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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-08-31 04:43:19 UTC

Update Date

2021-09-26 22:48:57 UTC

HMDB ID

HMDB0242452

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid

Description

3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid belongs to the class of organic compounds known as cyclopropanecarboxylic acids. These are organic compounds containing a carboxyl group attached to a cyclopropane ring. Based on a literature review very few articles have been published on 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). (1s,3r)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 31-AUG-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-AUG-21         0                                  
HETATM    1  C   UNK     0      -0.735   2.649   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.445   1.659   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.215   0.325   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.325   0.325   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.659  -0.445   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.993   0.325   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.659  -1.985   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.548  -0.445   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.548  -1.985   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0       3.882  -2.755   0.000  0.00  0.00          Cl+0
HETATM   11 Cl   UNK     0       1.215  -2.755   0.000  0.00  0.00          Cl+0
HETATM   12  C   UNK     0       1.624   2.649   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   12                                             
CONECT    3    2    4    8                                                  
CONECT    4    3    2    5                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    3    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    2                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate	Generator
(1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate	Generator
3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid	MeSH, HMDB
3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid, calcium salt	MeSH, HMDB
3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid, monosodium salt	MeSH, HMDB
CDCCA compound	MeSH, HMDB
CL2CA	MeSH, HMDB
TDCCA compound	MeSH, HMDB
cis-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid	MeSH, HMDB
trans-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid	MeSH, HMDB

Chemical Formula

C₈H₁₀Cl₂O₂

Average Molecular Weight

209.07

Monoisotopic Molecular Weight

208.005785

IUPAC Name

3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid

Traditional Name

3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(C)C(C=C(Cl)Cl)C1C(O)=O

InChI Identifier

InChI=1S/C8H10Cl2O2/c1-8(2)4(3-5(9)10)6(8)7(11)12/h3-4,6H,1-2H3,(H,11,12)

InChI Key

LLMLSUSAKZVFOA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclopropanecarboxylic acids. These are organic compounds containing a carboxyl group attached to a cyclopropane ring.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Cyclopropanecarboxylic acids and derivatives

Direct Parent

Cyclopropanecarboxylic acids

Alternative Parents

Substituents

Cyclopropanecarboxylic acid
Ketene acetal or derivatives
Carboxylic acid
Monocarboxylic acid or derivatives
Vinyl chloride
Vinyl halide
Haloalkene
Chloroalkene
Organochloride
Organohalogen compound
Organooxygen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

organochlorine compound (CHEBI:39308 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.7	ALOGPS
logP	2.33	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.89	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.66 m³·mol⁻¹	ChemAxon
Polarizability	19.28 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	139.719	30932474
DeepCCS	[M-H]-	135.891	30932474
DeepCCS	[M-2H]-	173.414	30932474
DeepCCS	[M+Na]+	148.953	30932474
AllCCS	[M+H]+	139.8	32859911
AllCCS	[M+H-H2O]+	136.0	32859911
AllCCS	[M+NH4]+	143.2	32859911
AllCCS	[M+Na]+	144.2	32859911
AllCCS	[M-H]-	140.1	32859911
AllCCS	[M+Na-2H]-	141.4	32859911
AllCCS	[M+HCOO]-	142.9	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid,1TMS,isomer #1	CC1(C)C(C=C(Cl)Cl)C1C(=O)O[Si](C)(C)C	1423.6	Semi standard non polar	33892256
(1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid,1TMS,isomer #1	CC1(C)C(C=C(Cl)Cl)C1C(=O)O[Si](C)(C)C	1381.2	Standard non polar	33892256
(1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid,1TMS,isomer #1	CC1(C)C(C=C(Cl)Cl)C1C(=O)O[Si](C)(C)C	1540.4	Standard polar	33892256
(1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid,1TBDMS,isomer #1	CC1(C)C(C=C(Cl)Cl)C1C(=O)O[Si](C)(C)C(C)(C)C	1683.4	Semi standard non polar	33892256
(1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid,1TBDMS,isomer #1	CC1(C)C(C=C(Cl)Cl)C1C(=O)O[Si](C)(C)C(C)(C)C	1627.2	Standard non polar	33892256
(1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid,1TBDMS,isomer #1	CC1(C)C(C=C(Cl)Cl)C1C(=O)O[Si](C)(C)C(C)(C)C	1707.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9600000000-252e5e6dfa41f184dd1a	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - (1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid 42V, Positive-QTOF	splash10-0a4i-0090000000-0effeefe77b71851030e	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid 10V, Positive-QTOF	splash10-02ta-9610000000-5e2dbe4cc6f351ce5792	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid 20V, Positive-QTOF	splash10-014j-9300000000-184aef8e37831ca90e76	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid 40V, Positive-QTOF	splash10-0006-9400000000-198c04b720dd1e3e0e22	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid 10V, Negative-QTOF	splash10-0a4i-0390000000-087e3f6e6c234777b195	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid 20V, Negative-QTOF	splash10-03di-0900000000-a639a4ff808922224d9b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid 40V, Negative-QTOF	splash10-0006-9610000000-d83f87957f84d5b69f97	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

82761

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

39308

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid (HMDB0242452)

MOL for HMDB0242452 ((1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid)

3D MOL for HMDB0242452 ((1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid)

3D SDF for HMDB0242452 ((1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid)

3D-SDF for HMDB0242452 ((1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid)

PDB for HMDB0242452 ((1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid)

3D PDB for HMDB0242452 ((1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid)

SMILES for HMDB0242452 ((1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid)

INCHI for HMDB0242452 ((1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid)

Structure for HMDB0242452 ((1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid)

3D Structure for HMDB0242452 ((1S,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra