(2E,4E,6E)-8-[3-Ethyl-2-isopropyl-cyclohex-2-en-(E)-ylidene]-3,7-dimethyl-octa-2,4,6-trienoic acid

ID: ALA46398

Chembl Id: CHEMBL46398

PubChem CID: 9883342

Max Phase: Preclinical

Molecular Formula: C21H30O2

Molecular Weight: 314.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC1=C(C(C)C)/C(=C/C(C)=C/C=C/C(C)=C/C(=O)O)CCC1

Standard InChI:  InChI=1S/C21H30O2/c1-6-18-11-8-12-19(21(18)15(2)3)13-16(4)9-7-10-17(5)14-20(22)23/h7,9-10,13-15H,6,8,11-12H2,1-5H3,(H,22,23)/b10-7+,16-9+,17-14+,19-13+

Standard InChI Key:  OZUIXDDSOLQKNK-WXVUQSRRSA-N

Alternative Forms

1. Parent:

   

   ALA46398

   (2E,4E,6Z)-3,7-Dimethyl-8-[(1E)-2-isopropyl-3-ethyl-2-cyclohexenylidene]-2,4,6-octatrienoic 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: 314.47

Molecular Weight (Monoisotopic): 314.2246

AlogP: 5.99

#Rotatable Bonds: 6

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: 4.56

CX Basic pKa: ┄

CX LogP: 5.40

CX LogD: 2.64

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.48

Np Likeness Score: 1.51

References

1. Muccio DD, Brouillette WJ, Breitman TR, Taimi M, Emanuel PD, Zhang X, Chen G, Sani BP, Venepally P, Reddy L, Alam M, Simpson-Herren L, Hill DL..  (1998)  Conformationally defined retinoic acid analogues. 4. Potential new agents for acute promyelocytic and juvenile myelomonocytic leukemias.,  41  (10): [PMID:9572893] [10.1021/jm970635h]

2. Alam M, Zhestkov V, Sani BP, Venepally P, Levin AA, Kazmer S, Li E, Norris AW, Zhang XK, Lee MO..  (1995)  Conformationally defined 6-s-trans-retinoic acid analogs. 2. Selective agonists for nuclear receptor binding and transcriptional activity.,  38  (13): [PMID:7608895] [10.1021/jm00013a006]

3. Muccio DD, Brouillette WJ, Alam M, Vaezi MF, Sani BP, Venepally P, Reddy L, Li E, Norris AW, Simpson-Herren L, Hill DL..  (1996)  Conformationally defined 6-s-trans-retinoic acid analogs. 3. Structure-activity relationships for nuclear receptor binding, transcriptional activity, and cancer chemopreventive activity.,  39  (19): [PMID:8809153] [10.1021/jm9603126]

Source

Source(1):

• Scientific Literature