NP-MRD: Showing NP-Card for Quinolonic acid (NP0006279)

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Record Information

Version

2.0

Created at

2020-12-09 03:20:22 UTC

Updated at

2021-07-15 16:54:20 UTC

NP-MRD ID

NP0006279

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Quinolonic acid

Provided By

NPAtlas

Description

Quinolonic acid is found in Penicillium citrinum. Quinolonic acid was first documented in 2006 (PMID: 16604219). Based on a literature review very few articles have been published on 3-(C-hydroxycarbonimidoyl)-1-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242121113D          

 28 29  0  0  0  0            999 V2000
   -0.0136   -2.6012    0.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0232   -1.1676    0.2140 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2275   -0.5289    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4670   -1.2969    0.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5692   -0.7203    0.0067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4765   -2.6715    0.4042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2433    0.8383   -0.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4064    1.6177   -0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3861    3.0419   -0.0779 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4641    1.2396   -0.8982 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0524    1.5606   -0.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0252    2.8175   -0.2469 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1233    0.9111    0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3059    1.6368    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304    1.0074    0.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4934   -0.3532    0.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3371   -1.1116    0.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1316   -0.4781    0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9539   -3.0927    0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6507   -2.9681   -0.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4648   -2.9941    1.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2019   -3.0221    0.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7304    3.7339   -0.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0257    3.3317    0.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2616    2.7084   -0.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469    1.5830    0.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4549   -0.8555    0.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3890   -2.1659    0.5495 H   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  3  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 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
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18  2  1  0  0  0  0
 18 13  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  6 22  1  0  0  0  0
  9 23  1  0  0  0  0
  9 24  1  0  0  0  0
 14 25  1  0  0  0  0
 15 26  1  0  0  0  0
 16 27  1  0  0  0  0
 17 28  1  0  0  0  0
M  END


  Mrv1652306242121113D          

 28 29  0  0  0  0            999 V2000
   -0.0136   -2.6012    0.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0232   -1.1676    0.2140 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2275   -0.5289    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4670   -1.2969    0.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5692   -0.7203    0.0067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4765   -2.6715    0.4042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2433    0.8383   -0.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4064    1.6177   -0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3861    3.0419   -0.0779 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4641    1.2396   -0.8982 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0524    1.5606   -0.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0252    2.8175   -0.2469 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1233    0.9111    0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3059    1.6368    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304    1.0074    0.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4934   -0.3532    0.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3371   -1.1116    0.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1316   -0.4781    0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9539   -3.0927    0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6507   -2.9681   -0.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4648   -2.9941    1.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2019   -3.0221    0.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7304    3.7339   -0.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0257    3.3317    0.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2616    2.7084   -0.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469    1.5830    0.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4549   -0.8555    0.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3890   -2.1659    0.5495 H   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  3  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 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
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18  2  1  0  0  0  0
 18 13  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  6 22  1  0  0  0  0
  9 23  1  0  0  0  0
  9 24  1  0  0  0  0
 14 25  1  0  0  0  0
 15 26  1  0  0  0  0
 16 27  1  0  0  0  0
 17 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006279

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C(C(=O)N([H])[H])C(=O)C2=C([H])C([H])=C([H])C([H])=C2N1C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H10N2O4/c1-14-7-5-3-2-4-6(7)10(15)8(11(13)16)9(14)12(17)18/h2-5H,1H3,(H2,13,16)(H,17,18)

> <INCHI_KEY>
CGKCBYCUHQKZMN-UHFFFAOYSA-N

> <FORMULA>
C12H10N2O4

> <MOLECULAR_WEIGHT>
246.222

> <EXACT_MASS>
246.06405681

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
23.594414506115474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-carbamoyl-1-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid

> <ALOGPS_LOGP>
0.20

> <JCHEM_LOGP>
0.19378932400000012

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.346353539859312

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.247126231270376

> <JCHEM_PKA_STRONGEST_BASIC>
-1.48370454077015

> <JCHEM_POLAR_SURFACE_AREA>
100.69999999999999

> <JCHEM_REFRACTIVITY>
64.45530000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-carbamoyl-1-methyl-4-oxoquinoline-2-carboxylic acid

> <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  C   UNK     0      -0.014  -2.601   0.317  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.023  -1.168   0.214  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.228  -0.529   0.048  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.467  -1.297   0.149  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.569  -0.720   0.007  0.00  0.00           O+0
HETATM    6  O   UNK     0      -2.477  -2.672   0.404  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.243   0.838  -0.114  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.406   1.618  -0.400  0.00  0.00           C+0
HETATM    9  N   UNK     0      -2.386   3.042  -0.078  0.00  0.00           N+0
HETATM   10  O   UNK     0      -3.464   1.240  -0.898  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.052   1.561  -0.103  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.025   2.817  -0.247  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.123   0.911   0.067  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.306   1.637   0.088  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.530   1.007   0.270  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.493  -0.353   0.424  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.337  -1.112   0.409  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.132  -0.478   0.227  0.00  0.00           C+0
HETATM   19  H   UNK     0       0.954  -3.093   0.078  0.00  0.00           H+0
HETATM   20  H   UNK     0      -0.651  -2.968  -0.551  0.00  0.00           H+0
HETATM   21  H   UNK     0      -0.465  -2.994   1.236  0.00  0.00           H+0
HETATM   22  H   UNK     0      -3.202  -3.022   0.996  0.00  0.00           H+0
HETATM   23  H   UNK     0      -2.730   3.734  -0.756  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.026   3.332   0.831  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.262   2.708  -0.040  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.447   1.583   0.284  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.455  -0.856   0.569  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.389  -2.166   0.550  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2    1    3   18                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4   22                                                       
CONECT    7    3    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   23   24                                                  
CONECT   10    8                                                            
CONECT   11    7   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15   25                                                  
CONECT   15   14   16   26                                                  
CONECT   16   15   17   27                                                  
CONECT   17   16   18   28                                                  
CONECT   18   17    2   13                                                  
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    6                                                            
CONECT   23    9                                                            
CONECT   24    9                                                            
CONECT   25   14                                                            
CONECT   26   15                                                            
CONECT   27   16                                                            
CONECT   28   17                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3-(C-Hydroxycarbonimidoyl)-1-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylate	Generator
Quinolonate	Generator

Chemical Formula

C₁₂H₁₀N₂O₄

Average Mass

246.2220 Da

Monoisotopic Mass

246.06406 Da

IUPAC Name

3-carbamoyl-1-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid

Traditional Name

3-carbamoyl-1-methyl-4-oxoquinoline-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CN1C2=CC=CC=C2C(=O)C(C(N)=O)=C1C(O)=O

InChI Identifier

InChI=1S/C12H10N2O4/c1-14-7-5-3-2-4-6(7)10(15)8(11(13)16)9(14)12(17)18/h2-5H,1H3,(H2,13,16)(H,17,18)

InChI Key

CGKCBYCUHQKZMN-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
Penicillium citrinum	NPAtlas	16604219

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as quinoline-3-carboxamides. These are quinolines in which the quinoline ring system is substituted by one carboxamide group at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinoline carboxamides

Direct Parent

Quinoline-3-carboxamides

Alternative Parents

Substituents

Quinoline-2-carboxylic acid
Quinoline-3-carboxamide
Dihydroquinolone
Dihydroquinoline
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Benzenoid
Pyridine
Vinylogous amide
Heteroaromatic compound
Carboxamide group
Primary carboxylic acid amide
Azacycle
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
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	0.2	ALOGPS
logP	0.19	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	2.25	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.7 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	64.46 m³·mol⁻¹	ChemAxon
Polarizability	23.59 Å³	ChemAxon
Number of Rings	2	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

NPAtlas ID

NPA009253

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9732591

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11557817

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Clark B, Capon RJ, Lacey E, Tennant S, Gill JH: Quinolactacins revisited: from lactams to imide and beyond. Org Biomol Chem. 2006 Apr 21;4(8):1512-9. doi: 10.1039/b600959j. Epub 2006 Mar 16. [PubMed:16604219 ]

Showing NP-Card for Quinolonic acid (NP0006279)

MOL for NP0006279 (Quinolonic acid)

3D MOL for NP0006279 (Quinolonic acid)

3D SDF for NP0006279 (Quinolonic acid)

3D-SDF for NP0006279 (Quinolonic acid)

PDB for NP0006279 (Quinolonic acid)

3D PDB for NP0006279 (Quinolonic acid)

SMILES for NP0006279 (Quinolonic acid)

INCHI for NP0006279 (Quinolonic acid)

Structure for NP0006279 (Quinolonic acid)

3D Structure for NP0006279 (Quinolonic acid)