ID: ALA271235

Max Phase: Preclinical

Molecular Formula: C26H26N4O4

Molecular Weight: 458.52

Molecule Type: Small molecule

Representations

Canonical SMILES:  C#CCN1C[C@H](C(=O)NO)[C@H](NC(=O)c2ccc(OCc3cc(C)nc4ccccc34)cc2)C1

Standard InChI:  InChI=1S/C26H26N4O4/c1-3-12-30-14-22(26(32)29-33)24(15-30)28-25(31)18-8-10-20(11-9-18)34-16-19-13-17(2)27-23-7-5-4-6-21(19)23/h1,4-11,13,22,24,33H,12,14-16H2,2H3,(H,28,31)(H,29,32)/t22-,24+/m0/s1

Standard InChI Key:  SIICAQVADMFEDB-LADGPHEKSA-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: 458.52

Molecular Weight (Monoisotopic): 458.1954

AlogP: 2.29

#Rotatable Bonds: 7

Polar Surface Area: 103.79

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.84

CX Basic pKa: 6.79

CX LogP: 1.90

CX LogD: 1.78

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.29

Np Likeness Score: -1.10

References

1. Ott GR, Asakawa N, Lu Z, Liu RQ, Covington MB, Vaddi K, Qian M, Newton RC, Christ DD, Traskos JM, Decicco CP, Duan JJ..  (2008)  Alpha,beta-cyclic-beta-benzamido hydroxamic acids: novel templates for the design, synthesis, and evaluation of selective inhibitors of TNF-alpha converting enzyme (TACE).,  18  (2): [PMID:18061445] [10.1016/j.bmcl.2007.11.059]

2. DasGupta S, Murumkar PR, Giridhar R, Yadav MR..  (2009)  Current perspective of TACE inhibitors: a review.,  17  (2): [PMID:19095454] [10.1016/j.bmc.2008.11.067]

Source

Source(1):

• Scientific Literature