NP-MRD: Showing NP-Card for 2-Naphthoic acid (NP0002854)

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Record Information

Version

2.0

Created at

2020-11-23 19:42:04 UTC

Updated at

2021-08-12 19:52:20 UTC

NP-MRD ID

NP0002854

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Naphthoic acid

Provided By

BMRB

Description

2-Naphthoic acid, also known as b-naphthoate, belongs to the class of organic compounds known as naphthalenecarboxylic acids. Naphthalenecarboxylic acids are compounds containing a naphthalene moiety, which bears a carboxylic acid group one or more positions. Naphthalene is a bicyclic compound that is made up of two fused benzene ring. 2-Naphthoic acid exists in all living organisms, ranging from bacteria to humans. 2-Naphthoic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 2-Naphthoic acid is found in Mus musculus. 2-Naphthoic acid was first documented in 1997 (PMID: 19005807). Based on a literature review a small amount of articles have been published on 2-Naphthoic acid (PMID: 19712381) (PMID: 30466032).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   -3.6213   -2.0980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3353   -0.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4675    0.3585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9171   -0.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6310    1.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2128    1.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9194    0.8401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3376    1.3286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4698    0.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1837   -1.1278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7655   -1.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6333   -0.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7849   -1.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8857   -0.1301    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7632    2.3195    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0732    3.2965    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6236    2.8011    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8880    0.8332    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3159   -2.1117    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4795   -3.0888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0709   -2.5934    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  4  1  0
 12  7  1  0
  3 14  1  0
  5 15  1  0
  6 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
 13 21  1  0
M  END
> <DATABASE_ID>
NP0002854

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC2=CC=CC=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H8O2/c12-11(13)10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,(H,12,13)

> <INCHI_KEY>
UOBYKYZJUGYBDK-UHFFFAOYSA-N

> <FORMULA>
C11H8O2

> <MOLECULAR_WEIGHT>
172.18

> <EXACT_MASS>
172.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
17.856366397803747

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
naphthalene-2-carboxylic acid

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
2.620305480666667

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9893572086945723

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
49.7644

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.82e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-naphthoic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    8                                                       
CONECT    4    2    9                                                       
CONECT    5    6    8                                                       
CONECT    6    5   10                                                       
CONECT    7    9   10                                                       
CONECT    8    3    5    9                                                  
CONECT    9    4    7    8                                                  
CONECT   10    6    7   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol

Synonyms

Value	Source
2-Naphthalenecarboxylic acid	ChEBI
beta-Naphthoic acid	ChEBI
Isonaphthoic acid	ChEBI
2-Naphthalenecarboxylate	Generator
b-Naphthoate	Generator
b-Naphthoic acid	Generator
beta-Naphthoate	Generator
Β-naphthoate	Generator
Β-naphthoic acid	Generator
Isonaphthoate	Generator
2-Naphthoate	Generator
2-Naphthoic acid, copper (2+) salt	HMDB
2-Naphthoic acid, palladium (2+) salt	HMDB
2-Naphthoic acid, potassium salt	HMDB
2-Naphthoic acid, sodium salt	HMDB
2-Naphthoic acid hydride	HMDB
2-Naphthoic acid, ammonium salt	HMDB

Chemical Formula

C₁₁H₈O₂

Average Mass

172.1800 Da

Monoisotopic Mass

172.05243 Da

IUPAC Name

naphthalene-2-carboxylic acid

Traditional Name

β-naphthoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC2=CC=CC=C2C=C1

InChI Identifier

InChI=1S/C11H8O2/c12-11(13)10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,(H,12,13)

InChI Key

UOBYKYZJUGYBDK-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, ethanol, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, ethanol, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, ethanol, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Mus musculus	LOTUS Database	35616633
Triticum aestivum	KNApSAcK Database	22123792

Species Where Detected

Species Name	Source	Reference
Escherichia coli	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenecarboxylic acids. Naphthalenecarboxylic acids are compounds containing a naphthalene moiety, which bears a carboxylic acid group one or more positions. Naphthalene is a bicyclic compound that is made up of two fused benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthalenecarboxylic acids and derivatives

Direct Parent

Naphthalenecarboxylic acids

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic homopolycyclic 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	2.79	ALOGPS
logP	2.62	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	49.76 m³·mol⁻¹	ChemAxon
Polarizability	17.86 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0245249

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000736

Chemspider ID

6856

KEGG Compound ID

C14101

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Naphthoic acid

METLIN ID

Not Available

PubChem Compound

7123

PDB ID

Not Available

ChEBI ID

36106

Good Scents ID

Not Available

References

General References

Schalk M, Pierrel MA, Zimmerlin A, Batard Y, Durst F, Werck-Reichhart D: Xenobiotics: Substrates and inhibitors of the plant cytochrome P450. Environ Sci Pollut Res Int. 1997;4(4):229-34. doi: 10.1007/BF02986353. [PubMed:19005807 ]
Meckenstock RU, Safinowski M, Griebler C: Anaerobic degradation of polycyclic aromatic hydrocarbons. FEMS Microbiol Ecol. 2004 Jul 1;49(1):27-36. doi: 10.1016/j.femsec.2004.02.019. [PubMed:19712381 ]
Li NN, Ma YQ, Sun XJ, Li MQ, Zeng S, Xing ZY, Li JL: A dual-function probe based on naphthalene for fluorescent turn-on recognition of Cu(2+) and colorimetric detection of Fe(3+) in neat H2O. Spectrochim Acta A Mol Biomol Spectrosc. 2019 Mar 5;210:266-274. doi: 10.1016/j.saa.2018.11.031. Epub 2018 Nov 14. [PubMed:30466032 ]

Showing NP-Card for 2-Naphthoic acid (NP0002854)

MOL for NP0002854 (2-Naphthoic acid)

3D MOL for NP0002854 (2-Naphthoic acid)

3D SDF for NP0002854 (2-Naphthoic acid)

3D-SDF for NP0002854 (2-Naphthoic acid)

PDB for NP0002854 (2-Naphthoic acid)

3D PDB for NP0002854 (2-Naphthoic acid)

SMILES for NP0002854 (2-Naphthoic acid)

INCHI for NP0002854 (2-Naphthoic acid)

Structure for NP0002854 (2-Naphthoic acid)

3D Structure for NP0002854 (2-Naphthoic acid)