(2E,4E,6Z)-7-((4aR,5S,6R)-4a,5-dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2-yl)-3-methylocta-2,4,6-trienoic acid

ID: ALA1773075

PubChem CID: 54586923

Max Phase: Preclinical

Molecular Formula: C24H32O2

Molecular Weight: 352.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)[C@@H]1CCC2=CC(/C(C)=C\C=C\C(C)=C\C(=O)O)=CC[C@]2(C)[C@H]1C

Standard InChI:  InChI=1S/C24H32O2/c1-16(2)22-11-10-21-15-20(12-13-24(21,6)19(22)5)18(4)9-7-8-17(3)14-23(25)26/h7-9,12,14-15,19,22H,1,10-11,13H2,2-6H3,(H,25,26)/b8-7+,17-14+,18-9-/t19-,22-,24+/m0/s1

Standard InChI Key:  UFMVIQBZDMJIDZ-VBWXPERGSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    1.2833   -1.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1333   -4.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1333   -5.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7083   -2.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4208   -3.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9958   -1.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4208   -2.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7083   -1.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8458   -5.4708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -5.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5703   -1.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5773   -2.9787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2864   -2.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1412   -2.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1372   -1.7418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8468   -1.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5650   -1.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5689   -2.5612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8548   -2.9801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1458   -3.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8576   -3.8051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2858   -2.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979   -2.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2906   -3.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 17  2  0
  2  5  2  0
 16 14  1  0
  3  2  1  0
 14 15  1  0
 15  1  2  0
 16 17  1  0
  4  8  1  0
  5  7  1  0
  6  1  1  0
  7  4  2  0
  8  6  2  0
  9  3  2  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 10  3  1  0
 16 22  1  1
 11  5  1  0
 21 23  1  1
 12  6  1  0
 20 24  1  6
 24 25  2  0
  1 13  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1773075

   (2E,4E,6Z)-7-[(4aR,5S,6R)-4a,5-dimethyl-6-prop-1-en-2-yl-5,6,7,8-tetrahydro-4H-naphthalen-2-yl]-3-methylocta-2,4,6-trienoic 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: 352.52

Molecular Weight (Monoisotopic): 352.2402

AlogP: 6.40

#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: 4.60

CX Basic pKa: ┄

CX LogP: 5.51

CX LogD: 2.78

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.35

Np Likeness Score: 2.06

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