4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)benzenesulfonic acid

ID: ALA4441103

Chembl Id: CHEMBL4441103

PubChem CID: 118343123

Max Phase: Preclinical

Molecular Formula: C22H26O4S

Molecular Weight: 386.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc2c(cc1C(=O)c1ccc(S(=O)(=O)O)cc1)C(C)(C)CCC2(C)C

Standard InChI:  InChI=1S/C22H26O4S/c1-14-12-18-19(22(4,5)11-10-21(18,2)3)13-17(14)20(23)15-6-8-16(9-7-15)27(24,25)26/h6-9,12-13H,10-11H2,1-5H3,(H,24,25,26)

Standard InChI Key:  VBCZKJPEMLTMIE-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA4441103

   4-(3,5,5,8,8-Pentamethyl-6,7-dihydronaphthalene-2-carbonyl)benzenesulfonic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 386.51

Molecular Weight (Monoisotopic): 386.1552

AlogP: 4.82

#Rotatable Bonds: 3

Polar Surface Area: 71.44

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -2.21

CX Basic pKa: ┄

CX LogP: 5.75

CX LogD: 3.38

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.61

Np Likeness Score: -0.08

References

1. Heck MC, Wagner CE, Shahani PH, MacNeill M, Grozic A, Darwaiz T, Shimabuku M, Deans DG, Robinson NM, Salama SH, Ziller JW, Ma N, van der Vaart A, Marshall PA, Jurutka PW..  (2016)  Modeling, Synthesis, and Biological Evaluation of Potential Retinoid X Receptor (RXR)-Selective Agonists: Analogues of 4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic Acid (Bexarotene) and 6-(Ethyl(5,5,8,8-tetrahydronaphthalen-2-yl)amino)nicotinic Acid (NEt-TMN).,  59  (19): [PMID:27592633] [10.1021/acs.jmedchem.6b00812]

Source

Source(1):

• Scientific Literature