NP-MRD: Showing NP-Card for Tannase (NP0334581)

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Record Information

Version

2.0

Created at

2024-09-10 18:59:59 UTC

Updated at

2024-09-10 19:00:00 UTC

NP-MRD ID

NP0334581

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tannase

Description

Nalidixic Acid, also known as acide nalidixique or nalidixate, belongs to the class of organic compounds known as naphthyridine carboxylic acids and derivatives. Naphthyridine carboxylic acids and derivatives are compounds containing a naphthyridine moiety, where one of the ring atoms bears a carboxylic acid group. A monocarboxylic acid comprising 1,8-naphthyridin-4-one substituted by carboxylic acid, ethyl and methyl groups at positions 3, 1, and 7, respectively. Nalidixic Acid is a drug which is used for the treatment of urinary tract infections caused by susceptible gram-negative microorganisms, including the majority of e. Coli, enterobacter species, klebsiella species, and proteus species. Tannase was first documented in 1964 (PMID: 14107587). Nalidixic Acid is a strong basic compound (based on its pKa) (PMID: 11321869) (PMID: 12002106) (PMID: 12399485) (PMID: 12702698).

Structure

MOL SDF PDB SMILES InChI

779
  Mrv0541 02231215002D          

 17 18  0  0  0  0            999 V2000
    4.2364    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -0.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6885   -0.6474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6885    1.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4359   -0.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4359    0.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1488   -0.6386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  2  0  0  0  0
  2 16  1  0  0  0  0
  3 16  2  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5 13  2  0  0  0  0
  6  7  2  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8 14  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 16  1  0  0  0  0
 12 15  2  0  0  0  0
 13 15  1  0  0  0  0
 13 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334581

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C=C(C(O)=O)C(=O)C2=C1N=C(C)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17)

> <INCHI_KEY>
MHWLWQUZZRMNGJ-UHFFFAOYSA-N

> <FORMULA>
C12H12N2O3

> <MOLECULAR_WEIGHT>
232.2353

> <EXACT_MASS>
232.08479226

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
23.649783745099587

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

> <ALOGPS_LOGP>
0.95

> <JCHEM_LOGP>
1.0082525712681194

> <ALOGPS_LOGS>
-2.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.950252968990619

> <JCHEM_PKA_STRONGEST_BASIC>
4.678220137258441

> <JCHEM_POLAR_SURFACE_AREA>
70.5

> <JCHEM_REFRACTIVITY>
62.8245

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.30e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nalidixic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 779                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       7.908   3.465   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.907   1.155   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.241   3.465   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       7.908  -1.155   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      10.619  -1.208   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.242  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.242   1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.908  -2.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.574  -0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.574   1.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.908   1.925   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.619   1.978   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.014  -0.417   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.574  -3.465   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.014   1.187   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.241   1.925   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.344  -1.192   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   16                                                            
CONECT    3   16                                                            
CONECT    4    6    8    9                                                  
CONECT    5    6   13                                                       
CONECT    6    4    5    7                                                  
CONECT    7    6   11   12                                                  
CONECT    8    4   14                                                       
CONECT    9    4   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11    1    7   10                                                  
CONECT   12    7   15                                                       
CONECT   13    5   15   17                                                  
CONECT   14    8                                                            
CONECT   15   12   13                                                       
CONECT   16    2    3   10                                                  
CONECT   17   13                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid	ChEBI
1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure	ChEBI
1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid	ChEBI
1-Ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylic acid	ChEBI
1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid	ChEBI
3-Carboxy-1-ethyl-7-methyl-1,8-naphthyridin-4-one	ChEBI
Acide nalidixique	ChEBI
Acido nalidixico	ChEBI
Acidum nalidixicum	ChEBI
NA	Kegg
NegGram	Kegg
1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate	Generator
1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate	Generator
1-Ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylate	Generator
1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylate	Generator
Nalidixate	Generator
Acid, nalidixic	HMDB
Nevigramon	HMDB
Sodium, nalidixate	HMDB
Nalidixate sodium	HMDB
Nalidixin	HMDB
Sodium nalidixic acid, anhydrous	HMDB
Anhydrous, nalidixate sodium	HMDB
Nalidixate sodium anhydrous	HMDB
Sodium anhydrous, nalidixate	HMDB
Sodium nalidixic acid, monohydrate	HMDB

Chemical Formula

C₁₂H₁₂N₂O₃

Average Mass

232.2353 Da

Monoisotopic Mass

232.08479 Da

IUPAC Name

1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Traditional Name

nalidixic acid

CAS Registry Number

Not Available

SMILES

CCN1C=C(C(O)=O)C(=O)C2=C1N=C(C)C=C2

InChI Identifier

InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17)

InChI Key

MHWLWQUZZRMNGJ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthyridine carboxylic acids and derivatives. Naphthyridine carboxylic acids and derivatives are compounds containing a naphthyridine moiety, where one of the ring atoms bears a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Naphthyridines

Direct Parent

Naphthyridine carboxylic acids and derivatives

Alternative Parents

Substituents

Naphthyridine carboxylic acid
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Methylpyridine
Pyridine
Heteroaromatic compound
Vinylogous amide
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:100147 )
1,8-naphthyridine derivative (CHEBI:100147 )
quinolone antibiotic (CHEBI:100147 )
4-Quinolones (C05079 )

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	0.95	ALOGPS
logP	1.01	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	5.95	ChemAxon
pKa (Strongest Basic)	4.68	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	70.5 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	62.82 m³·mol⁻¹	ChemAxon
Polarizability	23.65 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

HMDB0014917

DrugBank ID

DB00779

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020181

KNApSAcK ID

Not Available

Chemspider ID

4268

KEGG Compound ID

C05079

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nalidixic_Acid

METLIN ID

Not Available

PubChem Compound

4421

PDB ID

Not Available

ChEBI ID

100147

Good Scents ID

Not Available

References

General References

Mahmood A: Nalidixic acid is still the drug of choice for shigellosis in Pakistan. J Pak Med Assoc. 2001 Feb;51(2):101. [PubMed:11321869 ]
Mache A: Antibiotic resistance and sero-groups of shigella among paediatric out-patients in southwest Ethiopia. East Afr Med J. 2001 Jun;78(6):296-9. doi: 10.4314/eamj.v78i6.9022. [PubMed:12002106 ]
Kim N, Weeks DL, Shin JM, Scott DR, Young MK, Sachs G: Proteins released by Helicobacter pylori in vitro. J Bacteriol. 2002 Nov;184(22):6155-62. doi: 10.1128/JB.184.22.6155-6162.2002. [PubMed:12399485 ]
Andersson MI, MacGowan AP: Development of the quinolones. J Antimicrob Chemother. 2003 May;51 Suppl 1:1-11. doi: 10.1093/jac/dkg212. [PubMed:12702698 ]
NISHIURA T, YOKOYAMA S, ISHIGAMI Y: [NALIDIXIC ACID: A NEW ANTIBACTERIAL AGENT]. Hinyokika Kiyo. 1964 Jan;10:41-6. [PubMed:14107587 ]

Showing NP-Card for Tannase (NP0334581)

MOL for NP0334581 (Tannase)

3D MOL for NP0334581 (Tannase)

3D SDF for NP0334581 (Tannase)

3D-SDF for NP0334581 (Tannase)

PDB for NP0334581 (Tannase)

3D PDB for NP0334581 (Tannase)

SMILES for NP0334581 (Tannase)

INCHI for NP0334581 (Tannase)

Structure for NP0334581 (Tannase)

3D Structure for NP0334581 (Tannase)