Vibusambucin B; 3beta,12beta,17alpha-trihydroxy-20,21,22,23,24,25,26,27-octanordammar-15-one

ID: ALA4079407

PubChem CID: 137651743

Max Phase: Preclinical

Molecular Formula: C22H36O4

Molecular Weight: 364.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)[C@@H](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/C22H36O4/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/h12-16,18,23-25H,6-11H2,1-5H3/t12-,13-,14+,15-,16+,18-,20+,21-,22-/m1/s1

Standard InChI Key:  VNSZDCAXCXZALO-XSTTYIRUSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    8.9458   -8.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5374   -7.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1245   -8.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8291   -6.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8291   -7.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5411   -6.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2531   -6.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2496   -7.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9584   -7.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6751   -7.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9654   -6.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6787   -6.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6957   -5.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9708   -5.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4091   -5.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3956   -6.3131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1775   -6.5813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6743   -5.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1992   -5.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2457   -5.8832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6707   -5.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2416   -8.3541    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9583   -7.1207    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4040   -4.6582    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3874   -7.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1148   -7.9460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7059   -4.2390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4670   -4.4636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4196   -7.3700    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  1  1
 13 27  1  1
 19 28  1  6
 17 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4079407

   ---

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: 364.53

Molecular Weight (Monoisotopic): 364.2614

AlogP: 2.93

#Rotatable Bonds: ┄

Polar Surface Area: 77.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.31

CX LogD: 2.31

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.62

Np Likeness Score: 3.02

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