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

ID: ALA1773352

PubChem CID: 52952998

Max Phase: Preclinical

Molecular Formula: C21H28O2

Molecular Weight: 312.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)[C@@H]1CC[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/h6-9,11,13-14,18,20H,1,10,12H2,2-5H3,(H,22,23)/b8-6+,11-9+,16-7-,17-14+/t18-,20+/m1/s1

Standard InChI Key:  IADAPKLAERAWQU-PGCPYWQFSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    1.8125   -1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -1.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -2.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1000   -1.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417   -1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0917   -4.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0917   -5.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667   -2.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -3.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542   -1.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -3.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667   -1.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8042   -5.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3750   -5.5583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1000   -3.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3917   -1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3917   -2.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625   -4.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9625   -0.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0990   -3.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0989   -0.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8129   -0.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3839   -0.1842    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  1  1
  3  1  2  0
 21 22  2  0
  4  1  1  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1773352

   (2E,4E,6Z,8E)-3,7-dimethyl-9-[(3R,6S)-3-methyl-6-prop-1-en-2-ylcyclohexen-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: 5.62

#Rotatable Bonds: 6

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: 5.14

CX LogD: 2.55

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.39

Np Likeness Score: 2.26

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