3-O-Acetyl-28-O-mesylbetulin

ID: ALA1076459

PubChem CID: 12136706

Max Phase: Preclinical

Molecular Formula: C33H54O5S

Molecular Weight: 562.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)[C@@H]1CC[C@]2(COS(C)(=O)=O)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/C33H54O5S/c1-21(2)23-12-17-33(20-37-39(9,35)36)19-18-31(7)24(28(23)33)10-11-26-30(6)15-14-27(38-22(3)34)29(4,5)25(30)13-16-32(26,31)8/h23-28H,1,10-20H2,2-9H3/t23-,24+,25-,26+,27-,28+,30-,31+,32+,33+/m0/s1

Standard InChI Key:  SRWQTBNNXLUBTN-WAEOCRLMSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1076459

   [(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-(methylsulfonyloxymethyl)-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-9-yl] acetate

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: 562.86

Molecular Weight (Monoisotopic): 562.3692

AlogP: 7.55

#Rotatable Bonds: 5

Polar Surface Area: 69.67

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: 6.54

CX LogD: 6.54

Aromatic Rings: ┄

Heavy Atoms: 39

QED Weighted: 0.20

Np Likeness Score: 2.75

References

1. Pohjala L, Alakurtti S, Ahola T, Yli-Kauhaluoma J, Tammela P..  (2009)  Betulin-derived compounds as inhibitors of alphavirus replication.,  72  (11): [PMID:19839605] [10.1021/np9003245]

Source

Source(1):

• Scientific Literature