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Showing NP-Card for Allitridin (NP0046116)

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Record Information
Version2.0
Created at2022-03-17 19:48:42 UTC
Updated at2022-03-17 19:48:42 UTC
NP-MRD IDNP0046116
Secondary Accession NumbersNone
Natural Product Identification
Common NameAllitridin
DescriptionAllitridin, also known as allyl trisulfide or DATS, belongs to the class of organic compounds known as organic trisulfides. These are organosulfur compounds with the general formula RSSSR' (R,R'=alkyl, aryl). An organic trisulfide that is trisulfane in which both of the hydrogens are replaced by allyl groups. Allitridin is possibly neutral. Allitridin is a garlic, green, and metallic tasting compound. Outside of the human body, Allitridin has been detected, but not quantified in, several different foods, such as garden onions, garlics, onion-family vegetables, and soft-necked garlics. Allitridin is found in Allium chinense. Allitridin was first documented in 2000 (PMID: 10757551). This could make allitridin a potential biomarker for the consumption of these foods (PMID: 11020449) (PMID: 22020565) (PMID: 22137902) (PMID: 22143535) (PMID: 22525868) (PMID: 22578287).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046116 (Allitridin)


  Mrv0541 02241212382D          

  9  8  0  0  0  0            999 V2000
   -1.6059    3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8914    4.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1769    3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5375    4.1839    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2520    3.7714    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9665    4.1839    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6809    3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3954    4.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1099    3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
M  END
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3D MOL for NP0046116 (Allitridin)

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3D SDF for NP0046116 (Allitridin)

  Mrv0541 02241212382D          

  9  8  0  0  0  0            999 V2000
   -1.6059    3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8914    4.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1769    3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5375    4.1839    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2520    3.7714    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9665    4.1839    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6809    3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3954    4.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1099    3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0046116

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C=CCSSSCC=C

> <INCHI_IDENTIFIER>
InChI=1S/C6H10S3/c1-3-5-7-9-8-6-4-2/h3-4H,1-2,5-6H2

> <INCHI_KEY>
UBAXRAHSPKWNCX-UHFFFAOYSA-N

> <FORMULA>
C6H10S3

> <MOLECULAR_WEIGHT>
178.339

> <EXACT_MASS>
177.99446239

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
18.956486619039868

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
bis(prop-2-en-1-yl)trisulfane

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
3.355505386999999

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
51.17280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diallyl trisulfide

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0046116 (Allitridin)
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PDB for NP0046116 (Allitridin)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.998   7.040   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.664   7.810   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.330   7.040   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0       1.003   7.810   0.000  0.00  0.00           S+0
HETATM    5  S   UNK     0       2.337   7.040   0.000  0.00  0.00           S+0
HETATM    6  S   UNK     0       3.671   7.810   0.000  0.00  0.00           S+0
HETATM    7  C   UNK     0       5.004   7.040   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.338   7.810   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.672   7.040   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0046116 (Allitridin)
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SMILES for NP0046116 (Allitridin)
C=CCSSSCC=C
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INCHI for NP0046116 (Allitridin)
InChI=1S/C6H10S3/c1-3-5-7-9-8-6-4-2/h3-4H,1-2,5-6H2
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View in JSmol
Synonyms
ValueSource
(CH2=CHCH2S)2SChEBI
Allyl trisulfideChEBI
DATSChEBI
Di-2-propenyl trisulfideChEBI
Allyl trisulphideGenerator
Di-2-propenyl trisulphideGenerator
1,3-DiallyltrisulfaneHMDB
4,5,6-Trithia-1,8-nonadieneHMDB
AllitridumHMDB
Allyl trisulfide, 8ciHMDB
DasuansuHMDB
DATHMDB
Diallyl trisulfideHMDB
Diallyl trisulphideHMDB
DiallyltrisulfideHMDB
FEMA 3265HMDB
Prop-2-enyl prop-2-enylthio disulfideHMDB
Trisulfide, di-2-propenylHMDB
Trisulfide, di-2-propenyl (9ci)HMDB
AllitridiHMDB
AllitridinMeSH
Chemical FormulaC6H10S3
Average Mass178.3390 Da
Monoisotopic Mass177.99446 Da
IUPAC Namebis(prop-2-en-1-yl)trisulfane
Traditional Namediallyl trisulfide
CAS Registry Number2050-87-5
SMILES
C=CCSSSCC=C
InChI Identifier
InChI=1S/C6H10S3/c1-3-5-7-9-8-6-4-2/h3-4H,1-2,5-6H2
InChI KeyUBAXRAHSPKWNCX-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium cepaFooDB
    • Mans Boelens, Pieter J. de Valois, Henk J. Wobben, and Arne van der Gen. Volatile Flavor Compound...
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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic trisulfides. These are organosulfur compounds with the general formula RSSSR' (R,R'=alkyl, aryl).
KingdomOrganic compounds  
Super ClassOrganosulfur compounds  
ClassOrganic trisulfides  
Sub ClassNot Available
Direct ParentOrganic trisulfides  
Alternative Parents
Substituents
  • Organic trisulfide
    • 

  • Allyl sulfur compound
    • 

  • 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
logP2.74ALOGPS
logP3.36ChemAxon
logS-3.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity51.17 m³·mol⁻¹ChemAxon
Polarizability18.96 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031154  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003168  
KNApSAcK IDNot Available
Chemspider ID15481  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiallyl_trisulfide  
METLIN IDNot Available
PubChem Compound16315  
PDB IDNot Available
ChEBI ID78492  
Good Scents IDNot Available
References
General References
  1. Liu L, Yeh YY: Inhibition of cholesterol biosynthesis by organosulfur compounds derived from garlic. Lipids. 2000 Feb;35(2):197-203. doi: 10.1007/BF02664770. [PubMed:10757551  ] 
  2. Qi R, Liao F, Inoue K, Yatomi Y, Sato K, Ozaki Y: Inhibition by diallyl trisulfide, a garlic component, of intracellular Ca(2+) mobilization without affecting inositol-1,4, 5-trisphosphate (IP(3)) formation in activated platelets. Biochem Pharmacol. 2000 Nov 15;60(10):1475-83. doi: 10.1016/s0006-2952(00)00467-6. [PubMed:11020449  ] 
  3. Borkowska A, Sielicka-Dudzin A, Herman-Antosiewicz A, Wozniak M, Fedeli D, Falcioni G, Antosiewicz J: Diallyl trisulfide-induced prostate cancer cell death is associated with Akt/PKB dephosphorylation mediated by P-p66shc. Eur J Nutr. 2012 Oct;51(7):817-25. doi: 10.1007/s00394-011-0260-x. Epub 2011 Oct  22. [PubMed:22020565  ] 
  4. Lii CK, Huang CY, Chen HW, Chow MY, Lin YR, Huang CS, Tsai CW: Diallyl trisulfide suppresses the adipogenesis of 3T3-L1 preadipocytes through ERK activation. Food Chem Toxicol. 2012 Mar;50(3-4):478-84. doi: 10.1016/j.fct.2011.11.020. Epub  2011 Nov 25. [PubMed:22137902  ] 
  5. Chen M, Li B, Zhao X, Zuo H, He X, Li Z, Liu X, Chen L: Effect of diallyl trisulfide derivatives on the induction of apoptosis in human prostate cancer PC-3 cells. Mol Cell Biochem. 2012 Apr;363(1-2):75-84. doi: 10.1007/s11010-011-1159-9. Epub 2011 Dec 6. [PubMed:22143535  ] 
  6. Nkrumah-Elie YM, Reuben JS, Hudson A, Taka E, Badisa R, Ardley T, Israel B, Sadrud-Din SY, Oriaku E, Darling-Reed SF: Diallyl trisulfide as an inhibitor of benzo(a)pyrene-induced precancerous carcinogenesis in MCF-10A cells. Food Chem Toxicol. 2012 Jul;50(7):2524-30. doi: 10.1016/j.fct.2012.04.010. Epub 2012 Apr 16. [PubMed:22525868  ] 
  7. Choi YH, Park HS: Apoptosis induction of U937 human leukemia cells by diallyl trisulfide induces through generation of reactive oxygen species. J Biomed Sci. 2012 May 11;19:50. doi: 10.1186/1423-0127-19-50. [PubMed:22578287  ] 
  8. Li W, Tian H, Li L, Li S, Yue W, Chen Z, Qi L, Hu W, Zhu Y, Hao B, Gao C, Si L, Gao F: Diallyl trisulfide induces apoptosis and inhibits proliferation of A549 cells in vitro and in vivo. Acta Biochim Biophys Sin (Shanghai). 2012 Jul;44(7):577-83. doi: 10.1093/abbs/gms033. Epub 2012 May 17. [PubMed:22595511  ] 
  9. Yu CS, Huang AC, Lai KC, Huang YP, Lin MW, Yang JS, Chung JG: Diallyl trisulfide induces apoptosis in human primary colorectal cancer cells. Oncol Rep. 2012 Sep;28(3):949-54. doi: 10.3892/or.2012.1882. Epub 2012 Jun 20. [PubMed:22736270  ] 
  10. Xia Q, Wang ZY, Li HQ, Diao YT, Li XL, Cui J, Chen XL, Li H: Reversion of p-glycoprotein-mediated multidrug resistance in human leukemic cell line by diallyl trisulfide. Evid Based Complement Alternat Med. 2012;2012:719805. doi: 10.1155/2012/719805. Epub 2012 Jul 12. [PubMed:22919419  ] 
  11. Chen H, Zhu W, Feng J, Li S: Protective effect of diallyl trisulfide on liver in rats with sepsis and the mechanism. J Huazhong Univ Sci Technolog Med Sci. 2012 Oct;32(5):657-662. doi: 10.1007/s11596-012-1013-7. [PubMed:23073793  ] 
  12. Huang YT, Yao CH, Way CL, Lee KW, Tsai CY, Ou HC, Kuo WW: Diallyl trisulfide and diallyl disulfide ameliorate cardiac dysfunction by suppressing apoptotic and enhancing survival pathways in experimental diabetic rats. J Appl Physiol (1985). 2013 Feb;114(3):402-10. doi: 10.1152/japplphysiol.00672.2012. Epub 2012 Nov 8. [PubMed:23139364  ] 
  13. Chandra-Kuntal K, Lee J, Singh SV: Critical role for reactive oxygen species in apoptosis induction and cell migration inhibition by diallyl trisulfide, a cancer chemopreventive component of garlic. Breast Cancer Res Treat. 2013 Feb;138(1):69-79. doi: 10.1007/s10549-013-2440-2. Epub 2013 Feb 15. [PubMed:23412769  ] 
  14. Li Y, Zhang J, Zhang L, Si M, Yin H, Li J: Diallyl trisulfide inhibits proliferation, invasion and angiogenesis of osteosarcoma cells by switching on suppressor microRNAs and inactivating of Notch-1 signaling. Carcinogenesis. 2013 Jul;34(7):1601-10. doi: 10.1093/carcin/bgt065. Epub 2013 Feb 20. [PubMed:23430952  ] 
  15. Tsai CY, Wang CC, Lai TY, Tsu HN, Wang CH, Liang HY, Kuo WW: Antioxidant effects of diallyl trisulfide on high glucose-induced apoptosis are mediated by the PI3K/Akt-dependent activation of Nrf2 in cardiomyocytes. Int J Cardiol. 2013 Sep 30;168(2):1286-97. doi: 10.1016/j.ijcard.2012.12.004. Epub 2013 Feb 27. [PubMed:23453443  ]