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Record Information
Version3.6
Creation Date2006-08-13 10:24:21 UTC
Update Date2013-02-09 00:12:59 UTC
HMDB IDHMDB04078
Secondary Accession NumbersNone
Metabolite Identification
Common NameCinnavalininate
DescriptionCinnavalininate is an intermediate in the tryptophan metabolic pathway [Kegg: C05640]. It is generated from 3-hydroxyanthranilate via the enzyme catalase (EC:1.11.1.6).
Structure
Thumb
Synonyms
  1. 2-Amino-3-oxo-3H-phenoxazin-1,9-dicarboxylic acid
  2. 2-Amino-3H-phenoxazin-one-1,9-dicarboxylic acid
  3. Cinnabarinic acid
  4. Cinnavalininic acid
Chemical FormulaC14H8N2O6
Average Molecular Weight300.2231
Monoisotopic Molecular Weight300.038235998
IUPAC Name2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid
Traditional Namecinnabarinic acid
CAS Registry NumberNot Available
SMILES
NC1=C(C(O)=O)C2=NC3=C(C=CC=C3OC2=CC1=O)C(O)=O
InChI Identifier
InChI=1S/C14H8N2O6/c15-10-6(17)4-8-12(9(10)14(20)21)16-11-5(13(18)19)2-1-3-7(11)22-8/h1-4H,15H2,(H,18,19)(H,20,21)
InChI KeyInChIKey=FSBKJYLVDRVPTK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenoxazines. These are polycyclic aromatic compounds containing a phenoxazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a 1,4-oxazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxazines
Sub ClassPhenoxazines
Direct ParentPhenoxazines
Alternative Parents
Substituents
  • Phenoxazine
  • Aminobenzoic acid or derivatives
  • Aminobenzoic acid
  • Benzoyl
  • Benzenoid
  • Primary aromatic amine
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Vinylogous amide
  • Cyclic ketone
  • Oxacycle
  • Azacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.604Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.15 mg/mLALOGPS
logP0.7ALOGPS
logP0.44ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)2.37ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area139.28 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity76.9 m3·mol-1ChemAxon
Polarizability27.38 Å3ChemAxon
Number of Rings3ChemAxon
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
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063map00380
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 IDFDB023302
KNApSAcK IDNot Available
Chemspider ID102864
KEGG Compound IDC05640
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04078
Metagene LinkHMDB04078
METLIN IDNot Available
PubChem Compound114918
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in catalase activity
Specific function:
Occurs in almost all aerobically respiring organisms and serves to protect cells from the toxic effects of hydrogen peroxide. Promotes growth of cells including T-cells, B-cells, myeloid leukemia cells, melanoma cells, mastocytoma cells and normal and transformed fibroblast cells.
Gene Name:
CAT
Uniprot ID:
P04040
Molecular weight:
59755.82
Reactions
3-Hydroxyanthranilic acid + Oxygen → Cinnavalininate + Superoxide + Hydrogen peroxide + Hydrogen Iondetails