(2R,4aS,6aS,12bR,14aS,14bR)-benzyl 10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylate

ID: ALA1170915

Chembl Id: CHEMBL1170915

PubChem CID: 24861322

Max Phase: Preclinical

Molecular Formula: C36H44O4

Molecular Weight: 540.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(O)C(=O)C=C2C1=CC=C1[C@@]2(C)CC[C@@]2(C)[C@@H]3C[C@](C)(C(=O)OCc4ccccc4)CC[C@]3(C)CC[C@]12C

Standard InChI:  InChI=1S/C36H44O4/c1-23-25-12-13-28-34(4,26(25)20-27(37)30(23)38)17-19-36(6)29-21-33(3,15-14-32(29,2)16-18-35(28,36)5)31(39)40-22-24-10-8-7-9-11-24/h7-13,20,29,38H,14-19,21-22H2,1-6H3/t29-,32-,33-,34+,35-,36+/m1/s1

Standard InChI Key:  QVCXDBCRBHXXAD-WFVGHVPHSA-N

Alternative Forms

1. Parent:

   

   ALA1170915

   benzyl (2R,4aS,6aR,6aS,14aS,14bR)-10-hydroxy-2,4a,6a,6a,9,14a-hexamethyl-11-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate

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: 540.74

Molecular Weight (Monoisotopic): 540.3240

AlogP: 8.36

#Rotatable Bonds: 3

Polar Surface Area: 63.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.75

CX Basic pKa: ┄

CX LogP: 7.20

CX LogD: 7.20

Aromatic Rings: 1

Heavy Atoms: 40

QED Weighted: 0.39

Np Likeness Score: 2.56

References

1. Sun H, Xu L, Yu P, Jiang J, Zhang G, Wang Y..  (2010)  Synthesis and preliminary evaluation of neuroprotection of celastrol analogues in PC12 cells.,  20  (13): [PMID:20627556] [10.1016/j.bmcl.2010.05.066]

2. Shan WG, Wang HG, Chen Y, Wu R, Wen YT, Zhang LW, Ying YM, Wang JW, Zhan ZJ..  (2017)  Synthesis of 3- and 29-substituted celastrol derivatives and structure-activity relationship studies of their cytotoxic activities.,  27  (15): [PMID:28587825] [10.1016/j.bmcl.2017.05.083]

3. Salvador JAR, Leal AS, Valdeira AS, Gonçalves BMF, Alho DPS, Figueiredo SAC, Silvestre SM, Mendes VIS..  (2017)  Oleanane-, ursane-, and quinone methide friedelane-type triterpenoid derivatives: Recent advances in cancer treatment.,  142  [PMID:28754470] [10.1016/j.ejmech.2017.07.013]

4. He QW,Feng JH,Hu XL,Long H,Huang XF,Jiang ZZ,Zhang XQ,Ye WC,Wang H.  (2020)  Synthesis and Biological Evaluation of Celastrol Derivatives as Potential Immunosuppressive Agents.,  83  (9.0): [PMID:32822186] [10.1021/acs.jnatprod.0c00067]

5. Hu XL, He QW, Long H, Zhang LX, Wang R, Wang BL, Feng JH, Wang Q, Hou JQ, Zhang XQ, Ye WC, Wang H..  (2021)  Synthesis and Biological Evaluation of Celastrol Derivatives with Improved Cytotoxic Selectivity and Antitumor Activities.,  84  (7.0): [PMID:34170694] [10.1021/acs.jnatprod.1c00262]

Source

Source(1):

• Scientific Literature