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Record Information
Version3.6
Creation Date2009-07-25 00:09:11 UTC
Update Date2013-02-09 00:29:31 UTC
HMDB IDHMDB12884
Secondary Accession NumbersNone
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
  1. AdChr
  2. Adrenochrome O-quinone
  3. Adrenochrome oxidised
  4. N-Methyl-5,6-dioxo-2,3,5,6-tetrahydro-3-hydroxyindole
  5. N-Methyl-5,6-dioxo-2,3,5,6-tetrahydro-3-indolol
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 IUPAC 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
KingdomOrganic Compounds
Super ClassAliphatic Heteropolycyclic Compounds
ClassBenzoquinones
Sub ClassN/A
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • Enamine
  • Ketone
  • Pyrrolidine
  • Secondary Alcohol
Direct ParentBenzoquinones
Ontology
StatusExpected and 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 g/LALOGPS
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 area57.61ChemAxon
rotatable bond count0ChemAxon
refractivity48.56ChemAxon
polarizability17.25ChemAxon
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 LinkHMDB12884
Metagene LinkHMDB12884
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