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Showing metabocard for trans-3-Chloroallyl aldehyde (HMDB0060516)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:26:32 UTC
Update Date2023-02-21 17:30:04 UTC
HMDB IDHMDB0060516
Secondary Accession Numbers
  • HMDB60516
Metabolite Identification
Common Nametrans-3-Chloroallyl aldehyde
Descriptiontrans-3-Chloroallyl aldehyde, also known as trans-3-chloro-2-propenal, belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position. trans-3-Chloroallyl aldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). These are salts of enols (or of the tautomeric aldehydes or ketones), in which the anionic charge is delocalized over oxygen and carbon, or similar covalent metal derivatives in which the metal is bound to oxygen.
Structure
Data?1677000604
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0060516 (trans-3-Chloroallyl aldehyde)


  Mrv0541 05161318262D          

  5  4  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  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
M  END
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3D MOL for HMDB0060516 (trans-3-Chloroallyl aldehyde)

HMDB0060516
     RDKit          3D
trans-3-Chloroallyl aldehyde
  8  7  0  0  0  0  0  0  0  0999 V2000
   -1.6280   -0.9253   -0.6038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3147   -0.0205    0.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0993    0.3349    0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0314   -0.2357   -0.4099 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6906    0.2605   -0.2253 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0390    0.4747    0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4022    1.1167    1.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7582   -1.0054   -1.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  2  6  1  0
  3  7  1  0
  4  8  1  0
M  END
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3D SDF for HMDB0060516 (trans-3-Chloroallyl aldehyde)


  Mrv0541 05161318262D          

  5  4  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  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
M  END
> <DATABASE_ID>
HMDB0060516

> <DATABASE_NAME>
hmdb

> <SMILES>
Cl\C=C\C=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H3ClO/c4-2-1-3-5/h1-3H/b2-1+

> <INCHI_KEY>
ZSOPPQGHWJVKJB-OWOJBTEDSA-N

> <FORMULA>
C3H3ClO

> <MOLECULAR_WEIGHT>
90.508

> <EXACT_MASS>
89.987242425

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
7.669781446568479

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-chloroprop-2-enal

> <ALOGPS_LOGP>
0.43

> <JCHEM_LOGP>
0.6915285673333333

> <ALOGPS_LOGS>
-0.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.302310808467726

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
21.1676

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.78e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trans-3-chloroacrolein

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0060516 (trans-3-Chloroallyl aldehyde)

HMDB0060516
     RDKit          3D
trans-3-Chloroallyl aldehyde
  8  7  0  0  0  0  0  0  0  0999 V2000
   -1.6280   -0.9253   -0.6038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3147   -0.0205    0.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0993    0.3349    0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0314   -0.2357   -0.4099 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6906    0.2605   -0.2253 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0390    0.4747    0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4022    1.1167    1.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7582   -1.0054   -1.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  2  6  1  0
  3  7  1  0
  4  8  1  0
M  END
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PDB for HMDB0060516 (trans-3-Chloroallyl aldehyde)

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
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2                                                            
CONECT    5    3                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0060516 (trans-3-Chloroallyl aldehyde)

COMPND    HMDB0060516
HETATM    1  O1  UNL     1      -1.628  -0.925  -0.604  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.315  -0.020   0.213  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.099   0.335   0.305  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.031  -0.236  -0.410  1.00  0.00           C  
HETATM    5 CL1  UNL     1       2.691   0.261  -0.225  1.00  0.00          CL  
HETATM    6  H1  UNL     1      -2.039   0.475   0.819  1.00  0.00           H  
HETATM    7  H2  UNL     1       0.402   1.117   1.005  1.00  0.00           H  
HETATM    8  H3  UNL     1       0.758  -1.005  -1.104  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    6
CONECT    3    4    4    7
CONECT    4    5    8
END
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SMILES for HMDB0060516 (trans-3-Chloroallyl aldehyde)

Cl\C=C\C=O
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INCHI for HMDB0060516 (trans-3-Chloroallyl aldehyde)

InChI=1S/C3H3ClO/c4-2-1-3-5/h1-3H/b2-1+
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
trans-3-Chloro-2-propenalKegg
Chemical FormulaC3H3ClO
Average Molecular Weight90.508
Monoisotopic Molecular Weight89.987242425
IUPAC Name(2E)-3-chloroprop-2-enal
Traditional Nametrans-3-chloroacrolein
CAS Registry NumberNot Available
SMILES
Cl\C=C\C=O
InChI Identifier
InChI=1S/C3H3ClO/c4-2-1-3-5/h1-3H/b2-1+
InChI KeyZSOPPQGHWJVKJB-OWOJBTEDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentEnals
Alternative Parents
Substituents
  • Vinylogous halide
  • Enal
  • Chloroalkene
  • Haloalkene
  • Vinyl halide
  • Vinyl chloride
  • Organic oxide
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
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 Solubility37.8 g/LALOGPS
logP0.43ALOGPS
logP0.69ChemAxon
logS-0.38ALOGPS
pKa (Strongest Basic)-5.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity21.17 m³·mol⁻¹ChemAxon
Polarizability7.67 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]+120.76630932474
DeepCCS[M-H]-118.87130932474
DeepCCS[M-2H]-154.21230932474
DeepCCS[M+Na]+128.61930932474
AllCCS[M+H]+124.432859911
AllCCS[M+H-H2O]+120.032859911
AllCCS[M+NH4]+128.632859911
AllCCS[M+Na]+129.732859911
AllCCS[M-H]-135.632859911
AllCCS[M+Na-2H]-141.132859911
AllCCS[M+HCOO]-147.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
trans-3-Chloroallyl aldehydeCl\C=C\C=O1056.5Standard polar33892256
trans-3-Chloroallyl aldehydeCl\C=C\C=O693.2Standard non polar33892256
trans-3-Chloroallyl aldehydeCl\C=C\C=O742.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - trans-3-Chloroallyl aldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-0553-9000000000-5186243033c5ebaf7c972017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-3-Chloroallyl aldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-3-Chloroallyl aldehyde 10V, Positive-QTOFsplash10-0006-9000000000-2a706c1b597cb1842c0a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-3-Chloroallyl aldehyde 20V, Positive-QTOFsplash10-006x-9000000000-72b426157d36e6d1823e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-3-Chloroallyl aldehyde 40V, Positive-QTOFsplash10-076r-9000000000-2b8aafe5d6e724fe93382017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-3-Chloroallyl aldehyde 10V, Negative-QTOFsplash10-000i-9000000000-8aeecf083c0988ebc16d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-3-Chloroallyl aldehyde 20V, Negative-QTOFsplash10-000i-9000000000-a9b0fd6df86bd75a1ea72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-3-Chloroallyl aldehyde 40V, Negative-QTOFsplash10-0udi-9000000000-0cf276280f4ffb4dad6d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-3-Chloroallyl aldehyde 10V, Positive-QTOFsplash10-0006-9000000000-632f46ec507129a31a102021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-3-Chloroallyl aldehyde 20V, Positive-QTOFsplash10-03kc-9000000000-818e341da732705eaf812021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-3-Chloroallyl aldehyde 40V, Positive-QTOFsplash10-0ab9-9000000000-d4bd39bda5f710217aeb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-3-Chloroallyl aldehyde 10V, Negative-QTOFsplash10-001i-9000000000-c2fa753da65a4bac80a12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-3-Chloroallyl aldehyde 20V, Negative-QTOFsplash10-001i-9000000000-c2fa753da65a4bac80a12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-3-Chloroallyl aldehyde 40V, Negative-QTOFsplash10-001i-9000000000-c2fa753da65a4bac80a12021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
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 IDC06613
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280971
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
Enzyme Details
4. Alcohol dehydrogenase class-3
General function:
Involved in zinc ion binding
Specific function:
Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:
ADH5
Uniprot ID:
P11766
Molecular weight:
39723.945
Reactions
trans-3-Chloro-2-propene-1-ol + NAD → trans-3-Chloroallyl aldehyde + NADH + Hydrogen Iondetails