Vibusambucin A; 12beta,17alpha-dihydroxy-20,21,22,23,24,25,26,27-octanordammar-3,15-dione

ID: ALA4097443

PubChem CID: 137662246

Max Phase: Preclinical

Molecular Formula: C22H34O4

Molecular Weight: 362.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)C(=O)CC[C@]2(C)[C@H]3C[C@@H](O)[C@@H]4[C@H](O)CC(=O)[C@@]4(C)[C@]3(C)CC[C@@H]12

Standard InChI:  InChI=1S/C22H34O4/c1-19(2)14-6-9-21(4)15(20(14,3)8-7-16(19)25)10-12(23)18-13(24)11-17(26)22(18,21)5/h12-15,18,23-24H,6-11H2,1-5H3/t12-,13-,14+,15-,18-,20+,21-,22-/m1/s1

Standard InChI Key:  OJTDRFXIVHDTOA-VCPKPJSLSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    7.1666   -8.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7583   -7.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3454   -8.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0499   -6.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0499   -7.3041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7619   -6.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4740   -6.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4704   -7.3041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1792   -7.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8960   -7.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1862   -6.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8995   -6.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9166   -4.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1916   -5.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6299   -5.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6165   -6.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3984   -6.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8951   -5.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4201   -5.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4666   -5.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8916   -5.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4625   -8.1249    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1790   -6.8916    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6249   -4.4291    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6082   -6.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3356   -7.7169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9267   -4.0098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6877   -4.2344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6405   -7.1408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  4  6  1  0
  5  2  1  0
  2  8  1  0
  7  6  1  0
  7  8  1  0
  7 11  1  0
  8  9  1  0
  9 10  1  0
 10 12  1  0
 11 12  1  0
 11 14  1  0
 12 16  1  0
 15 13  1  0
 13 14  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
  7 20  1  1
 12 21  1  1
  8 22  1  6
 11 23  1  6
 15 24  1  1
 16 25  1  6
  5 26  2  0
 13 27  1  1
 19 28  1  6
 17 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4097443

   ---

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: 362.51

Molecular Weight (Monoisotopic): 362.2457

AlogP: 3.14

#Rotatable Bonds: ┄

Polar Surface Area: 74.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.88

CX LogD: 2.88

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.69

Np Likeness Score: 3.04

References

1. Nguyen TT, Truong BN, Doan Thi Mai H, Litaudon M, Nguyen VH, Do Thi T, Chau VM, Pham VC..  (2017)  Cytotoxic dammarane-type triterpenoids from the leaves of Viburnum sambucinum.,  27  (8): [PMID:28318944] [10.1016/j.bmcl.2017.03.014]

Source

Source(1):

• Scientific Literature