2alpha,3beta,23-Tris(acetyloxy)-N-(phenylmethyl)-urs-12-en-28-amide

ID: ALA4277168

PubChem CID: 71467321

Max Phase: Preclinical

Molecular Formula: C43H61NO7

Molecular Weight: 703.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@@]1(C)[C@@H]2CC[C@]3(C)[C@H](CC=C4[C@@H]5[C@@H](C)[C@H](C)CC[C@]5(C(=O)NCc5ccccc5)CC[C@]43C)[C@@]2(C)C[C@@H](OC(C)=O)[C@@H]1OC(C)=O

Standard InChI:  InChI=1S/C43H61NO7/c1-26-17-20-43(38(48)44-24-31-13-11-10-12-14-31)22-21-41(8)32(36(43)27(26)2)15-16-35-39(6)23-33(50-29(4)46)37(51-30(5)47)40(7,25-49-28(3)45)34(39)18-19-42(35,41)9/h10-15,26-27,33-37H,16-25H2,1-9H3,(H,44,48)/t26-,27+,33-,34-,35-,36+,37+,39+,40+,41-,42-,43+/m1/s1

Standard InChI Key:  GJUIQDAWVOGWRT-JSLFXHDISA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA4277168

   [(2R,3R,4R,4aR,6aR,6bS,8aS,11R,12S,12aS,14aR,14bR)-2,3-diacetyloxy-8a-(benzylcarbamoyl)-4,6a,6b,11,12,14b-hexamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picen-4-yl]methyl 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: 703.96

Molecular Weight (Monoisotopic): 703.4448

AlogP: 7.98

#Rotatable Bonds: 7

Polar Surface Area: 108.00

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 0.67

CX LogP: 6.69

CX LogD: 6.69

Aromatic Rings: 1

Heavy Atoms: 51

QED Weighted: 0.17

Np Likeness Score: 2.03

References

1. Kahnt M, Wiemann J, Fischer L, Sommerwerk S, Csuk R..  (2018)  Transformation of asiatic acid into a mitocanic, bimodal-acting rhodamine B conjugate of nanomolar cytotoxicity.,  159  [PMID:30278332] [10.1016/j.ejmech.2018.09.066]

Source

Source(1):

• Scientific Literature