NP-MRD: Showing NP-Card for 2,8-dihydroxyquinoline-4-carboxylic acid (NP0242782)

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Record Information

Version

1.0

Created at

2022-09-07 03:10:27 UTC

Updated at

2022-09-07 03:10:27 UTC

NP-MRD ID

NP0242782

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,8-dihydroxyquinoline-4-carboxylic acid

Description

Zeanic acid, also known as zeanate, belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions. Zeanic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Zeanic acid has been detected, but not quantified in, cereals and cereal products. 2,8-dihydroxyquinoline-4-carboxylic acid is found in Zea mays. This could make zeanic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061306492D          

 15 16  0  0  0  0            999 V2000
   -3.5444    0.3303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8299   -0.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1154    0.3303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8299   -0.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5444   -1.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5444   -2.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2589   -2.5572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8299   -2.5572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1154   -2.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1154   -1.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4010   -0.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6865   -1.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6865   -2.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4010   -2.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4010   -3.3822    0.0000 O   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
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 14  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0242782

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC(=O)NC2=C1C=CC=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C10H7NO4/c12-7-3-1-2-5-6(10(14)15)4-8(13)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15)

> <INCHI_KEY>
DVEVPRIOUKVFAM-UHFFFAOYSA-N

> <FORMULA>
C10H7NO4

> <MOLECULAR_WEIGHT>
205.1669

> <EXACT_MASS>
205.037507717

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
18.84271907397129

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-2-oxo-1,2-dihydroquinoline-4-carboxylic acid

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
0.784664224

> <ALOGPS_LOGS>
-1.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.624270907282533

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7881196068193175

> <JCHEM_PKA_STRONGEST_BASIC>
-2.646508499539036

> <JCHEM_POLAR_SURFACE_AREA>
86.63

> <JCHEM_REFRACTIVITY>
53.2593

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-2-oxo-1H-quinoline-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  O   UNK     0      -6.616   0.617   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -5.282  -0.153   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.949   0.617   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -5.282  -1.693   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.616  -2.463   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.616  -4.003   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.950  -4.773   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      -5.282  -4.773   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -3.949  -4.003   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.949  -2.463   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.615  -1.693   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.281  -2.463   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.281  -4.003   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.615  -4.773   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.615  -6.313   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    4    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14    9   13   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
Zeanate	Generator
1,2-Dihydro-8-hydroxy-2-oxo-4-quinolinecarboxylic acid	HMDB
2,8-Dihydroxycinchoninic acid	HMDB
8-Hydroxy-2(1H)-quinolinone-4-carboxylic acid	HMDB
2,8-Dihydroxyquinoline-4-carboxylate	Generator

Chemical Formula

C₁₀H₇NO₄

Average Mass

205.1669 Da

Monoisotopic Mass

205.03751 Da

IUPAC Name

8-hydroxy-2-oxo-1,2-dihydroquinoline-4-carboxylic acid

Traditional Name

8-hydroxy-2-oxo-1H-quinoline-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC(=O)NC2=C1C=CC=C2O

InChI Identifier

InChI=1S/C10H7NO4/c12-7-3-1-2-5-6(10(14)15)4-8(13)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15)

InChI Key

DVEVPRIOUKVFAM-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
Zea mays	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinoline carboxylic acids

Direct Parent

Quinoline carboxylic acids

Alternative Parents

Substituents

Quinoline-4-carboxylic acid
Dihydroquinolone
Hydroxyquinoline
8-hydroxyquinoline
Dihydroquinoline
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyridinone
Pyridine
Benzenoid
Heteroaromatic compound
Lactam
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen 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	1.58	ALOGPS
logP	0.78	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	2.79	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	53.26 m³·mol⁻¹	ChemAxon
Polarizability	18.84 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

HMDB ID

HMDB0032963

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010949

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

13988328

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,8-dihydroxyquinoline-4-carboxylic acid (NP0242782)

MOL for NP0242782 (2,8-dihydroxyquinoline-4-carboxylic acid)

3D MOL for NP0242782 (2,8-dihydroxyquinoline-4-carboxylic acid)

3D SDF for NP0242782 (2,8-dihydroxyquinoline-4-carboxylic acid)

3D-SDF for NP0242782 (2,8-dihydroxyquinoline-4-carboxylic acid)

PDB for NP0242782 (2,8-dihydroxyquinoline-4-carboxylic acid)

3D PDB for NP0242782 (2,8-dihydroxyquinoline-4-carboxylic acid)

SMILES for NP0242782 (2,8-dihydroxyquinoline-4-carboxylic acid)

INCHI for NP0242782 (2,8-dihydroxyquinoline-4-carboxylic acid)

Structure for NP0242782 (2,8-dihydroxyquinoline-4-carboxylic acid)

3D Structure for NP0242782 (2,8-dihydroxyquinoline-4-carboxylic acid)