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Showing metabocard for Methyl 2-propenyl disulfide (HMDB0041389)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-12 03:04:17 UTC
Update Date2023-02-21 17:28:40 UTC
HMDB IDHMDB0041389
Secondary Accession Numbers
  • HMDB41389
Metabolite Identification
Common NameMethyl 2-propenyl disulfide
DescriptionMethyl 2-propenyl disulfide, also known as 3-(methyldisulfanyl)-1-propene or allyl methyl disulphide, belongs to the class of organic compounds known as allyl sulfur compounds. Allyl sulfur compounds are compounds containing an allylsulfur group, with the general structure H2C(=CH2)CS. Methyl 2-propenyl disulfide is an alliaceous, garlic, and green tasting compound. Methyl 2-propenyl disulfide is found, on average, in the highest concentration within soft-necked garlics (Allium sativum L. var. sativum). Methyl 2-propenyl disulfide has also been detected, but not quantified in, several different foods, such as allia (Allium), garden onions (Allium cepa), red onion, chives (Allium schoenoprasum), and welsh onions (Allium fistulosum). This could make methyl 2-propenyl disulfide a potential biomarker for the consumption of these foods. Methyl 2-propenyl disulfide is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Methyl 2-propenyl disulfide.
Structure
Data?1677000519
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0041389 (Methyl 2-propenyl disulfide)

  Mrv1652312031723002D          

  6  5  0  0  0  0            999 V2000
    3.0787   -0.2063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643    0.2063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7932    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5076   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2219    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  4  6  2  0  0  0  0
M  END
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3D MOL for HMDB0041389 (Methyl 2-propenyl disulfide)

HMDB0041389
     RDKit          3D
Methyl 2-propenyl disulfide
 14 13  0  0  0  0  0  0  0  0999 V2000
    3.0021   -0.3575   -0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6828   -0.3404   -0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8525    0.8341    0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3593    0.3955    1.4502 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7207   -0.9947    0.6101 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1442   -0.2057   -0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5605    0.4951    0.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5687   -1.2395   -0.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1933   -1.2405   -0.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4863    1.6675    0.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2590    1.1489   -0.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0412   -0.4814    0.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0473    0.9080   -0.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2926   -0.5894   -1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  3 10  1  0
  3 11  1  0
  6 12  1  0
  6 13  1  0
  6 14  1  0
M  END
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3D SDF for HMDB0041389 (Methyl 2-propenyl disulfide)

  Mrv1652312031723002D          

  6  5  0  0  0  0            999 V2000
    3.0787   -0.2063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643    0.2063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7932    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5076   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2219    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  4  6  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041389

> <DATABASE_NAME>
hmdb

> <SMILES>
CSSCC=C

> <INCHI_IDENTIFIER>
InChI=1S/C4H8S2/c1-3-4-6-5-2/h3H,1,4H2,2H3

> <INCHI_KEY>
XNZOTQPMYMCTBZ-UHFFFAOYSA-N

> <FORMULA>
C4H8S2

> <MOLECULAR_WEIGHT>
120.236

> <EXACT_MASS>
120.006741636

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
12.998891716785643

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(methyldisulfanyl)prop-1-ene

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
2.055681254333333

> <ALOGPS_LOGS>
-2.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
36.2821

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.62e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
allyl methyl disulfide

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0041389 (Methyl 2-propenyl disulfide)

HMDB0041389
     RDKit          3D
Methyl 2-propenyl disulfide
 14 13  0  0  0  0  0  0  0  0999 V2000
    3.0021   -0.3575   -0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6828   -0.3404   -0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8525    0.8341    0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3593    0.3955    1.4502 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7207   -0.9947    0.6101 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1442   -0.2057   -0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5605    0.4951    0.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5687   -1.2395   -0.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1933   -1.2405   -0.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4863    1.6675    0.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2590    1.1489   -0.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0412   -0.4814    0.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0473    0.9080   -0.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2926   -0.5894   -1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  3 10  1  0
  3 11  1  0
  6 12  1  0
  6 13  1  0
  6 14  1  0
M  END
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PDB for HMDB0041389 (Methyl 2-propenyl disulfide)

HEADER    PROTEIN                                 03-DEC-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-DEC-17         0                                  
HETATM    1  S   UNK     0       5.747  -0.385   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0       4.413   0.385   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       7.081   0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.414  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.080  -0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.748   0.385   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1    5                                                       
CONECT    3    1    4                                                       
CONECT    4    3    6                                                       
CONECT    5    2                                                            
CONECT    6    4                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for HMDB0041389 (Methyl 2-propenyl disulfide)

COMPND    HMDB0041389
HETATM    1  C1  UNL     1       3.002  -0.358  -0.084  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.683  -0.340  -0.211  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.853   0.834   0.144  1.00  0.00           C  
HETATM    4  S1  UNL     1      -0.359   0.395   1.450  1.00  0.00           S  
HETATM    5  S2  UNL     1      -1.721  -0.995   0.610  1.00  0.00           S  
HETATM    6  C4  UNL     1      -3.144  -0.206  -0.157  1.00  0.00           C  
HETATM    7  H1  UNL     1       3.561   0.495   0.292  1.00  0.00           H  
HETATM    8  H2  UNL     1       3.569  -1.239  -0.357  1.00  0.00           H  
HETATM    9  H3  UNL     1       1.193  -1.241  -0.598  1.00  0.00           H  
HETATM   10  H4  UNL     1       1.486   1.668   0.524  1.00  0.00           H  
HETATM   11  H5  UNL     1       0.259   1.149  -0.719  1.00  0.00           H  
HETATM   12  H6  UNL     1      -4.041  -0.481   0.457  1.00  0.00           H  
HETATM   13  H7  UNL     1      -3.047   0.908  -0.208  1.00  0.00           H  
HETATM   14  H8  UNL     1      -3.293  -0.589  -1.208  1.00  0.00           H  
CONECT    1    2    2    7    8
CONECT    2    3    9
CONECT    3    4   10   11
CONECT    4    5
CONECT    5    6
CONECT    6   12   13   14
END
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SMILES for HMDB0041389 (Methyl 2-propenyl disulfide)

CSSCC=C
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INCHI for HMDB0041389 (Methyl 2-propenyl disulfide)

InChI=1S/C4H8S2/c1-3-4-6-5-2/h3H,1,4H2,2H3
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC4H8S2
Average Molecular Weight120.236
Monoisotopic Molecular Weight120.006741636
IUPAC Name3-(methyldisulfanyl)prop-1-ene
Traditional Nameallyl methyl disulfide
CAS Registry Number2179-58-0
SMILES
CSSCC=C
InChI Identifier
InChI=1S/C4H8S2/c1-3-4-6-5-2/h3H,1,4H2,2H3
InChI KeyXNZOTQPMYMCTBZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as allyl sulfur compounds. Allyl sulfur compounds are compounds containing an allylsulfur group, with the general structure H2C(=CH2)CS.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassAllyl sulfur compounds
Sub ClassNot Available
Direct ParentAllyl sulfur compounds
Alternative Parents
Substituents
  • Allyl sulfur compound
  • Dialkyldisulfide
  • Organic disulfide
  • Sulfenyl compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point30.00 to 33.00 °C. @ 20.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP2.871 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease 		details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Ulcerative colitis
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021321
KNApSAcK IDC00001257
Chemspider ID56217
KEGG Compound IDC08383
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound62434
PDB IDNot Available
ChEBI ID6854
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1009831
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .