28-O-(N-Acetylanthraniloyl)betulin

ID: ALA1076490

PubChem CID: 23627401

Max Phase: Preclinical

Molecular Formula: C39H57NO4

Molecular Weight: 603.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)[C@@H]1CC[C@]2(COC(=O)c3ccccc3NC(C)=O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12

Standard InChI:  InChI=1S/C39H57NO4/c1-24(2)26-15-20-39(23-44-34(43)27-11-9-10-12-29(27)40-25(3)41)22-21-37(7)28(33(26)39)13-14-31-36(6)18-17-32(42)35(4,5)30(36)16-19-38(31,37)8/h9-12,26,28,30-33,42H,1,13-23H2,2-8H3,(H,40,41)/t26-,28+,30-,31+,32-,33+,36-,37+,38+,39+/m0/s1

Standard InChI Key:  QNDIGNIVTOJCRU-GTUFNTTASA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1076490

   [(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-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]methyl 2-acetamidobenzoate

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: 603.89

Molecular Weight (Monoisotopic): 603.4288

AlogP: 8.82

#Rotatable Bonds: 5

Polar Surface Area: 75.63

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.95

CX Basic pKa: ┄

CX LogP: 8.55

CX LogD: 8.55

Aromatic Rings: 1

Heavy Atoms: 44

QED Weighted: 0.26

Np Likeness Score: 2.04

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