6-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-cyclopropyl]-nicotinic acid

ID: ALA288436

Chembl Id: CHEMBL288436

Cas Number: 153559-76-3

PubChem CID: 3922

Product Number: L132783

Max Phase: Preclinical

Molecular Formula: C24H29NO2

Molecular Weight: 363.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc2c(cc1C1(c3ccc(C(=O)O)cn3)CC1)C(C)(C)CCC2(C)C

Standard InChI:  InChI=1S/C24H29NO2/c1-15-12-18-19(23(4,5)9-8-22(18,2)3)13-17(15)24(10-11-24)20-7-6-16(14-25-20)21(26)27/h6-7,12-14H,8-11H2,1-5H3,(H,26,27)

Standard InChI Key:  SLXTWXQUEZSSTJ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA288436

   6-(1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopropyl)nicotinic acid

Molecule Features

Natural Product: Yes

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: 363.50

Molecular Weight (Monoisotopic): 363.2198

AlogP: 5.52

#Rotatable Bonds: 3

Polar Surface Area: 50.19

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.93

CX Basic pKa: 2.53

CX LogP: 5.82

CX LogD: 2.87

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.78

Np Likeness Score: 0.16

References

1. Michellys PY, D'Arrigo J, Grese TA, Karanewsky DS, Leibowitz MD, Mais DA, Mapes CM, Reifel-Miller A, Rungta D, Boehm MF..  (2004)  Design, synthesis and structure-activity relationship of novel RXR-selective modulators.,  14  (6): [PMID:15006411] [10.1016/j.bmcl.2003.12.089]

2. Michellys PY, Ardecky RJ, Chen JH, Crombie DL, Etgen GJ, Faul MM, Faulkner AL, Grese TA, Heyman RA, Karanewsky DS, Klausing K, Leibowitz MD, Liu S, Mais DA, Mapes CM, Marschke KB, Reifel-Miller A, Ogilvie KM, Rungta D, Thompson AW, Tyhonas JS, Boehm MF..  (2003)  Novel (2E,4E,6Z)-7-(2-alkoxy-3,5-dialkylbenzene)-3-methylocta-2,4,6-trienoic acid retinoid X receptor modulators are active in models of type 2 diabetes.,  46  (13): [PMID:12801232] [10.1021/jm020340q]

3. Boehm MF, Zhang L, Zhi L, McClurg MR, Berger E, Wagoner M, Mais DE, Suto CM, Davies JA, Heyman RA..  (1995)  Design and synthesis of potent retinoid X receptor selective ligands that induce apoptosis in leukemia cells.,  38  (16): [PMID:7636877] [10.1021/jm00016a018]

4. Michellys PY, Boehm MF, Chen JH, Grese TA, Karanewsky DS, Leibowitz MD, Liu S, Mais DA, Mapes CM, Reifel-Miller A, Ogilvie KM, Rungta D, Thompson AW, Tyhonas JS, Yumibe N, Ardecky RJ..  (2003)  Design and synthesis of novel RXR-selective modulators with improved pharmacological profile.,  13  (22): [PMID:14592510] [10.1016/j.bmcl.2003.08.048]

5. Michellys PY, Ardecky RJ, Chen JH, D'Arrigo J, Grese TA, Karanewsky DS, Leibowitz MD, Liu S, Mais DA, Mapes CM, Montrose-Rafizadeh C, Ogilvie KM, Reifel-Miller A, Rungta D, Thompson AW, Tyhonas JS, Boehm MF..  (2003)  Design, synthesis, and structure-activity relationship studies of novel 6,7-locked-[7-(2-alkoxy-3,5-dialkylbenzene)-3-methylocta]-2,4,6-trienoic acids.,  46  (19): [PMID:12954061] [10.1021/jm020401k]

6. PubChem BioAssay data set, 

7. Conda-Sheridan M, Park EJ, Beck DE, Reddy PV, Nguyen TX, Hu B, Chen L, White JJ, van Breemen RB, Pezzuto JM, Cushman M..  (2013)  Design, synthesis, and biological evaluation of indenoisoquinoline rexinoids with chemopreventive potential.,  56  (6): [PMID:23472886] [10.1021/jm400026k]

8.  (2021)  EUbOPEN Chemogenomics Library wave 1,  [10.6019/CHEMBL4689842]

9. EUbOPEN.  (2022)  EUbOPEN Chemogenomics Library wave 2 - DSF,  [10.6019/CHEMBL5060014]

10. Willems S, Zaienne D, Merk D..  (2021)  Targeting Nuclear Receptors in Neurodegeneration and Neuroinflammation.,  64  (14.0): [PMID:34251209] [10.1021/acs.jmedchem.1c00186]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• EUbOPEN Chemogenomic Library