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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:29 UTC

Update Date

2022-03-07 02:53:07 UTC

HMDB ID

HMDB0031792

Secondary Accession Numbers

HMDB31792

Metabolite Identification

Common Name

Folpet

Description

Folpet, also known as orthophaltan or fungitrol, belongs to the class of organic compounds known as phthalimides. These are aromatic heterocyclic compounds containing a 1,3-dioxoisoindoline moiety. They are imide derivatives of phthalic anhydrides. Based on a literature review a significant number of articles have been published on Folpet.

Structure

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


  Mrv1652305271900122D          

 16 17  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
   -0.5837    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9962    0.0940    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982    1.2210    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1308    0.3960    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  2  0  0  0  0
  6  4  2  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  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14  7  2  0  0  0  0
 15  8  2  0  0  0  0
 16  9  1  0  0  0  0
 16 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031792

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC(Cl)(Cl)SN1C(=O)C2=CC=CC=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H4Cl3NO2S/c10-9(11,12)16-13-7(14)5-3-1-2-4-6(5)8(13)15/h1-4H

> <INCHI_KEY>
HKIOYBQGHSTUDB-UHFFFAOYSA-N

> <FORMULA>
C9H4Cl3NO2S

> <MOLECULAR_WEIGHT>
296.558

> <EXACT_MASS>
294.902832188

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
25.035986361469675

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(trichloromethyl)sulfanyl]-2,3-dihydro-1H-isoindole-1,3-dione

> <ALOGPS_LOGP>
2.92

> <JCHEM_LOGP>
3.783400406666666

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
37.38

> <JCHEM_REFRACTIVITY>
66.58840000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.85e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
folpet

> <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      -1.090   1.509   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0      -1.860   0.175   0.000  0.00  0.00          Cl+0
HETATM   11 Cl   UNK     0      -2.423   2.279   0.000  0.00  0.00          Cl+0
HETATM   12 Cl   UNK     0       0.244   0.739   0.000  0.00  0.00          Cl+0
HETATM   13  N   UNK     0       1.220   2.843   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       1.650   0.132   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.650   5.553   0.000  0.00  0.00           O+0
HETATM   16  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   13   14                                                  
CONECT    8    6   13   15                                                  
CONECT    9   10   11   12   16                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13    7    8   16                                                  
CONECT   14    7                                                            
CONECT   15    8                                                            
CONECT   16    9   13                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Acryptan	ChEBI
Cosan I	ChEBI
Faltan	ChEBI
Faltex	ChEBI
Folpel	ChEBI
N-(Trichlor-methylthio)-phthalamid	ChEBI
N-(Trichloromethanesulfenyl)phthalimide	ChEBI
N-(Trichloromethanesulphenyl)phthalimide	ChEBI
N-(Trichloromethylthio)phthalimide	ChEBI
Orthophaltan	ChEBI
Phthaltan	ChEBI
Trichloromethylthiophthalimide	ChEBI
2-(Trichloromethylsulphanyl)isoindole-1,3-dione	HMDB
2-((Trichloromethyl)thio)-1H-isoindole-1,3(2H)-dione	HMDB
2-[(Trichloromethyl)sulfanyl]-1H-isoindole-1,3(2H)-dione	HMDB
2-[(Trichloromethyl)thio]-1H-isoindole-1,3(2H)-dione	HMDB
2-[(Trichloromethyl)thio]-1H-isoindole-1,3(2H)-dione, 9ci	HMDB
Cosan T	HMDB
Diutrid	HMDB
Folnit	HMDB
Folpan	HMDB
Folpex	HMDB
Ftalan	HMDB
Fungitrol	HMDB
Fungitrol 11	HMDB
Fungitrol II	HMDB
Intercide TMP	HMDB
Murphy'S rose fungicide	HMDB
N-((Trichloromethyl)thio)-phthalimide	HMDB
N-(Trichlormethylthio)phthalimide	HMDB
N-(Trichloromethyl)thiophthalimide	HMDB
N-(Trichloromethylmercapto)phthalimide	HMDB
N-[(Trichloromethyl)thio]-phthalimide	HMDB
N-[(Trichloromethyl)thio]phthalimide	HMDB
Ortho phaltan 50W	HMDB
Phaltan	HMDB
Phaltane	HMDB
Phalton	HMDB
Phthalan	HMDB
Phthalic acid,imide,N-trichloromethyl sulfenyl	HMDB
Spolacid	HMDB
Thiophal	HMDB
Trichlormethylthioimid kyseliny ftalove	HMDB
Trichloromethyl(thio)phthalimide	HMDB
Trifol	HMDB
Troysan anti-mildew O	HMDB
Vinicoll	HMDB
Folpet	HMDB

Chemical Formula

C₉H₄Cl₃NO₂S

Average Molecular Weight

296.558

Monoisotopic Molecular Weight

294.902832188

IUPAC Name

2-[(trichloromethyl)sulfanyl]-2,3-dihydro-1H-isoindole-1,3-dione

Traditional Name

folpet

CAS Registry Number

133-07-3

SMILES

ClC(Cl)(Cl)SN1C(=O)C2=CC=CC=C2C1=O

InChI Identifier

InChI=1S/C9H4Cl3NO2S/c10-9(11,12)16-13-7(14)5-3-1-2-4-6(5)8(13)15/h1-4H

InChI Key

HKIOYBQGHSTUDB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phthalimides. These are aromatic heterocyclic compounds containing a 1,3-dioxoisoindoline moiety. They are imide derivatives of phthalic anhydrides.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindolines

Direct Parent

Phthalimides

Alternative Parents

Substituents

Phthalimide
Isoindole
Benzenoid
Trihalomethane
Carboxylic acid derivative
Sulfenyl compound
Azacycle
Hydrocarbon derivative
Organic oxygen compound
Alkyl halide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Alkyl chloride
Halomethane
Organopnictogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:82019 )
organosulfur compound (CHEBI:82019 )
phthalimide fungicide (CHEBI:82019 )
Dicarboximide fungicides (C18860 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031792)
Cell membrane (HMDB: HMDB0031792)

Source

Endogenous

Endogenous (HMDB: HMDB0031792)

Exogenous

Food

Food (HMDB: HMDB0031792)

Synthetic

Synthetic (HMDB: HMDB0031792)

Exogenous (HMDB: HMDB0031792)

Process

Not Available

Role

Environmental role

Air pollutant (HMDB: HMDB0031792)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	177 °C	Not Available
Boiling Point	333.80 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.0008 mg/mL at 25 °C	Not Available
LogP	2.85	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0068 g/L	ALOGPS
logP	2.92	ALOGPS
logP	3.78	ChemAxon
logS	-4.6	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	37.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	66.59 m³·mol⁻¹	ChemAxon
Polarizability	25.04 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]+	145.288	30932474
DeepCCS	[M-H]-	142.93	30932474
DeepCCS	[M-2H]-	177.006	30932474
DeepCCS	[M+Na]+	152.255	30932474
AllCCS	[M+H]+	150.0	32859911
AllCCS	[M+H-H2O]+	146.7	32859911
AllCCS	[M+NH4]+	153.1	32859911
AllCCS	[M+Na]+	154.0	32859911
AllCCS	[M-H]-	141.5	32859911
AllCCS	[M+Na-2H]-	141.2	32859911
AllCCS	[M+HCOO]-	140.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.19 minutes	32390414
Predicted by Siyang on May 30, 2022	15.2046 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.07 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2388.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	557.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	198.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	375.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	283.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	615.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	882.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	438.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1301.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	540.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1571.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	450.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	497.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	766.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	481.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	180.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Folpet	ClC(Cl)(Cl)SN1C(=O)C2=CC=CC=C2C1=O	3208.2	Standard polar	33892256
Folpet	ClC(Cl)(Cl)SN1C(=O)C2=CC=CC=C2C1=O	2047.5	Standard non polar	33892256
Folpet	ClC(Cl)(Cl)SN1C(=O)C2=CC=CC=C2C1=O	2060.0	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 - Folpet GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-2970000000-ce3d024021bb47b3e92e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Folpet GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Folpet GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0ik9-7890000000-a8d2179fab1f35de18fa	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 - Folpet 10V, Positive-QTOF	splash10-0002-0090000000-603864eafce4a511f45a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Folpet 20V, Positive-QTOF	splash10-0002-0090000000-7af6ec761aecf753cd39	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Folpet 40V, Positive-QTOF	splash10-0002-4190000000-3591d051eee991ced479	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Folpet 10V, Negative-QTOF	splash10-0006-0090000000-0b57ab4a82c78d652d41	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Folpet 20V, Negative-QTOF	splash10-0006-0090000000-0b57ab4a82c78d652d41	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Folpet 40V, Negative-QTOF	splash10-0udl-0790000000-a732d6b345e46ae2a4d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Folpet 10V, Negative-QTOF	splash10-0006-0090000000-d7eb720fc3b923375bd6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Folpet 20V, Negative-QTOF	splash10-0006-0090000000-d7eb720fc3b923375bd6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Folpet 40V, Negative-QTOF	splash10-0006-0090000000-d7eb720fc3b923375bd6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Folpet 10V, Positive-QTOF	splash10-0002-0090000000-54ee2d84e6cf77e97b69	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Folpet 20V, Positive-QTOF	splash10-0002-0090000000-54ee2d84e6cf77e97b69	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Folpet 40V, Positive-QTOF	splash10-0900-4920000000-ec2cca1807a1023e19ec	2021-09-22	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

FDB008465

KNApSAcK ID

Not Available

Chemspider ID

8288

KEGG Compound ID

C18860

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Folpet

METLIN ID

Not Available

PubChem Compound

8607

PDB ID

Not Available

ChEBI ID

82019

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1332371

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 Folpet (HMDB0031792)

MOL for HMDB0031792 (Folpet)

3D MOL for HMDB0031792 (Folpet)

3D SDF for HMDB0031792 (Folpet)

3D-SDF for HMDB0031792 (Folpet)

PDB for HMDB0031792 (Folpet)

3D PDB for HMDB0031792 (Folpet)

SMILES for HMDB0031792 (Folpet)

INCHI for HMDB0031792 (Folpet)

Structure for HMDB0031792 (Folpet)

3D Structure for HMDB0031792 (Folpet)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra