ID: ALA516093

Max Phase: Preclinical

Molecular Formula: C27H41N3O5

Molecular Weight: 487.64

Molecule Type: Small molecule

Representations

Synonyms (1): Beauveriolide I
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](CC(C)C)C(=O)O1

Standard InChI:  InChI=1S/C27H41N3O5/c1-6-7-11-18(4)23-16-24(31)29-21(15-20-12-9-8-10-13-20)26(33)28-19(5)25(32)30-22(14-17(2)3)27(34)35-23/h8-10,12-13,17-19,21-23H,6-7,11,14-16H2,1-5H3,(H,28,33)(H,29,31)(H,30,32)/t18-,19-,21-,22+,23-/m0/s1

Standard InChI Key:  ZKSLFHXTWGEITF-JIORRVSTSA-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: 10.94

CX Basic pKa:

CX LogP: 3.80

CX LogD: 3.80

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.49

Np Likeness Score: 1.72

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, 

Source

Source(3):

• Scientific Literature
• BindingDB Database
• Patent Bioactivity Data