(1S,2S,4'R,5S)-4'-isobutyl-6,6,6',6',8',8'-hexamethyl-3',4'-dihydro-1'H-spiro[bicyclo[3.1.1]heptane-2,2'-naphthalene]-5',7'(6'H,8'H)-dione

ID: ALA3354991

PubChem CID: 10949067

Max Phase: Preclinical

Molecular Formula: C25H38O3

Molecular Weight: 386.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@@H]1C[C@@]2(CC[C@H]3C[C@@H]2C3(C)C)OC2=C1C(=O)C(C)(C)C(=O)C2(C)C

Standard InChI:  InChI=1S/C25H38O3/c1-14(2)11-15-13-25(10-9-16-12-17(25)22(16,3)4)28-20-18(15)19(26)23(5,6)21(27)24(20,7)8/h14-17H,9-13H2,1-8H3/t15-,16+,17-,25-/m1/s1

Standard InChI Key:  KLOIQEXOEVJBFB-PDVBNWKYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   12.6752   -3.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5002   -3.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0877   -2.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6169   -5.6251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2085   -4.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7957   -5.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3461   -4.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3419   -5.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0504   -5.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7676   -5.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7717   -4.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0587   -4.0972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5002   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2122   -3.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9243   -3.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9208   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6296   -4.9174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3499   -3.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6366   -3.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6389   -2.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3546   -2.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3570   -1.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0679   -2.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0544   -4.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9836   -3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5961   -4.5126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2122   -2.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7858   -4.9170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0544   -3.2709    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.4795   -5.7501    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
  6  5  1  0
  7  8  1  1
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  2 13  1  0
  2 14  1  0
 13  5  1  0
  5 16  1  0
 15 14  1  0
 15 16  2  0
 15 19  1  0
 16 17  1  0
 17  7  1  0
  7 18  1  0
 18 19  1  0
 19 20  1  6
 20 21  1  0
 21 22  1  0
 21 23  1  0
 12 24  1  0
 24 10  1  0
 11 25  1  0
 11 26  1  0
 14 27  2  0
 13 28  2  0
 12 29  1  6
 10 30  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3354991

   (1'R,2R,4R,5'S)-6,6,6',6',8,8-hexamethyl-4-(2-methylpropyl)spiro[3,4-dihydrochromene-2,2'-bicyclo[3.1.1]heptane]-5,7-dione

Molecule Features

Natural Product: Yes

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: 386.58

Molecular Weight (Monoisotopic): 386.2821

AlogP: 5.72

#Rotatable Bonds: 2

Polar Surface Area: 43.37

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.34

CX LogD: 6.34

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.57

Np Likeness Score: 2.31

References

1. Nishiwaki H, Fujiwara S, Wukirsari T, Iwamoto H, Mori S, Nishi K, Sugahara T, Yamauchi S, Shuto Y..  (2015)  Revised stereochemistry of ficifolidione and its biological activities against insects and cells.,  78  (1): [PMID:25495518] [10.1021/np5006746]

Source

Source(1):

• Scientific Literature