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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 10:24:21 UTC
Update Date2020-02-26 21:24:57 UTC
HMDB IDHMDB0004078
Secondary Accession Numbers
  • HMDB04078
Metabolite Identification
Common NameCinnavalininate
DescriptionCinnavalininate, also known as cinnabarinic acid or cinnabarinate, 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. Cinnavalininate is an extremely weak basic (essentially neutral) compound (based on its pKa). Cinnavalininate exists in all living organisms, ranging from bacteria to humans. cinnavalininate can be biosynthesized from 3-hydroxyanthranilic acid; which is mediated by the enzyme catalase. In humans, cinnavalininate is involved in tryptophan metabolism.
Structure
Data?1582752297
Synonyms
ValueSource
Cinnabarinic acidKegg
CinnabarinateGenerator
Cinnavalininic acidGenerator
2-Amino-3-oxo-3H-phenoxazin-1,9-dicarboxylic acidHMDB
2-Amino-3H-phenoxazin-one-1,9-dicarboxylic acidHMDB
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 KeyFSBKJYLVDRVPTK-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Cyclic ketone
  • Amino acid
  • Amino acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Azacycle
  • Primary amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Process

Naturally occurring process:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity76.9 m³·mol⁻¹ChemAxon
Polarizability27.38 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kal-1090000000-a9b3f04e0154e56a34acSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05fr-7019200000-9d027bf9474c784d794fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0093000000-6eec5362c826437aa9f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0090000000-ea4d6ec354a7ad615bcdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5i-2090000000-a1cd4541b5bfb101f231Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-7b8418c9fe543cb0ddfcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-0090000000-3aa6f5b7cbca4210c35fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-0390000000-10af92579df64b8720cbSpectrum
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 IDFDB023302
KNApSAcK IDNot Available
Chemspider ID102864
KEGG Compound IDC05640
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound114918
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDM01572
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