(+)-(2E,4E,6Z,8E)-3,7-Dimethyl-9-[(3R,6R)-6-methyl-3-(prop-1-en-2-yl)-cyclohex-1-ene]nona-2,4,6,8-tetraenoic Acid

ID: ALA2021516

PubChem CID: 70683410

Max Phase: Preclinical

Molecular Formula: C21H30O2

Molecular Weight: 314.47

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H30O2/c1-15(2)19-12-10-18(5)20(14-19)11-9-16(3)7-6-8-17(4)13-21(22)23/h6-9,11,13,18-20H,1,10,12,14H2,2-5H3,(H,22,23)/b8-6+,11-9+,16-7-,17-13+/t18-,19-,20?/m1/s1

Standard InChI Key:  ICHOXYDNXCNWBS-FRRZSWROSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    3.9261  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2116  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4971  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4971  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2116  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9261  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2116  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9261  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4971  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6406  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2116  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3550  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0695  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7840  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0695  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7840  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4984  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4984  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2129  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7840  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2129  -16.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9274  -16.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4984  -16.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  1  1  0
  5  7  1  6
  7  8  2  0
  7  9  1  0
  1 10  1  0
  2 11  1  1
 10 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 19 21  1  0
 21 22  2  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2021516

   (2E,4E,6Z,8E)-3,7-dimethyl-9-[(2R,5R)-2-methyl-5-prop-1-en-2-ylcyclohexyl]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: 314.47

Molecular Weight (Monoisotopic): 314.2246

AlogP: 5.70

#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: 4.70

CX Basic pKa: ┄

CX LogP: 5.55

CX LogD: 2.90

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.39

Np Likeness Score: 2.27

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]

Source

Source(1):

• Scientific Literature