(2E,4E,6Z,8E)-3,7-Dimethyl-9-((1S,4R,5R)-1-isopropyl-4-methylbicyclo[3.1.0]hex-2-en-3-yl)-2,4,6,8-nonatetraenoic acid

ID: ALA1773360

PubChem CID: 54581148

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@]2(C(C)C)C[C@@H]2[C@H]1C

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

Standard InChI Key:  DKRKJWTYVYDMRU-GQADQPKISA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    2.0625   -1.3438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -1.3438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -1.3438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -1.3438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -0.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    0.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -2.0583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -0.6293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9920    1.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8205    0.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356    1.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2775    2.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9920    2.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1425    1.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125    1.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1480    0.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2974    2.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750   -0.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -2.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2074    2.7728    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  1 10  2  0
  1 11  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 12 17  1  0
 12 16  1  0
 15 18  1  6
 19 20  1  0
 19 21  1  0
 12 19  1  6
  9 14  1  0
  7 22  1  0
  3 23  1  0
 16 24  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1773360

   (2E,4E,6Z,8E)-3,7-dimethyl-9-[(1S,4R,5R)-4-methyl-1-propan-2-yl-3-bicyclo[3.1.0]hex-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: 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: 4.72

CX LogD: 2.13

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.53

Np Likeness Score: 2.17

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