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

ID: ALA560824

PubChem CID: 45269609

Max Phase: Preclinical

Molecular Formula: C20H24O5

Molecular Weight: 344.41

Molecule Type: Small molecule

Names and Identifiers

Synonyms: durumolide L | DURUMOLIDE L|CHEMBL560824

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

Standard InChI:  InChI=1S/C20H24O5/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/h7-8,11,15-16,18H,3-6,9-10H2,1-2H3/b12-7+,13-8+/t15-,16-,18-,20+/m1/s1

Standard InChI Key:  OBSSCZVQJAGPOE-KMKNQKDISA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    9.7551  -18.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0716  -19.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7788  -19.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4186  -20.2978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1070  -19.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8924  -19.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4103  -18.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8780  -20.1425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2476  -17.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9315  -17.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0636  -17.7156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4767  -18.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7148  -17.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5974  -18.6210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9362  -19.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5790  -19.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8785  -20.3959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5404  -19.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1849  -20.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1588  -21.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1113  -19.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7678  -19.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5762  -18.4687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5595  -20.5772    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4763  -18.2937    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3344  -19.0521    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4324  -19.0733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4358  -16.3964    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  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA560824

   DURUMOLIDE L

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: 344.41

Molecular Weight (Monoisotopic): 344.1624

AlogP: 2.85

#Rotatable Bonds: 1

Polar Surface Area: 72.97

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.53

CX LogD: 3.53

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.24

Np Likeness Score: 3.02

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