(3S,3aS,6aR,8R,9aS,9bS)-6a,8,9a-trihydroxy-3-methyl-6,9-dimethylenedecahydroazuleno[4,5-b]furan-2(9bH)-one

ID: ALA2270095

PubChem CID: 76308714

Max Phase: Preclinical

Molecular Formula: C15H20O5

Molecular Weight: 280.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC[C@H]2[C@H](C)C(=O)O[C@@H]2[C@@]2(O)C(=C)[C@H](O)C[C@@]12O

Standard InChI:  InChI=1S/C15H20O5/c1-7-4-5-10-8(2)13(17)20-12(10)15(19)9(3)11(16)6-14(7,15)18/h8,10-12,16,18-19H,1,3-6H2,2H3/t8-,10-,11+,12-,14+,15-/m0/s1

Standard InChI Key:  GAQIBPNSCLHKPN-BWNUQWIFSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   27.4204  -29.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0415  -30.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7330  -28.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7419  -29.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5454  -28.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0441  -28.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8609  -28.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3814  -28.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6734  -27.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9778  -30.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2164  -29.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4849  -30.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6085  -30.8492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4203  -30.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7951  -30.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7862  -31.7090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9508  -30.4803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9628  -28.3249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6123  -30.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6254  -29.7845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  4  1  0
  5  3  1  0
  3  1  1  0
  4  5  1  0
  5  6  1  0
  4 12  1  0
  6  7  1  0
  7  8  1  0
 11  8  1  1
  6  9  2  0
  2 10  2  0
 11 12  1  0
 12 13  1  6
 13 14  1  0
 14 15  1  0
 11 15  1  0
 14 16  2  0
  4 17  1  6
  5 18  1  6
 15 19  1  6
  1 20  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2270095

   (3S,3aS,6aR,8R,9aS,9bS)-6a,8,9a-trihydroxy-3-methyl-6,9-dimethylidene-3a,4,5,7,8,9b-hexahydro-3H-azuleno[4,5-b]furan-2-one

Molecule Features

Natural Product: No

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: 280.32

Molecular Weight (Monoisotopic): 280.1311

AlogP: 0.30

#Rotatable Bonds: ┄

Polar Surface Area: 86.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.06

CX Basic pKa: ┄

CX LogP: -0.14

CX LogD: -0.14

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.44

Np Likeness Score: 2.84

References

1. Macías FA, Galindo JC, Castellano D, Velasco RF..  (2000)  Sesquiterpene lactones with potential use as natural herbicide models. 2. guaianolides.,  48  (11): [PMID:11087474] [10.1021/jf0005364]

Source

Source(1):

• Scientific Literature