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Showing NP-Card for 4-Chlorophenoxyacetic acid (NP0002827)

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Record Information
Version2.0
Created at2020-11-23 19:41:26 UTC
Updated at2024-09-03 04:16:40 UTC
NP-MRD IDNP0002827
Natural Product DOIhttps://doi.org/10.57994/0754
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Chlorophenoxyacetic acid
Provided ByBMRBBMRB logo
Description(4-Chlorophenoxy)acetic acid is also known as 4-CPA or 4-chlorphenoxyessigsaeure. 4-Chlorophenoxyacetic acid was first documented in 2001 (PMID: 11523589). Based on a literature review very few articles have been published on (4-chlorophenoxy)acetic acid (PMID: 17215075).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0002827 (4-Chlorophenoxyacetic acid)

 
  Mrv1533006051513292D          
 
 12 12  0  0  0  0            999 V2000
   16.6451  -10.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9336  -10.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3601  -10.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6486   -9.1797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9336  -11.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3601  -11.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3635   -8.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6451  -11.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3635   -7.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6486  -12.4865    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.0819   -7.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6486   -7.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  2  0  0  0  0
  6  8  2  0  0  0  0
M  END
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3D MOL for NP0002827 (4-Chlorophenoxyacetic acid)

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3D SDF for NP0002827 (4-Chlorophenoxyacetic acid)
 
  Mrv1533006051513292D          
 
 12 12  0  0  0  0            999 V2000
   16.6451  -10.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9336  -10.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3601  -10.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6486   -9.1797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9336  -11.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3601  -11.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3635   -8.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6451  -11.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3635   -7.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6486  -12.4865    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.0819   -7.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6486   -7.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  2  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0002827

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)COC1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H7ClO3/c9-6-1-3-7(4-2-6)12-5-8(10)11/h1-4H,5H2,(H,10,11)

> <INCHI_KEY>
SODPIMGUZLOIPE-UHFFFAOYSA-N

> <FORMULA>
C8H7ClO3

> <MOLECULAR_WEIGHT>
186.59

> <EXACT_MASS>
186.0083718

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
17.245346095859624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-chlorophenoxy)acetic acid

> <ALOGPS_LOGP>
2.11

> <JCHEM_LOGP>
1.8976025349999996

> <ALOGPS_LOGS>
-2.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1395449324524694

> <JCHEM_PKA_STRONGEST_BASIC>
-4.890346208865694

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
43.4106

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sure-set

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0002827 (4-Chlorophenoxyacetic acid)
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PDB for NP0002827 (4-Chlorophenoxyacetic acid)
HEADER    PROTEIN                                 05-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-JUN-15         0                                  
HETATM    1  C   UNK     0      31.071 -18.675   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.743 -19.445   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      32.406 -19.445   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      31.077 -17.135   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      29.743 -20.985   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.406 -20.985   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.412 -16.359   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.071 -21.762   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.412 -14.819   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0      31.077 -23.308   0.000  0.00  0.00          Cl+0
HETATM   11  O   UNK     0      33.753 -14.049   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      31.077 -14.049   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7                                                       
CONECT    5    2    8                                                       
CONECT    6    3    8                                                       
CONECT    7    4    9                                                       
CONECT    8    5   10    6                                                  
CONECT    9    7   11   12                                                  
CONECT   10    8                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0002827 (4-Chlorophenoxyacetic acid)
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SMILES for NP0002827 (4-Chlorophenoxyacetic acid)
OC(=O)COC1=CC=C(Cl)C=C1
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INCHI for NP0002827 (4-Chlorophenoxyacetic acid)
InChI=1S/C8H7ClO3/c9-6-1-3-7(4-2-6)12-5-8(10)11/h1-4H,5H2,(H,10,11)
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View in JSmol
Synonyms
ValueSource
(p-Chlorophenoxy)acetic acidChEBI
4-ChlorophenoxyacetateChEBI
4-Chlorophenoxyacetic acidChEBI
4-ChlorphenoxyessigsaeureChEBI
4-CPAChEBI
Para-chlorophenoxyacetic acidChEBI
(p-Chlorophenoxy)acetateGenerator
Para-chlorophenoxyacetateGenerator
(4-Chlorophenoxy)acetateGenerator
4-Chlorophenoxyacetic acid, sodium saltMeSH
4-Chlorophenoxyacetic acid, ammonium saltMeSH
4-Chlorophenoxyacetic acid, potassium saltMeSH
P-Chlorophenoxyacetic acidMeSH
Chemical FormulaC8H7ClO3
Average Mass186.5900 Da
Monoisotopic Mass186.00837 Da
IUPAC Name2-(4-chlorophenoxy)acetic acid
Traditional Namesure-set
CAS Registry NumberNot Available
SMILES
OC(=O)COC1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C8H7ClO3/c9-6-1-3-7(4-2-6)12-5-8(10)11/h1-4H,5H2,(H,10,11)
InChI KeySODPIMGUZLOIPE-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-07-25View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-07-25View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as chlorophenoxyacetates. These are compounds containing a phenoxyacetate that carries one or more chlorine atoms on the benzene ring.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassPhenoxyacetic acid derivatives  
Direct ParentChlorophenoxyacetates  
Alternative Parents
Substituents
  • Chlorophenoxyacetate
    • 

  • Phenoxy compound
    • 

  • Phenol ether
    • 

  • Alkyl aryl ether
    • 

  • Chlorobenzene
    • 

  • Halobenzene
    • 

  • Aryl chloride
    • 

  • Aryl halide
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Ether
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organochloride
    • 

  • Hydrocarbon derivative
    • 

  • Organohalogen compound
    • 

  • 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
logP2.11ALOGPS
logP1.9ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.14ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.41 m³·mol⁻¹ChemAxon
Polarizability17.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24438  
KEGG Compound IDC07088  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Chlorophenoxyacetic_acid  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID1808  
Good Scents IDNot Available
References
General References
  1. Aliciguzel Y, Ozdem S, Demir AY, Unal F, Kumbul D, Ozdem SS, Perry G, Smith MA: Effect of the herbicide 4-CPA on human erythrocyte antioxidant enzymes in vitro. Redox Rep. 2001;6(3):153-4. doi: 10.1179/135100001101536256. [PubMed:11523589  ] 
  2. Sidell N, Kirma N, Morgan ET, Nair H, Tekmal RR: Inhibition of estrogen-induced mammary tumor formation in MMTV-aromatase transgenic mice by 4-chlorophenylacetate. Cancer Lett. 2007 Jun 28;251(2):302-10. doi: 10.1016/j.canlet.2006.11.031. Epub 2007 Jan 9. [PubMed:17215075  ]