(1R,3R,4R,13S,14R,7E,11E)-13-hydroxy-3,4-epoxycembra-7,11,15(17)-trien-16,14-olide

ID: ALA557212

PubChem CID: 11427555

Max Phase: Preclinical

Molecular Formula: C20H28O4

Molecular Weight: 332.44

Molecule Type: Small molecule

Names and Identifiers

Synonyms: durumolide J | DURUMOLIDE J|CHEMBL557212

Canonical SMILES:  C=C1C(=O)O[C@@H]2[C@@H]1C[C@H]1O[C@]1(C)CC/C=C(\C)CC/C=C(\C)[C@H]2O

Standard InChI:  InChI=1S/C20H28O4/c1-12-7-5-9-13(2)17(21)18-15(14(3)19(22)23-18)11-16-20(4,24-16)10-6-8-12/h8-9,15-18,21H,3,5-7,10-11H2,1-2,4H3/b12-8+,13-9+/t15-,16-,17-,18-,20-/m1/s1

Standard InChI Key:  HVJGVUTXXJGUKC-CZAZWBCNSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -0.3293  -11.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9870  -12.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6943  -13.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3341  -13.5289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0224  -13.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8078  -12.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3255  -11.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7932  -13.3736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8367  -11.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528  -10.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209  -10.9470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6075  -11.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3694  -11.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4868  -11.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1479  -12.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5052  -12.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2058  -13.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5438  -13.1340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8994  -13.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9256  -14.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9728  -12.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3167  -13.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917  -11.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750  -13.8083    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917  -11.5250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2500  -12.2833    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6519  -12.3045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 14 15  2  0
  5  8  2  0
 15 16  1  0
  3  4  1  0
 16 17  1  0
  1  9  1  0
 17 18  1  0
  4  5  1  0
 18 19  2  0
  9 10  1  6
 19 20  1  0
  5  6  1  0
 15 21  1  0
  9 11  1  0
 19 22  1  0
 22  3  1  0
  2  6  1  0
  1 23  1  0
  2 23  1  0
  9 12  1  0
  3 24  1  6
  2  3  1  0
  2 25  1  1
  1 11  1  0
 12 13  1  0
  1 26  1  1
  6  7  2  0
 22 27  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA557212

   DURUMOLIDE J

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: 332.44

Molecular Weight (Monoisotopic): 332.1988

AlogP: 3.46

#Rotatable Bonds: ┄

Polar Surface Area: 59.06

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.58

CX Basic pKa: ┄

CX LogP: 3.50

CX LogD: 3.50

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.32

Np Likeness Score: 3.76

References

1. Cheng SY, Wen ZH, Wang SK, Chiou SF, Hsu CH, Dai CF, Duh CY..  (2009)  Anti-inflammatory cembranolides from the soft coral Lobophytum durum.,  17  (11): [PMID:19433363] [10.1016/j.bmc.2009.04.053]

Source

Source(1):

• Scientific Literature