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

ID: ALA1078062

PubChem CID: 46883138

Max Phase: Preclinical

Molecular Formula: C20H30O5

Molecular Weight: 350.46

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(CO[C@@H](O)C1)O2

Standard InChI:  InChI=1S/C20H30O5/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/h12-15,21H,4-11H2,1-3H3/t12-,13-,14-,15+,17+,18+,19-,20-/m1/s1

Standard InChI Key:  IACFKHAQKGTVTR-GWVZFCQUSA-N

Molfile:  

     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
    4.7255    1.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5235    1.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9728    1.8617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4524    2.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6817    2.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894    0.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6851    0.5574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9539    1.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367    1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7525   -0.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7525   -0.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667   -1.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667    0.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1768   -0.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1784   -0.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870   -1.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6009   -0.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6035   -0.0738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6754   -2.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6557   -2.0731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1814   -2.7657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7440   -1.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1719   -1.7210    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3185    0.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6658    3.3025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6000   -1.7214    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9580    0.7270    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  1  6
  2  3  1  0
 16 26  1  6
  3  4  1  0
 14 27  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1078062

   CID 46883138

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: 350.46

Molecular Weight (Monoisotopic): 350.2093

AlogP: 2.79

#Rotatable Bonds: ┄

Polar Surface Area: 64.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.38

CX Basic pKa: ┄

CX LogP: 2.88

CX LogD: 2.88

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.68

Np Likeness Score: 3.70

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