Np mrd loader

Showing NP-Card for cis-Ajoene (NP0046186)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-03-17 19:49:52 UTC
Updated at2022-03-17 19:49:53 UTC
NP-MRD IDNP0046186
Secondary Accession NumbersNone
Natural Product Identification
Common Namecis-Ajoene
DescriptionAjoene, also known as trans-ajoene, belongs to the class of organic compounds known as sulfoxides. Sulfoxides are compounds containing a sulfoxide functional group, with the structure RS(=O)R' (R,R' not H). Ajoene is an extremely weak basic (essentially neutral) compound (based on its pKa). Ajoene is also found in garlic extract. Outside of the human body, Ajoene has been detected, but not quantified in, soft-necked garlics. This could make ajoene a potential biomarker for the consumption of these foods. For example, Ajoene has been shown to have activity against the human dermatophyte Trichophyton rubrum, the most common cause of tinea pedis, commonly known as Athlete's Foot. The structure of ajoene was determined and it was synthesized based on biosynthetic considerations in 1984, correcting an incorrect structure published in 1983. Ajoene also has antithrombotic (anti-clotting) properties, which helps prevent platelets in the blood from forming blood clots, potentially reducing the risk of heart disease and stroke in humans. cis-Ajoene was first documented in 1993 (PMID: 8328978). In a randomized study by Ledezma et al (2000), 70 soldiers from the Venezuelan Armed Forces with KOH or culture proven tinea pedis interdigitalis were randomly distributed into 3 treatment groups: 0.6% Ajoene, 1% ajoene, and 1% terbinafine (commercially available as Lamisil AT®) applied twice daily for 1 week (PMID: 8900018) (PMID: 16854181) (PMID: 20108330) (PMID: 8415808).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0046186 (cis-Ajoene)


  Mrv0541 05061307122D          

 13 12  0  0  0  0            999 V2000
   -2.6664    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    2.5559    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    2.1434    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    0.9059    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  3  1  0  0  0  0
  7  5  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  1  0  0  0  0
 13  8  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  2  0  0  0  0
M  END
Download

3D MOL for NP0046186 (cis-Ajoene)

Download
3D SDF for NP0046186 (cis-Ajoene)

  Mrv0541 05061307122D          

 13 12  0  0  0  0            999 V2000
   -2.6664    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    2.5559    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    2.1434    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    0.9059    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  3  1  0  0  0  0
  7  5  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  1  0  0  0  0
 13  8  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0046186

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C=CCSS\C=C/CS(=O)CC=C

> <INCHI_IDENTIFIER>
InChI=1S/C9H14OS3/c1-3-6-11-12-7-5-9-13(10)8-4-2/h3-5,7H,1-2,6,8-9H2/b7-5-

> <INCHI_KEY>
IXELFRRANAOWSF-ALCCZGGFSA-N

> <FORMULA>
C9H14OS3

> <MOLECULAR_WEIGHT>
234.402

> <EXACT_MASS>
234.02067714

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
24.80598183598837

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[(1Z)-3-(prop-2-ene-1-sulfinyl)prop-1-en-1-yl]disulfanyl}prop-1-ene

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
1.6583815063333331

> <ALOGPS_LOGS>
-2.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.617060635165

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.01318253603882

> <JCHEM_PKA_STRONGEST_BASIC>
-6.574096816323368

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
69.00370000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(1Z)-3-(prop-2-ene-1-sulfinyl)prop-1-en-1-yl]disulfanyl}prop-1-ene

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0046186 (cis-Ajoene)
Download
PDB for NP0046186 (cis-Ajoene)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.977   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.358   0.151   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.644   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.025  -0.619   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.025   4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.310   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.691   4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.691   0.151   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.025   2.461   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.357   2.461   0.000  0.00  0.00           O+0
HETATM   11  S   UNK     0      -0.976   4.771   0.000  0.00  0.00           S+0
HETATM   12  S   UNK     0       0.357   4.001   0.000  0.00  0.00           S+0
HETATM   13  S   UNK     0       1.691   1.691   0.000  0.00  0.00           S+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    6                                                       
CONECT    4    2    8                                                       
CONECT    5    7    9                                                       
CONECT    6    3   11                                                       
CONECT    7    5   12                                                       
CONECT    8    4   13                                                       
CONECT    9    5   13                                                       
CONECT   10   13                                                            
CONECT   11    6   12                                                       
CONECT   12    7   11                                                       
CONECT   13    8    9   10                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

Download
3D PDB for NP0046186 (cis-Ajoene)
Download
SMILES for NP0046186 (cis-Ajoene)
C=CCSS\C=C/CS(=O)CC=C
Download
INCHI for NP0046186 (cis-Ajoene)
InChI=1S/C9H14OS3/c1-3-6-11-12-7-5-9-13(10)8-4-2/h3-5,7H,1-2,6,8-9H2/b7-5-
Download
View in JSmol
Synonyms
ValueSource
2-Propenyl 3-(2-propenylsulfinyl)-1-propenyl disulfide, 9ciHMDB
2-Propenyl-3-(2-propenylsulfinyl)-1-propenyl disulfideHMDB
4,5,9-Trithia-1,6,11-dodecatriene 9-oxideHMDB
4,5,9-Trithiadodeca-1,6,11-triene 9-oxideHMDB
Allyl 3-allylsulfinyl-1-propenyl disulfideHMDB
Disulfide, 2-propenyl 3-(2-propenylsulfinyl)-1-propenylHMDB
trans-AjoeneHMDB
Chemical FormulaC9H14OS3
Average Mass234.4020 Da
Monoisotopic Mass234.02068 Da
IUPAC Name3-{[(1Z)-3-(prop-2-ene-1-sulfinyl)prop-1-en-1-yl]disulfanyl}prop-1-ene
Traditional Name3-{[(1Z)-3-(prop-2-ene-1-sulfinyl)prop-1-en-1-yl]disulfanyl}prop-1-ene
CAS Registry Number92285-00-2
SMILES
C=CCSS\C=C/CS(=O)CC=C
InChI Identifier
InChI=1S/C9H14OS3/c1-3-6-11-12-7-5-9-13(10)8-4-2/h3-5,7H,1-2,6,8-9H2/b7-5-
InChI KeyIXELFRRANAOWSF-ALCCZGGFSA-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 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 sulfoxides. Sulfoxides are compounds containing a sulfoxide functional group, with the structure RS(=O)R' (R,R' not H).
KingdomOrganic compounds  
Super ClassOrganosulfur compounds  
ClassSulfoxides  
Sub ClassNot Available
Direct ParentSulfoxides  
Alternative Parents
Substituents
  • Allyl sulfur compound
    • 

  • Sulfoxide
    • 

  • Organic disulfide
    • 

  • Sulfenyl compound
    • 

  • Sulfinyl compound
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • 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
logP2.58ALOGPS
logP1.66ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)16.01ChemAxon
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity69 m³·mol⁻¹ChemAxon
Polarizability24.81 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033566  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003580  
KNApSAcK IDNot Available
Chemspider ID8056824  
KEGG Compound IDC16757  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAjoene  
METLIN IDNot Available
PubChem Compound9881148  
PDB IDNot Available
ChEBI ID80707  
Good Scents IDNot Available
References
General References
  1. Naganawa R, Iwata N, Ishikawa K, Fukuda H, Fujino T, Suzuki A: Inhibition of microbial growth by ajoene, a sulfur-containing compound derived from garlic. Appl Environ Microbiol. 1996 Nov;62(11):4238-42. doi: 10.1128/aem.62.11.4238-4242.1996. [PubMed:8900018  ] 
  2. Ledezma E, Apitz-Castro R: [Ajoene the main active compound of garlic (Allium sativum): a new antifungal agent]. Rev Iberoam Micol. 2006 Jun;23(2):75-80. doi: 10.1016/s1130-1406(06)70017-1. [PubMed:16854181  ] 
  3. Urbina JA, Marchan E, Lazardi K, Visbal G, Apitz-Castro R, Gil F, Aguirre T, Piras MM, Piras R: Inhibition of phosphatidylcholine biosynthesis and cell proliferation in Trypanosoma cruzi by ajoene, an antiplatelet compound isolated from garlic. Biochem Pharmacol. 1993 Jun 22;45(12):2381-7. doi: 10.1016/0006-2952(93)90217-k. [PubMed:8328978  ] 
  4. Kaschula CH, Hunter R, Parker MI: Garlic-derived anticancer agents: structure and biological activity of ajoene. Biofactors. 2010 Jan-Feb;36(1):78-85. doi: 10.1002/biof.76. [PubMed:20108330  ] 
  5. Srivastava KC, Tyagi OD: Effects of a garlic-derived principle (ajoene) on aggregation and arachidonic acid metabolism in human blood platelets. Prostaglandins Leukot Essent Fatty Acids. 1993 Aug;49(2):587-95. doi: 10.1016/0952-3278(93)90165-s. [PubMed:8415808  ]