NP-MRD: Showing NP-Card for Cinnavalininate (NP0087134)

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Record Information

Version

2.0

Created at

2022-05-11 16:41:04 UTC

Updated at

2022-05-11 16:41:04 UTC

NP-MRD ID

NP0087134

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cinnavalininate

Description

Cinnavalininate, 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 through the action of the enzyme catalase. Cinnavalininate is found in Mus musculus. In humans, cinnavalininate is involved in tryptophan metabolism.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
    4.5085   -0.0609   -0.8936 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2339   -0.5020   -0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0896    0.2885   -0.5984 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2269    1.5693   -1.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3992    1.9130   -1.6211 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1839    2.4434   -1.4507 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8617   -0.1651   -0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2785    0.5781   -0.2844 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4122    0.0285    0.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6307    0.6807    0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7380    1.9974   -0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7360    2.5570   -0.9477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9500    2.6621   -0.5755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8150    0.1051    0.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7862   -1.1195    1.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5820   -1.7715    1.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4038   -1.2291    0.7901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3181   -1.9454    0.9237 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8358   -1.4773    0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9869   -2.2166    0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1801   -1.7385    0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2342   -2.4507    0.2956 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2276    0.3667   -0.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7350   -0.1778   -1.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3840    3.4362   -1.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3316    3.0560    0.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7286    0.6757    0.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7074   -1.5564    1.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5633   -2.7579    1.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8942   -3.1890    1.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  6  1  0
  4  5  2  0
  3  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 10 11  1  0
 11 13  1  0
 11 12  2  0
 21  2  1  0
 19  7  1  0
 17  9  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 20 30  1  0
 13 26  1  0
M  END


  Mrv0541 02231219522D          

 22 24  0  0  0  0            999 V2000
   13.8935   -2.5309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7609   -2.5309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8272   -5.3386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5217   -2.5468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1328   -2.5468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6234   -5.3577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6234   -3.7353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8272   -3.7544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2121   -2.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4423   -2.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5133   -4.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5133   -4.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1412   -4.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9390   -4.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9390   -4.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1412   -4.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2213   -3.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4332   -3.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2213   -5.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4332   -5.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7155   -4.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7155   -4.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2 10  1  0  0  0  0
  3 11  1  0  0  0  0
  3 13  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  2  0  0  0  0
  6 14  2  0  0  0  0
  7 15  1  0  0  0  0
  8 12  2  0  0  0  0
  8 16  1  0  0  0  0
  9 17  1  0  0  0  0
 10 18  1  0  0  0  0
 11 12  1  0  0  0  0
 11 19  2  0  0  0  0
 12 17  1  0  0  0  0
 13 16  1  0  0  0  0
 13 20  2  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  2  0  0  0  0
 18 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0087134

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
FSBKJYLVDRVPTK-UHFFFAOYSA-N

> <FORMULA>
C14H8N2O6

> <MOLECULAR_WEIGHT>
300.2231

> <EXACT_MASS>
300.038235998

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
27.383447390351158

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid

> <ALOGPS_LOGP>
0.70

> <JCHEM_LOGP>
0.4385754573333333

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.882453523470117

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.366796983750847

> <JCHEM_PKA_STRONGEST_BASIC>
-1.719341367235418

> <JCHEM_POLAR_SURFACE_AREA>
139.27999999999997

> <JCHEM_REFRACTIVITY>
76.89910000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cinnabarinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      25.935  -4.724   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      18.220  -4.724   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      22.077  -9.965   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      23.374  -4.754   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      20.781  -4.754   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      27.297 -10.001   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      27.297  -6.973   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      22.077  -7.008   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      24.663  -5.478   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.492  -5.478   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.358  -9.226   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.358  -7.747   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.797  -9.226   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.019  -9.257   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.019  -7.717   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.797  -7.747   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.680  -6.957   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.475  -6.957   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.680 -10.017   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.475 -10.017   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.136  -7.717   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.136  -9.257   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   11   13                                                       
CONECT    4    9                                                            
CONECT    5   10                                                            
CONECT    6   14                                                            
CONECT    7   15                                                            
CONECT    8   12   16                                                       
CONECT    9    1    4   17                                                  
CONECT   10    2    5   18                                                  
CONECT   11    3   12   19                                                  
CONECT   12    8   11   17                                                  
CONECT   13    3   16   20                                                  
CONECT   14    6   15   19                                                  
CONECT   15    7   14   17                                                  
CONECT   16    8   13   18                                                  
CONECT   17    9   12   15                                                  
CONECT   18   10   16   21                                                  
CONECT   19   11   14                                                       
CONECT   20   13   22                                                       
CONECT   21   18   22                                                       
CONECT   22   20   21                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
Cinnabarinic acid	Kegg
Cinnabarinate	Generator
Cinnavalininic acid	Generator
2-Amino-3-oxo-3H-phenoxazin-1,9-dicarboxylic acid	HMDB
2-Amino-3H-phenoxazin-one-1,9-dicarboxylic acid	HMDB

Chemical Formula

C₁₄H₈N₂O₆

Average Mass

300.2231 Da

Monoisotopic Mass

300.03824 Da

IUPAC Name

2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid

Traditional Name

cinnabarinic acid

CAS Registry Number

Not 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 Key

FSBKJYLVDRVPTK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazines

Sub Class

Phenoxazines

Direct Parent

Phenoxazines

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenoxazine (CHEBI:3715 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.7	ALOGPS
logP	0.44	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	2.37	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.28 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.9 m³·mol⁻¹	ChemAxon
Polarizability	27.38 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0004078

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023302

KNApSAcK ID

Not Available

Chemspider ID

102864

KEGG Compound ID

C05640

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

114918

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cinnavalininate (NP0087134)

MOL for NP0087134 (Cinnavalininate)

3D MOL for NP0087134 (Cinnavalininate)

3D SDF for NP0087134 (Cinnavalininate)

3D-SDF for NP0087134 (Cinnavalininate)

PDB for NP0087134 (Cinnavalininate)

3D PDB for NP0087134 (Cinnavalininate)

SMILES for NP0087134 (Cinnavalininate)

INCHI for NP0087134 (Cinnavalininate)

Structure for NP0087134 (Cinnavalininate)

3D Structure for NP0087134 (Cinnavalininate)