2-((1-Hydroxy-4-(4-phenoxyphenylsulfonamido)naphthalen-2-yl)thio)acetic Acid

ID: ALA3265299

Chembl Id: CHEMBL3265299

PubChem CID: 86765310

Max Phase: Preclinical

Molecular Formula: C24H19NO6S2

Molecular Weight: 481.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CSc1cc(NS(=O)(=O)c2ccc(Oc3ccccc3)cc2)c2ccccc2c1O

Standard InChI:  InChI=1S/C24H19NO6S2/c26-23(27)15-32-22-14-21(19-8-4-5-9-20(19)24(22)28)25-33(29,30)18-12-10-17(11-13-18)31-16-6-2-1-3-7-16/h1-14,25,28H,15H2,(H,26,27)

Standard InChI Key:  CTGZINWTGVOSRK-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3265299

   2-[1-Hydroxy-4-[(4-phenoxyphenyl)sulfonylamino]naphthalen-2-yl]sulfanylacetic acid

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: 481.55

Molecular Weight (Monoisotopic): 481.0654

AlogP: 5.32

#Rotatable Bonds: 8

Polar Surface Area: 112.93

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.28

CX Basic pKa:

CX LogP: 4.44

CX LogD: 0.88

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.23

Np Likeness Score: -1.02

References

1. Abulwerdi FA, Liao C, Mady AS, Gavin J, Shen C, Cierpicki T, Stuckey JA, Showalter HD, Nikolovska-Coleska Z..  (2014)  3-Substituted-N-(4-hydroxynaphthalen-1-yl)arylsulfonamides as a novel class of selective Mcl-1 inhibitors: structure-based design, synthesis, SAR, and biological evaluation.,  57  (10): [PMID:24749893] [10.1021/jm500010b]

2. Fang C, D'Souza B, Thompson CF, Clifton MC, Fairman JW, Fulroth B, Leed A, McCarren P, Wang L, Wang Y, Feau C, Kaushik VK, Palmer M, Wei G, Golub TR, Hubbard BK, Serrano-Wu MH..  (2014)  Single Diastereomer of a Macrolactam Core Binds Specifically to Myeloid Cell Leukemia 1 (MCL1).,  5  (12): [PMID:25516789] [10.1021/ml500388q]

Source

Source(1):

• Scientific Literature