NP-MRD: Showing NP-Card for MSD-819 (NP0021732)

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Record Information

Version

2.0

Created at

2021-01-06 07:00:27 UTC

Updated at

2021-07-15 17:37:07 UTC

NP-MRD ID

NP0021732

Secondary Accession Numbers

None

Natural Product Identification

Common Name

MSD-819

Provided By

NPAtlas

Description

MSD-819 is found in Streptomyces ambofaciens. MSD-819 was first documented in 1968 (PMID: 5735369). Based on a literature review very few articles have been published on 6-chloro-1,4-dioxo-1λ⁵,4λ⁵-quinoxaline-2-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105183D          

 21 22  0  0  0  0            999 V2000
   -3.2858   -1.9103   -0.8355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1375   -0.7677   -0.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2177    0.0111   -0.0248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7974   -0.2586   -0.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5897    1.0125    0.3882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3234    1.4757    0.5791 N   0  3  0  0  0  4  0  0  0  0  0  0
   -0.1923    2.7393    1.1099 O   0  5  0  0  0  1  0  0  0  0  0  0
    0.7456    0.7234    0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0230    1.1933    0.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1253    0.4305    0.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7692    1.0118    0.3685 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9271   -0.8279   -0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6444   -1.3006   -0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5435   -0.5342   -0.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7025   -0.9962   -0.4590 N   0  3  0  0  0  4  0  0  0  0  0  0
   -0.9418   -2.2417   -0.9820 O   0  5  0  0  0  1  0  0  0  0  0  0
   -4.5383    0.1669    0.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4641    1.5837    0.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1820    2.1892    0.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7685   -1.4296   -0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4620   -2.2703   -1.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  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
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15  4  1  0  0  0  0
 14  8  1  0  0  0  0
  3 17  1  0  0  0  0
  5 18  1  0  0  0  0
  9 19  1  0  0  0  0
 12 20  1  0  0  0  0
 13 21  1  0  0  0  0
M  CHG  4   6   1   7  -1  15   1  16  -1
M  END
> <DATABASE_ID>
NP0021732

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])[N+]([O-])=C2C([H])=C(Cl)C([H])=C([H])C2=[N+]1[O-]

> <INCHI_IDENTIFIER>
InChI=1S/C9H5ClN2O4/c10-5-1-2-6-7(3-5)11(15)4-8(9(13)14)12(6)16/h1-4H,(H,13,14)

> <INCHI_KEY>
OREKRDMCWBYLFR-UHFFFAOYSA-N

> <FORMULA>
C9H5ClN2O4

> <MOLECULAR_WEIGHT>
240.6

> <EXACT_MASS>
239.9937843

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
20.846465703264943

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-carboxy-7-chloroquinoxaline-1,4-diium-1,4-bis(olate)

> <ALOGPS_LOGP>
0.30

> <JCHEM_LOGP>
-1.2449992547377973

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.062083492444344

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.5019364632246281

> <JCHEM_PKA_STRONGEST_BASIC>
0.911999948300658

> <JCHEM_POLAR_SURFACE_AREA>
91.17999999999999

> <JCHEM_REFRACTIVITY>
56.5125

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-carboxy-7-chloroquinoxaline-1,4-diium-1,4-bis(olate)

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -3.286  -1.910  -0.836  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.138  -0.768  -0.356  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.218   0.011  -0.025  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.797  -0.259  -0.146  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.590   1.012   0.388  0.00  0.00           C+0
HETATM    6  N   UNK     0      -0.323   1.476   0.579  0.00  0.00           N+1
HETATM    7  O   UNK     0      -0.192   2.739   1.110  0.00  0.00           O-1
HETATM    8  C   UNK     0       0.746   0.723   0.260  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.023   1.193   0.453  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.125   0.431   0.129  0.00  0.00           C+0
HETATM   11 Cl   UNK     0       4.769   1.012   0.369  0.00  0.00          Cl+0
HETATM   12  C   UNK     0       2.927  -0.828  -0.399  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.644  -1.301  -0.594  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.544  -0.534  -0.269  0.00  0.00           C+0
HETATM   15  N   UNK     0      -0.703  -0.996  -0.459  0.00  0.00           N+1
HETATM   16  O   UNK     0      -0.942  -2.242  -0.982  0.00  0.00           O-1
HETATM   17  H   UNK     0      -4.538   0.167   0.931  0.00  0.00           H+0
HETATM   18  H   UNK     0      -2.464   1.584   0.631  0.00  0.00           H+0
HETATM   19  H   UNK     0       2.182   2.189   0.871  0.00  0.00           H+0
HETATM   20  H   UNK     0       3.769  -1.430  -0.655  0.00  0.00           H+0
HETATM   21  H   UNK     0       1.462  -2.270  -1.001  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2   17                                                       
CONECT    4    2    5   15                                                  
CONECT    5    4    6   18                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   14                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   20                                                  
CONECT   13   12   14   21                                                  
CONECT   14   13   15    8                                                  
CONECT   15   14   16    4                                                  
CONECT   16   15                                                            
CONECT   17    3                                                            
CONECT   18    5                                                            
CONECT   19    9                                                            
CONECT   20   12                                                            
CONECT   21   13                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
6-Chloro-1,4-dioxo-1,4-quinoxaline-2-carboxylate	Generator
6-Chloro-1,4-dioxo-1λ⁵,4λ⁵-quinoxaline-2-carboxylate	Generator

Chemical Formula

C₉H₅ClN₂O₄

Average Mass

240.6000 Da

Monoisotopic Mass

239.99378 Da

IUPAC Name

3-carboxy-7-chloroquinoxaline-1,4-diium-1,4-bis(olate)

Traditional Name

3-carboxy-7-chloroquinoxaline-1,4-diium-1,4-bis(olate)

CAS Registry Number

Not Available

SMILES

OC(=O)C1=[N+]([O-])C2=C(C=C(Cl)C=C2)[N+]([O-])=C1

InChI Identifier

InChI=1S/C9H5ClN2O4/c10-5-1-2-6-7(3-5)11(15)4-8(9(13)14)12(6)16/h1-4H,(H,13,14)

InChI Key

OREKRDMCWBYLFR-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
Streptomyces ambofaciens	NPAtlas	5735369

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as quinoxalines. These are compounds containing a quinoxaline moiety, a bicyclic heterocycle made up of a benzene ring fused to a pyrazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Quinoxalines

Alternative Parents

Substituents

Quinoxaline
Pyrazine carboxylic acid
Pyrazine carboxylic acid or derivatives
Aryl chloride
Aryl halide
Pyrazine
Benzenoid
Pyrazinium
Heteroaromatic compound
Vinylogous amide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organic zwitterion
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	0.3	ALOGPS
logP	-1.2	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	-1.5	ChemAxon
pKa (Strongest Basic)	0.91	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	91.18 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	56.51 m³·mol⁻¹	ChemAxon
Polarizability	20.85 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA005505

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

57460122

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54690348

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Miller TW, Walker RW, Trenner NR, Arison BA, Wolf FJ: Antibiotic MSD-819. II. Isolation and chemical characterization as 6-chloro-2-quinoxalinecarboxylic acid 1,4-dioxide. Antimicrob Agents Chemother (Bethesda). 1968;8:255-9. [PubMed:5735369 ]

Showing NP-Card for MSD-819 (NP0021732)

MOL for NP0021732 (MSD-819)

3D MOL for NP0021732 (MSD-819)

3D SDF for NP0021732 (MSD-819)

3D-SDF for NP0021732 (MSD-819)

PDB for NP0021732 (MSD-819)

3D PDB for NP0021732 (MSD-819)

SMILES for NP0021732 (MSD-819)

INCHI for NP0021732 (MSD-819)

Structure for NP0021732 (MSD-819)

3D Structure for NP0021732 (MSD-819)