ID: ALA409855

Max Phase: Preclinical

Molecular Formula: C27H41N3O5

Molecular Weight: 487.64

Molecule Type: Small molecule

Representations

Synonyms (1): Beauveriolide III
Synonyms from Alternative Forms(1):

Canonical SMILES:  CCCC[C@H](C)[C@@H]1CC(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@@H](C)C(=O)N[C@H]([C@@H](C)CC)C(=O)O1

Standard InChI:  InChI=1S/C27H41N3O5/c1-6-8-12-18(4)22-16-23(31)29-21(15-20-13-10-9-11-14-20)26(33)28-19(5)25(32)30-24(17(3)7-2)27(34)35-22/h9-11,13-14,17-19,21-22,24H,6-8,12,15-16H2,1-5H3,(H,28,33)(H,29,31)(H,30,32)/t17-,18-,19-,21-,22-,24+/m0/s1

Standard InChI Key:  VEELKRGSLCNVAR-QVZGIDAOSA-N

Molecule Features

Natural Product: Yes

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

Properties

Molecular Weight: 487.64

Molecular Weight (Monoisotopic): 487.3046

AlogP: 2.89

#Rotatable Bonds: 8

Polar Surface Area: 113.60

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.92

CX Basic pKa:

CX LogP: 3.88

CX LogD: 3.88

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.49

Np Likeness Score: 1.81

References

1. Nagai K, Doi T, Ohshiro T, Sunazuka T, Tomoda H, Takahashi T, Omura S..  (2008)  Synthesis and biological evaluation of a focused library of beauveriolides.,  18  (15): [PMID:18620856] [10.1016/j.bmcl.2008.06.054]

2. Doi T, Muraoka T, Ohshiro T, Matsuda D, Yoshida M, Takahashi T, Omura S, Tomoda H..  (2012)  Conformationally restricted analog and biotin-labeled probe based on beauveriolide III.,  22  (1): [PMID:22079027] [10.1016/j.bmcl.2011.10.045]

3.  (2014)  Method for selectively inhibiting ACAT1 in the treatment of neurodegenerative diseases, 

4.  (2015)  Method for selectively inhibiting ACAT1 in the treatment of alzheimer's disease, 

5. Kapojos MM, Abdjul DB, Yamazaki H, Ohshiro T, Rotinsulu H, Wewengkang DS, Sumilat DA, Tomoda H, Namikoshi M, Uchida R..  (2018)  Callyspongiamides A and B, sterol O-acyltransferase inhibitors, from the Indonesian marine sponge Callyspongia sp.,  28  (10): [PMID:29631961] [10.1016/j.bmcl.2018.03.077]

6. Bhattacharjee P, Rutland N, Iyer MR..  (2022)  Targeting Sterol O-Acyltransferase/Acyl-CoA:Cholesterol Acyltransferase (ACAT): A Perspective on Small-Molecule Inhibitors and Their Therapeutic Potential.,  65  (24.0): [PMID:36473091] [10.1021/acs.jmedchem.2c01265]

Source

Source(3):

• Scientific Literature
• BindingDB Database
• Patent Bioactivity Data