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Showing NP-Card for p-Fluorobenzoic acid (NP0002887)

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Record Information
Version2.0
Created at2020-11-23 19:42:51 UTC
Updated at2021-08-12 19:52:25 UTC
NP-MRD IDNP0002887
Secondary Accession NumbersNone
Natural Product Identification
Common Namep-Fluorobenzoic acid
Provided ByBMRBBMRB logo
Description4-Fluorobenzoic acid, also known as p-fluorobenzoate, belongs to the class of organic compounds known as halobenzoic acids. These are benzoic acids carrying a halogen atom on the benzene ring. 4-Fluorobenzoic acid exists in all living organisms, ranging from bacteria to humans. 4-Fluorobenzoic 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. p-Fluorobenzoic acid was first documented in 2001 (PMID: 11693292). Based on a literature review a small amount of articles have been published on 4-Fluorobenzoic acid (PMID: 21097599) (PMID: 23439662) (PMID: 33302215) (PMID: 32622178) (PMID: 28364617).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002887 (p-Fluorobenzoic acid)


     RDKit          2D

 15 15  0  0  0  0  0  0  0  0999 V2000
   -2.6791   -1.7755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1171   -0.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0404    0.7974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6316   -0.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0696    1.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4158    1.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3392    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8246    0.4496    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.7771   -1.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -1.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5259    0.5888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9929    2.3967    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9779    2.8139    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7005   -2.3318    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2703   -2.7490    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
  7  9  1  0
  9 10  2  0
 10  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  9 14  1  0
 10 15  1  0
M  END
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3D MOL for NP0002887 (p-Fluorobenzoic acid)

NP0002887
     RDKit          3D

 15 15  0  0  0  0  0  0  0  0999 V2000
    2.6606    1.2015    0.5050 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0816    0.1298    0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8644   -0.9754   -0.0621 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6230    0.0792    0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0639   -1.0588   -0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4381   -1.1035   -0.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1556    0.0295    0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5099    0.0259   -0.0394 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5145    1.2012    0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1248    1.2094    0.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6218   -0.9903   -0.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5054   -1.9550   -0.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9375   -2.0066   -0.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0471    2.1103    0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4345    2.1026    0.6585 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
  7  9  1  0
  9 10  2  0
 10  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  9 14  1  0
 10 15  1  0
M  END
Download

3D SDF for NP0002887 (p-Fluorobenzoic acid)


     RDKit          2D

 15 15  0  0  0  0  0  0  0  0999 V2000
   -2.6791   -1.7755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1171   -0.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0404    0.7974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6316   -0.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0696    1.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4158    1.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3392    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8246    0.4496    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.7771   -1.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -1.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5259    0.5888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9929    2.3967    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9779    2.8139    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7005   -2.3318    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2703   -2.7490    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
  7  9  1  0
  9 10  2  0
 10  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  9 14  1  0
 10 15  1  0
M  END
> <DATABASE_ID>
NP0002887

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC=C(F)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C7H5FO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,(H,9,10)

> <INCHI_KEY>
BBYDXOIZLAWGSL-UHFFFAOYSA-N

> <FORMULA>
C7H5FO2

> <MOLECULAR_WEIGHT>
140.113

> <EXACT_MASS>
140.027357564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
12.07970060410392

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-fluorobenzoic acid

> <ALOGPS_LOGP>
1.66

> <JCHEM_LOGP>
1.773530660333333

> <ALOGPS_LOGS>
-1.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.218549969566019

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
33.5306

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.11e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-fluorobenzoic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002887 (p-Fluorobenzoic acid)

NP0002887
     RDKit          3D

 15 15  0  0  0  0  0  0  0  0999 V2000
    2.6606    1.2015    0.5050 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0816    0.1298    0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8644   -0.9754   -0.0621 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6230    0.0792    0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0639   -1.0588   -0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4381   -1.1035   -0.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1556    0.0295    0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5099    0.0259   -0.0394 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5145    1.2012    0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1248    1.2094    0.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6218   -0.9903   -0.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5054   -1.9550   -0.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9375   -2.0066   -0.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0471    2.1103    0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4345    2.1026    0.6585 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
  7  9  1  0
  9 10  2  0
 10  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  9 14  1  0
 10 15  1  0
M  END
Download

PDB for NP0002887 (p-Fluorobenzoic acid)

HEADER    PROTEIN                                 04-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-15         0                                  
HETATM    1  C   UNK     0      20.196 -15.047   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.189 -13.516   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.869 -15.805   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.536 -15.805   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      21.515 -12.758   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      18.862 -12.765   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      18.869 -17.349   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.536 -17.349   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.196 -18.128   0.000  0.00  0.00           C+0
HETATM   10  F   UNK     0      20.189 -19.658   0.000  0.00  0.00           F+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    3    9                                                       
CONECT    8    4    9                                                       
CONECT    9    7   10    8                                                  
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for NP0002887 (p-Fluorobenzoic acid)

COMPND    NP0002887
HETATM    1  O1  UNL     1       2.661   1.201   0.505  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.082   0.130   0.200  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.864  -0.975  -0.062  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.623   0.079   0.131  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.064  -1.059  -0.195  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.438  -1.103  -0.259  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.156   0.029   0.013  1.00  0.00           C  
HETATM    8  F1  UNL     1      -3.510   0.026  -0.039  1.00  0.00           F  
HETATM    9  C6  UNL     1      -1.515   1.201   0.347  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.125   1.209   0.401  1.00  0.00           C  
HETATM   11  H1  UNL     1       3.622  -0.990  -0.743  1.00  0.00           H  
HETATM   12  H2  UNL     1       0.505  -1.955  -0.410  1.00  0.00           H  
HETATM   13  H3  UNL     1      -1.937  -2.007  -0.516  1.00  0.00           H  
HETATM   14  H4  UNL     1      -2.047   2.110   0.566  1.00  0.00           H  
HETATM   15  H5  UNL     1       0.434   2.103   0.658  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   11
CONECT    4    5    5   10
CONECT    5    6   12
CONECT    6    7    7   13
CONECT    7    8    9
CONECT    9   10   10   14
CONECT   10   15
END
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SMILES for NP0002887 (p-Fluorobenzoic acid)

OC(=O)C1=CC=C(F)C=C1
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INCHI for NP0002887 (p-Fluorobenzoic acid)

InChI=1S/C7H5FO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,(H,9,10)
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View in JSmol
Synonyms
ValueSource
p-Fluorobenzoic acidChEBI
Para-fluorobenzoic acidChEBI
p-FluorobenzoateGenerator
Para-fluorobenzoateGenerator
4-FluorobenzoateGenerator
4-Fluorobenzoic acid, 18F-labeledHMDB
4-Fluorobenzoic acid, anhydrideHMDB
4-Fluorobenzoic acid, copper (+1) saltHMDB
4-Fluorobenzoic acid, monosodium saltHMDB
4-Fluorobenzoic acid, potassium saltHMDB
4-Fluorobenzoic acid, ion(1-)HMDB
4-Fluorobenzoic acid, copper (+2) salt dihydrateHMDB
4-Fluorobenzoic acid, silver (+1) saltHMDB
4-Fluorobenzoic acid, copper (+2) saltHMDB
Chemical FormulaC7H5FO2
Average Mass140.1130 Da
Monoisotopic Mass140.02736 Da
IUPAC Name4-fluorobenzoic acid
Traditional Name4-fluorobenzoic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1=CC=C(F)C=C1
InChI Identifier
InChI=1S/C7H5FO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,(H,9,10)
InChI KeyBBYDXOIZLAWGSL-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as halobenzoic acids. These are benzoic acids carrying a halogen atom on the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHalobenzoic acids
Alternative Parents
Substituents
  • 4-halobenzoic acid or derivatives
  • 4-halobenzoic acid
  • Halobenzoic acid
  • Benzoic acid
  • Benzoyl
  • Halobenzene
  • Fluorobenzene
  • Aryl halide
  • Aryl fluoride
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.66ALOGPS
logP1.77ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.53 m³·mol⁻¹ChemAxon
Polarizability12.08 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0246425
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9579
KEGG Compound IDC02371
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Fluorobenzoic_acid
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID20364
Good Scents IDNot Available
References
General References
  1. dos Santos LM, Spicq A, New AP, Lo Biundo G, Wolff JC, Edwards A: Aerobic biotransformation of 4-fluorocinnamic acid to 4-fluorobenzoic acid. Biodegradation. 2001;12(1):23-9. doi: 10.1023/a:1011973824171. [PubMed:11693292 ]
  2. Hasan SA, Ferreira MI, Koetsier MJ, Arif MI, Janssen DB: Complete biodegradation of 4-fluorocinnamic acid by a consortium comprising Arthrobacter sp. strain G1 and Ralstonia sp. strain H1. Appl Environ Microbiol. 2011 Jan;77(2):572-9. doi: 10.1128/AEM.00393-10. Epub 2010 Nov 19. [PubMed:21097599 ]
  3. Pan H, Gu L, Sun S, Chen Z, Zhou H, Zeng S, Jiang H: Metabolism of bis(4-fluorobenzyl)trisulfide and its formation of hemoglobin adduct in rat erythrocytes. Drug Metab Dispos. 2013 May;41(5):1082-93. doi: 10.1124/dmd.112.048801. Epub 2013 Feb 25. [PubMed:23439662 ]
  4. Selimoglu F, Unal N, Ceren Ertekin Z, Dinc E: PARAFAC and MCR-ALS approaches to the pKa determination of benzoic acid and its derivatives. Spectrochim Acta A Mol Biomol Spectrosc. 2021 Mar 5;248:119253. doi: 10.1016/j.saa.2020.119253. Epub 2020 Nov 28. [PubMed:33302215 ]
  5. Czarnecka K, Lisiecki P, Szewczyk E, Chufarova N, Wojtowicz P, Krecisz P, Szymanski P: New acridine derivatives as promising agents against methicillin-resistant staphylococci - From tests to in silico analysis. Comput Biol Chem. 2020 Oct;88:107321. doi: 10.1016/j.compbiolchem.2020.107321. Epub 2020 Jun 25. [PubMed:32622178 ]
  6. Li X, Liu Z, Xu Y, Wang D: Synthesis, crystal structure and hydrolysis activity of a novel heterobinuclear cobalt(capital I, Ukrainiancapital I, Ukrainiancapital I, Ukrainian) sodium(capital I, Ukrainian) Schiff base complex. J Inorg Biochem. 2017 Jun;171:37-44. doi: 10.1016/j.jinorgbio.2017.03.005. Epub 2017 Mar 28. [PubMed:28364617 ]