(2R,2a'S,2a1'R,5a'S,7'R,8a'R)-2a',5a',7'-trimethyloctahydro-3H-spiro[furan-2,6'-naphtho[1,8-bc]furan]-2',5(2a'H,4H)-dione

ID: ALA1078053

PubChem CID: 46883095

Max Phase: Preclinical

Molecular Formula: C17H24O4

Molecular Weight: 292.38

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@@]12CCC(=O)O2

Standard InChI:  InChI=1S/C17H24O4/c1-10-9-11-13-15(2,14(19)20-11)6-4-7-16(13,3)17(10)8-5-12(18)21-17/h10-11,13H,4-9H2,1-3H3/t10-,11-,13+,15+,16+,17-/m1/s1

Standard InChI Key:  DFQREMVEHMYQMW-MZIBEIOLSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   -2.2661    0.9181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4699    1.1346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4302    1.9566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2015    2.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7190    1.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4043    0.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4043   -0.3235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6896   -0.7353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6896    0.9163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9791    0.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9775   -0.3235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2685   -0.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5542   -0.3249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5516    0.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4809   -1.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4999   -1.4974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9751   -2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4127   -1.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9840   -1.1451    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7405    2.4098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8362    0.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5551   -1.1455    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1980    1.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  5  1  1
  6  7  1  0
  6  9  1  0
  7  8  1  0
  8 11  1  0
 10  9  1  0
 10 11  1  0
 10  1  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14  1  1  0
  8 15  1  0
 15 16  1  0
 12 16  1  0
 15 17  2  0
  8 18  1  6
 11 19  1  6
  3 20  2  0
 14 21  1  6
 12 22  1  6
  1  2  1  0
 10 23  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1078053

   (1R,4S,8S,9R,10R,12R)-4,8,10-trimethylspiro[2-oxatricyclo[6.3.1.04,12]dodecane-9,5'-oxolane]-2',3-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: 292.38

Molecular Weight (Monoisotopic): 292.1675

AlogP: 2.84

#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: ┄

CX Basic pKa: ┄

CX LogP: 2.83

CX LogD: 2.83

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.64

Np Likeness Score: 3.43

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