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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 22:44:24 UTC

Update Date

2021-09-26 23:17:36 UTC

HMDB ID

HMDB0259812

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Vinclozolin M2

Description

Vinclozolin M2 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 a significant number of articles have been published on Vinclozolin M2. This compound has been identified in human blood as reported by (PMID: 31557052 ). Vinclozolin m2 is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Vinclozolin M2 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

  Mrv1652309122100442D          

 16 16  0  0  0  0            999 V2000
    0.8250    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    3.3000    0.0000 O   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  2  0  0  0  0
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  0  0  0  0
 10 15  1  0  0  0  0
  2 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259812

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(O)(C=C)C(=O)NC1=CC(Cl)=CC(Cl)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H11Cl2NO2/c1-3-11(2,16)10(15)14-9-5-7(12)4-8(13)6-9/h3-6,16H,1H2,2H3,(H,14,15)

> <INCHI_KEY>
FBYYIBNYONAZCU-UHFFFAOYSA-N

> <FORMULA>
C11H11Cl2NO2

> <MOLECULAR_WEIGHT>
260.11

> <EXACT_MASS>
259.016684

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
24.879317978861792

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(3,5-dichlorophenyl)-2-hydroxy-2-methylbut-3-enamide

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
2.9777694869999998

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.49079238808514

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.036276224148493

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8527191171426063

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
65.8541

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(3,5-dichlorophenyl)-2-hydroxy-2-methylbut-3-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-21         0                                  
HETATM    1  C   UNK     0       1.540   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0      -1.334  -0.770   0.000  0.00  0.00          Cl+0
HETATM   15 Cl   UNK     0       4.001  -0.770   0.000  0.00  0.00          Cl+0
HETATM   16  O   UNK     0      -1.540   6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5   16                                             
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    8                                                       
CONECT   14   12                                                            
CONECT   15   10                                                            
CONECT   16    2                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0259812
HETATM    1  C1  UNL     1      -3.113   1.458   1.008  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.055   0.165   0.701  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.243  -0.294  -0.462  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.684  -1.638  -0.969  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.270   0.694  -1.419  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.834  -0.449   0.025  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.681  -1.322   0.901  1.00  0.00           O  
HETATM    8  N1  UNL     1       0.222   0.320  -0.460  1.00  0.00           N  
HETATM    9  C6  UNL     1       1.545   0.219  -0.046  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.461   1.087  -0.661  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.792   1.064  -0.320  1.00  0.00           C  
HETATM   12 CL1  UNL     1       4.891   2.188  -1.136  1.00  0.00          CL  
HETATM   13  C9  UNL     1       4.261   0.193   0.631  1.00  0.00           C  
HETATM   14  C10 UNL     1       3.393  -0.672   1.255  1.00  0.00           C  
HETATM   15 CL2  UNL     1       3.956  -1.796   2.471  1.00  0.00          CL  
HETATM   16  C11 UNL     1       2.045  -0.621   0.882  1.00  0.00           C  
HETATM   17  H1  UNL     1      -2.565   2.180   0.407  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.689   1.803   1.837  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.581  -0.570   1.271  1.00  0.00           H  
HETATM   20  H4  UNL     1      -3.428  -2.072  -0.241  1.00  0.00           H  
HETATM   21  H5  UNL     1      -1.844  -2.389  -0.981  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.108  -1.620  -1.982  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.261   0.362  -2.352  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.062   1.030  -1.211  1.00  0.00           H  
HETATM   25  H9  UNL     1       2.109   1.796  -1.427  1.00  0.00           H  
HETATM   26  H10 UNL     1       5.322   0.194   0.885  1.00  0.00           H  
HETATM   27  H11 UNL     1       1.421  -1.310   1.395  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3   19
CONECT    3    4    5    6
CONECT    4   20   21   22
CONECT    5   23
CONECT    6    7    7    8
CONECT    8    9   24
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
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-(3,5-Dichlorophenyl)-2-hydroxy-2-methyl-3-butenamide	Kegg
3',5'-Dichloro-2-hydroxy-2-methylbut-3-enanilide	Kegg
N-(3,5-Dichlorophenyl)-2-hydroxy-2-methylbut-3-enimidate	HMDB
2-OH-2-Me-dicl-butenanilide	HMDB

Chemical Formula

C₁₁H₁₁Cl₂NO₂

Average Molecular Weight

260.11

Monoisotopic Molecular Weight

259.016684

IUPAC Name

N-(3,5-dichlorophenyl)-2-hydroxy-2-methylbut-3-enamide

Traditional Name

N-(3,5-dichlorophenyl)-2-hydroxy-2-methylbut-3-enamide

CAS Registry Number

Not Available

SMILES

CC(O)(C=C)C(=O)NC1=CC(Cl)=CC(Cl)=C1

InChI Identifier

InChI=1S/C11H11Cl2NO2/c1-3-11(2,16)10(15)14-9-5-7(12)4-8(13)6-9/h3-6,16H,1H2,2H3,(H,14,15)

InChI Key

FBYYIBNYONAZCU-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
Aryl chloride
Aryl halide
Tertiary alcohol
Carboximidic acid
Carboximidic acid derivative
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organopnictogen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

anilide (CHEBI:34827 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	2.91	ALOGPS
logP	2.98	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.04	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	65.85 m³·mol⁻¹	ChemAxon
Polarizability	24.88 Å³	ChemAxon
Number of Rings	1	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]+	152.739	32859911
AllCCS	[M+H-H2O]+	149.192	32859911
AllCCS	[M+Na]+	156.979	32859911
AllCCS	[M+NH4]+	156.032	32859911
AllCCS	[M-H]-	150.678	32859911
AllCCS	[M+Na-2H]-	151.042	32859911
AllCCS	[M+HCOO]-	151.534	32859911
DeepCCS	[M+H]+	151.631	30932474
DeepCCS	[M-H]-	149.235	30932474
DeepCCS	[M-2H]-	182.147	30932474
DeepCCS	[M+Na]+	157.638	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vinclozolin M2	CC(O)(C=C)C(=O)NC1=CC(Cl)=CC(Cl)=C1	3223.0	Standard polar	33892256
Vinclozolin M2	CC(O)(C=C)C(=O)NC1=CC(Cl)=CC(Cl)=C1	1937.0	Standard non polar	33892256
Vinclozolin M2	CC(O)(C=C)C(=O)NC1=CC(Cl)=CC(Cl)=C1	2020.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vinclozolin M2,2TMS,isomer #1	C=CC(C)(O[Si](C)(C)C)C(=O)N(C1=CC(Cl)=CC(Cl)=C1)[Si](C)(C)C	1908.1	Semi standard non polar	33892256
Vinclozolin M2,2TMS,isomer #1	C=CC(C)(O[Si](C)(C)C)C(=O)N(C1=CC(Cl)=CC(Cl)=C1)[Si](C)(C)C	1971.2	Standard non polar	33892256
Vinclozolin M2,2TMS,isomer #1	C=CC(C)(O[Si](C)(C)C)C(=O)N(C1=CC(Cl)=CC(Cl)=C1)[Si](C)(C)C	2171.2	Standard polar	33892256
Vinclozolin M2,2TBDMS,isomer #1	C=CC(C)(O[Si](C)(C)C(C)(C)C)C(=O)N(C1=CC(Cl)=CC(Cl)=C1)[Si](C)(C)C(C)(C)C	2406.3	Semi standard non polar	33892256
Vinclozolin M2,2TBDMS,isomer #1	C=CC(C)(O[Si](C)(C)C(C)(C)C)C(=O)N(C1=CC(Cl)=CC(Cl)=C1)[Si](C)(C)C(C)(C)C	2390.1	Standard non polar	33892256
Vinclozolin M2,2TBDMS,isomer #1	C=CC(C)(O[Si](C)(C)C(C)(C)C)C(=O)N(C1=CC(Cl)=CC(Cl)=C1)[Si](C)(C)C(C)(C)C	2377.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Vinclozolin M2 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0itl-9500000000-43698cc310b6505f6383	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vinclozolin M2 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vinclozolin M2 GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vinclozolin M2 GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vinclozolin M2 GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vinclozolin M2 GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	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

103085

KEGG Compound ID

C14207

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

115209

PDB ID

Not Available

ChEBI ID

Not Available

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 M2 (HMDB0259812)

MOL for HMDB0259812 (Vinclozolin M2)

3D MOL for HMDB0259812 (Vinclozolin M2)

3D SDF for HMDB0259812 (Vinclozolin M2)

3D-SDF for HMDB0259812 (Vinclozolin M2)

PDB for HMDB0259812 (Vinclozolin M2)

3D PDB for HMDB0259812 (Vinclozolin M2)

SMILES for HMDB0259812 (Vinclozolin M2)

INCHI for HMDB0259812 (Vinclozolin M2)

Structure for HMDB0259812 (Vinclozolin M2)

3D Structure for HMDB0259812 (Vinclozolin M2)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra