(1''S,3R,4''R,5'R,6''R,8''S,12''R)-1'',6'',8''-trimethyldispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0^{4,12}]dodecane]-2'',5-dione

ID: ALA1079715

PubChem CID: 46883183

Max Phase: Preclinical

Molecular Formula: C20H28O5

Molecular Weight: 348.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1C[C@H]2OC(=O)[C@@]3(C)CCC[C@@](C)([C@@H]23)[C@@]12CC[C@@]1(COC(=O)C1)O2

Standard InChI:  InChI=1S/C20H28O5/c1-12-9-13-15-17(2,16(22)24-13)5-4-6-18(15,3)20(12)8-7-19(25-20)10-14(21)23-11-19/h12-13,15H,4-11H2,1-3H3/t12-,13-,15+,17+,18+,19-,20-/m1/s1

Standard InChI Key:  UHVBVZOAJOXFRA-WBTYJLFFSA-N

Molfile:  

     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
    5.8160  -13.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6139  -13.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0632  -12.7696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428  -12.1281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7721  -12.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9799  -14.2903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7756  -14.0739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0444  -12.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5272  -13.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8429  -14.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8429  -15.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5571  -15.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5571  -14.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2673  -14.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2689  -15.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9775  -15.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6913  -15.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6939  -14.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7658  -16.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7462  -16.7045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2719  -17.3971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8345  -16.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2624  -16.3523    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4090  -14.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7562  -11.3288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6904  -16.3526    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0485  -13.9044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  5  1  1  0
  1  2  1  0
  6  7  1  0
  7  1  1  0
  1  8  1  1
  8  9  1  0
  6  9  1  1
 10 11  1  0
 10 13  1  0
 11 12  1  0
 12 15  1  0
 14 13  1  0
 14 15  1  0
 14  6  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  6  1  0
 12 19  1  0
 19 20  1  0
 16 20  1  0
 19 21  2  0
 12 22  1  6
 15 23  1  6
 18 24  1  6
  4 25  2  0
  2  3  1  0
 16 26  1  6
  3  4  1  0
 14 27  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1079715

   CID 46883183

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: 348.44

Molecular Weight (Monoisotopic): 348.1937

AlogP: 3.00

#Rotatable Bonds: ┄

Polar Surface Area: 61.83

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.88

CX LogD: 2.88

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.63

Np Likeness Score: 3.48

References

1. Rigano D, Aviello G, Bruno M, Formisano C, Rosselli S, Capasso R, Senatore F, Izzo AA, Borrelli F..  (2009)  Antispasmodic effects and structure-activity relationships of labdane diterpenoids from Marrubium globosum ssp. libanoticum.,  72  (8): [PMID:19650652] [10.1021/np9002756]

Source

Source(1):

• Scientific Literature