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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 22:44:20 UTC

Update Date

2022-11-23 22:29:21 UTC

HMDB ID

HMDB0259811

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Vinclozolin

Description

Vinclozolin belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it. Based on a literature review very few articles have been published on Vinclozolin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Vinclozolin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Vinclozolin 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


  Mrv0541 04251301072D          

 18 19  0  0  0  0            999 V2000
    1.1270   -2.5070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665   -1.4675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3095   -0.5187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7294    0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1195   -0.5187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830   -3.1745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4324   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9173   -3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7378   -3.6695    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5817   -4.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7613   -4.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2763   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4257   -5.3493    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  4  9  1  0  0  0  0
  2 10  2  0  0  0  0
  1 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 11 17  1  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259811

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(OC(=O)N(C1=O)C1=CC(Cl)=CC(Cl)=C1)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C12H9Cl2NO3/c1-3-12(2)10(16)15(11(17)18-12)9-5-7(13)4-8(14)6-9/h3-6H,1H2,2H3

> <INCHI_KEY>
FSCWZHGZWWDELK-UHFFFAOYSA-N

> <FORMULA>
C12H9Cl2NO3

> <MOLECULAR_WEIGHT>
286.111

> <EXACT_MASS>
284.995948573

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.193033458615048

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-1,3-oxazolidine-2,4-dione

> <ALOGPS_LOGP>
3.14

> <JCHEM_LOGP>
3.7446360003333328

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.282967397384969

> <JCHEM_POLAR_SURFACE_AREA>
46.61

> <JCHEM_REFRACTIVITY>
67.00150000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vinclozolin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-13         0                                  
HETATM    1  N   UNK     0       2.104  -4.680   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.088  -3.215   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.580  -3.215   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.044  -2.739   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.578  -0.968   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.362   0.357   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.090  -0.968   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.342  -5.926   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.009  -5.926   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.540  -5.765   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.446  -7.011   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0       6.977  -6.850   0.000  0.00  0.00          Cl+0
HETATM   15  C   UNK     0       4.819  -8.418   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.288  -8.578   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.382  -7.333   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0       2.661  -9.985   0.000  0.00  0.00          Cl+0
CONECT    1    2    5   11                                                  
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7    9                                             
CONECT    5    4    1    6                                                  
CONECT    6    5                                                            
CONECT    7    4    8                                                       
CONECT    8    7                                                            
CONECT    9    4                                                            
CONECT   10    2                                                            
CONECT   11    1   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16   11                                                       
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0259811
HETATM    1  C1  UNL     1      -3.793   1.016   1.002  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.460  -0.250   0.839  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.176  -0.579   0.221  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.139  -0.318  -1.268  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.746  -1.887   0.434  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.376  -1.903   0.234  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.325  -2.906  -0.090  1.00  0.00           O  
HETATM    8  N1  UNL     1       0.108  -0.578   0.458  1.00  0.00           N  
HETATM    9  C6  UNL     1       1.451  -0.124   0.367  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.251  -0.527  -0.682  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.562  -0.083  -0.776  1.00  0.00           C  
HETATM   12 CL1  UNL     1       4.575  -0.595  -2.103  1.00  0.00          CL  
HETATM   13  C9  UNL     1       4.114   0.767   0.161  1.00  0.00           C  
HETATM   14  C10 UNL     1       3.279   1.153   1.206  1.00  0.00           C  
HETATM   15 CL2  UNL     1       3.937   2.238   2.431  1.00  0.00          CL  
HETATM   16  C11 UNL     1       1.978   0.721   1.313  1.00  0.00           C  
HETATM   17  C12 UNL     1      -1.027   0.211   0.795  1.00  0.00           C  
HETATM   18  O3  UNL     1      -0.997   1.276   1.411  1.00  0.00           O  
HETATM   19  H1  UNL     1      -3.144   1.822   0.690  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.739   1.265   1.457  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.154  -1.020   1.172  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.963  -0.834  -1.768  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.198   0.765  -1.476  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.121  -0.655  -1.624  1.00  0.00           H  
HETATM   25  H7  UNL     1       1.907  -1.188  -1.463  1.00  0.00           H  
HETATM   26  H8  UNL     1       5.136   1.132   0.108  1.00  0.00           H  
HETATM   27  H9  UNL     1       1.409   1.079   2.166  1.00  0.00           H  
CONECT    1    2    2   19   20
CONECT    2    3   21
CONECT    3    4    5   17
CONECT    4   22   23   24
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9   17
CONECT    9   10   10   16
CONECT   10   11   25
CONECT   11   12   13   13
CONECT   13   14   26
CONECT   14   15   16   16
CONECT   16   27
CONECT   17   18   18
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(3,5-Dichlorophenyl)-5-methyl-5-vinyl-1,3-oxazolidine-2,4-dione	MeSH
Ronilan	MeSH

Chemical Formula

C₁₂H₉Cl₂NO₃

Average Molecular Weight

286.111

Monoisotopic Molecular Weight

284.995948573

IUPAC Name

3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-1,3-oxazolidine-2,4-dione

Traditional Name

vinclozolin

CAS Registry Number

Not Available

SMILES

CC1(OC(=O)N(C1=O)C1=CC(Cl)=CC(Cl)=C1)C=C

InChI Identifier

InChI=1S/C12H9Cl2NO3/c1-3-12(2)10(16)15(11(17)18-12)9-5-7(13)4-8(14)6-9/h3-6H,1H2,2H3

InChI Key

FSCWZHGZWWDELK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Dichlorobenzenes

Alternative Parents

Substituents

1,3-dichlorobenzene
Oxazolidinedione
Aryl chloride
Aryl halide
Oxazolidinone
Dicarboximide
Oxazolidine
Carbamic acid ester
Carbonic acid derivative
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dicarboximide (CHEBI:83732 )
dichlorobenzene (CHEBI:83732 )
olefinic compound (CHEBI:83732 )
oxazolidinone (CHEBI:83732 )
Carbamate pesticides (C10981 )
Dicarboximide fungicides (C10981 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0259811)

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	3.14	ALOGPS
logP	3.74	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	46.61 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	67 m³·mol⁻¹	ChemAxon
Polarizability	26.19 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	157.165	32859911
AllCCS	[M+H-H2O]+	153.615	32859911
AllCCS	[M+Na]+	161.407	32859911
AllCCS	[M+NH4]+	160.46	32859911
AllCCS	[M-H]-	153.561	32859911
AllCCS	[M+Na-2H]-	153.117	32859911
AllCCS	[M+HCOO]-	152.734	32859911
DeepCCS	[M+H]+	161.579	30932474
DeepCCS	[M-H]-	159.221	30932474
DeepCCS	[M-2H]-	192.107	30932474
DeepCCS	[M+Na]+	167.672	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
VINCLOZOLIN	CC1(OC(=O)N(C1=O)C1=CC(Cl)=CC(Cl)=C1)C=C	2830.0	Standard polar	33892256
VINCLOZOLIN	CC1(OC(=O)N(C1=O)C1=CC(Cl)=CC(Cl)=C1)C=C	2114.8	Standard non polar	33892256
VINCLOZOLIN	CC1(OC(=O)N(C1=O)C1=CC(Cl)=CC(Cl)=C1)C=C	2050.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Vinclozolin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ug0-9240000000-bf89f1f40075773094c2	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vinclozolin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01p9-7980000000-95f8d8d8e2f4e48d2ccd	2014-10-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vinclozolin 90V, Positive-QTOF	splash10-00di-0900000000-c0e2e62c921a42b43ce7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vinclozolin 75V, Positive-QTOF	splash10-00di-0900000000-4ca08b47b3259fbd8b41	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vinclozolin 45V, Positive-QTOF	splash10-02or-0970000000-9694f61d4f6098f1c1b0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vinclozolin 60V, Positive-QTOF	splash10-00di-0920000000-de70432cb5cf65b3c319	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vinclozolin 30V, Positive-QTOF	splash10-02ti-0190000000-095efceffc704e6077b2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vinclozolin 15V, Positive-QTOF	splash10-000i-0090000000-c98c4e21d4b81274112a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vinclozolin 10V, Positive-QTOF	splash10-000i-0090000000-b3300389257f8faff5ca	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vinclozolin 20V, Positive-QTOF	splash10-0gbi-9030000000-06d3f48418764eb1a617	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vinclozolin 40V, Positive-QTOF	splash10-0udi-9000000000-942d3569d2c68aa5db43	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vinclozolin 10V, Negative-QTOF	splash10-001i-0090000000-7ac69daa2d2d030d875b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vinclozolin 20V, Negative-QTOF	splash10-001i-0090000000-758f586c440fea004f5e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vinclozolin 40V, Negative-QTOF	splash10-000i-1900000000-4cdfab3c8d249dc4f7e7	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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

36278

KEGG Compound ID

C10981

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Vinclozolin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

83732

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 Vinclozolin (HMDB0259811)

MOL for HMDB0259811 (Vinclozolin)

3D MOL for HMDB0259811 (Vinclozolin)

3D SDF for HMDB0259811 (Vinclozolin)

3D-SDF for HMDB0259811 (Vinclozolin)

PDB for HMDB0259811 (Vinclozolin)

3D PDB for HMDB0259811 (Vinclozolin)

SMILES for HMDB0259811 (Vinclozolin)

INCHI for HMDB0259811 (Vinclozolin)

Structure for HMDB0259811 (Vinclozolin)

3D Structure for HMDB0259811 (Vinclozolin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra