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Record Information
Version3.6
Creation Date2009-07-25 00:09:11 UTC
Update Date2017-08-16 08:16:00 UTC
HMDB IDHMDB0012884
Secondary Accession Numbers
  • HMDB12884
Metabolite Identification
Common NameAdrenochrome
DescriptionAdrenochrome, chemical formula C9H9NO3, is a pigment obtained by the oxidation of adrenaline (epinephrine). Adrenochrome monosemicarbazone, also known as carbazochrome, is a hemostatic, meaning it reduces capillary bleeding.
Structure
Thumb
Synonyms
ValueSource
AdChrHMDB
Adrenochrome O-quinoneHMDB
Adrenochrome oxidisedHMDB
N-Methyl-5,6-dioxo-2,3,5,6-tetrahydro-3-hydroxyindoleHMDB
N-Methyl-5,6-dioxo-2,3,5,6-tetrahydro-3-indololHMDB
Chemical FormulaC9H9NO3
Average Molecular Weight179.1727
Monoisotopic Molecular Weight179.058243159
IUPAC Name3-hydroxy-1-methyl-2,3,5,6-tetrahydro-1H-indole-5,6-dione
Traditional Nameadrenochrome
CAS Registry Number54-06-8
SMILES
CN1CC(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
InChI KeyRPHLQSHHTJORHI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassIndoles and derivatives
Direct ParentIndoles and derivatives
Alternative Parents
Substituents
  • Indole or derivatives
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Vinylogous amide
  • Ketone
  • Secondary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Cyclic ketone
  • Enamine
  • Azacycle
  • Carbonyl group
  • Amine
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point125 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility68.0 mg/mLALOGPS
logP0.08ALOGPS
logP-0.31ChemAxon
logS-0.42ALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)3.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.61 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity48.56 m3·mol-1ChemAxon
Polarizability17.25 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029199
KNApSAcK IDNot Available
Chemspider ID5687
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Linkadrenochrome
NuGOwiki LinkHMDB0012884
METLIN IDNot Available
PubChem Compound5898
PDB IDNot Available
ChEBI ID838058
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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