NP-MRD: Showing NP-Card for Cinnabarin (NP0078984)

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Record Information

Version

2.0

Created at

2022-04-29 00:03:37 UTC

Updated at

2022-04-29 00:03:37 UTC

NP-MRD ID

NP0078984

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cinnabarin

Description

2-Amino-9-(hydroxymethyl)-3-oxo-3H-phenoxazine-1-carboxylic acid 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. Cinnabarin is found in Trametes cinnabarina and Pycnoporus sanguineus . 2-Amino-9-(hydroxymethyl)-3-oxo-3H-phenoxazine-1-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
    4.5390   -0.1540    0.9958 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3474   -0.6081    0.3793 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1557    0.0904    0.6179 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1361    1.2569    1.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1848    1.6571    2.0216 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9660    1.9364    1.7081 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9597   -0.3086    0.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1802    0.3981    0.2981 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3032   -0.0661   -0.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5160    0.5957   -0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4822    1.7942    0.7937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7476    2.3323    0.8959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7010    0.2005   -0.6745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6657   -0.9091   -1.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4875   -1.5840   -1.7136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2856   -1.1742   -1.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1747   -1.8538   -1.3711 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9417   -1.4730   -0.8267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1420   -2.1404   -1.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3089   -1.7101   -0.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3903   -2.3424   -0.6625 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9298   -0.6548    1.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0278    0.6814    0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6414    2.6886    1.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7203    2.4790    0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1733    1.4946    1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6386    3.2976    1.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6189    0.7539   -0.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6032   -1.2242   -1.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4810   -2.4511   -2.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1083   -3.0028   -1.6879 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 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20  2  1  0
 18  7  1  0
 16  9  1  0
  1 22  1  0
  1 23  1  0
  6 24  1  0
 11 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 19 31  1  0
M  END


  Mrv1533004181500482D          

 21 23  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0078984

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=C(C(O)=O)C2=NC3=C(CO)C=CC=C3OC2=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H10N2O5/c15-11-7(18)4-9-13(10(11)14(19)20)16-12-6(5-17)2-1-3-8(12)21-9/h1-4,17H,5,15H2,(H,19,20)

> <INCHI_KEY>
BHUPIKYIGMWGAD-UHFFFAOYSA-N

> <FORMULA>
C14H10N2O5

> <MOLECULAR_WEIGHT>
286.243

> <EXACT_MASS>
286.05897143

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
27.21783369259373

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-amino-9-(hydroxymethyl)-3-oxo-3H-phenoxazine-1-carboxylic acid

> <ALOGPS_LOGP>
0.47

> <JCHEM_LOGP>
0.01364278200000023

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.572231651297344

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7035676770982606

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9866509513634076

> <JCHEM_POLAR_SURFACE_AREA>
122.21000000000001

> <JCHEM_REFRACTIVITY>
76.4588

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-9-(hydroxymethyl)-3-oxophenoxazine-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    9   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    7   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    2   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
2-Amino-9-(hydroxymethyl)-3-oxo-3H-phenoxazine-1-carboxylate	Generator

Chemical Formula

C₁₄H₁₀N₂O₅

Average Mass

286.2430 Da

Monoisotopic Mass

286.05897 Da

IUPAC Name

2-amino-9-(hydroxymethyl)-3-oxo-3H-phenoxazine-1-carboxylic acid

Traditional Name

2-amino-9-(hydroxymethyl)-3-oxophenoxazine-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

NC1=C(C(O)=O)C2=NC3=C(CO)C=CC=C3OC2=CC1=O

InChI Identifier

InChI=1S/C14H10N2O5/c15-11-7(18)4-9-13(10(11)14(19)20)16-12-6(5-17)2-1-3-8(12)21-9/h1-4,17H,5,15H2,(H,19,20)

InChI Key

BHUPIKYIGMWGAD-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
Trametes cinnabarina	LOTUS Database	35616633
Trametes sanguinea	Fungi	KNApSAcK

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
Benzenoid
Vinylogous amide
Heteroaromatic compound
Amino acid or derivatives
Cyclic ketone
Amino acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Oxacycle
Aromatic alcohol
Primary amine
Primary alcohol
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	0.47	ALOGPS
logP	0.014	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	2.7	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.21 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.46 m³·mol⁻¹	ChemAxon
Polarizability	27.22 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72626

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cinnabarin (NP0078984)

MOL for NP0078984 (Cinnabarin)

3D MOL for NP0078984 (Cinnabarin)

3D SDF for NP0078984 (Cinnabarin)

3D-SDF for NP0078984 (Cinnabarin)

PDB for NP0078984 (Cinnabarin)

3D PDB for NP0078984 (Cinnabarin)

SMILES for NP0078984 (Cinnabarin)

INCHI for NP0078984 (Cinnabarin)

Structure for NP0078984 (Cinnabarin)

3D Structure for NP0078984 (Cinnabarin)