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Showing NP-Card for 4-chloroacetophenone (NP0002769)

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Record Information
Version1.0
Created at2020-11-23 19:39:58 UTC
Updated at2021-08-19 23:59:21 UTC
NP-MRD IDNP0002769
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-chloroacetophenone
Provided ByBMRBBMRB logo
DescriptionP-Chloroacetophenone belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. It was first documented in 2003 (PMID: 14629135). Based on a literature review a significant number of articles have been published on P-Chloroacetophenone (PMID: 17984079) (PMID: 26955713) (PMID: 22905505) (PMID: 22594255) (PMID: 22523964) (PMID: 25374684).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002769 (4-chloroacetophenone)


     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
   -2.7744    0.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7017   -0.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0733   -2.2476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2574   -0.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1143    1.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5586    1.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6313    0.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0757    0.8248    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.2597   -1.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8154   -1.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8229   -0.8186    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7260    1.3268    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8472    1.3026    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9585    2.1121    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9302    2.9217    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3324   -2.0817    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4437   -2.8912    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
  1 11  1  1
  1 12  1  0
  1 13  1  0
  5 14  1  0
  6 15  1  0
  9 16  1  0
 10 17  1  0
M  END
Download

3D MOL for NP0002769 (4-chloroacetophenone)

NP0002769
     RDKit          3D

 17 17  0  0  0  0  0  0  0  0999 V2000
    2.6641    0.3110    0.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6409   -0.7475    0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9552   -1.9627    0.3465 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2529   -0.3660    0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1405    0.9540   -0.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4602    1.3139   -0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4375    0.3567   -0.4220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1191    0.8008   -0.7166 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0476   -0.9645   -0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7245   -1.3251   -0.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0020    0.6010   -0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3048    1.1733    1.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5615   -0.1349    0.9884 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5873    1.7344    0.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7845    2.3499   -0.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8238   -1.7327   -0.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4311   -2.3615   -0.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
  1 11  1  0
  1 12  1  0
  1 13  1  0
  5 14  1  0
  6 15  1  0
  9 16  1  0
 10 17  1  0
M  END
Download

3D SDF for NP0002769 (4-chloroacetophenone)


     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
   -2.7744    0.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7017   -0.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0733   -2.2476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2574   -0.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1143    1.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5586    1.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6313    0.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0757    0.8248    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.2597   -1.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8154   -1.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8229   -0.8186    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7260    1.3268    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8472    1.3026    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9585    2.1121    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9302    2.9217    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3324   -2.0817    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4437   -2.8912    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
  1 11  1  1
  1 12  1  0
  1 13  1  0
  5 14  1  0
  6 15  1  0
  9 16  1  0
 10 17  1  0
M  END
> <DATABASE_ID>
NP0002769

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H7ClO/c1-6(10)7-2-4-8(9)5-3-7/h2-5H,1H3

> <INCHI_KEY>
BUZYGTVTZYSBCU-UHFFFAOYSA-N

> <FORMULA>
C8H7ClO

> <MOLECULAR_WEIGHT>
154.594

> <EXACT_MASS>
154.018542553

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
15.349909305287927

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(4-chlorophenyl)ethan-1-one

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.134938011

> <ALOGPS_LOGS>
-2.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.056455198414668

> <JCHEM_PKA_STRONGEST_BASIC>
-7.388219466297953

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
41.265600000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-chloroacetophenone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002769 (4-chloroacetophenone)

NP0002769
     RDKit          3D

 17 17  0  0  0  0  0  0  0  0999 V2000
    2.6641    0.3110    0.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6409   -0.7475    0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9552   -1.9627    0.3465 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2529   -0.3660    0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1405    0.9540   -0.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4602    1.3139   -0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4375    0.3567   -0.4220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1191    0.8008   -0.7166 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0476   -0.9645   -0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7245   -1.3251   -0.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0020    0.6010   -0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3048    1.1733    1.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5615   -0.1349    0.9884 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5873    1.7344    0.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7845    2.3499   -0.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8238   -1.7327   -0.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4311   -2.3615   -0.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
  1 11  1  0
  1 12  1  0
  1 13  1  0
  5 14  1  0
  6 15  1  0
  9 16  1  0
 10 17  1  0
M  END
Download

PDB for NP0002769 (4-chloroacetophenone)

HEADER    PROTEIN                                 07-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-14         0                                  
HETATM    1  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9 Cl   UNK     0       1.334   3.850   0.000  0.00  0.00          Cl+0
HETATM   10  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    4    7                                                       
CONECT    3    5    7                                                       
CONECT    4    2    8                                                       
CONECT    5    3    8                                                       
CONECT    6    1    7   10                                                  
CONECT    7    2    3    6                                                  
CONECT    8    4    5    9                                                  
CONECT    9    8                                                            
CONECT   10    6                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for NP0002769 (4-chloroacetophenone)

COMPND    NP0002769
HETATM    1  C1  UNL     1       2.664   0.311   0.472  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.641  -0.747   0.292  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.955  -1.963   0.346  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.253  -0.366   0.049  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.141   0.954  -0.019  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.460   1.314  -0.250  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.437   0.357  -0.422  1.00  0.00           C  
HETATM    8 CL1  UNL     1      -4.119   0.801  -0.717  1.00  0.00          CL  
HETATM    9  C7  UNL     1      -2.048  -0.964  -0.355  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.724  -1.325  -0.123  1.00  0.00           C  
HETATM   11  H1  UNL     1       3.002   0.601  -0.559  1.00  0.00           H  
HETATM   12  H2  UNL     1       2.305   1.173   1.056  1.00  0.00           H  
HETATM   13  H3  UNL     1       3.561  -0.135   0.988  1.00  0.00           H  
HETATM   14  H4  UNL     1       0.587   1.734   0.109  1.00  0.00           H  
HETATM   15  H5  UNL     1      -1.784   2.350  -0.306  1.00  0.00           H  
HETATM   16  H6  UNL     1      -2.824  -1.733  -0.491  1.00  0.00           H  
HETATM   17  H7  UNL     1      -0.431  -2.362  -0.072  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    3    4
CONECT    4    5    5   10
CONECT    5    6   14
CONECT    6    7    7   15
CONECT    7    8    9
CONECT    9   10   10   16
CONECT   10   17
END
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SMILES for NP0002769 (4-chloroacetophenone)

CC(=O)C1=CC=C(Cl)C=C1
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INCHI for NP0002769 (4-chloroacetophenone)

InChI=1S/C8H7ClO/c1-6(10)7-2-4-8(9)5-3-7/h2-5H,1H3
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Synonyms
ValueSource
4-ChloroacetophenoneMeSH
Chemical FormulaC8H7ClO
Average Mass154.5940 Da
Monoisotopic Mass154.01854 Da
IUPAC Name1-(4-chlorophenyl)ethan-1-one
Traditional Name4-chloroacetophenone
CAS Registry NumberNot Available
SMILES
CC(=O)C1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C8H7ClO/c1-6(10)7-2-4-8(9)5-3-7/h2-5H,1H3
InChI KeyBUZYGTVTZYSBCU-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, 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 alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Acetophenone
  • Aryl alkyl ketone
  • Benzoyl
  • Halobenzene
  • Chlorobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Organic oxide
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point14.00 to 18.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point231.00 to 233.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility755.9 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.350The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP2.41ALOGPS
logP2.13ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)16.06ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity41.27 m³·mol⁻¹ChemAxon
Polarizability15.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID13835126
KEGG Compound IDC06647
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenacyl chloride
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDrw1012611
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. Sun X, Che C, Ji J, Zheng J, Yang G: [Heterologous expression and substrate specificity of ketoreductase domain in bacillaene polyketide synthase]. Sheng Wu Gong Cheng Xue Bao. 2015 Sep;31(9):1355-62. [PubMed:26955713 ]
  3. Mandal G, Chakraborty A, Sur UK, Ankamwar B, De A, Ganguly T: Synthesis, characterization, photophysical properties of a novel organic photoswitchable dyad in its pristine and hybrid nanocomposite forms. J Nanosci Nanotechnol. 2012 Jun;12(6):4591-600. doi: 10.1166/jnn.2012.6208. [PubMed:22905505 ]
  4. Fahmy HH, Khalifa NM, Nossier ES, Abdalla MM, Ismai MM: Synthesis and anti-inflammatory evaluation of new substituted 1-(3-chlorophenyl)-3-(4-methoxyphenyl)-1H-pyrazole derivatives. Acta Pol Pharm. 2012 May-Jun;69(3):411-21. [PubMed:22594255 ]
  5. Mandal G, Bhattacharya S, Das S, Ganguly T: The rates of charge separation and energy destructive charge recombination processes within an organic dyad in presence of metal-semiconductor core shell nanocomposites. J Nanosci Nanotechnol. 2012 Jan;12(1):187-94. doi: 10.1166/jnn.2012.5728. [PubMed:22523964 ]
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  7. Mandal G, Bhattacharya S, Ganguly T: Development of a nanocomposite system by combining an organic dyad 1-(4-chloro-phenyl)-3-(4-methoxy-naphthalen-1-yl)-Propenone with semiconductor TiO2 nanoparticles. J Nanosci Nanotechnol. 2010 Jan;10(1):579-87. doi: 10.1166/jnn.2010.1820. [PubMed:20352895 ]
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