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

ID: ALA2111790

Chembl Id: CHEMBL2111790

PubChem CID: 10357464

Max Phase: Preclinical

Molecular Formula: C20H28O2

Molecular Weight: 300.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(C(C)C)/C(=C/C(C)=C\C=C\C(C)=C\C(=O)O)CCC1

Standard InChI:  InChI=1S/C20H28O2/c1-14(2)20-17(5)10-7-11-18(20)12-15(3)8-6-9-16(4)13-19(21)22/h6,8-9,12-14H,7,10-11H2,1-5H3,(H,21,22)/b9-6+,15-8-,16-13+,18-12+

Standard InChI Key:  BYHSFJNWVLBCIM-AORJTVFCSA-N

Alternative Forms

1. Parent:

   

   ALA2111790

   (2E,4E,6Z,8E)-3,7-dimethyl-8-(3-methyl-2-propan-2-ylcyclohex-2-en-1-ylidene)octa-2,4,6-trienoic 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: 300.44

Molecular Weight (Monoisotopic): 300.2089

AlogP: 5.60

#Rotatable Bonds: 5

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: 4.96

CX LogD: 2.20

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.53

Np Likeness Score: 1.52

References

1. 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]

2. Vaezi MF, Alam M, Sani BP, Rogers TS, Simpson-Herren L, Wille JJ, Hill DL, Doran TI, Brouillette WJ, Muccio DD..  (1994)  A conformationally defined 6-s-trans-retinoic acid isomer: synthesis, chemopreventive activity, and toxicity.,  37  (26): [PMID:7799400] [10.1021/jm00052a009]

3. Vaezi MF, Alam M, Sani BP, Rogers TS, Simpson-Herren L, Wille JJ, Hill DL, Doran TI, Brouillette WJ, Muccio DD..  (1994)  A conformationally defined 6-s-trans-retinoic acid isomer: synthesis, chemopreventive activity, and toxicity.,  37  (26): [PMID:7799400] [10.1021/jm00052a009]

4. Vaezi MF, Alam M, Sani BP, Rogers TS, Simpson-Herren L, Wille JJ, Hill DL, Doran TI, Brouillette WJ, Muccio DD..  (1994)  A conformationally defined 6-s-trans-retinoic acid isomer: synthesis, chemopreventive activity, and toxicity.,  37  (26): [PMID:7799400] [10.1021/jm00052a009]

Source

Source(1):

• Scientific Literature