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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:45 UTC

Update Date

2022-03-07 02:53:04 UTC

HMDB ID

HMDB0031669

Secondary Accession Numbers

HMDB31669

Metabolite Identification

Common Name

Captafol

Description

Captafol, also known as difolatan or haipen, belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. Captafol is formally rated as a probable carcinogen (by IARC 2A) and is also a potentially toxic compound. Based on a literature review a significant number of articles have been published on Captafol.

Structure

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


  Mrv1652305271900052D          

 18 19  0  0  0  0            999 V2000
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9962    2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    2.9519    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    3.6664    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1308    2.6499    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982    1.8249    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 S   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  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 10  1  0  0  0  0
 15  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16  7  2  0  0  0  0
 17  8  2  0  0  0  0
 18 10  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031669

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC(Cl)C(Cl)(Cl)SN1C(=O)C2CC=CCC2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H9Cl4NO2S/c11-9(12)10(13,14)18-15-7(16)5-3-1-2-4-6(5)8(15)17/h1-2,5-6,9H,3-4H2

> <INCHI_KEY>
JHRWWRDRBPCWTF-UHFFFAOYSA-N

> <FORMULA>
C10H9Cl4NO2S

> <MOLECULAR_WEIGHT>
349.061

> <EXACT_MASS>
346.910810055

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
30.031629413182117

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1,1,2,2-tetrachloroethyl)sulfanyl]-2,3,3a,4,7,7a-hexahydro-1H-isoindole-1,3-dione

> <ALOGPS_LOGP>
3.57

> <JCHEM_LOGP>
3.948791137333333

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.892796004799543

> <JCHEM_POLAR_SURFACE_AREA>
37.38

> <JCHEM_REFRACTIVITY>
77.48929999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.75e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
crisfolatan

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.860   5.510   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.090   4.176   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0      -3.400   5.510   0.000  0.00  0.00          Cl+0
HETATM   12 Cl   UNK     0      -1.090   6.844   0.000  0.00  0.00          Cl+0
HETATM   13 Cl   UNK     0       0.244   4.946   0.000  0.00  0.00          Cl+0
HETATM   14 Cl   UNK     0      -2.423   3.406   0.000  0.00  0.00          Cl+0
HETATM   15  N   UNK     0       1.220   2.843   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       1.650   0.132   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.650   5.553   0.000  0.00  0.00           O+0
HETATM   18  S   UNK     0      -0.320   2.843   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6    7                                                  
CONECT    6    4    5    8                                                  
CONECT    7    5   15   16                                                  
CONECT    8    6   15   17                                                  
CONECT    9   10   11   12                                                  
CONECT   10    9   13   14   18                                             
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13   10                                                            
CONECT   14   10                                                            
CONECT   15    7    8   18                                                  
CONECT   16    7                                                            
CONECT   17    8                                                            
CONECT   18   10   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0031669
HETATM    1  O1  UNL     1       0.597   2.168  -0.466  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.117   1.039  -0.203  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.255   0.603  -0.414  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.327   1.602  -0.066  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.625   0.890  -0.163  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.694  -0.420  -0.037  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.550  -1.339   0.208  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.397  -0.513   0.631  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.065  -1.141   0.524  1.00  0.00           C  
HETATM   10  O2  UNL     1       0.191  -2.352   0.566  1.00  0.00           O  
HETATM   11  N1  UNL     1       0.850  -0.034   0.362  1.00  0.00           N  
HETATM   12  S1  UNL     1       2.543  -0.070   0.809  1.00  0.00           S  
HETATM   13  C9  UNL     1       3.677  -0.203  -0.558  1.00  0.00           C  
HETATM   14 CL1  UNL     1       3.651   1.246  -1.618  1.00  0.00          CL  
HETATM   15 CL2  UNL     1       3.490  -1.654  -1.537  1.00  0.00          CL  
HETATM   16  C10 UNL     1       5.085  -0.232   0.061  1.00  0.00           C  
HETATM   17 CL3  UNL     1       5.269  -1.623   1.160  1.00  0.00          CL  
HETATM   18 CL4  UNL     1       5.273   1.242   1.076  1.00  0.00          CL  
HETATM   19  H1  UNL     1      -1.374   0.162  -1.425  1.00  0.00           H  
HETATM   20  H2  UNL     1      -2.265   2.507  -0.685  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.164   1.847   1.019  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.531   1.454  -0.341  1.00  0.00           H  
HETATM   23  H5  UNL     1      -4.679  -0.917  -0.116  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.261  -1.899  -0.708  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.890  -2.052   1.009  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.523  -0.073   1.639  1.00  0.00           H  
HETATM   27  H9  UNL     1       5.857  -0.239  -0.726  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4    8   19
CONECT    4    5   20   21
CONECT    5    6    6   22
CONECT    6    7   23
CONECT    7    8   24   25
CONECT    8    9   26
CONECT    9   10   10   11
CONECT   11   12
CONECT   12   13
CONECT   13   14   15   16
CONECT   16   17   18   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Tetrachloroethylthio)tetrahydrophthalimide	ChEBI
1,2,3,6-Tetrahydro-N-(1,1,2,2-tetrachloroethylthio)phthalimide	ChEBI
3a,4,7,7a-Tetrahydro-2-[(1,1,2,2-tetrachloroethyl)thio]-1H-isoindole-1,3(2H)-dione	ChEBI
3a,4,7,7a-Tetrahydro-N-(1,1,2,2-tetrachloroethanesulphenyl)phthalimide	ChEBI
Captaspor	ChEBI
Difolatan	ChEBI
Difosan	ChEBI
Folcid	ChEBI
Haipen	ChEBI
Kenofol	ChEBI
Merpafol	ChEBI
N-(1,1,2,2-Tetrachloroethylthio)-Delta(4)-tetrahydrophthalimide	ChEBI
N-1,1,2,2-Tetrachloroethylmercapto-4-cyclohexene-1,2-carboximide	ChEBI
N-[(1,1,2,2-Tetrachloroethyl)sulfenyl]-4-cyclohexene-1,2-dicarboximide	ChEBI
Sanspor	ChEBI
Terrazol	ChEBI
3a,4,7,7a-Tetrahydro-N-(1,1,2,2-tetrachloroethanesulfenyl)phthalimide	Generator
N-(1,1,2,2-Tetrachloroethylthio)-δ(4)-tetrahydrophthalimide	Generator
N-[(1,1,2,2-Tetrachloroethyl)sulphenyl]-4-cyclohexene-1,2-dicarboximide	Generator
3a,4,7,7a-Tetrahydro-2-[(1,1,2,2-tetrachloroethyl)thio]-1H-isoindole-1,3(2H)-dione, 9ci	HMDB
Alfloc	HMDB
Arborseal	HMDB
Difolatan, jmaf	HMDB
Foltaf	HMDB
Haipen 50	HMDB
N-(1,1,2,2-Tetrachloroethylthio)-4-cyclohexene-1,2-dicarboximide, 8ci	HMDB
Nalco 7046	HMDB
Proxel ef	HMDB
Saprirearine	HMDB
Tetrachloroethylthiotetrahydrophthalimide	HMDB
N-(Tetrachloroethylthio)tetrahydrophthalimide	HMDB
Captafol, (cis)-isomer	HMDB
Captefol	HMDB
Captofol	HMDB

Chemical Formula

C₁₀H₉Cl₄NO₂S

Average Molecular Weight

349.061

Monoisotopic Molecular Weight

346.910810055

IUPAC Name

2-[(1,1,2,2-tetrachloroethyl)sulfanyl]-2,3,3a,4,7,7a-hexahydro-1H-isoindole-1,3-dione

Traditional Name

crisfolatan

CAS Registry Number

2425-06-1

SMILES

ClC(Cl)C(Cl)(Cl)SN1C(=O)C2CC=CCC2C1=O

InChI Identifier

InChI=1S/C10H9Cl4NO2S/c11-9(12)10(13,14)18-15-7(16)5-3-1-2-4-6(5)8(15)17/h1-2,5-6,9H,3-4H2

InChI Key

JHRWWRDRBPCWTF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindolines

Direct Parent

Isoindolones

Alternative Parents

Substituents

Isoindolone
Isoindole
Pyrrolidone
2-pyrrolidone
Dicarboximide
Pyrrolidine
Lactam
Carboxylic acid derivative
Azacycle
Sulfenyl compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Alkyl chloride
Alkyl halide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:81938 )
organosulfur compound (CHEBI:81938 )
isoindoles (CHEBI:81938 )
phthalimide fungicide (CHEBI:81938 )
Dicarboximide fungicides (C18754 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0031669)

Cellular substructure

Membrane (HMDB: HMDB0031669)

Source

Endogenous

Endogenous (HMDB: HMDB0031669)

Exogenous

Food

Food (HMDB: HMDB0031669)

Synthetic

Synthetic (HMDB: HMDB0031669)

Process

Not Available

Role

Environmental role

Environmental contaminant (HMDB: HMDB0031669)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	160 - 161 °C	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
Water Solubility	0.018 g/L	ALOGPS
logP	3.57	ALOGPS
logP	3.95	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	17.89	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	37.38 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	77.49 m³·mol⁻¹	ChemAxon
Polarizability	30.03 Å³	ChemAxon
Number of Rings	2	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]+	158.547	30932474
DeepCCS	[M-H]-	156.189	30932474
DeepCCS	[M-2H]-	189.284	30932474
DeepCCS	[M+Na]+	164.64	30932474
AllCCS	[M+H]+	162.0	32859911
AllCCS	[M+H-H2O]+	159.2	32859911
AllCCS	[M+NH4]+	164.5	32859911
AllCCS	[M+Na]+	165.3	32859911
AllCCS	[M-H]-	162.3	32859911
AllCCS	[M+Na-2H]-	162.5	32859911
AllCCS	[M+HCOO]-	162.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Captafol	ClC(Cl)C(Cl)(Cl)SN1C(=O)C2CC=CCC2C1=O	3272.6	Standard polar	33892256
Captafol	ClC(Cl)C(Cl)(Cl)SN1C(=O)C2CC=CCC2C1=O	2369.4	Standard non polar	33892256
Captafol	ClC(Cl)C(Cl)(Cl)SN1C(=O)C2CC=CCC2C1=O	2285.4	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 - Captafol GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9700000000-7c112c6aff5bc992788b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Captafol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Captafol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-9512000000-ea55ac48cb3b2d20f9da	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Captafol 10V, Positive-QTOF	splash10-0002-0109000000-5273503de88addacd050	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Captafol 20V, Positive-QTOF	splash10-01q9-0900000000-731117cd44833cb4f1a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Captafol 40V, Positive-QTOF	splash10-0w29-7930000000-d436fd19ac460c146bdc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Captafol 10V, Negative-QTOF	splash10-001i-0901000000-33d988dc5870bfed800c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Captafol 20V, Negative-QTOF	splash10-053r-0914000000-a0ecdec0fd1e79ec9e1b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Captafol 40V, Negative-QTOF	splash10-0002-3900000000-ca9ad7ba56ff30cd6b02	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Captafol 10V, Positive-QTOF	splash10-0002-0009000000-829864d315d3707de67f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Captafol 20V, Positive-QTOF	splash10-0002-0009000000-cca0800d42f20fdb2d03	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Captafol 40V, Positive-QTOF	splash10-003r-6900000000-d74d3c0c1f38dcc80969	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Captafol 10V, Negative-QTOF	splash10-0002-0009000000-8e640e8707a5054f2e48	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Captafol 20V, Negative-QTOF	splash10-0002-1409000000-9ba3ebf26414178ae16a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Captafol 40V, Negative-QTOF	splash10-0g4u-9843000000-52bfa296d6531325a760	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB008329

KNApSAcK ID

Not Available

Chemspider ID

16139

KEGG Compound ID

C18754

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Captafol

METLIN ID

Not Available

PubChem Compound

17038

PDB ID

Not Available

ChEBI ID

81938

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Captafol (HMDB0031669)

MOL for HMDB0031669 (Captafol)

3D MOL for HMDB0031669 (Captafol)

3D SDF for HMDB0031669 (Captafol)

3D-SDF for HMDB0031669 (Captafol)

PDB for HMDB0031669 (Captafol)

3D PDB for HMDB0031669 (Captafol)

SMILES for HMDB0031669 (Captafol)

INCHI for HMDB0031669 (Captafol)

Structure for HMDB0031669 (Captafol)

3D Structure for HMDB0031669 (Captafol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra