((1R,3aS,5aR,5bR,9S,11aS,11bR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-3a-yl)methyl 3-(prop-2-ynylcarbamoyl)benzoate

ID: ALA4856456

PubChem CID: 164610854

Max Phase: Preclinical

Molecular Formula: C41H57NO4

Molecular Weight: 627.91

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C#CCNC(=O)c1cccc(C(=O)OC[C@]23CC[C@@H](C(=C)C)[C@@H]2[C@H]2CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]2(C)CC3)c1

Standard InChI:  InChI=1S/C41H57NO4/c1-9-23-42-35(44)27-11-10-12-28(24-27)36(45)46-25-41-20-15-29(26(2)3)34(41)30-13-14-32-38(6)18-17-33(43)37(4,5)31(38)16-19-40(32,8)39(30,7)21-22-41/h1,10-12,24,29-34,43H,2,13-23,25H2,3-8H3,(H,42,44)/t29-,30+,31-,32+,33-,34+,38-,39+,40+,41+/m0/s1

Standard InChI Key:  ADWJKMWXTNQKGS-RDNVVGNZSA-N

Molfile:  

 
     RDKit          2D

 50 55  0  0  0  0  0  0  0  0999 V2000
   15.2124  -21.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8041  -21.0416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3913  -21.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0958  -19.8082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0958  -20.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8078  -19.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5199  -19.8082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5209  -20.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2319  -21.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9465  -20.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2298  -19.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9474  -19.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9462  -18.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2260  -18.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6636  -18.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6625  -19.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3757  -19.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0945  -19.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3778  -18.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0948  -18.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7152  -18.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3816  -17.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5552  -17.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0066  -16.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2659  -15.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1986  -16.8909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3814  -21.0460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5125  -18.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9416  -18.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8041  -18.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2249  -20.2166    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.3708  -18.9749    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.5166  -21.4541    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.6583  -20.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6583  -17.7416    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.5199  -18.5729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2330  -18.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2306  -19.8126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9488  -18.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6601  -18.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3753  -18.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3783  -17.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6600  -17.3427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9478  -17.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0883  -18.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0854  -19.8231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8042  -18.5881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5173  -19.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2331  -18.5930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9416  -18.1750    0.0000 C   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
 15 19  1  0
 16 17  1  0
 17 18  1  0
 18 20  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
 23 24  1  6
 24 25  2  0
 24 26  1  0
  5 27  1  1
  7 28  1  1
 12 29  1  1
 20 30  1  1
 11 31  1  6
 19 32  1  6
  8 33  1  6
 16 34  1  6
 15 35  1  1
 30 36  1  0
 36 37  1  0
 37 38  2  0
 37 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 43 44  2  0
 44 39  1  0
 41 45  1  0
 45 46  2  0
 45 47  1  0
 47 48  1  0
 48 49  1  0
 49 50  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4856456

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 627.91

Molecular Weight (Monoisotopic): 627.4288

AlogP: 8.22

#Rotatable Bonds: 6

Polar Surface Area: 75.63

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 7.96

CX LogD: 7.96

Aromatic Rings: 1

Heavy Atoms: 46

QED Weighted: 0.19

Np Likeness Score: 1.80

References

1. Pęcak P, Orzechowska B, Chrobak E, Boryczka S..  (2021)  Novel betulin dicarboxylic acid ester derivatives as potent antiviral agents: Design, synthesis, biological evaluation, structure-activity relationship and in-silico study.,  225  [PMID:34425312] [10.1016/j.ejmech.2021.113738]

Source

Source(1):

• Scientific Literature