[(3S,5R,8R,9R,10R,12R,13R,14R,17R)-12-hydroxy-4,4,8,10,14-pentamethyl-17-[(2R)-2,6,6-trimethyltetrahydropyran-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]-2-[(5-cyano-6-oxo-4-phenyl-1H-pyrimidin-2-yl)sulfanyl]acetate

ID: ALA5271693

Max Phase: Preclinical

Molecular Formula: C43H59N3O5S

Molecular Weight: 730.03

Names and Identifiers

Canonical SMILES:  CC1(C)CCC[C@](C)([C@@H]2CC[C@]3(C)[C@@H]2[C@H](O)C[C@@H]2[C@@]4(C)CC[C@H](OC(=O)CSc5nc(-c6ccccc6)c(C#N)c(=O)[nH]5)C(C)(C)[C@@H]4CC[C@]23C)O1

Standard InChI:  InChI=1S/C43H59N3O5S/c1-38(2)18-12-19-43(8,51-38)28-15-21-42(7)34(28)29(47)23-31-40(5)20-17-32(39(3,4)30(40)16-22-41(31,42)6)50-33(48)25-52-37-45-35(26-13-10-9-11-14-26)27(24-44)36(49)46-37/h9-11,13-14,28-32,34,47H,12,15-23,25H2,1-8H3,(H,45,46,49)/t28-,29-,30+,31-,32+,34+,40+,41-,42-,43-/m1/s1

Standard InChI Key:  LDJAJJAUOXYWGC-SHDMEPQVSA-N

Molfile:  

 
     RDKit          2D

 56 62  0  0  0  0  0  0  0  0999 V2000
   -4.2297   -1.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5151   -1.4078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8033   -1.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8033   -2.6447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5133   -3.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2297   -2.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9444   -3.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6589   -3.4737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5133   -3.8819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0884   -1.4071    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3741   -1.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6593   -1.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0550   -1.8197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7698   -1.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7698   -0.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842   -0.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1989   -0.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1989   -1.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4843   -1.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0709   -2.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8960   -2.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9136   -1.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6280   -1.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6280   -0.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9136   -0.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9136    0.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6282    1.0681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3429    0.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3428   -0.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1257   -0.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6177    0.2522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1470    0.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3605    1.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7771    2.2863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9906    3.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7877    3.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3710    2.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1576    1.9164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7766    3.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1928    3.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9440    1.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9673    0.8194    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330   -0.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6282    1.8934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6280    0.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1989    0.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6593   -0.5820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9444   -1.4074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6592   -1.8199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3710   -1.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3710   -0.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6607   -0.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9444   -0.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1989   -2.2323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4342    1.4754    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8273   -0.9897    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  3  1  0
  5  4  1  0
  1  6  2  0
  6  5  1  0
  6  7  1  0
  7  8  3  0
  5  9  2  0
  3 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 14 13  1  1
 15 14  1  0
 16 15  1  0
 17 16  1  0
 18 17  1  0
 19 18  1  0
 14 19  1  0
 19 20  1  0
 19 21  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
 17 25  1  0
 24 25  1  0
 25 26  1  0
 27 26  1  0
 28 27  1  0
 29 28  1  0
 24 29  1  0
 29 30  1  0
 30 31  1  0
 28 32  1  0
 32 31  1  0
 33 32  1  0
 33 34  1  0
 35 34  1  0
 36 35  1  0
 37 36  1  0
 33 38  1  0
 38 37  1  0
 35 39  1  0
 35 40  1  0
 33 41  1  1
 32 42  1  1
 29 43  1  6
 27 44  1  1
 24 45  1  1
 17 46  1  1
 12 47  2  0
  1 48  1  0
 49 48  2  0
 50 49  1  0
 51 50  2  0
 52 51  1  0
 53 52  2  0
 48 53  1  0
 18 54  1  6
 28 55  1  1
 25 56  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5271693

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 730.03

Molecular Weight (Monoisotopic): 729.4175

AlogP: 8.71

#Rotatable Bonds: 6

Polar Surface Area: 125.30

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 6.79

CX Basic pKa: ┄

CX LogP: 7.43

CX LogD: 6.89

Aromatic Rings: 2

Heavy Atoms: 52

QED Weighted: 0.17

Np Likeness Score: 1.18

References

1. Teng J, Chen Y, Xiao S, Li T, Su G, Wang G, Zhao Y..  (2022)  Novel ginsenoside derivatives induce apoptosis in HepG-2 cells via the MDM2-p53 signaling pathway.,  78  [PMID:36336316] [10.1016/j.bmcl.2022.129045]

Source

Source(1):

• Scientific Literature