(2E,4E,6Z)-7-((2S,4aR)-1,2,3,4,4a,5-Hexahydro-1,1,5,5-tetramethyl-2,4a-methanonaphthalen-7-yl)-3-methyl-2,4,6-octatrienoic acid

ID: ALA1773363

PubChem CID: 54581149

Max Phase: Preclinical

Molecular Formula: C24H32O2

Molecular Weight: 352.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=C/C=C/C(C)=C/C(=O)O)C1=CC(C)(C)[C@@]23CC[C@@H](C2)C(C)(C)C3=C1

Standard InChI:  InChI=1S/C24H32O2/c1-16(12-21(25)26)8-7-9-17(2)18-13-20-23(5,6)19-10-11-24(20,15-19)22(3,4)14-18/h7-9,12-14,19H,10-11,15H2,1-6H3,(H,25,26)/b8-7+,16-12+,17-9-/t19-,24-/m0/s1

Standard InChI Key:  RKEVEOWVENZGLD-LHFASWIXSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    0.0001    1.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8501   -1.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8501   -2.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4251    0.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1376   -0.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7126    1.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1376   -0.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4251    1.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5626   -2.4812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4210   -1.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7210    2.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7129    1.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7059    0.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0032    0.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4244    0.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4204    1.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1300    1.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8482    1.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8521    0.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1380    0.0095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1249   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2999   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7207    2.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5499    2.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2499    0.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5626    1.6671    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1335   -2.4771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  2  0
  3  2  1  0
  4  8  1  0
  5  7  1  0
  6  1  1  0
  7  4  2  0
  8  6  2  0
  9  3  2  0
 10  5  1  0
 11  6  1  0
  1 12  1  0
 12 16  2  0
 15 13  1  0
 13 14  1  0
 14  1  2  0
 15 16  1  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 13 21  1  0
 13 22  1  0
 17 23  1  0
 17 24  1  0
 15 25  1  1
 18 25  1  0
 18 26  1  1
  3 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1773363

   (2E,4E,6Z)-3-methyl-7-[(1R,8S)-2,2,7,7-tetramethyl-4-tricyclo[6.2.1.01,6]undeca-3,5-dienyl]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: 352.52

Molecular Weight (Monoisotopic): 352.2402

AlogP: 6.24

#Rotatable Bonds: 4

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: 4.60

CX Basic pKa: ┄

CX LogP: 5.10

CX LogD: 2.37

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.48

Np Likeness Score: 2.05

References

1. Okitsu T, Sato K, Iwatsuka K, Sawada N, Nakagawa K, Okano T, Yamada S, Kakuta H, Wada A..  (2011)  Replacement of the hydrophobic part of 9-cis-retinoic acid with cyclic terpenoid moiety results in RXR-selective agonistic activity.,  19  (9): [PMID:21489804] [10.1016/j.bmc.2011.03.033]

Source

Source(1):

• Scientific Literature