Ethyl (+)-(2E,4E,6Z,8E)-3,7-dimethyl-9-[(3R,6S)-6-isopropyl-3-methylcyclohex-1-en-1-il]nona-2,4,6,8-tetraenoate

ID: ALA508378

PubChem CID: 25147656

Max Phase: Preclinical

Molecular Formula: C21H30O2

Molecular Weight: 314.47

Molecule Type: Small molecule

Names and Identifiers

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

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

Standard InChI Key:  FDKJJFZTALFHMZ-PGCPYWQFSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
   -4.7500    0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7500    0.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0380   -0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3260    0.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3260    0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0380    1.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0380    2.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3235    2.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7525    2.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0380   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6103    1.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8970    0.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1814    1.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4681    0.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1789    2.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4705    0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2428   -0.3188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2403   -1.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9536   -1.5584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4753   -1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9512   -2.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2357   -2.7939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6646   -2.7981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  2  0
 11 12  2  0
  5  6  1  0
 12 13  1  0
 13 14  2  0
  6  7  1  1
 13 15  1  0
  1  2  1  0
 14 16  1  0
  7  8  1  0
 16 17  2  0
  1  6  1  0
 17 18  1  0
  7  9  1  0
 18 19  2  0
  2  3  1  0
 18 20  1  0
  3 10  1  6
 19 21  1  0
  3  4  1  0
  5 11  1  0
 21 22  1  0
 21 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA508378

   (2E,4E,6Z,8E)-3,7-dimethyl-9-[(3R,6S)-3-methyl-6-propan-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: 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: 4.76

CX Basic pKa: ┄

CX LogP: 5.49

CX LogD: 2.90

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.50

Np Likeness Score: 2.16

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]

2. 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]

3. Zhang, L L and 7 more authors.  1996-07-05  Discovery of novel retinoic acid receptor agonists having potent antiproliferative activity in cervical cancer cells.  [PMID:8709094]

4. Canan Koch, S S SS and 6 more authors.  1999-02-25  Synthesis of retinoid X receptor-specific ligands that are potent inducers of adipogenesis in 3T3-L1 cells.  [PMID:10052980]

5. Haffner, Curt D CD and 13 more authors.  2004-04-08  Structure-based design of potent retinoid X receptor alpha agonists.  [PMID:15056000]

6. Patch, Raymond J RJ and 16 more authors.  2011-02-10  Identification of diaryl ether-based ligands for estrogen-related receptor α as potential antidiabetic agents.  [PMID:21218783]

7. Gege, Christian C, Schlüter, Thomas T and Hoffmann, Thomas T.  2014-11-15  Identification of the first inverse agonist of retinoid-related orphan receptor (ROR) with dual selectivity for RORβ and RORγt.  [PMID:25305688]

8. Haffez, Hesham and 7 more authors.  2018-05-01  Probing biological activity through structural modelling of ligand-receptor interactions of 2,4-disubstituted thiazole retinoids.  [PMID:29439915]

Source

Source(1):

• Scientific Literature