3beta-Hydroxy-urs-12-en-28-methyl acetoacetate

ID: ALA2283545

PubChem CID: 76327281

Max Phase: Preclinical

Molecular Formula: C33H52O5

Molecular Weight: 528.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)COC(=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/C33H52O5/c1-20-11-16-33(28(36)38-19-26(35)37-8)18-17-31(6)22(27(33)21(20)2)9-10-24-30(5)14-13-25(34)29(3,4)23(30)12-15-32(24,31)7/h9,20-21,23-25,27,34H,10-19H2,1-8H3/t20-,21+,23+,24-,25+,27+,30+,31-,32-,33+/m1/s1

Standard InChI Key:  XIHMPCMESUXEIB-XHVSEXIISA-N

Molfile:  

     RDKit          2D

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    4.1561  -28.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5676  -26.3235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4462  -29.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8577  -26.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7446  -28.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1047  -26.7527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.4237  -25.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2693  -28.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3989  -27.9785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5635  -27.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1520  -27.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0294  -29.8976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7303  -24.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1066  -28.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8143  -27.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8143  -27.1613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5220  -28.3871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5220  -29.2043    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
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  6  4  1  0
  7 15  1  1
  8  5  1  0
  9  1  2  0
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  4 12  1  6
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 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  2  0
 35 37  1  0
 37 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2283545

   3BETA-HYDROXY-URS-12-EN-28-METHYL ACETOACETATE

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: 528.77

Molecular Weight (Monoisotopic): 528.3815

AlogP: 6.72

#Rotatable Bonds: 3

Polar Surface Area: 72.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.35

CX LogD: 6.35

Aromatic Rings: ┄

Heavy Atoms: 38

QED Weighted: 0.33

Np Likeness Score: 2.66

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. Wei H, Guo J, Sun X, Gou W, Ning H, Fang Z, Liu Q, Hou W, Li Y..  (2022)  Discovery and radiosensitization research of ursolic acid derivatives as SENP1 inhibitors.,  227  [PMID:34688014] [10.1016/j.ejmech.2021.113918]

Source

Source(1):

• Scientific Literature