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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:09:11 UTC
Update Date2021-09-14 15:45:11 UTC
HMDB IDHMDB0012884
Secondary Accession Numbers
  • HMDB12884
Metabolite Identification
Common NameAdrenochrome
DescriptionAdrenochrome (CAS: 54-06-8) 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. Adrenochrome is a red-coloured oxidation product of adrenaline (epinephrine) that was first isolated and identified by Green and Richter in 1937 (PMID: 16746378 ). It is highly soluble in water. Adrenochrome can be synthesized from adrenalin via oxidation with silver oxide (PMID: 4581204 ).
Structure
Data?1592259720
Synonyms
ValueSource
(-)-AdrenochromeHMDB
(3R)-2,3-Dihydro-3-hydroxy-1-methyl-1H-indole-5,6-dioneHMDB
(3R)-3-Hydroxy-1-methyl-2,3,5,6-tetrahydro-1H-indole-5,6-dioneHMDB
(R)-3-Hydroxy-1-methyl-indoline-5,6-dioneHMDB
1-Methyl-3-hydroxy-5,6-dioxo-2,3,5,6-tetrahydroindoleHMDB
2,3-Dihydro-3-hydroxy-1-methyl-1H-indole-5,6-dioneHMDB
2,3-Dihydro-3-hydroxy-N-methylindole-5,6-quinoneHMDB
3-Hydroxy-1-methyl-2,3,5,6-tetrahydro-1H-indole-5,6-dioneHMDB
3-Hydroxy-1-methyl-2,3-dihydro-1H-indole-5,6-dioneHMDB
3-Hydroxy-1-methyl-2,3-dihydroindole-5,6-dioneHMDB
3-Hydroxy-1-methyl-5,6-indolinedioneHMDB
AdChrHMDB
AdrenochromeHMDB
Chemical FormulaC9H9NO3
Average Molecular Weight179.175
Monoisotopic Molecular Weight179.058243154
IUPAC Name(3R)-3-hydroxy-1-methyl-2,3,5,6-tetrahydro-1H-indole-5,6-dione
Traditional Name(3R)-3-hydroxy-1-methyl-2,3-dihydroindole-5,6-dione
CAS Registry Number7506-92-5
SMILES
CN1C[C@H](O)C2=CC(=O)C(=O)C=C12
InChI Identifier
InChI=1S/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3/t9-/m0/s1
InChI KeyRPHLQSHHTJORHI-VIFPVBQESA-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassNot Available
Direct ParentIndoles and derivatives
Alternative Parents
Substituents
  • Indole or derivatives
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Vinylogous amide
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Tertiary amine
  • Tertiary aliphatic amine
  • Enamine
  • Azacycle
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Amine
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point125 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility68 g/LALOGPS
logP10(0.08) g/LALOGPS
logP10(-0.31) g/LChemAxon
logS10(-0.42) g/LALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.61 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity48.56 m³·mol⁻¹ChemAxon
Polarizability17.33 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AdrenochromeCN1C[C@H](O)C2=CC(=O)C(=O)C=C122973.8Standard polar33892256
AdrenochromeCN1C[C@H](O)C2=CC(=O)C(=O)C=C121706.1Standard non polar33892256
AdrenochromeCN1C[C@H](O)C2=CC(=O)C(=O)C=C121964.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Adrenochrome,1TMS,isomer #1CN1C[C@H](O[Si](C)(C)C)C2=CC(=O)C(=O)C=C211996.9Semi standard non polar33892256
Adrenochrome,1TBDMS,isomer #1CN1C[C@H](O[Si](C)(C)C(C)(C)C)C2=CC(=O)C(=O)C=C212223.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Adrenochrome GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adrenochrome 10V, Positive-QTOFsplash10-001i-0900000000-94871f99bc2bfbd56c302021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adrenochrome 20V, Positive-QTOFsplash10-001i-0900000000-3154aaa502c96a443eb22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adrenochrome 40V, Positive-QTOFsplash10-0036-4900000000-b1472b1e530e52911e9d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adrenochrome 10V, Negative-QTOFsplash10-004i-0900000000-f7139a1e768d1e55c0da2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adrenochrome 20V, Negative-QTOFsplash10-01sr-0900000000-5cdea3150754d86c0e942021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adrenochrome 40V, Negative-QTOFsplash10-001i-0900000000-a2a6cc6eee7ec69f1a3d2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029199
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAdrenochrome
METLIN IDNot Available
PubChem Compound24884154
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Green DE, Richter D: Adrenaline and adrenochrome. Biochem J. 1937 Apr;31(4):596-616. doi: 10.1042/bj0310596. [PubMed:16746378 ]
  2. Heacock RA, Powell WS: Adrenochrome and related compounds. Prog Med Chem. 1972;9(2):275-339. doi: 10.1016/s0079-6468(08)70401-6. [PubMed:4581204 ]

Enzymes

General function:
Posttranslational modification, protein turnover, chaperones
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Has a sulfatase activity.
Gene Name:
GSTT2
Uniprot ID:
P0CG29
Molecular weight:
Not Available