(rel)-(1S,7S,8R,11S,12R,3E,)-1:12,8:11-diepoxy-7-hydroxycembr-3-en-5-one

ID: ALA3634664

PubChem CID: 122196285

Max Phase: Preclinical

Molecular Formula: C20H32O4

Molecular Weight: 336.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C1=C\C[C@]2(C(C)C)CC[C@@](C)(O2)[C@@H]2CC[C@@](C)(O2)[C@@H](O)CC1=O

Standard InChI:  InChI=1S/C20H32O4/c1-13(2)20-9-6-14(3)15(21)12-16(22)18(4)8-7-17(23-18)19(5,24-20)10-11-20/h6,13,16-17,22H,7-12H2,1-5H3/b14-6+/t16-,17-,18+,19+,20+/m0/s1

Standard InChI Key:  WUZGXABGCGIHCY-RWKKOLHOSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    2.0756    1.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9966    2.3397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4558    2.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6671    1.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6112    0.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8387   -0.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167   -1.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3638   -2.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3445   -1.7059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5714   -0.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9223    2.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2502    1.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5814    3.4452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7591    0.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0562    1.4481    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2240   -4.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4182   -3.9351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7293   -5.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0989   -3.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3080   -2.3026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2912   -0.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2716   -0.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6161   -0.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5837   -0.9046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8260    1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  6  1  0
  1 10  1  0
  3 11  1  0
  3 12  1  1
 11 13  1  6
 10 14  1  1
  1 15  1  1
  8 16  1  1
 16 17  1  0
 16 18  1  0
  8 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 11 25  1  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3634664

   ---

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: 336.47

Molecular Weight (Monoisotopic): 336.2301

AlogP: 3.56

#Rotatable Bonds: 1

Polar Surface Area: 55.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.81

CX Basic pKa: ┄

CX LogP: 3.34

CX LogD: 3.34

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.80

Np Likeness Score: 3.05

References

1. Ren J, Wang YG, Wang AG, Wu LQ, Zhang HJ, Wang WJ, Su YL, Qin HL..  (2015)  Cembranoids from the Gum Resin of Boswellia carterii as Potential Antiulcerative Colitis Agents.,  78  (10): [PMID:26457560] [10.1021/acs.jnatprod.5b00104]

Source

Source(1):

• Scientific Literature