5-((3R,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid{6-[4-(4,2',3'-trihydroxy-5',6'-dimethyl-[1,1';4',1'']terphenyl-4''-yloxymethyl)-[1,2,3]triazol-1-yl]-hexyl}amide

ID: ALA2013072

Chembl Id: CHEMBL2013072

PubChem CID: 70691637

Max Phase: Preclinical

Molecular Formula: C39H48N6O6S

Molecular Weight: 728.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(C)c(-c2ccc(OCc3cn(CCCCCCNC(=O)CCCC[C@@H]4SC[C@@H]5NC(=O)N[C@@H]54)nn3)cc2)c(O)c(O)c1-c1ccc(O)cc1

Standard InChI:  InChI=1S/C39H48N6O6S/c1-24-25(2)35(38(49)37(48)34(24)26-11-15-29(46)16-12-26)27-13-17-30(18-14-27)51-22-28-21-45(44-43-28)20-8-4-3-7-19-40-33(47)10-6-5-9-32-36-31(23-52-32)41-39(50)42-36/h11-18,21,31-32,36,46,48-49H,3-10,19-20,22-23H2,1-2H3,(H,40,47)(H2,41,42,50)/t31-,32-,36-/m0/s1

Standard InChI Key:  WPVFVPRCILRHRE-QOVAEWSBSA-N

Alternative Forms

1. Parent:

   

   ALA2013072

   5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[6-[4-[[4-[2,3-dihydroxy-4-(4-hydroxyphenyl)-5,6-dimethylphenyl]phenoxy]methyl]triazol-1-yl]hexyl]pentanamide

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

Calculated Properties

Molecular Weight: 728.92

Molecular Weight (Monoisotopic): 728.3356

AlogP: 6.33

#Rotatable Bonds: 17

Polar Surface Area: 170.86

Molecular Species: NEUTRAL

HBA: 10

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 4

CX Acidic pKa: 9.30

CX Basic pKa: ┄

CX LogP: 6.11

CX LogD: 6.10

Aromatic Rings: 4

Heavy Atoms: 52

QED Weighted: 0.04

Np Likeness Score: -0.60

References

1. Ye YQ, Onose J, Abe N, Koshino H, Takahashi S..  (2012)  Design and synthesis of a vialinin A analog with a potent inhibitory activity of TNF-α production and its transformation into a couple of bioprobes.,  22  (7): [PMID:22410084] [10.1016/j.bmcl.2012.02.034]

2. Okada K, Ye YQ, Taniguchi K, Yoshida A, Akiyama T, Yoshioka Y, Onose J, Koshino H, Takahashi S, Yajima A, Abe N, Yajima S..  (2013)  Vialinin A is a ubiquitin-specific peptidase inhibitor.,  23  (15): [PMID:23791076] [10.1016/j.bmcl.2013.05.093]

3. Yoshioka Y, Namiki D, Makiuchi M, Sugaya K, Onose J, Ashida H, Abe N..  (2016)  Vialinin A and thelephantin G, potent inhibitors of tumor necrosis factor-α production, inhibit sentrin/SUMO-specific protease 1 enzymatic activity.,  26  (17): [PMID:27491710] [10.1016/j.bmcl.2016.07.051]

Source

Source(1):

• Scientific Literature