(1R,2E,6E,10S,11E,13R)-10-isopropyl-13-methoxy-3,7,13-trimethylcyclotetradeca-2,6,11-trienol

ID: ALA2407302

PubChem CID: 73353581

Max Phase: Preclinical

Molecular Formula: C21H36O2

Molecular Weight: 320.52

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H36O2/c1-16(2)19-11-10-17(3)8-7-9-18(4)14-20(22)15-21(5,23-6)13-12-19/h8,12-14,16,19-20,22H,7,9-11,15H2,1-6H3/b13-12+,17-8+,18-14+/t19-,20+,21+/m1/s1

Standard InChI Key:  UCWVMPCRFWCDGY-QSBDLPQCSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
   26.0811   -1.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8688   -2.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6673   -2.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4756   -4.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0251   -3.4093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0354   -4.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2074   -3.5154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2224   -4.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8935   -5.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0396   -2.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0685   -5.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7201   -3.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7324   -4.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9099   -3.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9204   -4.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4710   -4.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3000   -4.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7141   -4.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7101   -3.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1316   -4.2457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2659   -4.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6732   -4.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2514   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  4  5  1  0
  4  6  1  0
  5  7  2  0
  6  8  1  0
  7  2  1  0
  8  9  1  0
  2 10  1  0
  9 11  2  0
 10 12  1  0
 11 13  1  0
 12 14  1  0
 13 15  1  0
 14 16  2  0
 15 16  1  0
  4 17  1  6
 17 18  1  0
 17 19  1  0
 12 20  1  1
 16 21  1  0
  9 22  1  0
  3 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2407302

   (1R,2Z,6Z,10S,11E,13R)-13-methoxy-3,7,13-trimethyl-10-propan-2-ylcyclotetradeca-2,6,11-trien-1-ol

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: 320.52

Molecular Weight (Monoisotopic): 320.2715

AlogP: 5.44

#Rotatable Bonds: 2

Polar Surface Area: 29.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.03

CX LogD: 5.03

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.69

Np Likeness Score: 3.04

References

1. Eterović VA, Del Valle-Rodriguez A, Pérez D, Carrasco M, Khanfar MA, El Sayed KA, Ferchmin PA..  (2013)  Protective activity of (1S,2E,4R,6R,7E,11E)-2,7,11-cembratriene-4,6-diol analogues against diisopropylfluorophosphate neurotoxicity: preliminary structure-activity relationship and pharmacophore modeling.,  21  (15): [PMID:23769165] [10.1016/j.bmc.2013.05.018]

Source

Source(1):

• Scientific Literature