(2aS,5aR,9bS,9cS)-9,9c-Dimethyl-3,4,5,5a,6,6a,9b,9c-octahydro-2aH-1,7-dioxa-cyclopenta[d]acenaphthylene-2,8-dione

ID: ALA2252625

PubChem CID: 12095918

Max Phase: Preclinical

Molecular Formula: C15H18O4

Molecular Weight: 262.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C2[C@H](C[C@H]3CCC[C@@H]4C(=O)O[C@@H]2[C@@]34C)OC1=O

Standard InChI:  InChI=1S/C15H18O4/c1-7-11-10(18-13(7)16)6-8-4-3-5-9-14(17)19-12(11)15(8,9)2/h8-10,12H,3-6H2,1-2H3/t8-,9-,10+,12+,15+/m1/s1

Standard InChI Key:  XTSBENNQJJYWQF-HGBDMZGYSA-N

Molfile:  

     RDKit          2D

 19 22  0  0  0  0  0  0  0  0999 V2000
   16.8197   -2.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8197   -3.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5362   -1.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2506   -2.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9587   -3.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9631   -1.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8393   -2.4986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2516   -3.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5356   -3.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7111   -4.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7857   -4.2985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1932   -4.9408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6752   -2.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6701   -3.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4531   -3.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9418   -2.6762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4598   -2.0069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7031   -4.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7653   -2.6812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  9  2  1  1
  4  3  1  6
  4  8  1  0
  4  6  1  0
  8  5  1  0
  5 14  1  0
 13  6  1  6
  8  7  1  1
  8  9  1  0
  9 10  1  0
 10 11  1  0
  5 11  1  6
 10 12  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 13 17  1  0
 15 18  1  0
 16 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252625

   (1R,6S,8R,12S,15S)-3,15-dimethyl-5,14-dioxatetracyclo[6.6.1.02,6.012,15]pentadec-2-ene-4,13-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: 262.30

Molecular Weight (Monoisotopic): 262.1205

AlogP: 1.98

#Rotatable Bonds: ┄

Polar Surface Area: 52.60

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.89

CX Basic pKa: ┄

CX LogP: 2.21

CX LogD: 2.21

Aromatic Rings: ┄

Heavy Atoms: 19

QED Weighted: 0.63

Np Likeness Score: 2.96

References

1. Cantrell CL, Duke SO, Fronczek FR, Osbrink WL, Mamonov LK, Vassilyev JI, Wedge DE, Dayan FE..  (2007)  Phytotoxic Eremophilanes from Ligularia macrophylla.,  55  (26): [PMID:18044832] [10.1021/jf072548w]

Source

Source(1):

• Scientific Literature