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Showing NP-Card for Allicin (NP0047801)

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Record Information
Version2.0
Created at2022-03-17 20:46:12 UTC
Updated at2022-03-17 20:46:12 UTC
NP-MRD IDNP0047801
Secondary Accession NumbersNone
Natural Product Identification
Common NameAllicin
DescriptionAllicin, also known as allimin or allitridi, belongs to the class of organic compounds known as thiosulfinic acid esters. These are organic compounds containing an ester of thiosulfinic acid with the general structure RS(=S)OR' (R, R'=alkyl, aryl). Allicin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Allicin is found, on average, in the highest concentration within soft-necked garlics. Allicin has also been detected, but not quantified in, several different foods, such as triticales, sunflowers, dates, pepper (c. Frutescens), and napa cabbages. This could make allicin a potential biomarker for the consumption of these foods. Allicin was discovered as part of efforts to create thiamine derivatives in the 1950s, mainly in Japan. The compound is not present in garlic unless tissue damage occurs, and is formed by the action of the enzyme alliinase on alliin. Allicin is chiral but occurs naturally only as a racemate. The enzyme alliinase, which contains pyridoxal phosphate (PLP), cleaves alliin, generating allysulfenic acid (CH2CHCH2SOH), pyruvate, and ammonium. Allicin is found in Allium chinense, Allium obliquum and Allium schoenoprasum. Allicin was first documented in 1990 (PMID: 2111084). Its biological activity can be attributed to both its antioxidant activity and its reaction with thiol-containing proteins (PMID: 19105898) (PMID: 20591093) (PMID: 17303073) (PMID: 15911108).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047801 (Allicin)


  Mrv0541 02241212372D          

  9  8  0  0  0  0            999 V2000
    1.7143   -0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9821    0.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3123   -0.2223    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4185    0.2070    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1708   -0.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8204    0.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3123   -1.0474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5514   -0.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4352    0.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  8  2  0  0  0  0
  1  9  2  0  0  0  0
M  END
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3D MOL for NP0047801 (Allicin)

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3D SDF for NP0047801 (Allicin)

  Mrv0541 02241212372D          

  9  8  0  0  0  0            999 V2000
    1.7143   -0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9821    0.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3123   -0.2223    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4185    0.2070    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1708   -0.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8204    0.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3123   -1.0474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5514   -0.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4352    0.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  8  2  0  0  0  0
  1  9  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0047801

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C=CCSS(=O)CC=C

> <INCHI_IDENTIFIER>
InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2

> <INCHI_KEY>
JDLKFOPOAOFWQN-UHFFFAOYSA-N

> <FORMULA>
C6H10OS2

> <MOLECULAR_WEIGHT>
162.273

> <EXACT_MASS>
162.017306322

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
17.00941417288128

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(prop-2-ene-1-sulfinyl)sulfanyl]prop-1-ene

> <ALOGPS_LOGP>
1.16

> <JCHEM_LOGP>
2.0214

> <ALOGPS_LOGS>
-1.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.684360672307594

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
44.932599999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.13e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
allicin

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047801 (Allicin)
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PDB for NP0047801 (Allicin)
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       3.200  -0.480   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.833   0.321   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0       0.583  -0.415   0.000  0.00  0.00           S+0
HETATM    4  S   UNK     0      -0.781   0.386   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0      -2.185  -0.346   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.398   0.452   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.583  -1.955   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.763  -0.262   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.546   0.269   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    8                                                       
CONECT    7    3                                                            
CONECT    8    6                                                            
CONECT    9    1                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0047801 (Allicin)
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SMILES for NP0047801 (Allicin)
C=CCSS(=O)CC=C
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INCHI for NP0047801 (Allicin)
InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2
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Synonyms
ValueSource
2-Propene-1-sulfinothioic acid S-2-propenyl esterChEBI
Thio-2-propene-1-sulfinic acid S-allyl esterChEBI
2-Propene-1-sulfinothioate S-2-propenyl esterGenerator
2-Propene-1-sulphinothioate S-2-propenyl esterGenerator
2-Propene-1-sulphinothioic acid S-2-propenyl esterGenerator
Thio-2-propene-1-sulfinate S-allyl esterGenerator
Thio-2-propene-1-sulphinate S-allyl esterGenerator
Thio-2-propene-1-sulphinic acid S-allyl esterGenerator
2-Propene-1-sulfinic acid, thio-, S-allyl esterHMDB
2-Propene-1-sulfinothioic acid, S-2-propenyl esterHMDB
2-Propene-1-sulfinothioic acid, S-2-propenyl ester (9ci)HMDB
AlliminHMDB
AllitridiHMDB
AllylthiosulfinateHMDB
Allylthiosulphinic acid allyl esterHMDB
DadsoHMDB
Diallyl disulfide-oxideHMDB
Diallyl thiosulfinateHMDB
Diallyldisulfid-S-oxidHMDB
S-2-Propenyl 2-propene-1-sulfinothioate, 9ciHMDB
S-Allyl 2-propene-1-sulfinothioateHMDB
S-Allyl acrylo-1-sulphinothioateHMDB
S-Allyl prop-2-ene-1-sulfinothioateHMDB
S-Prop-2-en-1-yl prop-2-ene-1-sulfinothioateHMDB
Chemical FormulaC6H10OS2
Average Mass162.2730 Da
Monoisotopic Mass162.01731 Da
IUPAC Name3-[(prop-2-ene-1-sulfinyl)sulfanyl]prop-1-ene
Traditional Nameallicin
CAS Registry Number539-86-6
SMILES
C=CCSS(=O)CC=C
InChI Identifier
InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2
InChI KeyJDLKFOPOAOFWQN-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium cepaFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Allium cepa L.FooDB
Allium chinenseLOTUS Database
Allium fistulosumFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Allium obliquumPlant
Allium sativumFooDB
Allium schoenoprasumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thiosulfinic acid esters. These are organic compounds containing an ester of thiosulfinic acid with the general structure RS(=S)OR' (R, R'=alkyl, aryl).
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassThiosulfinic acid esters  
Sub ClassNot Available
Direct ParentThiosulfinic acid esters  
Alternative Parents
Substituents
  • Thiosulfinic acid ester
    • 

  • Allyl sulfur compound
    • 

  • Sulfenyl compound
    • 

  • Sulfinyl compound
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organosulfur compound
    • 

  • 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
logP1.16ALOGPS
logP2.02ChemAxon
logS-1.4ALOGPS
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity44.93 m³·mol⁻¹ChemAxon
Polarizability17.01 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033963  
DrugBank IDDB11780  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012190  
KNApSAcK IDC00001242  
Chemspider ID58548  
KEGG Compound IDC07600  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAllicin  
METLIN IDNot Available
PubChem Compound65036  
PDB IDNot Available
ChEBI ID28411  
Good Scents IDNot Available
References
General References
  1. Luo DQ, Guo JH, Wang FJ, Jin ZX, Cheng XL, Zhu JC, Peng CQ, Zhang C: Anti-fungal efficacy of polybutylcyanoacrylate nanoparticles of allicin and comparison with pure allicin. J Biomater Sci Polym Ed. 2009;20(1):21-31. doi: 10.1163/156856208X393473. [PubMed:19105898  ] 
  2. Younis F, Mirelman D, Rabinkov A, Rosenthal T: S-allyl-mercapto-captopril: a novel compound in the treatment of Cohen-Rosenthal diabetic hypertensive rats. J Clin Hypertens (Greenwich). 2010 Jun;12(6):451-5. doi: 10.1111/j.1751-7176.2010.00270.x. [PubMed:20591093  ] 
  3. Makheja AN, Bailey JM: Antiplatelet constituents of garlic and onion. Agents Actions. 1990 Mar;29(3-4):360-3. doi: 10.1007/BF01966468. [PubMed:2111084  ] 
  4. Hasan N, Siddiqui MU, Toossi Z, Khan S, Iqbal J, Islam N: Allicin-induced suppression of Mycobacterium tuberculosis 85B mRNA in human monocytes. Biochem Biophys Res Commun. 2007 Apr 6;355(2):471-6. doi: 10.1016/j.bbrc.2007.01.174. Epub 2007 Feb 7. [PubMed:17303073  ] 
  5. Park SY, Cho SJ, Kwon HC, Lee KR, Rhee DK, Pyo S: Caspase-independent cell death by allicin in human epithelial carcinoma cells: involvement of PKA. Cancer Lett. 2005 Jun 16;224(1):123-32. doi: 10.1016/j.canlet.2004.10.009. Epub 2004 Nov 14. [PubMed:15911108  ]