(3S,2R)-3-[3beta-Acetoxy-28-norlup-20(29)-en-17beta-yl]-oxirane-2-carboxylic acid methyl ester

ID: ALA590488

PubChem CID: 46230769

Max Phase: Preclinical

Molecular Formula: C36H56O5

Molecular Weight: 568.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)[C@@H]1CC[C@]2([C@@H]3O[C@H]3C(=O)OCC)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](OC(C)=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12

Standard InChI:  InChI=1S/C36H56O5/c1-10-39-31(38)29-30(41-29)36-18-13-23(21(2)3)28(36)24-11-12-26-33(7)16-15-27(40-22(4)37)32(5,6)25(33)14-17-35(26,9)34(24,8)19-20-36/h23-30H,2,10-20H2,1,3-9H3/t23-,24+,25-,26+,27-,28+,29+,30+,33-,34+,35+,36-/m0/s1

Standard InChI Key:  RQWDTTBBLJVAJG-OWKALYNRSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA590488

   ethyl (2R,3S)-3-[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-acetyloxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-3a-yl]oxirane-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: 568.84

Molecular Weight (Monoisotopic): 568.4128

AlogP: 7.91

#Rotatable Bonds: 5

Polar Surface Area: 65.13

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 7.33

CX LogD: 7.33

Aromatic Rings: ┄

Heavy Atoms: 41

QED Weighted: 0.19

Np Likeness Score: 2.46

References

1. Csuk R, Barthel A, Kluge R, Ströhl D, Kommera H, Paschke R..  (2010)  Synthesis and biological evaluation of antitumour-active betulin derivatives.,  18  (3): [PMID:20034802] [10.1016/j.bmc.2009.12.024]

Source

Source(1):

• Scientific Literature