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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:09:10 UTC

Update Date

2021-09-14 15:45:29 UTC

HMDB ID

HMDB0012883

Secondary Accession Numbers

HMDB12883

Metabolite Identification

Common Name

Adrenochrome o-semiquinone

Description

Adrenochrome o-semiquinone belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Based on a literature review a significant number of articles have been published on Adrenochrome o-semiquinone.

Structure

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

  Mrv1652303102016462D          

 13 14  0  0  0  0            999 V2000
   12.3054  -23.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4772  -22.2450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2308  -21.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1446  -21.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7574  -20.5376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3377  -20.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9252  -20.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1003  -20.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6878  -19.4887    0.0000 O   0  0  0  0  0  1  0  0  0  0  0  0
   10.6878  -20.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8628  -20.9178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1003  -21.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9252  -21.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 13  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 13  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012883

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CC(O)C2=C1C=C(O)C([O])=C2

> <INCHI_IDENTIFIER>
InChI=1S/C9H10NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,12-13H,4H2,1H3

> <INCHI_KEY>
YNKQTALYBHMWCC-UHFFFAOYSA-N

> <FORMULA>
C9H10NO3

> <MOLECULAR_WEIGHT>
180.1806

> <EXACT_MASS>
180.066068191

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.00474658100965

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3,6-dihydroxy-1-methyl-2,3-dihydro-1H-indol-5-yl)oxidanyl

> <ALOGPS_LOGP>
0.11

> <JCHEM_LOGP>
0.6397000000000002

> <ALOGPS_LOGS>
-0.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.966779837543957

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.092872483578649

> <JCHEM_PKA_STRONGEST_BASIC>
-2.210640680029252

> <JCHEM_POLAR_SURFACE_AREA>
43.7

> <JCHEM_REFRACTIVITY>
59.515800000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,6-dihydroxy-1-methyl-2,3-dihydroindol-5-yloxidanyl

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      22.970 -43.030   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      23.291 -41.524   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      24.697 -40.898   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.537 -39.367   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      25.680 -38.337   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      23.030 -39.047   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.260 -37.713   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.721 -37.713   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      19.951 -36.379   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      19.951 -39.047   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      18.411 -39.047   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      20.721 -40.380   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.260 -40.380   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13    2    6   12                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
AdcSq	HMDB

Chemical Formula

C₉H₁₀NO₃

Average Molecular Weight

180.1806

Monoisotopic Molecular Weight

180.066068191

IUPAC Name

(3,6-dihydroxy-1-methyl-2,3-dihydro-1H-indol-5-yl)oxidanyl

Traditional Name

3,6-dihydroxy-1-methyl-2,3-dihydroindol-5-yloxidanyl

CAS Registry Number

Not Available

SMILES

CN1CC(O)C2=C1C=C(O)C([O])=C2

InChI Identifier

InChI=1S/C9H10NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,12-13H,4H2,1H3

InChI Key

YNKQTALYBHMWCC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Not Available

Direct Parent

Indoles and derivatives

Alternative Parents

Substituents

Indole or derivatives
Tertiary aliphatic/aromatic amine
Dialkylarylamine
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
1,2-aminoalcohol
Secondary alcohol
Tertiary amine
Azacycle
Amine
Organic oxygen compound
Alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0012883)

Process

Not Available

Role

Not Available

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	110 g/L	ALOGPS
logP	0.11	ALOGPS
logP	0.64	ChemAxon
logS	-0.22	ALOGPS
pKa (Strongest Acidic)	7.09	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	43.7 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	59.52 m³·mol⁻¹	ChemAxon
Polarizability	18 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	140.636	31661259
DarkChem	[M-H]-	137.94	31661259
DeepCCS	[M+H]+	137.247	30932474
DeepCCS	[M-H]-	134.178	30932474
DeepCCS	[M-2H]-	170.703	30932474
DeepCCS	[M+Na]+	146.242	30932474
AllCCS	[M+H]+	138.5	32859911
AllCCS	[M+H-H2O]+	134.1	32859911
AllCCS	[M+NH4]+	142.6	32859911
AllCCS	[M+Na]+	143.8	32859911
AllCCS	[M-H]-	137.7	32859911
AllCCS	[M+Na-2H]-	138.2	32859911
AllCCS	[M+HCOO]-	138.8	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Adrenochrome o-semiquinone,1TMS,isomer #1	CN1CC(O[Si](C)(C)C)C2=CC([O])=C(O)C=C21	1887.7	Semi standard non polar	33892256
Adrenochrome o-semiquinone,1TMS,isomer #2	CN1CC(O)C2=CC([O])=C(O[Si](C)(C)C)C=C21	1890.4	Semi standard non polar	33892256
Adrenochrome o-semiquinone,2TMS,isomer #1	CN1CC(O[Si](C)(C)C)C2=CC([O])=C(O[Si](C)(C)C)C=C21	1913.8	Semi standard non polar	33892256
Adrenochrome o-semiquinone,1TBDMS,isomer #1	CN1CC(O[Si](C)(C)C(C)(C)C)C2=CC([O])=C(O)C=C21	2162.8	Semi standard non polar	33892256
Adrenochrome o-semiquinone,1TBDMS,isomer #2	CN1CC(O)C2=CC([O])=C(O[Si](C)(C)C(C)(C)C)C=C21	2160.2	Semi standard non polar	33892256
Adrenochrome o-semiquinone,2TBDMS,isomer #1	CN1CC(O[Si](C)(C)C(C)(C)C)C2=CC([O])=C(O[Si](C)(C)C(C)(C)C)C=C21	2413.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Adrenochrome o-semiquinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zg3-5900000000-6b1e67862de7cc09ea82	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adrenochrome o-semiquinone GC-MS (2 TMS) - 70eV, Positive	splash10-03xu-6690000000-98024984cb322ffebdee	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adrenochrome o-semiquinone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adrenochrome o-semiquinone 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrenochrome o-semiquinone 10V, Positive-QTOF	splash10-03di-0900000000-1ec6adce96507f4fdbbd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrenochrome o-semiquinone 20V, Positive-QTOF	splash10-03di-0900000000-a5918be2ed0fc29e99dc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrenochrome o-semiquinone 40V, Positive-QTOF	splash10-007t-0900000000-59212910425c701fcacc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrenochrome o-semiquinone 10V, Negative-QTOF	splash10-03di-0900000000-e7a61b498c894247b9c2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrenochrome o-semiquinone 20V, Negative-QTOF	splash10-03di-0900000000-e7a61b498c894247b9c2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrenochrome o-semiquinone 40V, Negative-QTOF	splash10-023a-0900000000-f9955b9b285b9bcda712	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrenochrome o-semiquinone 10V, Positive-QTOF	splash10-03di-0900000000-2a99e149c8734fadf763	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrenochrome o-semiquinone 20V, Positive-QTOF	splash10-03di-0900000000-24abf8e9b7c6673f8997	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrenochrome o-semiquinone 40V, Positive-QTOF	splash10-052f-3900000000-751f944c7845a25d4834	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029198

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

132551346

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Adrenochrome o-semiquinone (HMDB0012883)

MOL for HMDB0012883 (Adrenochrome o-semiquinone)

3D MOL for HMDB0012883 (Adrenochrome o-semiquinone)

3D SDF for HMDB0012883 (Adrenochrome o-semiquinone)

3D-SDF for HMDB0012883 (Adrenochrome o-semiquinone)

PDB for HMDB0012883 (Adrenochrome o-semiquinone)

3D PDB for HMDB0012883 (Adrenochrome o-semiquinone)

SMILES for HMDB0012883 (Adrenochrome o-semiquinone)

INCHI for HMDB0012883 (Adrenochrome o-semiquinone)

Structure for HMDB0012883 (Adrenochrome o-semiquinone)

3D Structure for HMDB0012883 (Adrenochrome o-semiquinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra