv1927 06032115113D

62 61 0 0 0 0 999 V2000

-6.3720 0.2720 -0.7760 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.1940 -2.7030 -1.0950 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.6800 -2.2100 0.2330 C 0 0 1 0 0 0 0 0 0 0 0 0

0.3210 -3.1940 0.7810 C 0 0 0 0 0 0 0 0 0 0 0 0

1.8360 -1.3150 1.1470 C 0 0 1 0 0 0 0 0 0 0 0 0

2.3800 -0.9300 2.4990 C 0 0 0 0 0 0 0 0 0 0 0 0

4.5280 1.6580 1.4880 C 0 0 0 0 0 0 0 0 0 0 0 0

6.8020 1.1540 0.7580 C 0 0 1 0 0 0 0 0 0 0 0 0

7.4620 1.7810 -0.4720 C 0 0 1 0 0 0 0 0 0 0 0 0

8.5310 0.8320 -1.0170 C 0 0 1 0 0 0 0 0 0 0 0 0

10.2600 0.5100 -2.7920 C 0 0 0 0 0 0 0 0 0 0 0 0

4.2140 0.1920 1.3420 C 0 0 1 0 0 0 0 0 0 0 0 0

5.7500 2.0890 1.2950 C 0 0 0 0 0 0 0 0 0 0 0 0

-7.3260 0.9270 -0.0860 N 0 0 0 0 0 0 0 0 0 0 0 0

-6.2870 0.4130 -1.9780 O 0 0 0 0 0 0 0 0 0 0 0 0

-8.2620 1.8090 -0.7880 C 0 0 1 0 0 0 0 0 0 0 0 0

-9.2360 2.4240 0.2190 C 0 0 1 0 0 0 0 0 0 0 0 0

-8.5190 3.2720 1.1190 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.4840 -2.7590 -1.3170 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.4470 -2.1580 -0.3260 C 0 0 1 0 0 0 0 0 0 0 0 0

-4.4280 -1.2410 -1.0600 C 0 0 1 0 0 0 0 0 0 0 0 0

-5.4050 -0.6310 -0.0530 C 0 0 1 0 0 0 0 0 0 0 0 0

1.5140 -2.7870 1.1360 C 0 0 0 0 0 0 0 0 0 0 0 0

3.5260 -0.3020 2.5880 C 0 0 0 0 0 0 0 0 0 0 0 0

9.1910 1.4590 -2.2470 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.5000 -3.0110 -1.8620 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1990 -1.2400 0.0990 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.5110 -2.1100 0.9310 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0530 -4.2360 0.8830 H 0 0 0 0 0 0 0 0 0 0 0 0

0.9290 -0.7440 0.9450 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5800 -1.0990 0.3810 H 0 0 0 0 0 0 0 0 0 0 0 0

1.8260 -1.1730 3.3930 H 0 0 0 0 0 0 0 0 0 0 0 0

3.7460 2.3540 1.7530 H 0 0 0 0 0 0 0 0 0 0 0 0

6.3390 0.2080 0.4790 H 0 0 0 0 0 0 0 0 0 0 0 0

7.5570 0.9770 1.5250 H 0 0 0 0 0 0 0 0 0 0 0 0

6.7080 1.9580 -1.2380 H 0 0 0 0 0 0 0 0 0 0 0 0

7.9250 2.7280 -0.1920 H 0 0 0 0 0 0 0 0 0 0 0 0

9.2850 0.6550 -0.2500 H 0 0 0 0 0 0 0 0 0 0 0 0

8.0680 -0.1140 -1.2960 H 0 0 0 0 0 0 0 0 0 0 0 0

10.7300 0.9570 -3.6680 H 0 0 0 0 0 0 0 0 0 0 0 0

11.0140 0.3330 -2.0260 H 0 0 0 0 0 0 0 0 0 0 0 0

9.7970 -0.4360 -3.0720 H 0 0 0 0 0 0 0 0 0 0 0 0

3.5600 0.0440 0.4830 H 0 0 0 0 0 0 0 0 0 0 0 0

5.1400 -0.3650 1.1930 H 0 0 0 0 0 0 0 0 0 0 0 0

6.0030 3.1150 1.5200 H 0 0 0 0 0 0 0 0 0 0 0 0

-7.3940 0.8140 0.8750 H 0 0 0 0 0 0 0 0 0 0 0 0

-7.7080 2.6030 -1.2880 H 0 0 0 0 0 0 0 0 0 0 0 0

-8.8190 1.2340 -1.5270 H 0 0 0 0 0 0 0 0 0 0 0 0

-9.9870 3.0100 -0.3120 H 0 0 0 0 0 0 0 0 0 0 0 0

-9.7260 1.6300 0.7820 H 0 0 0 0 0 0 0 0 0 0 0 0

-9.0750 3.6970 1.7860 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.8570 -3.2360 -2.2120 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.9980 -2.9540 0.1740 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.8930 -1.5790 0.4130 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.8770 -0.4450 -1.5600 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.9820 -1.8190 -1.7990 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.8510 -0.0520 0.6860 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.9560 -1.4270 0.4470 H 0 0 0 0 0 0 0 0 0 0 0 0

2.2680 -3.5070 1.4190 H 0 0 0 0 0 0 0 0 0 0 0 0

3.9770 -0.1370 3.5560 H 0 0 0 0 0 0 0 0 0 0 0 0

8.4370 1.6360 -3.0130 H 0 0 0 0 0 0 0 0 0 0 0 0

9.6540 2.4060 -1.9670 H 0 0 0 0 0 0 0 0 0 0 0 0

11 25 1 0 0 0 0

25 10 1 0 0 0 0

9 10 1 0 0 0 0

9 8 1 0 0 0 0

13 7 2 0 0 0 0

13 8 1 0 0 0 0

7 12 1 0 0 0 0

12 24 1 0 0 0 0

24 6 2 0 0 0 0

6 5 1 0 0 0 0

20 21 1 0 0 0 0

20 19 1 0 0 0 0

3 4 1 0 0 0 0

3 2 1 0 0 0 0

21 22 1 0 0 0 0

5 23 1 0 0 0 0

4 23 2 0 0 0 0

19 2 2 0 0 0 0

17 18 1 0 0 0 0

17 16 1 0 0 0 0

22 1 1 0 0 0 0

1 15 2 0 0 0 0

1 14 1 0 0 0 0

14 16 1 0 0 0 0

2 26 1 0 0 0 0

3 27 1 0 0 0 0

3 28 1 0 0 0 0

4 29 1 0 0 0 0

5 30 1 0 0 0 0

5 31 1 0 0 0 0

6 32 1 0 0 0 0

7 33 1 0 0 0 0

8 34 1 0 0 0 0

8 35 1 0 0 0 0

9 36 1 0 0 0 0

9 37 1 0 0 0 0

10 38 1 0 0 0 0

10 39 1 0 0 0 0

11 40 1 0 0 0 0

11 41 1 0 0 0 0

11 42 1 0 0 0 0

12 43 1 0 0 0 0

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13 45 1 0 0 0 0

14 46 1 0 0 0 0

16 47 1 0 0 0 0

16 48 1 0 0 0 0

17 49 1 0 0 0 0

17 50 1 0 0 0 0

18 51 1 0 0 0 0

19 52 1 0 0 0 0

20 53 1 0 0 0 0

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21 55 1 0 0 0 0

21 56 1 0 0 0 0

22 57 1 0 0 0 0

22 58 1 0 0 0 0

23 59 1 0 0 0 0

24 60 1 0 0 0 0

25 61 1 0 0 0 0

25 62 1 0 0 0 0

M END): 17 ms

reading 62 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

62 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
Anandamide (ANA), also referred to as N-arachidonoylethanolamine (AEA) is a fatty acid neurotransmitter belonging to the fatty acid derivative group known as N-acylethanolamine (NAE). Anandamide takes its name from the Sanskrit word ananda (आनन्द), meaning "joy, bliss, delight," plus amide. Anandamide, the first discovered endocannabinoid, engages with the body's endocannabinoid system by binding to the same cannabinoid receptors that THC found in cannabis acts on. Anandamide can be found within tissues in a wide range of animals. It has also been found in plants, such as the cacao tree. Anandamide is derived from the non-oxidative metabolism of arachidonic acid, an essential omega-6 fatty acid. It is synthesized from N-arachidonoyl phosphatidylethanolamine by multiple pathways. It is degraded primarily by the fatty acid amide hydrolase (FAAH) enzyme, which converts anandamide into ethanolamine and arachidonic acid. As such, inhibitors of FAAH lead to elevated anandamide levels and are being pursued for possible therapeutic use.
Read full article at Wikipedia

Formula

C22H37NO2

Net Charge

Average Mass

347.543

Monoisotopic Mass

347.28243

InChI

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-

InChIKey

LGEQQWMQCRIYKG-DOFZRALJSA-N

SMILES

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

Metabolite of Species	Details
Homo sapiens (NCBI:txid9606)	See: DOI
Homo sapiens (NCBI:txid9606)	Found in blood (UBERON:0000178). See: PubMed
Homo sapiens (NCBI:txid9606)	Found in cerebrospinal fluid (UBERON:0001359). See: PubMed

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	human blood serum metabolite Any metabolite (endogenous or exogenous) found in human blood serum samples. neurotransmitter An endogenous compound that is used to transmit information across the synapse between a neuron and another cell. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via endocannabinoid ) cannabinoid receptor agonist An agonist that binds to and activates cannabinoid receptors. (via cannabinoid )

Application(s):	vasodilator agent A drug used to cause dilation of the blood vessels.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	anandamide (CHEBI:2700) has functional parent arachidonic acid (CHEBI:15843) anandamide (CHEBI:2700) has role human blood serum metabolite (CHEBI:85234) anandamide (CHEBI:2700) has role neurotransmitter (CHEBI:25512) anandamide (CHEBI:2700) has role vasodilator agent (CHEBI:35620) anandamide (CHEBI:2700) is a N-acylethanolamine 20:4 (CHEBI:134161) anandamide (CHEBI:2700) is a endocannabinoid (CHEBI:67197)

Incoming	N-(20-hydroxyarachidonoyl)ethanolamine (CHEBI:136992) has functional parent anandamide (CHEBI:2700) N-[(5Z,11Z,14Z)-8,9-epoxyicosatrienoyl]ethanolamine (CHEBI:136989) has functional parent anandamide (CHEBI:2700) N-[(5Z,8Z,11Z)-14,15-epoxyicosatrienoyl]ethanolamine (CHEBI:136991) has functional parent anandamide (CHEBI:2700) N-[(5Z,8Z,14Z)-11,12-epoxyicosatrienoyl]ethanolamine (CHEBI:136990) has functional parent anandamide (CHEBI:2700) N-[(8Z,11Z,14Z)-5,6-epoxyicosatrienoyl]ethanolamine (CHEBI:136988) has functional parent anandamide (CHEBI:2700) N-arachidonoylethanolamine phosphate(2−) (CHEBI:131894) has functional parent anandamide (CHEBI:2700) O-oleoylanandamide (CHEBI:76070) has functional parent anandamide (CHEBI:2700)

IUPAC Name

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

Synonyms	Sources
(5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)-5,8,11,14-eicosatetraenamide	ChemIDplus
(all-Z)-N-(2-hydroxyethyl)-5,8,11,14-eicosatetraenamide	ChemIDplus
AEA	KEGG COMPOUND
Anandamide	KEGG COMPOUND
Anandamide (20.4, N-6)	HMDB
Anandamide(20:4, N-6)	HMDB
Arachidonic acid N-(hydroxyethyl)amide	HMDB
arachidonoyl ethanolamide	ChemIDplus
Arachidonylethanolamide	KEGG COMPOUND
N-(2-Hydroxyethyl)anachidonamide	HMDB
N-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-ethanolamine	HMDB
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine	UniProt
N-(5Z,8Z,11Z,14Z-icosatetraenoyl)-ethanolamide	KEGG COMPOUND
N-arachidonoyl ethanolamine	HMDB
N-arachidonoyl-2-hydroxyethylamide	ChemIDplus
N-arachidonoylethanolamine	ChEBI

Manual Xrefs	Databases
4445241	ChemSpider
Anandamide	Wikipedia
C11695	KEGG COMPOUND
CPD-7598	MetaCyc
E7Y	PDBeChem
FDB023303	FooDB
HMDB0004080	HMDB
LMFA08040001	LIPID MAPS
View more database links

Registry Numbers	Types	Sources
7079463	Reaxys Registry Number	Reaxys
94421-68-8	CAS Registry Number	KEGG COMPOUND
94421-68-8	CAS Registry Number	ChemIDplus

Citations	Types	Sources
15047233	PubMed citation	Europe PMC
15797258	PubMed citation	Europe PMC
15944392	PubMed citation	Europe PMC
15997233	PubMed citation	Europe PMC
16118355	PubMed citation	Europe PMC
16957004	PubMed citation	Europe PMC
18227059	PubMed citation	Europe PMC
18691603	PubMed citation	Europe PMC
19330032	PubMed citation	Europe PMC
29363071	PubMed citation	Europe PMC
29546791	PubMed citation	Europe PMC
31610409	PubMed citation	Europe PMC
32195347	PubMed citation	Europe PMC
33551019	PubMed citation	Europe PMC
33713246	PubMed citation	Europe PMC
33731590	PubMed citation	Europe PMC

Last Modified

24 March 2022

CHEBI:2700 - anandamide

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