(2E,4E,6Z,8E)-3,7-Dimethyl-9-((1R,4S,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-2-en-3-yl)-2,4,6,8-nonatetraenoic acid

ID: ALA1773357

PubChem CID: 52952997

Max Phase: Preclinical

Molecular Formula: C21H28O2

Molecular Weight: 312.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=C/C=C/C(C)=C/C(=O)O)/C=C/C1=C[C@H]2C[C@@H]([C@@H]1C)C2(C)C

Standard InChI:  InChI=1S/C21H28O2/c1-14(7-6-8-15(2)11-20(22)23)9-10-17-12-18-13-19(16(17)3)21(18,4)5/h6-12,16,18-19H,13H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7-,15-11+/t16-,18+,19+/m1/s1

Standard InChI Key:  WJILZFDTSGYVEL-MGWDKRDRSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   -1.3729    1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6562    1.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3729    0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0854    1.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0562    1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9062   -1.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9062   -2.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4813    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937   -0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7688    1.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937   -0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4813    1.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6187   -2.4833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7937    1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7937    0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4771   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7771    2.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0865    2.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0812    0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0854    0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6187    0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7979   -0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0854   -0.8208    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5906    1.4552    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1896   -2.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  1  1  0
  5  2  2  0
  6  9  2  0
  7  6  1  0
  8 12  1  0
  9 11  1  0
 10  5  1  0
 11  8  2  0
 12 10  2  0
 13  7  2  0
 20  3  1  0
 14  4  1  0
 15 14  1  0
 16  9  1  0
 17 10  1  0
 15 20  1  0
  4 18  1  6
 14 19  1  0
 20 19  1  0
 15 21  1  0
 15 22  1  0
 20 23  1  1
 14 24  1  1
  7 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1773357

   (2E,4E,6Z,8E)-3,7-dimethyl-9-[(1R,4S,5S)-4,6,6-trimethyl-3-bicyclo[3.1.1]hept-2-enyl]nona-2,4,6,8-tetraenoic 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: 312.45

Molecular Weight (Monoisotopic): 312.2089

AlogP: 5.31

#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: 4.76

CX Basic pKa: ┄

CX LogP: 4.72

CX LogD: 2.13

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.55

Np Likeness Score: 2.30

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