NP-MRD: Showing NP-Card for 8-[(1-hydroxyethylidene)amino]-7-oxophenoxazine-2-carboxylic acid (NP0315050)

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Record Information

Version

2.0

Created at

2022-09-11 13:29:21 UTC

Updated at

2022-09-11 13:29:21 UTC

NP-MRD ID

NP0315050

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-[(1-hydroxyethylidene)amino]-7-oxophenoxazine-2-carboxylic acid

Description

Carboxyexfoliazone 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. 8-[(1-hydroxyethylidene)amino]-7-oxophenoxazine-2-carboxylic acid is found in Streptomyces venezuelae. 8-[(1-hydroxyethylidene)amino]-7-oxophenoxazine-2-carboxylic acid was first documented in 2013 (PMID: 23164710). Based on a literature review a small amount of articles have been published on Carboxyexfoliazone (PMID: 32708048) (PMID: 23656313).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
    6.1868    0.5156    0.8790 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8997    0.1061    0.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -1.0711   -0.4396 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8993    0.8755    0.3932 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6066    0.6141   -0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4745    0.6220    0.6407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2003    0.3678    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8903    0.3777    0.8981 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0846    0.1180    0.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2492    0.1177    1.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4728   -0.1412    0.4963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6595   -0.1290    1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7655   -0.3670    0.8045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6176    0.1288    2.6862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5522   -0.4059   -0.8593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4288   -0.4183   -1.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2097   -0.1501   -1.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1360   -0.1648   -1.8261 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0341    0.0803   -1.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1923    0.0813   -2.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4282    0.3401   -1.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4707    0.3315   -2.2184 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9199   -0.3165    0.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5261    1.4241    0.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0282    0.7580    1.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2662   -1.8713   -0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5920    0.8357    1.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1177    0.3337    2.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4146   -0.5758    3.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5453   -0.6034   -1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4964   -0.6258   -2.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0986   -0.1326   -3.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 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
 11 12  1  0
 12 14  1  0
 12 13  2  0
 21  5  1  0
 19  7  1  0
 17  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  6 27  1  0
 10 28  1  0
 15 30  1  0
 16 31  1  0
 20 32  1  0
 14 29  1  0
M  END


  Mrv1652309112215292D          

 22 24  0  0  0  0            999 V2000
   -0.7145   -1.2375    0.0000 C   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
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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
    2.8579   -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
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   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  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  4  0  0  0
  5  6  2  0  0  0  0
  6  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
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 11 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0315050

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)=NC1=CC2=NC3=CC(=CC=C3OC2=CC1=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H10N2O5/c1-7(18)16-9-5-11-14(6-12(9)19)22-13-3-2-8(15(20)21)4-10(13)17-11/h2-6H,1H3,(H,16,18)(H,20,21)

> <INCHI_KEY>
XYAHGPPEMKOZBC-UHFFFAOYSA-N

> <FORMULA>
C15H10N2O5

> <MOLECULAR_WEIGHT>
298.254

> <EXACT_MASS>
298.05897143

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
29.334636532663072

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1-hydroxyethylidene)amino]-3-oxo-3H-phenoxazine-8-carboxylic acid

> <JCHEM_LOGP>
1.4897830989999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
5.406641876882318

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.599517070734844

> <JCHEM_PKA_STRONGEST_BASIC>
0.46623008809258315

> <JCHEM_POLAR_SURFACE_AREA>
108.55000000000001

> <JCHEM_REFRACTIVITY>
80.79029999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
8-[(1-hydroxyethylidene)amino]-7-oxophenoxazine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+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      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    9   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18    7   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    5   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₀N₂O₅

Average Mass

298.2540 Da

Monoisotopic Mass

298.05897 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(O)=NC1=CC2=NC3=CC(=CC=C3OC2=CC1=O)C(O)=O

InChI Identifier

InChI=1S/C15H10N2O5/c1-7(18)16-9-5-11-14(6-12(9)19)22-13-3-2-8(15(20)21)4-10(13)17-11/h2-6H,1H3,(H,16,18)(H,20,21)

InChI Key

XYAHGPPEMKOZBC-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Streptomyces venezuelae	LOTUS Database	35616633

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
N-acetylarylamine
N-arylamide
Benzenoid
Acetamide
Heteroaromatic compound
Carboxamide group
Secondary carboxylic acid amide
Cyclic ketone
Carboxylic acid
Carboxylic acid derivative
Azacycle
Oxacycle
Organic oxide
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
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

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

28677381

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71339187

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ren J, Liu D, Tian L, Wei Y, Proksch P, Zeng J, Lin W: Venezuelines A-G, new phenoxazine-based alkaloids and aminophenols from Streptomyces venezuelae and the regulation of gene target Nur77. Bioorg Med Chem Lett. 2013 Jan 1;23(1):301-4. doi: 10.1016/j.bmcl.2012.10.096. Epub 2012 Oct 30. [PubMed:23164710 ]
Elmallah MIY, Cogo S, Constantinescu AA, Elifio-Esposito S, Abdelfattah MS, Micheau O: Marine Actinomycetes-Derived Secondary Metabolites Overcome TRAIL-Resistance via the Intrinsic Pathway through Downregulation of Survivin and XIAP. Cells. 2020 Jul 22;9(8):1760. doi: 10.3390/cells9081760. [PubMed:32708048 ]
Abdelfattah MS: A new bioactive aminophenoxazinone alkaloid from a marine-derived actinomycete. Nat Prod Res. 2013;27(22):2126-31. doi: 10.1080/14786419.2013.793686. Epub 2013 May 9. [PubMed:23656313 ]
LOTUS database [Link]

Showing NP-Card for 8-[(1-hydroxyethylidene)amino]-7-oxophenoxazine-2-carboxylic acid (NP0315050)

MOL for NP0315050 (8-[(1-hydroxyethylidene)amino]-7-oxophenoxazine-2-carboxylic acid)

3D MOL for NP0315050 (8-[(1-hydroxyethylidene)amino]-7-oxophenoxazine-2-carboxylic acid)

3D SDF for NP0315050 (8-[(1-hydroxyethylidene)amino]-7-oxophenoxazine-2-carboxylic acid)

3D-SDF for NP0315050 (8-[(1-hydroxyethylidene)amino]-7-oxophenoxazine-2-carboxylic acid)

PDB for NP0315050 (8-[(1-hydroxyethylidene)amino]-7-oxophenoxazine-2-carboxylic acid)

3D PDB for NP0315050 (8-[(1-hydroxyethylidene)amino]-7-oxophenoxazine-2-carboxylic acid)

SMILES for NP0315050 (8-[(1-hydroxyethylidene)amino]-7-oxophenoxazine-2-carboxylic acid)

INCHI for NP0315050 (8-[(1-hydroxyethylidene)amino]-7-oxophenoxazine-2-carboxylic acid)

Structure for NP0315050 (8-[(1-hydroxyethylidene)amino]-7-oxophenoxazine-2-carboxylic acid)

3D Structure for NP0315050 (8-[(1-hydroxyethylidene)amino]-7-oxophenoxazine-2-carboxylic acid)