SMILAGENIN ACETATE

ID: ALA3138727

Cas Number: 4947-75-5

PubChem CID: 225766

Max Phase: Preclinical

Molecular Formula: C29H46O4

Molecular Weight: 458.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H]4[C@H](C[C@@H]32)O[C@]2(CC[C@@H](C)CO2)[C@H]4C)C1

Standard InChI:  InChI=1S/C29H46O4/c1-17-8-13-29(31-16-17)18(2)26-25(33-29)15-24-22-7-6-20-14-21(32-19(3)30)9-11-27(20,4)23(22)10-12-28(24,26)5/h17-18,20-26H,6-16H2,1-5H3/t17-,18+,20-,21+,22-,23+,24+,25+,26+,27+,28+,29-/m1/s1

Standard InChI Key:  LVRAKYNQYKVPIK-BSPYNPCNSA-N

Molfile:  

     RDKit          2D

 39 44  0  0  0  0  0  0  0  0999 V2000
    0.3843    0.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4708    1.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3843   -0.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7681   -0.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1640    0.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4379    0.4722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6582    0.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0542   -0.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3294   -0.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1640   -0.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6582    1.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7681   -1.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3294    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0542    0.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4708   -0.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3294   -1.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8987   -2.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4708   -1.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0542   -1.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9061   -1.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1956   -1.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4668   -3.0183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4549    1.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1956   -0.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7658    0.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4766    2.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3243   -3.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7662   -1.9884    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0542   -1.0117    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3294    0.2210    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3843   -1.0117    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0707   -0.4948    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9505    0.0816    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8998    2.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1853    2.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4708    2.0549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1853    0.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8998    1.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6143    2.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 11  1  0
  3  1  1  0
  4  8  1  0
  5  1  1  0
  6  7  1  0
  7  5  1  0
  8 14  1  0
  9  3  1  0
 10  3  1  0
 11  5  1  0
 12  4  1  0
 13  1  1  0
 14 13  1  0
 15  4  1  0
 16  9  1  0
 17 20  1  0
 12 18  1  0
 19 16  1  0
 21 20  1  1
 21 24  1  0
 22 17  2  0
  1 23  1  1
 24 15  1  0
  4 25  1  1
 11 26  1  6
 27 17  1  0
  7 10  1  0
  9  8  1  0
  2  6  1  0
 12 19  1  0
 18 21  1  0
 12 28  1  1
  8 29  1  6
  9 30  1  1
  3 31  1  6
  7 32  1  6
  5 33  1  6
  2 36  1  6
  2 37  1  0
 34 35  1  0
 35 36  1  0
 37 38  1  0
 38 34  1  0
 34 39  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3138727

   Smilagenin acetate

Molecule Features

Natural Product: Yes

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: 458.68

Molecular Weight (Monoisotopic): 458.3396

AlogP: 6.36

#Rotatable Bonds: 1

Polar Surface Area: 44.76

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.77

CX LogD: 5.77

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.43

Np Likeness Score: 2.89

References

1. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

Source

Source(1):

• Scientific Literature