(1R*,3R*,4S*,14R*,7E,11E)-18-hydroxy-13-oxo-3,4-epoxycembra-7,11,15(17)-trien-16,14-olide

ID: ALA560157

PubChem CID: 44188459

Max Phase: Preclinical

Molecular Formula: C20H26O5

Molecular Weight: 346.42

Molecule Type: Small molecule

Names and Identifiers

Synonyms: durumolide K | DURUMOLIDE K|CHEMBL560157

Canonical SMILES:  C=C1C(=O)O[C@H]2C(=O)/C(C)=C/CC/C(C)=C/CC[C@@]3(CO)O[C@@H]3C[C@H]12

Standard InChI:  InChI=1S/C20H26O5/c1-12-6-4-8-13(2)17(22)18-15(14(3)19(23)24-18)10-16-20(11-21,25-16)9-5-7-12/h7-8,15-16,18,21H,3-6,9-11H2,1-2H3/b12-7+,13-8+/t15-,16-,18-,20+/m1/s1

Standard InChI Key:  JPIGOPYINYLNIZ-KMKNQKDISA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   -0.1710  -19.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1455  -19.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8527  -20.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4926  -20.9229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1809  -20.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9663  -19.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4842  -19.0379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9519  -20.7676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6785  -18.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9946  -17.6745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1375  -18.3407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4494  -18.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2112  -18.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3287  -19.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9899  -19.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3471  -20.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0476  -21.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3857  -20.5279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7412  -21.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7673  -21.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8148  -19.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1583  -20.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6501  -19.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6334  -21.2023    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5502  -18.9188    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4083  -19.6771    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4937  -19.6984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4903  -17.0215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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  2  0
 13 14  1  0
 10 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA560157

   DURUMOLIDE K

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: 346.42

Molecular Weight (Monoisotopic): 346.1780

AlogP: 2.64

#Rotatable Bonds: 1

Polar Surface Area: 76.13

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.22

CX LogD: 3.22

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.34

Np Likeness Score: 3.22

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