(2E,4E,6Z,8E)-3,7-Dimethyl-9-((R)-3-methyl-6-(propan-2-ylidene)-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid

ID: ALA1773355

PubChem CID: 54585064

Max Phase: Preclinical

Molecular Formula: C21H28O2

Molecular Weight: 312.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=C1CC[C@@H](C)C=C1/C=C/C(C)=C\C=C\C(C)=C\C(=O)O

Standard InChI:  InChI=1S/C21H28O2/c1-15(2)20-12-10-18(5)13-19(20)11-9-16(3)7-6-8-17(4)14-21(22)23/h6-9,11,13-14,18H,10,12H2,1-5H3,(H,22,23)/b8-6+,11-9+,16-7-,17-14+/t18-/m1/s1

Standard InChI Key:  ATZZATZDMGYEFF-OAWKLDIGSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
   10.9542   -2.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6708   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9542   -2.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2417   -1.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3833   -2.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2333   -4.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2333   -5.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8083   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5208   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0958   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5208   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8083   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9458   -5.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5167   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2417   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5333   -2.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5333   -2.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8042   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1042   -0.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2406   -4.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2406   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9546   -0.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5256   -0.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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  7  1  0
 15  3  1  0
 16  4  1  0
 17 16  1  0
 18  9  1  0
 19 10  1  0
 17 15  1  0
 15 20  1  6
  2  1  1  0
  4 21  2  0
  3  1  2  0
 21 22  1  0
  4  1  1  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1773355

   (2E,4E,6Z,8E)-3,7-dimethyl-9-[(3R)-3-methyl-6-propan-2-ylidenecyclohexen-1-yl]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: 5.77

#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: 5.04

CX LogD: 2.45

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.52

Np Likeness Score: 2.12

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