(1S,4E,6S,8R,9E,11S,14S)-11-isopropyl-8-methoxy-4,8,14-trimethyl-15-oxabicyclo[12.1.0]pentadeca-4,9-dien-6-yl acetate

ID: ALA2407299

PubChem CID: 73352123

Max Phase: Preclinical

Molecular Formula: C23H38O4

Molecular Weight: 378.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@@]1(C)/C=C/[C@H](C(C)C)CC[C@]2(C)O[C@H]2CC/C(C)=C\[C@@H](OC(C)=O)C1

Standard InChI:  InChI=1S/C23H38O4/c1-16(2)19-10-12-22(5,25-7)15-20(26-18(4)24)14-17(3)8-9-21-23(6,27-21)13-11-19/h10,12,14,16,19-21H,8-9,11,13,15H2,1-7H3/b12-10+,17-14+/t19-,20+,21-,22-,23-/m0/s1

Standard InChI Key:  QZKGTJRIDWIYSB-SQSFQOCOSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   15.9656  -10.4294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0135  -12.7121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3793   -9.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7817  -14.0664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3652  -11.4213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5205  -12.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7745  -12.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0174  -11.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2175  -12.7109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2070  -11.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3661  -13.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0096  -11.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1669  -10.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3372  -10.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3597   -9.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5991  -14.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7678  -12.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5992  -11.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7748  -10.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5502  -11.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3237  -11.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5055  -11.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5997  -10.7022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0297  -12.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1923  -13.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3341  -12.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5632  -12.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6317  -13.7283    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  4  1  0
 19 15  1  0
 18 12  1  0
  9 17  1  0
 13 14  1  0
 17 27  1  0
 18  2  1  0
 13  3  1  0
 13 22  1  0
 25 16  1  1
 11 25  1  0
 23 19  1  0
  1 20  1  0
 19  5  2  0
  7 26  1  0
  7 18  1  6
  8 10  1  0
 11 24  1  0
 25  4  1  0
 21 22  2  0
 24  9  1  0
 14  8  1  0
 10 17  2  0
  7 21  1  0
 25  6  1  0
  8 23  1  6
 13  1  1  1
 26  6  1  0
 11 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2407299

   [(1S,4Z,6S,8R,9E,11S,14S)-8-methoxy-4,8,14-trimethyl-11-propan-2-yl-15-oxabicyclo[12.1.0]pentadeca-4,9-dien-6-yl] acetate

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: 378.55

Molecular Weight (Monoisotopic): 378.2770

AlogP: 5.22

#Rotatable Bonds: 3

Polar Surface Area: 48.06

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.57

CX LogD: 4.57

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.38

Np Likeness Score: 3.16

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