ID: ALA170458

Max Phase: Preclinical

Molecular Formula: C6H10S

Molecular Weight: 114.21

Molecule Type: Small molecule

Representations

Synonyms (3): 3-Allylsulfanyl-Propene | Diallyl Sulfide | Diallylsulfide
Synonyms from Alternative Forms(3):

Canonical SMILES:  C=CCSCC=C

Standard InChI:  InChI=1S/C6H10S/c1-3-5-7-6-4-2/h3-4H,1-2,5-6H2

Standard InChI Key:  UBJVUCKUDDKUJF-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

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: 114.21

Molecular Weight (Monoisotopic): 114.0503

AlogP: 2.09

#Rotatable Bonds: 4

Polar Surface Area: 0.00

Molecular Species:

HBA: 1

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 0

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 2.48

CX LogD: 2.48

Aromatic Rings: 0

Heavy Atoms: 7

QED Weighted: 0.40

Np Likeness Score: 0.05

References

1. 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]

2. Baraldi PG, Preti D, Materazzi S, Geppetti P..  (2010)  Transient receptor potential ankyrin 1 (TRPA1) channel as emerging target for novel analgesics and anti-inflammatory agents.,  53  (14): [PMID:20356305] [10.1021/jm100062h]

3. PubChem BioAssay data set, 

4. Krumm P, Giraldez T, Alvarez de la Rosa D, Clauss WG, Fronius M, Althaus M..  (2012)  Thiol-reactive compounds from garlic inhibit the epithelial sodium channel (ENaC).,  20  (13): [PMID:22668601] [10.1016/j.bmc.2012.05.021]

5. Arora A, Seth K, Shukla Y..  (2004)  Reversal of P-glycoprotein-mediated multidrug resistance by diallyl sulfide in K562 leukemic cells and in mouse liver.,  25  (1): [PMID:14729595] [10.1093/carcin/bgh060]

6. Brady JM, Cherrington NJ, Hartley DP, Buist SC, Li N, Klaassen CD..  (2002)  Tissue distribution and chemical induction of multiple drug resistance genes in rats.,  30  (1): [PMID:12065443] [10.1124/dmd.30.7.838]

7. Guo GL, Choudhuri S, Klaassen CD..  (2002)  Induction profile of rat organic anion transporting polypeptide 2 (oatp2) by prototypical drug-metabolizing enzyme inducers that activate gene expression through ligand-activated transcription factor pathways.,  300  (1): [PMID:11752118] [10.1124/jpet.300.1.206]

8. Slitt AL, Cherrington NJ, Maher JM, Klaassen CD..  (2003)  Induction of multidrug resistance protein 3 in rat liver is associated with altered vectorial excretion of acetaminophen metabolites.,  31  (1): [PMID:12920174] [10.1124/dmd.31.9.1176]

9. Cherrington NJ, Slitt AL, Maher JM, Zhang XX, Zhang J, Huang W, Wan YJ, Moore DD, Klaassen CD..  (2003)  Induction of multidrug resistance protein 3 (mrp3) in vivo is independent of constitutive androstane receptor.,  31  (1): [PMID:14570762] [10.1124/dmd.31.11.1315]

10. Jan CR, Lo HR, Chen CY, Kuo SY..  (2012)  Effect of allyl sulfides from garlic essential oil on intracellular ca2+ levels in renal tubular cells.,  75  (12): [PMID:23163425] [10.1021/np3005248]

11. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

12. Schneider T, Ba LA, Khairan K, Zwergel C, Bach ND, Bernhardt I, Brandt W, Wessjohann L, Diederich M, Jacob C.  (2011)  Interactions of polysulfanes with components of red blood cells,  2  (3): [10.1039/C0MD00203H]

13. Sinha S, Doble M, Manju SL..  (2019)  5-Lipoxygenase as a drug target: A review on trends in inhibitors structural design, SAR and mechanism based approach.,  27  (17): [PMID:31331653] [10.1016/j.bmc.2019.06.040]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• TP-search Transporter Database