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Record Information
Version1.0
Created at2020-11-23 19:38:47 UTC
Updated at2021-08-12 19:51:57 UTC
NP-MRD IDNP0002722
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Chlorophenylacetate
Provided ByBMRBBMRB logo
Description4-Chlorophenylacetic acid, also known as (p-chlorophenyl)acetate or 4-chlorobenzeneacetate, belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety. 4-Chlorophenylacetic 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. 4-Chlorophenylacetate is found in Apis cerana. It was first documented in 1978 (PMID: 637537). Based on a literature review a significant number of articles have been published on 4-Chlorophenylacetic acid (PMID: 17984079) (PMID: 3994362) (PMID: 6240395) (PMID: 7076135).
Structure
Thumb
Synonyms
ValueSource
(p-Chlorophenyl)acetic acidChEBI
4-Chlorobenzeneacetic acidChEBI
p-Chlorophenylacetic acidChEBI
(p-Chlorophenyl)acetateGenerator
4-ChlorobenzeneacetateGenerator
p-ChlorophenylacetateGenerator
4-ChlorophenylacetateGenerator
4-Chlorophenylacetic acid, potassium saltHMDB
4-Chlorophenylacetic acid, sodium saltHMDB
Chemical FormulaC8H7ClO2
Average Mass170.5930 Da
Monoisotopic Mass170.01346 Da
IUPAC Name2-(4-chlorophenyl)acetic acid
Traditional Name(4-chlorophenyl)acetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CC1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C8H7ClO2/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4H,5H2,(H,10,11)
InChI KeyCDPKJZJVTHSESZ-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 Origin
Species NameSourceReference
Apis ceranaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentChlorobenzenes
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
logP2.34ALOGPS
logP2.22ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.17 m³·mol⁻¹ChemAxon
Polarizability16.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0246401
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID15093
KEGG Compound IDC03077
BioCyc IDCPD-1786
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15880
PDB IDNot Available
ChEBI ID30749
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Subba-Rao RV, Alexander M: Bacterial and fungal cometabolism of 1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane (DDT) and its breakdown products. Appl Environ Microbiol. 1985 Mar;49(3):509-16. doi: 10.1128/aem.49.3.509-516.1985. [PubMed:3994362 ]
  3. Loo YH, Rabe A, Potempska A, Wang P, Fersko R, Wisniewski HM: Experimental maternal phenylketonuria: an examination of two animal models. Dev Neurosci. 1983-1984;6(4-5):227-34. doi: 10.1159/000112349. [PubMed:6240395 ]
  4. Francis AJ, Spanggord RJ, Ouchi GI, Bohonos N: Cometabolism of DDT analogs by a Pseudomonas sp. Appl Environ Microbiol. 1978 Feb;35(2):364-7. doi: 10.1128/aem.35.2.364-367.1978. [PubMed:637537 ]
  5. Markus A, Klages U, Lingens F: [Microbial degradation and 4-chlorophenylacetic acid. Chemical synthesis of 3-chloro-4-hydroxy-, 4-chloro-3-hydroxy- and 4-chloro-2-hydroxyphenylacetic acid (author's transl)]. Hoppe Seylers Z Physiol Chem. 1982 Apr;363(4):431-7. [PubMed:7076135 ]