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Showing NP-Card for cis-3-chloroacrylic acid (NP0002715)

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Record Information
Version2.0
Created at2020-11-23 19:38:37 UTC
Updated at2021-08-12 19:51:56 UTC
NP-MRD IDNP0002715
Secondary Accession NumbersNone
Natural Product Identification
Common Namecis-3-chloroacrylic acid
Provided ByBMRBBMRB logo
DescriptionCis-3-Chloroacrylic acid belongs to the class of organic compounds known as acrylic acids and derivatives. These are organic compounds containing acrylic acid CH2=CHCO2H or a derivative thereof. Cis-3-Chloroacrylic acid exists in all living organisms, ranging from bacteria to humans. Cis-3-Chloroacrylic 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. cis-3-chloroacrylic acid was first documented in 2017 (PMID: 29111295). Based on a literature review a small amount of articles have been published on cis-3-Chloroacrylic acid (PMID: 34019384) (PMID: 29184004).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002715 (cis-3-chloroacrylic acid)


     RDKit          2D

  9  8  0  0  0  0  0  0  0  0999 V2000
   -0.9132   -1.6413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8704   -0.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1475    0.6448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4495    0.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7266   -0.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6838   -1.7154    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.4674   -0.0678    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4922    2.0701    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0465    0.4967    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
  3  7  1  0
  4  8  1  0
  5  9  1  0
M  END
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3D MOL for NP0002715 (cis-3-chloroacrylic acid)

NP0002715
     RDKit          3D

  9  8  0  0  0  0  0  0  0  0999 V2000
    0.9071    1.3254    0.5364 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8664    0.1159    0.2542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0259   -0.6142    0.2627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4108   -0.4712   -0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5327    0.2381   -0.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.9385    0.3235 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5819   -0.8004   -0.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5281   -1.5193   -0.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4808   -0.2128   -0.3263 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
  3  7  1  0
  4  8  1  0
  5  9  1  0
M  END
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3D SDF for NP0002715 (cis-3-chloroacrylic acid)


     RDKit          2D

  9  8  0  0  0  0  0  0  0  0999 V2000
   -0.9132   -1.6413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8704   -0.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1475    0.6448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4495    0.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7266   -0.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6838   -1.7154    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.4674   -0.0678    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4922    2.0701    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0465    0.4967    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
  3  7  1  0
  4  8  1  0
  5  9  1  0
M  END
> <DATABASE_ID>
NP0002715

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)\C=C/Cl

> <INCHI_IDENTIFIER>
InChI=1S/C3H3ClO2/c4-2-1-3(5)6/h1-2H,(H,5,6)/b2-1-

> <INCHI_KEY>
MHMUCYJKZUZMNJ-UPHRSURJSA-N

> <FORMULA>
C3H3ClO2

> <MOLECULAR_WEIGHT>
106.508

> <EXACT_MASS>
105.982157047

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
8.285484472863587

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-3-chloroprop-2-enoic acid

> <ALOGPS_LOGP>
0.87

> <JCHEM_LOGP>
0.8501448196666668

> <ALOGPS_LOGS>
-0.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2338706750255533

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
22.093

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.84e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cis-3-chloroacrylic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0002715 (cis-3-chloroacrylic acid)

NP0002715
     RDKit          3D

  9  8  0  0  0  0  0  0  0  0999 V2000
    0.9071    1.3254    0.5364 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8664    0.1159    0.2542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0259   -0.6142    0.2627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4108   -0.4712   -0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5327    0.2381   -0.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.9385    0.3235 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5819   -0.8004   -0.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5281   -1.5193   -0.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4808   -0.2128   -0.3263 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
  3  7  1  0
  4  8  1  0
  5  9  1  0
M  END
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PDB for NP0002715 (cis-3-chloroacrylic acid)

HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         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  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       1.540  -2.667   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2                                                            
CONECT    5    3                                                            
CONECT    6    3                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for NP0002715 (cis-3-chloroacrylic acid)

COMPND    NP0002715
HETATM    1  O1  UNL     1       0.907   1.325   0.536  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.866   0.116   0.254  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.026  -0.614   0.263  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.411  -0.471  -0.073  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.533   0.238  -0.080  1.00  0.00           C  
HETATM    6 CL1  UNL     1      -1.429   1.939   0.323  1.00  0.00          CL  
HETATM    7  H1  UNL     1       2.582  -0.800  -0.568  1.00  0.00           H  
HETATM    8  H2  UNL     1      -0.528  -1.519  -0.330  1.00  0.00           H  
HETATM    9  H3  UNL     1      -2.481  -0.213  -0.326  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3    7
CONECT    4    5    5    8
CONECT    5    6    9
END
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SMILES for NP0002715 (cis-3-chloroacrylic acid)

OC(=O)\C=C/Cl
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INCHI for NP0002715 (cis-3-chloroacrylic acid)

InChI=1S/C3H3ClO2/c4-2-1-3(5)6/h1-2H,(H,5,6)/b2-1-
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Synonyms
ValueSource
cis-3-ChloroacrylateGenerator
Chemical FormulaC3H3ClO2
Average Mass106.5080 Da
Monoisotopic Mass105.98216 Da
IUPAC Name(2Z)-3-chloroprop-2-enoic acid
Traditional Namecis-3-chloroacrylic acid
CAS Registry NumberNot Available
SMILES
OC(=O)\C=C/Cl
InChI Identifier
InChI=1S/C3H3ClO2/c4-2-1-3(5)6/h1-2H,(H,5,6)/b2-1-
InChI KeyMHMUCYJKZUZMNJ-UPHRSURJSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 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 acrylic acids and derivatives. These are organic compounds containing acrylic acid CH2=CHCO2H or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAcrylic acids and derivatives
Direct ParentAcrylic acids and derivatives
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic 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
logP0.87ALOGPS
logP0.85ChemAxon
logS-0.19ALOGPS
pKa (Strongest Acidic)3.23ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.09 m³·mol⁻¹ChemAxon
Polarizability8.29 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0060457
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID558892
KEGG Compound IDC06615
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound643794
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Baas BJ, Medellin BP, LeVieux JA, Erwin K, Lancaster EB, Johnson WH Jr, Kaoud TS, Moreno RY, de Ruijter M, Babbitt PC, Zhang YJ, Whitman CP: Kinetic and Structural Analysis of Two Linkers in the Tautomerase Superfamily: Analysis and Implications. Biochemistry. 2021 Jun 8;60(22):1776-1786. doi: 10.1021/acs.biochem.1c00220. Epub 2021 May 21. [PubMed:34019384 ]
  2. Davidson R, Baas BJ, Akiva E, Holliday GL, Polacco BJ, LeVieux JA, Pullara CR, Zhang YJ, Whitman CP, Babbitt PC: A global view of structure-function relationships in the tautomerase superfamily. J Biol Chem. 2018 Feb 16;293(7):2342-2357. doi: 10.1074/jbc.M117.815340. Epub 2017 Nov 28. [PubMed:29184004 ]
  3. LeVieux JA, Baas BJ, Kaoud TS, Davidson R, Babbitt PC, Zhang YJ, Whitman CP: Kinetic and structural characterization of a cis-3-Chloroacrylic acid dehalogenase homologue in Pseudomonas sp. UW4: A potential step between subgroups in the tautomerase superfamily. Arch Biochem Biophys. 2017 Dec 15;636:50-56. doi: 10.1016/j.abb.2017.10.018. Epub 2017 Oct 27. [PubMed:29111295 ]