(-)-(2E,4E,6Z,8E)-3,7-Dimethyl-9-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl]nona-2,4,6,8-tetraenoic acid

ID: ALA2021515

PubChem CID: 70693908

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]2CC[C@]1(C)C2(C)C

Standard InChI:  InChI=1S/C21H28O2/c1-15(7-6-8-16(2)13-19(22)23)9-10-18-14-17-11-12-21(18,5)20(17,3)4/h6-10,13-14,17H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,15-7-,16-13+/t17-,21-/m0/s1

Standard InChI Key:  OLTHLBHNRAIYMD-HBMGFIGGSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   -1.6312    1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9146    1.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6312    0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3437    1.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2021    1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6479   -1.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6479   -2.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2229    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9354   -0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5104    1.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9354   -0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2229    1.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3604   -2.4833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3437    0.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0521    1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0521    0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2187   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5187    2.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5604    0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3604    1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3604    0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3479    2.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3437   -0.8167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9312   -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
 14  3  1  0
 15  4  1  0
 16 15  1  0
 17  9  1  0
 18 10  1  0
 14 16  1  0
  4 19  1  0
 14 19  1  0
 19 20  1  0
 19 21  1  0
  4 22  1  6
 14 23  1  1
  7 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2021515

   (2E,4E,6Z,8E)-3,7-dimethyl-9-[(1R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]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: 5.46

#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: 4.74

CX LogD: 2.15

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.54

Np Likeness Score: 2.08

References

1. Alvarez S, Pazos-Randulfe Y, Khanwalkar H, Germain P, Alvarez R, Gronemeyer H, de Lera AR..  (2008)  New retinoid chemotypes: 9-cis-retinoic acid analogs with hydrophobic rings derived from terpenes as selective RAR agonists.,  16  (22): [PMID:18951029] [10.1016/j.bmc.2008.09.069]

2. 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