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Showing NP-Card for Methyl 2-propenyl disulfide (NP0049840)

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Record Information
Version2.0
Created at2022-03-17 21:18:58 UTC
Updated at2022-03-17 21:18:58 UTC
NP-MRD IDNP0049840
Secondary Accession NumbersNone
Natural Product Identification
Common NameMethyl 2-propenyl disulfide
DescriptionMethyl 2-propenyl disulfide, also known as 3-(methyldisulfanyl)-1-propene or methyl allyl 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. An organic disulfide having allyl and methyl as the two organic groups. Methyl 2-propenyl disulfide is possibly neutral. Methyl 2-propenyl disulfide is an alliaceous, garlic, and green tasting compound. Outside of the human body, Methyl 2-propenyl disulfide is found, on average, in the highest concentration within soft-necked garlics. Methyl 2-propenyl disulfide has also been detected, but not quantified in, several different foods, such as allium (onion), chives, garden onions, and onion-family vegetables. Methyl 2-propenyl disulfide is found in Allium ampeloprasum, Allium chinense, Allium spp., Allium tuberosum , Allium victorialis and Mansoa alliacea. Methyl 2-propenyl disulfide was first documented in 2011 (PMID: 20609277). This could make methyl 2-propenyl disulfide a potential biomarker for the consumption of these foods (PMID: 23865201) (PMID: 24592995).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049840 (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 NP0049840 (Methyl 2-propenyl disulfide)

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3D SDF for NP0049840 (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>
NP0049840

> <DATABASE_NAME>
NP-MRD

> <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 NP0049840 (Methyl 2-propenyl disulfide)
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PDB for NP0049840 (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 NP0049840 (Methyl 2-propenyl disulfide)
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SMILES for NP0049840 (Methyl 2-propenyl disulfide)
CSSCC=C
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INCHI for NP0049840 (Methyl 2-propenyl disulfide)
InChI=1S/C4H8S2/c1-3-4-6-5-2/h3H,1,4H2,2H3
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Synonyms
ValueSource
3-(Methyldisulfanyl)-1-propeneChEBI
3-(Methyldithio)prop-1-eneChEBI
4,5-Dithia-1-hexeneChEBI
Allyl methyl disulphideChEBI
Methyl allyl disulfideChEBI
Methylallyl disulphideChEBI
Allyl methyl disulfideKegg
3-(Methyldisulphanyl)-1-propeneGenerator
Methyl allyl disulphideGenerator
Methylallyl disulfideGenerator
Methyl 2-propenyl disulphideGenerator
2-PropenylmethyldisulfideHMDB
3-(Methyldisulfanyl)prop-1-eneHMDB
Disulfide, allyl methylHMDB
Disulfide, methyl 2-propenylHMDB
FEMA 3127HMDB
Methyl 2-propenyl disulfideChEBI
Chemical FormulaC4H8S2
Average Mass120.2360 Da
Monoisotopic Mass120.00674 Da
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
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium ampeloprasumLOTUS Database
Allium cepaFooDB
    • Heikki Kallio and Lea Salorinne. Comparison of Onion Varieties by Headspace Gas Chromatography-Ma...
Allium cepa L.FooDB
Allium chinenseLOTUS Database
Allium fistulosumFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium spp.Plant
Allium tuberosumPlant
Allium victorialisPlant
Mansoa alliaceaLOTUS Database
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.82ALOGPS
logP2.06ChemAxon
logS-2.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity36.28 m³·mol⁻¹ChemAxon
Polarizability13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0041389  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
General References
  1. Mann RS, Rouseff RL, Smoot JM, Castle WS, Stelinski LL: Sulfur volatiles from Allium spp. affect Asian citrus psyllid, Diaphorina citri Kuwayama (Hemiptera: Psyllidae), response to citrus volatiles. Bull Entomol Res. 2011 Feb;101(1):89-97. doi: 10.1017/S0007485310000222. Epub 2010 Jul 8. [PubMed:20609277  ] 
  2. Zhao NN, Zhang H, Zhang XC, Luan XB, Zhou C, Liu QZ, Shi WP, Liu ZL: Evaluation of acute toxicity of essential oil of garlic (Allium sativum) and its selected major constituent compounds against overwintering Cacopsylla chinensis (Hemiptera: Psyllidae). J Econ Entomol. 2013 Jun;106(3):1349-54. doi: 10.1603/ec12191. [PubMed:23865201  ] 
  3. Munch R, Barringer SA: Deodorization of garlic breath volatiles by food and food components. J Food Sci. 2014 Apr;79(4):C526-33. doi: 10.1111/1750-3841.12394. Epub 2014 Mar 4. [PubMed:24592995  ]