ID: ALA25361

Max Phase: Preclinical

Molecular Formula: C25H26O2

Molecular Weight: 358.48

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC1(C)CCC(C)(C)c2cc(-c3ccc4cc(C(=O)O)ccc4c3)ccc21

Standard InChI:  InChI=1S/C25H26O2/c1-24(2)11-12-25(3,4)22-15-19(9-10-21(22)24)17-5-6-18-14-20(23(26)27)8-7-16(18)13-17/h5-10,13-15H,11-12H2,1-4H3,(H,26,27)

Standard InChI Key:  UHFICAKXFHFOCN-UHFFFAOYSA-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: 358.48

Molecular Weight (Monoisotopic): 358.1933

AlogP: 6.55

#Rotatable Bonds: 2

Polar Surface Area: 37.30

Molecular Species: ACID

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.99

CX Basic pKa:

CX LogP: 6.89

CX LogD: 3.73

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.56

Np Likeness Score: 0.35

References

1. Dawson MI, Jong L, Hobbs PD, Xiao D, Feng KC, Chao WR, Pan C, Fontana JA, Zhang XK..  (2000)  4-[3-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)phenyl]benzoic acid and heterocyclic-bridged analogues are novel retinoic acid receptor subtype and retinoid X receptor alpha agonists.,  10  (12): [PMID:10890153] [10.1016/s0960-894x(00)00244-4]

2. Dawson MI, Hobbs PD, Derdzinski KA, Chao WR, Frenking G, Loew GH, Jetten AM, Napoli JL, Williams JB, Sani BP..  (1989)  Effect of structural modifications in the C7-C11 region of the retinoid skeleton on biological activity in a series of aromatic retinoids.,  32  (7): [PMID:2738885] [10.1021/jm00127a018]

3. Dawson MI, Hobbs PD, Derdzinski K, Chan RL, Gruber J, Chao WR, Smith S, Thies RW, Schiff LJ..  (1984)  Conformationally restricted retinoids.,  27  (11): [PMID:6208361] [10.1021/jm00377a022]

4. Dawson MI, Chan RL, Derdzinski K, Hobbs PD, Chao WR, Schiff LJ..  (1983)  Synthesis and pharmacological activity of 6-[(E)-2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethen-1-yl]- and 6-(1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-naphthyl)-2-naphthalenecarboxylic acids.,  26  (11): [PMID:6195339] [10.1021/jm00365a021]

5. Diaz P, Michel S, Stella L, Charpentier B.  (1997)  Synthesis and biological activities of new heterocyclic aromatic retinoids,  7  (17): [10.1016/S0960-894X(97)00405-8]

6. Charpentier B, Bernardon JM, Eustache J, Millois C, Martin B, Michel S, Shroot B..  (1995)  Synthesis, structure-affinity relationships, and biological activities of ligands binding to retinoic acid receptor subtypes.,  38  (26): [PMID:8544175] [10.1021/jm00026a006]

7. Dawson MI, Xia Z, Liu G, Ye M, Fontana JA, Farhana L, Patel BB, Arumugarajah S, Bhuiyan M, Zhang XK, Han YH, Stallcup WB, Fukushi J, Mustelin T, Tautz L, Su Y, Harris DL, Waleh N, Hobbs PD, Jong L, Chao WR, Schiff LJ, Sani BP..  (2007)  An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and protein-tyrosine phosphatase activity.,  50  (11): [PMID:17489579] [10.1021/jm0613323]

Source

Source(1):

• Scientific Literature