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Showing NP-Card for cis-1,3-dichloropropene (NP0002869)

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Record Information
Version1.0
Created at2020-11-23 19:42:26 UTC
Updated at2021-08-12 19:52:22 UTC
NP-MRD IDNP0002869
Secondary Accession NumbersNone
Natural Product Identification
Common Namecis-1,3-dichloropropene
Provided ByBMRBBMRB logo
DescriptionTrans-1,3-Dichloropropene, also known as (1Z)-1,3-dichloro-1-propene, belongs to the class of organic compounds known as vinyl chlorides. These are vinyl halides in which a chlorine atom is bonded to an sp2-hybridised carbon atom. Trans-1,3-Dichloropropene is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. It was first documented in 2008 (PMID: 17984079). Based on a literature review a significant number of articles have been published on trans-1,3-Dichloropropene (PMID: 23899962) (PMID: 21074239) (PMID: 19722521) (PMID: 19018104).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002869 (cis-1,3-dichloropropene)


     RDKit          2D

  9  8  0  0  0  0  0  0  0  0999 V2000
    1.4095    1.6954    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4397    0.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1560   -0.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1578    0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4717    0.8671    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7536   -0.5280    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1862   -2.0800    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8815   -1.1705    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4341    1.4573    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  2  6  1  0
  3  7  1  0
  4  8  1  6
  4  9  1  0
M  END
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3D MOL for NP0002869 (cis-1,3-dichloropropene)

NP0002869
     RDKit          3D

  9  8  0  0  0  0  0  0  0  0999 V2000
    0.8870    1.9478   -0.6970 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3361    0.3817   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3904   -0.5221    0.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0477   -0.1758   -0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0208   -0.2934    1.3627 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3896    0.2080    0.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6475   -1.4864    0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4854   -0.9121   -0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0967    0.8524   -0.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  2  6  1  0
  3  7  1  0
  4  8  1  0
  4  9  1  0
M  END
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3D SDF for NP0002869 (cis-1,3-dichloropropene)


     RDKit          2D

  9  8  0  0  0  0  0  0  0  0999 V2000
    1.4095    1.6954    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4397    0.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1560   -0.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1578    0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4717    0.8671    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7536   -0.5280    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1862   -2.0800    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8815   -1.1705    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4341    1.4573    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  2  6  1  0
  3  7  1  0
  4  8  1  6
  4  9  1  0
M  END
> <DATABASE_ID>
NP0002869

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(Cl)=C(/[H])CCl

> <INCHI_IDENTIFIER>
InChI=1S/C3H4Cl2/c4-2-1-3-5/h1-2H,3H2/b2-1-

> <INCHI_KEY>
UOORRWUZONOOLO-UPHRSURJSA-N

> <FORMULA>
C3H4Cl2

> <MOLECULAR_WEIGHT>
110.97

> <EXACT_MASS>
109.969005542

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
9.619755169622907

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1Z)-1,3-dichloroprop-1-ene

> <ALOGPS_LOGP>
2.07

> <JCHEM_LOGP>
1.8844621376666664

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
25.276600000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.30e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
telone II

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0002869 (cis-1,3-dichloropropene)

NP0002869
     RDKit          3D

  9  8  0  0  0  0  0  0  0  0999 V2000
    0.8870    1.9478   -0.6970 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3361    0.3817   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3904   -0.5221    0.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0477   -0.1758   -0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0208   -0.2934    1.3627 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3896    0.2080    0.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6475   -1.4864    0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4854   -0.9121   -0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0967    0.8524   -0.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  2  6  1  0
  3  7  1  0
  4  8  1  0
  4  9  1  0
M  END
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PDB for NP0002869 (cis-1,3-dichloropropene)

HEADER    PROTEIN                                 06-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-14         0                                  
HETATM    1  C   UNK     0       1.540   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       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    4 Cl   UNK     0      -0.770  -1.334   0.000  0.00  0.00          Cl+0
HETATM    5 Cl   UNK     0       3.850  -1.334   0.000  0.00  0.00          Cl+0
HETATM    6  H   UNK     0       2.310   1.334   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0      -0.770   1.334   0.000  0.00  0.00           H+0
CONECT    1    2    3    6                                                  
CONECT    2    1    4    7                                                  
CONECT    3    1    5                                                       
CONECT    4    2                                                            
CONECT    5    3                                                            
CONECT    6    1                                                            
CONECT    7    2                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for NP0002869 (cis-1,3-dichloropropene)

COMPND    NP0002869
HETATM    1 CL1  UNL     1       0.887   1.948  -0.697  1.00  0.00          CL  
HETATM    2  C1  UNL     1       1.336   0.382  -0.050  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.390  -0.522   0.174  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.048  -0.176  -0.135  1.00  0.00           C  
HETATM    5 CL2  UNL     1      -2.021  -0.293   1.363  1.00  0.00          CL  
HETATM    6  H1  UNL     1       2.390   0.208   0.147  1.00  0.00           H  
HETATM    7  H2  UNL     1       0.648  -1.486   0.570  1.00  0.00           H  
HETATM    8  H3  UNL     1      -1.485  -0.912  -0.830  1.00  0.00           H  
HETATM    9  H4  UNL     1      -1.097   0.852  -0.542  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    3    6
CONECT    3    4    7
CONECT    4    5    8    9
END
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SMILES for NP0002869 (cis-1,3-dichloropropene)

[H]\C(Cl)=C(/[H])CCl
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INCHI for NP0002869 (cis-1,3-dichloropropene)

InChI=1S/C3H4Cl2/c4-2-1-3-5/h1-2H,3H2/b2-1-
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View in JSmol
Synonyms
ValueSource
(1Z)-1,3-Dichloro-1-propeneChEBI
(Z)-1,3-Dichloro-1-propeneChEBI
cis-1,3-Dichloro-1-propeneChEBI
cis-1,3-DichloropropeneChEBI
cis-1,3-DichloropropyleneChEBI
1,3-dichloro-1-PropeneMeSH
1,3-dichloro-1-Propene, (e)-isomerMeSH
1,3-dichloro-1-Propene, (Z)-isomerMeSH
Telone IIMeSH
1,3-DichloropropeneMeSH
1,3-DichloropropyleneMeSH
Telone ecMeSH
Chemical FormulaC3H4Cl2
Average Mass110.9700 Da
Monoisotopic Mass109.96901 Da
IUPAC Name(1Z)-1,3-dichloroprop-1-ene
Traditional Nametelone II
CAS Registry NumberNot Available
SMILES
[H]\C(Cl)=C(/[H])CCl
InChI Identifier
InChI=1S/C3H4Cl2/c4-2-1-3-5/h1-2H,3H2/b2-1-
InChI KeyUOORRWUZONOOLO-UPHRSURJSA-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 vinyl chlorides. These are vinyl halides in which a chlorine atom is bonded to an sp2-hybridised carbon atom.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassVinyl halides
Sub ClassVinyl chlorides
Direct ParentVinyl chlorides
Alternative Parents
Substituents
  • Chloroalkene
  • Haloalkene
  • Vinyl chloride
  • Hydrocarbon derivative
  • Organochloride
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
logP2.07ALOGPS
logP1.88ChemAxon
logS-1.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity25.28 m³·mol⁻¹ChemAxon
Polarizability9.62 ųChemAxon
Number of Rings0ChemAxon
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 ID4444456
KEGG Compound IDC06610
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID18809
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. Dohoo C, Read Guernsey J, Gibson MD, VanLeeuwen J: Impact of biogas digesters on cookhouse volatile organic compound exposure for rural Kenyan farmwomen. J Expo Sci Environ Epidemiol. 2015 Mar-Apr;25(2):167-74. doi: 10.1038/jes.2013.42. Epub 2013 Jul 31. [PubMed:23899962 ]
  3. Guo Y, Serrano H, Johnson WH Jr, Ernst S, Hackert ML, Whitman CP: Crystal structures of native and inactivated cis-3-chloroacrylic acid dehalogenase: Implications for the catalytic and inactivation mechanisms. Bioorg Chem. 2011 Feb;39(1):1-9. doi: 10.1016/j.bioorg.2010.10.001. Epub 2010 Oct 20. [PubMed:21074239 ]
  4. Qin R, Gao S, Ajwa H, Hanson BD, Trout TJ, Wang D, Guo M: Interactive effect of organic amendment and environmental factors on degradation of 1,3-dichloropropene and chloropicrin in soil. J Agric Food Chem. 2009 Oct 14;57(19):9063-70. doi: 10.1021/jf901737a. [PubMed:19722521 ]
  5. Pegan SD, Serrano H, Whitman CP, Mesecar AD: Structural and mechanistic analysis of trans-3-chloroacrylic acid dehalogenase activity. Acta Crystallogr D Biol Crystallogr. 2008 Dec;64(Pt 12):1277-82. doi: 10.1107/S0907444908034707. Epub 2008 Nov 18. [PubMed:19018104 ]