NP-MRD: Showing NP-Card for 8-methoxykynurenate (NP0256766)

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Record Information

Version

2.0

Created at

2022-09-07 21:41:56 UTC

Updated at

2022-09-07 21:41:56 UTC

NP-MRD ID

NP0256766

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-methoxykynurenate

Description

8-Methoxykynurenate 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. 8-Methoxykynurenate is an extremely weak basic (essentially neutral) compound (based on its pKa). 8-Methoxykynurenate exists in all living organisms, ranging from bacteria to humans. 8-methoxykynurenate is found in Trypanosoma brucei. 8-methoxykynurenate was first documented in 1984 (PMID: 6435892). These are Quinolines in which the quinoline ring system is substituted by a carboxyl group at at least one position.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05161318022D          

 16 17  0  0  0  0            999 V2000
    0.7145    3.7125    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    2.1434    2.0625    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
    2.8579    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  5  2  0  0  0  0
  8  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  4  2  0  0  0  0
 10  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  2  0  0  0  0
 13  8  1  0  0  0  0
 14 11  2  0  0  0  0
 15 11  1  0  0  0  0
 16  1  1  0  0  0  0
 16  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256766

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=CC2=C(O)C=C(N=C12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H9NO4/c1-16-9-4-2-3-6-8(13)5-7(11(14)15)12-10(6)9/h2-5H,1H3,(H,12,13)(H,14,15)

> <INCHI_KEY>
BXZSKDOPGDPDEG-UHFFFAOYSA-N

> <FORMULA>
C11H9NO4

> <MOLECULAR_WEIGHT>
219.1935

> <EXACT_MASS>
219.053157781

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
21.037616824540954

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-8-methoxyquinoline-2-carboxylic acid

> <ALOGPS_LOGP>
2.21

> <JCHEM_LOGP>
1.7130971176666674

> <ALOGPS_LOGS>
-2.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.475866667619183

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.849519789964662

> <JCHEM_PKA_STRONGEST_BASIC>
0.6348877039165869

> <JCHEM_POLAR_SURFACE_AREA>
79.65

> <JCHEM_REFRACTIVITY>
55.30760000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-methoxykynurenate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   2.310   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       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       5.335   4.620   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2    3    4                                                       
CONECT    3    2    6                                                       
CONECT    4    2    9                                                       
CONECT    5    7    8                                                       
CONECT    6    3    8   10                                                  
CONECT    7    5   11   12                                                  
CONECT    8    5    6   13                                                  
CONECT    9    4   10   16                                                  
CONECT   10    6    9   12                                                  
CONECT   11    7   14   15                                                  
CONECT   12    7   10                                                       
CONECT   13    8                                                            
CONECT   14   11                                                            
CONECT   15   11                                                            
CONECT   16    1    9                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
8-Methoxy-4-hydroxyquinoline-2-carboxylic acid	ChEBI
Xanthurenic acid 8-methyl ether	ChEBI
8-Methoxy-4-hydroxyquinoline-2-carboxylate	Generator
Xanthurenate 8-methyl ether	Generator
8-Methoxykynurenic acid	Generator
4-Hydroxy-8-methoxyquinaldate	HMDB
8-Methyl ether OF xanthurenic acid	HMDB
8-Methoxyxanthurenic acid	HMDB
8-Methoxykynurenate	ChEBI

Chemical Formula

C₁₁H₉NO₄

Average Mass

219.1935 Da

Monoisotopic Mass

219.05316 Da

IUPAC Name

4-hydroxy-8-methoxyquinoline-2-carboxylic acid

Traditional Name

8-methoxykynurenate

CAS Registry Number

Not Available

SMILES

COC1=CC=CC2=C(O)C=C(N=C12)C(O)=O

InChI Identifier

InChI=1S/C11H9NO4/c1-16-9-4-2-3-6-8(13)5-7(11(14)15)12-10(6)9/h2-5H,1H3,(H,12,13)(H,14,15)

InChI Key

BXZSKDOPGDPDEG-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
Trypanosoma brucei	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-2-carboxylic acid
Hydroxyquinoline
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Anisole
Alkyl aryl ether
Hydroxypyridine
Pyridine
Benzenoid
Heteroaromatic compound
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monohydroxyquinoline (CHEBI:2323 )
quinolinemonocarboxylic acid (CHEBI:2323 )

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	2.21	ALOGPS
logP	1.71	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.85	ChemAxon
pKa (Strongest Basic)	0.63	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.65 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	55.31 m³·mol⁻¹	ChemAxon
Polarizability	21.04 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

HMDB0060426

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

C05830

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76230

PDB ID

Not Available

ChEBI ID

2323

Good Scents ID

Not Available

References

General References

Suzuki M, Tabara M, Iinuma F, Watanabe M: Enzymatic formation of xanthurenic acid 8-methyl ether, an endogenous carcinogen, in animal tissues. Chem Pharm Bull (Tokyo). 1984 Jun;32(6):2340-5. doi: 10.1248/cpb.32.2340. [PubMed:6435892 ]
LOTUS database [Link]

Showing NP-Card for 8-methoxykynurenate (NP0256766)

MOL for NP0256766 (8-methoxykynurenate)

3D MOL for NP0256766 (8-methoxykynurenate)

3D SDF for NP0256766 (8-methoxykynurenate)

3D-SDF for NP0256766 (8-methoxykynurenate)

PDB for NP0256766 (8-methoxykynurenate)

3D PDB for NP0256766 (8-methoxykynurenate)

SMILES for NP0256766 (8-methoxykynurenate)

INCHI for NP0256766 (8-methoxykynurenate)

Structure for NP0256766 (8-methoxykynurenate)

3D Structure for NP0256766 (8-methoxykynurenate)