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Cinnavalininate (M2MDB001425)

Record Information
Version2.0
Creation Date2012-05-31 14:54:10 -0600
Update Date2015-06-03 17:20:24 -0600
Secondary Accession Numbers
  • ECMDB21005
Identification
Name:Cinnavalininate
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
MOLSDFPDBSMILESInChI
Synonyms:
  • 2-Amino-3-oxo-3H-phenoxazin-1,9-dicarboxylate
  • 2-Amino-3-oxo-3H-phenoxazin-1,9-dicarboxylic acid
  • 2-Amino-3H-phenoxazin-one-1,9-dicarboxylate
  • 2-Amino-3H-phenoxazin-one-1,9-dicarboxylic acid
  • Cinnabarinate
  • Cinnabarinic acid
  • Cinnavalininic acid
Chemical Formula:C14H8N2O6
Weight:Average: 300.2231
Monoisotopic: 300.038235998
InChI Key:FSBKJYLVDRVPTK-UHFFFAOYSA-N
InChI: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)
CAS number:Not Available
IUPAC Name:2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid
Traditional IUPAC Name:cinnabarinic acid
SMILES:NC1=C(C(O)=O)C2=NC3=C(C=CC=C3OC2=CC1=O)C(O)=O
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
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:0.604PhysProp
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
2 3-Hydroxyanthranilic acid + 4 Oxygen <> Cinnavalininate +2 Superoxide anion +2 Hydrogen peroxide +2 Hydrogen ion
SMPDB Pathways:
Tryptophan metabolismPW000815 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kal-1090000000-a9b3f04e0154e56a34acView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05fr-7019200000-9d027bf9474c784d794fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0093000000-6eec5362c826437aa9f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0090000000-ea4d6ec354a7ad615bcdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5i-2090000000-a1cd4541b5bfb101f231View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-7b8418c9fe543cb0ddfcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-0090000000-3aa6f5b7cbca4210c35fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-0390000000-10af92579df64b8720cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-fb1be335f42676557e20View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bti-0090000000-54b079267e6329486c07View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-0190000000-40328130c8a319d1d980View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-24fd7e79c1bc515afadeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-0090000000-dadf0f0bb8448267e058View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0090000000-362869951e6e3adac9c6View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB04078
Pubchem Compound ID114918
Kegg IDC05640
ChemSpider ID102864
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Catalase-peroxidase
General function:
Involved in catalase activity
Specific function:
Bifunctional enzyme with both catalase and broad- spectrum peroxidase activity. Displays also NADH oxidase, INH lyase and isonicotinoyl-NAD synthase activity
Gene Name:
katG
Uniprot ID:
P13029
Molecular weight:
80023
Reactions
Donor + H(2)O(2) = oxidized donor + 2 H(2)O.
2 H(2)O(2) = O(2) + 2 H(2)O.
Protein Details
2. Catalase HPII
General function:
Involved in catalase activity
Specific function:
Decomposes hydrogen peroxide into water and oxygen; serves to protect cells from the toxic effects of hydrogen peroxide
Gene Name:
katE
Uniprot ID:
P21179
Molecular weight:
84162
Reactions
2 H(2)O(2) = O(2) + 2 H(2)O.