ID: ALA122890

Max Phase: Preclinical

Molecular Formula: C9H14OS3

Molecular Weight: 234.41

Molecule Type: Small molecule

Representations

Synonyms (2): Ajoene | E-Ajoene
Synonyms from Alternative Forms(2):

Canonical SMILES:  C=CCSS/C=C/C[S+]([O-])CC=C

Standard InChI:  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+

Standard InChI Key:  IXELFRRANAOWSF-FNORWQNLSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 234.41

Molecular Weight (Monoisotopic): 234.0207

AlogP: 3.00

#Rotatable Bonds: 8

Polar Surface Area: 23.06

Molecular Species: NEUTRAL

HBA: 3

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 1

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 1.66

CX LogD: 1.66

Aromatic Rings: 0

Heavy Atoms: 13

QED Weighted: 0.28

Np Likeness Score: 1.31

References

1. Gallwitz H, Bonse S, Martinez-Cruz A, Schlichting I, Schumacher K, Krauth-Siegel RL..  (1999)  Ajoene is an inhibitor and subversive substrate of human glutathione reductase and Trypanosoma cruzi trypanothione reductase: crystallographic, kinetic, and spectroscopic studies.,  42  (3): [PMID:9986706] [10.1021/jm980471k]

2. Lipinski B, Egyud LG.  (1992)  Thiol-induced crosslinking of human blood proteins: implications for tumor immunity.,  2  (9): [10.1016/S0960-894X(00)80588-0]

3. Hunter R, Kaschula CH, Parker IM, Caira MR, Richards P, Travis S, Taute F, Qwebani T..  (2008)  Substituted ajoenes as novel anti-cancer agents.,  18  (19): [PMID:18774712] [10.1016/j.bmcl.2008.08.056]

4. Larsson J, Gottfries J, Bohlin L, Backlund A..  (2005)  Expanding the ChemGPS chemical space with natural products.,  68  (7): [PMID:16038536] [10.1021/np049655u]

5. Kaschula CH, Hunter R, Stellenboom N, Caira MR, Winks S, Ogunleye T, Richards P, Cotton J, Zilbeyaz K, Wang Y, Siyo V, Ngarande E, Parker MI..  (2012)  Structure-activity studies on the anti-proliferation activity of ajoene analogues in WHCO1 oesophageal cancer cells.,  50  [PMID:22381354] [10.1016/j.ejmech.2012.01.058]

6. PubChem BioAssay data set, 

7. Fong J, Yuan M, Jakobsen TH, Mortensen KT, Delos Santos MM, Chua SL, Yang L, Tan CH, Nielsen TE, Givskov M..  (2017)  Disulfide Bond-Containing Ajoene Analogues As Novel Quorum Sensing Inhibitors of Pseudomonas aeruginosa.,  60  (1): [PMID:27977197] [10.1021/acs.jmedchem.6b01025]

8. Soukarieh F, Williams P, Stocks MJ, Cámara M..  (2018)  Pseudomonas aeruginosa Quorum Sensing Systems as Drug Discovery Targets: Current Position and Future Perspectives.,  61  (23): [PMID:29999316] [10.1021/acs.jmedchem.8b00540]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays