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

ID: ALA556102

PubChem CID: 45271265

Max Phase: Preclinical

Molecular Formula: C24H34O8

Molecular Weight: 450.53

Molecule Type: Small molecule

Names and Identifiers

Synonyms: durumolide G | DURUMOLIDE G|CHEMBL556102

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

Standard InChI:  InChI=1S/C24H34O8/c1-14-8-6-10-15(2)21(27)22-19(16(3)23(28)32-22)12-20(31-18(5)26)24(29,11-7-9-14)13-30-17(4)25/h9-10,19-22,27,29H,3,6-8,11-13H2,1-2,4-5H3/b14-9+,15-10+/t19-,20+,21-,22-,24+/m1/s1

Standard InChI Key:  KOXLNTVHCAHJPE-AVGSJBJPSA-N

Molfile:  

     RDKit          2D

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   10.8537    0.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5609   -0.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2007   -0.9039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8890   -0.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6745    0.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.6599   -0.7486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0299    1.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.3441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2181    2.9970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8458    1.6780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.5400    3.5397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3490    2.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3228   -0.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9672   -1.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9411   -1.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8939    0.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5500   -0.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3583    0.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1760    0.1819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3417   -1.1833    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2583    1.1000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7625   -1.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3530    0.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8914    0.8077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6333   -0.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 20 21  1  0
 10 11  1  0
 21 22  1  0
  2  6  1  0
 22 23  2  0
  9 12  1  0
 23 24  1  0
  2  3  1  0
 19 25  1  0
 11 13  1  0
 23 26  1  0
 26  3  1  0
  6  7  2  0
  1 27  1  0
  2 27  1  0
 13 14  2  0
  1 28  1  6
  3 29  1  6
 13 15  1  0
  2 30  1  1
  5  8  2  0
 26 31  1  1
  9 16  1  0
 28 32  1  0
  3  4  1  0
 32 33  2  0
 16 17  1  0
 32 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA556102

   DURUMOLIDE G

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: 450.53

Molecular Weight (Monoisotopic): 450.2254

AlogP: 2.53

#Rotatable Bonds: 3

Polar Surface Area: 119.36

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.91

CX Basic pKa: ┄

CX LogP: 2.17

CX LogD: 2.17

Aromatic Rings: ┄

Heavy Atoms: 32

QED Weighted: 0.29

Np Likeness Score: 3.01

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