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Showing metabocard for trans-3-Chloroacrylic acid (HMDB0060515)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:26:28 UTC
Update Date2023-02-21 17:30:04 UTC
HMDB IDHMDB0060515
Secondary Accession Numbers
  • HMDB60515
Metabolite Identification
Common Nametrans-3-Chloroacrylic acid
Descriptiontrans-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. These are compounds containing the enone functional group, with the structure RC(=O)CR'. trans-3-Chloroacrylic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. trans-3-Chloroacrylic acid exists in all living organisms, ranging from bacteria to humans.
Structure
Data?1677000604
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0060515 (trans-3-Chloroacrylic acid)


  Mrv0541 05161318262D          

  6  5  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  3  1  0  0  0  0
M  END
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3D MOL for HMDB0060515 (trans-3-Chloroacrylic acid)

HMDB0060515
     RDKit          3D
trans-3-Chloroacrylic acid
  9  8  0  0  0  0  0  0  0  0999 V2000
   -1.0881   -1.5443   -0.2515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0092   -0.3099   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1488    0.4640   -0.1015 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3137    0.2966    0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4190   -0.4287    0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9739    0.3364    0.4392 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2379    1.3163   -0.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4265    1.3572    0.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3508   -1.4875    0.0215 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 HMDB0060515 (trans-3-Chloroacrylic acid)


  Mrv0541 05161318262D          

  6  5  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  3  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060515

> <DATABASE_NAME>
hmdb

> <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-OWOJBTEDSA-N

> <FORMULA>
C3H3ClO2

> <MOLECULAR_WEIGHT>
106.508

> <EXACT_MASS>
105.982157047

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
8.489990767049644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-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>
3.5338706750255535

> <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>
trans-3-chloroacrylic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0060515 (trans-3-Chloroacrylic acid)

HMDB0060515
     RDKit          3D
trans-3-Chloroacrylic acid
  9  8  0  0  0  0  0  0  0  0999 V2000
   -1.0881   -1.5443   -0.2515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0092   -0.3099   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1488    0.4640   -0.1015 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3137    0.2966    0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4190   -0.4287    0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9739    0.3364    0.4392 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2379    1.3163   -0.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4265    1.3572    0.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3508   -1.4875    0.0215 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 HMDB0060515 (trans-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       1.540   2.667   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.850   1.334   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 HMDB0060515 (trans-3-Chloroacrylic acid)

COMPND    HMDB0060515
HETATM    1  O1  UNL     1      -1.088  -1.544  -0.251  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.009  -0.310  -0.080  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.149   0.464  -0.101  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.314   0.297   0.144  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.419  -0.429   0.169  1.00  0.00           C  
HETATM    6 CL1  UNL     1       2.974   0.336   0.439  1.00  0.00          CL  
HETATM    7  H1  UNL     1      -2.238   1.316  -0.638  1.00  0.00           H  
HETATM    8  H2  UNL     1       0.426   1.357   0.297  1.00  0.00           H  
HETATM    9  H3  UNL     1       1.351  -1.488   0.021  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 HMDB0060515 (trans-3-Chloroacrylic acid)

OC(=O)\C=C\Cl
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INCHI for HMDB0060515 (trans-3-Chloroacrylic acid)

InChI=1S/C3H3ClO2/c4-2-1-3(5)6/h1-2H,(H,5,6)/b2-1+
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
trans-3-ChloroacrylateGenerator
3-Chloroacrylic acidHMDB
(e)-3-ChloroacrylateGenerator
Chemical FormulaC3H3ClO2
Average Molecular Weight106.508
Monoisotopic Molecular Weight105.982157047
IUPAC Name(2E)-3-chloroprop-2-enoic acid
Traditional Nametrans-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-OWOJBTEDSA-N
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 Parents
Substituents
  • Acrylic acid or derivatives
  • Vinylogous halide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Vinyl chloride
  • Chloroalkene
  • Haloalkene
  • Vinyl halide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility68.4 g/LALOGPS
logP0.87ALOGPS
logP0.85ChemAxon
logS-0.19ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.09 m³·mol⁻¹ChemAxon
Polarizability8.49 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+116.6930932474
DeepCCS[M-H]-114.74830932474
DeepCCS[M-2H]-150.50530932474
DeepCCS[M+Na]+125.0830932474
AllCCS[M+H]+126.232859911
AllCCS[M+H-H2O]+121.932859911
AllCCS[M+NH4]+130.332859911
AllCCS[M+Na]+131.532859911
AllCCS[M-H]-128.732859911
AllCCS[M+Na-2H]-133.332859911
AllCCS[M+HCOO]-138.432859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.3.33 minutes32390414
Predicted by Siyang on May 30, 202210.9387 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.05 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid757.3 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid387.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid112.8 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid290.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid108.7 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid296.9 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid345.1 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)538.3 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid648.0 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid76.1 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid934.1 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid249.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid327.6 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate780.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA301.2 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water342.4 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
trans-3-Chloroacrylic acidOC(=O)\C=C\Cl1948.7Standard polar33892256
trans-3-Chloroacrylic acidOC(=O)\C=C\Cl1060.8Standard non polar33892256
trans-3-Chloroacrylic acidOC(=O)\C=C\Cl1003.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
trans-3-Chloroacrylic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/Cl1006.8Semi standard non polar33892256
trans-3-Chloroacrylic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/Cl1228.9Semi standard non polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC06614
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound638124
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details
1. Aldehyde dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
trans-3-Chloroallyl aldehyde + Water → trans-3-Chloroacrylic acid + Hydrogen Iondetails
Enzyme Details
2. Fatty aldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
trans-3-Chloroallyl aldehyde + Water → trans-3-Chloroacrylic acid + Hydrogen Iondetails
Enzyme Details
3. Aldehyde dehydrogenase X, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
trans-3-Chloroallyl aldehyde + Water → trans-3-Chloroacrylic acid + Hydrogen Iondetails