3beta-Hydroxy-urs-12-en-28-propargylate

ID: ALA2283544

PubChem CID: 46873065

Max Phase: Preclinical

Molecular Formula: C33H50O3

Molecular Weight: 494.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCOC(=O)[C@]12CC[C@@H](C)[C@H](C)[C@H]1C1=CC[C@@H]3[C@@]4(C)CC[C@H](O)C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)CC2

Standard InChI:  InChI=1S/C33H50O3/c1-9-20-36-28(35)33-17-12-21(2)22(3)27(33)23-10-11-25-30(6)15-14-26(34)29(4,5)24(30)13-16-32(25,8)31(23,7)18-19-33/h1,10,21-22,24-27,34H,11-20H2,2-8H3/t21-,22+,24+,25-,26+,27+,30+,31-,32-,33+/m1/s1

Standard InChI Key:  YPJZTZJGWLTHSA-ABODYXKQSA-N

Molfile:  

     RDKit          2D

 36 40  0  0  0  0  0  0  0  0999 V2000
   20.0666  -13.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0542  -14.1853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3526  -14.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7723  -12.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9369  -14.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4781  -13.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6427  -14.1812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9411  -15.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3526  -12.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2312  -15.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1839  -13.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7847  -12.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7600  -14.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3526  -15.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6427  -13.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4781  -14.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2312  -14.1812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6427  -15.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1962  -12.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5296  -15.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8896  -13.3763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5029  -11.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5296  -14.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2086  -12.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0542  -15.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1839  -14.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3484  -13.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9369  -13.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8143  -16.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6315  -16.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8197  -15.8197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0707  -11.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5152  -10.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8916  -15.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5993  -14.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3011  -14.1853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  1  0
  5  7  1  0
  6  4  1  0
  7 15  1  1
  8  5  1  0
  9  1  2  0
 10  8  1  0
  6 11  1  1
  4 12  1  6
 13  2  1  0
 14  3  1  0
 15  9  1  0
 16  6  1  0
 17  5  1  0
 18 14  1  0
 19  6  1  0
 20 23  1  0
 21 11  2  0
 22 12  1  0
 23 17  1  0
 24 22  1  0
  2 25  1  6
 26 11  1  0
  3 27  1  1
  5 28  1  1
 29 10  1  0
 30 10  1  0
 20 31  1  1
 12 32  1  1
 22 33  1  6
  3  7  1  0
 13 16  1  0
 19 24  1  0
  8 18  1  1
 10 20  1  0
 26 34  1  0
 34 35  1  0
 35 36  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA2283544

   3BETA-HYDROXY-URS-12-EN-28-PROPARGYLATE

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: 494.76

Molecular Weight (Monoisotopic): 494.3760

AlogP: 7.18

#Rotatable Bonds: 2

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.96

CX LogD: 6.96

Aromatic Rings: ┄

Heavy Atoms: 36

QED Weighted: 0.25

Np Likeness Score: 2.70

References

1. Mallavadhani UV, Mahapatra A, Pattnaik B, Vanga N, Suri N, Saxena AK.  (2013)  Synthesis and anti-cancer activity of some novel C-17 analogs of ursolic and oleanolic acids,  22  (3): [10.1007/s00044-012-0106-y]

2. Dang Thi TA, Kim Tuyet NT, Pham The C, Thanh Nguyen H, Ba Thi C, Doan Duy T, D'hooghe M, Van Nguyen T..  (2014)  Synthesis and cytotoxic evaluation of novel ester-triazole-linked triterpenoid-AZT conjugates.,  24  (22): [PMID:25442310] [10.1016/j.bmcl.2014.09.079]

Source

Source(1):

• Scientific Literature