NP-MRD: Showing NP-Card for 2-amino-9-formyl-3-oxophenoxazine-1-carboxylic acid (NP0329011)

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Record Information

Version

2.0

Created at

2022-09-12 12:59:09 UTC

Updated at

2022-09-12 12:59:09 UTC

NP-MRD ID

NP0329011

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-amino-9-formyl-3-oxophenoxazine-1-carboxylic acid

Description

2-Amino-9-formyl-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. 2-Amino-9-formyl-3-oxo-3H-phenoxazine-1-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004231523072D          

 21 23  0  0  0  0            999 V2000
   -2.1434   -2.8875    0.0000 N   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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 N   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   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 O   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
    2.8579   -1.6500    0.0000 C   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
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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
  7 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0329011

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=C(C(O)=O)C2=NC3=C(OC2=CC1=O)C=CC=C3C=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H8N2O5/c15-11-7(18)4-9-13(10(11)14(19)20)16-12-6(5-17)2-1-3-8(12)21-9/h1-5H,15H2,(H,19,20)

> <INCHI_KEY>
GIEFYHDAQLAMLG-UHFFFAOYSA-N

> <FORMULA>
C14H8N2O5

> <MOLECULAR_WEIGHT>
284.227

> <EXACT_MASS>
284.043321366

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
26.44489616268089

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-amino-9-formyl-3-oxo-3H-phenoxazine-1-carboxylic acid

> <ALOGPS_LOGP>
1.08

> <JCHEM_LOGP>
0.493494894

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.94397091447698

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.510810628600015

> <JCHEM_PKA_STRONGEST_BASIC>
-4.930761544623537

> <JCHEM_POLAR_SURFACE_AREA>
119.05000000000001

> <JCHEM_REFRACTIVITY>
76.22690000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-9-formyl-3-oxophenoxazine-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  N   UNK     0      -4.001  -5.390   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.000  -7.700   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.334  -5.390   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+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       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13    2   15                                                  
CONECT   15   14                                                            
CONECT   16   10   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    9   20                                                  
CONECT   20   19   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-formyl-3-oxo-3H-phenoxazine-1-carboxylate	Generator

Chemical Formula

C₁₄H₈N₂O₅

Average Mass

284.2270 Da

Monoisotopic Mass

284.04332 Da

IUPAC Name

2-amino-9-formyl-3-oxo-3H-phenoxazine-1-carboxylic acid

Traditional Name

2-amino-9-formyl-3-oxophenoxazine-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

NC1=C(C(O)=O)C2=NC3=C(OC2=CC1=O)C=CC=C3C=O

InChI Identifier

InChI=1S/C14H8N2O5/c15-11-7(18)4-9-13(10(11)14(19)20)16-12-6(5-17)2-1-3-8(12)21-9/h1-5H,15H2,(H,19,20)

InChI Key

GIEFYHDAQLAMLG-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Aryl-aldehyde
Benzenoid
Heteroaromatic compound
Vinylogous amide
Amino acid or derivatives
Cyclic ketone
Amino acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Primary amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aldehyde
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	1.08	ALOGPS
logP	0.49	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	2.51	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.05 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.23 m³·mol⁻¹	ChemAxon
Polarizability	26.44 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

14160621

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-amino-9-formyl-3-oxophenoxazine-1-carboxylic acid (NP0329011)

MOL for NP0329011 (2-amino-9-formyl-3-oxophenoxazine-1-carboxylic acid)

3D MOL for NP0329011 (2-amino-9-formyl-3-oxophenoxazine-1-carboxylic acid)

3D SDF for NP0329011 (2-amino-9-formyl-3-oxophenoxazine-1-carboxylic acid)

3D-SDF for NP0329011 (2-amino-9-formyl-3-oxophenoxazine-1-carboxylic acid)

PDB for NP0329011 (2-amino-9-formyl-3-oxophenoxazine-1-carboxylic acid)

3D PDB for NP0329011 (2-amino-9-formyl-3-oxophenoxazine-1-carboxylic acid)

SMILES for NP0329011 (2-amino-9-formyl-3-oxophenoxazine-1-carboxylic acid)

INCHI for NP0329011 (2-amino-9-formyl-3-oxophenoxazine-1-carboxylic acid)

Structure for NP0329011 (2-amino-9-formyl-3-oxophenoxazine-1-carboxylic acid)

3D Structure for NP0329011 (2-amino-9-formyl-3-oxophenoxazine-1-carboxylic acid)