(1R,2R,4S,5E,7S,10E,14S)-7-isopropyl-4-methoxy-4,10,14-trimethyl-15-oxabicyclo[12.1.0]pentadeca-5,10-dien-2-ol

ID: ALA2407300

PubChem CID: 73349054

Max Phase: Preclinical

Molecular Formula: C21H36O3

Molecular Weight: 336.52

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@]2(C)O[C@@H]2[C@H](O)C1

Standard InChI:  InChI=1S/C21H36O3/c1-15(2)17-10-9-16(3)8-7-12-21(5)19(24-21)18(22)14-20(4,23-6)13-11-17/h8,11,13,15,17-19,22H,7,9-10,12,14H2,1-6H3/b13-11+,16-8+/t17-,18-,19-,20-,21+/m1/s1

Standard InChI Key:  TWRIPAVLXRTSCN-JXFGJMBUSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   13.5307   -7.5238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3184   -8.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1167   -8.1073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9249   -9.6783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4745   -8.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4849  -10.3739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6570   -9.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6718  -10.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3431  -11.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4892   -8.3304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5181  -11.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1697   -9.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1821  -10.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3701  -10.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7492   -9.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1633  -10.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1594   -8.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5813   -9.8111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1227  -10.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7009   -8.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9209   -9.6916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3552   -8.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5321   -8.9656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1203   -9.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4212   -8.1695    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  6
  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 22  1  0
 13 14  1  0
 14 21  1  0
  4 15  1  6
 15 16  1  0
 15 17  1  0
 12 18  1  1
  9 19  1  0
  3 20  1  0
 22 21  1  0
 22 23  1  0
 21 23  1  0
 21 24  1  1
 22 25  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2407300

   (1R,2R,4S,5E,7S,10Z,14S)-4-methoxy-4,10,14-trimethyl-7-propan-2-yl-15-oxabicyclo[12.1.0]pentadeca-5,10-dien-2-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: 336.52

Molecular Weight (Monoisotopic): 336.2664

AlogP: 4.65

#Rotatable Bonds: 2

Polar Surface Area: 41.99

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.29

CX LogD: 4.29

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.59

Np Likeness Score: 3.41

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