Beauveriolide III

ID: ALA409855

Chembl Id: CHEMBL409855

Cas Number: 221111-70-2

PubChem CID: 9848317

Max Phase: Preclinical

Molecular Formula: C27H41N3O5

Molecular Weight: 487.64

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Beauveriolide III | Beauveriolide III|221111-70-2|CHEMBL409855|(3R,6S,9S,13S)-9-benzyl-3-[(2S)-butan-2-yl]-13-[(2S)-hexan-2-yl]-6-methyl-1-oxa-4,7,10-triazacyclotridecane-2,5,8,11-tetrone|cyclo[L-alanyl-D-alloisoleucyl-(3S,4S)-3-hydroxy-4-methyloctanoyl-L-phenylalanyl]|SCHEMBL16174055|HY-P2792|BDBM50360305|AKOS040755134|CS-0142914

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

Alternative Forms

1. Parent:

   

   ALA409855

   BEAUVERIOLIDE III

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

Calculated 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: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

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