N-Formyl-D-leucine-(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl Ester

ID: ALA458622

Chembl Id: CHEMBL458622

Cas Number: 104872-28-8

PubChem CID: 13817938

Max Phase: Preclinical

Molecular Formula: C29H53NO5

Molecular Weight: 495.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@@H](CC(C)C)NC=O

Standard InChI:  InChI=1S/C29H53NO5/c1-5-7-9-11-12-13-14-15-16-18-24(34-29(33)26(30-22-31)20-23(3)4)21-27-25(28(32)35-27)19-17-10-8-6-2/h22-27H,5-21H2,1-4H3,(H,30,31)/t24-,25-,26+,27-/m0/s1

Standard InChI Key:  AHLBNYSZXLDEJQ-NFGXINMFSA-N

Alternative Forms

1. Parent:

   

   ALA458622

   Leucine orlistat, (-)-

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: 495.75

Molecular Weight (Monoisotopic): 495.3924

AlogP: 6.88

#Rotatable Bonds: 23

Polar Surface Area: 81.70

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.74

CX Basic pKa: ┄

CX LogP: 8.11

CX LogD: 8.11

Aromatic Rings: ┄

Heavy Atoms: 35

QED Weighted: 0.09

Np Likeness Score: 1.18

References

1. Ortar G, Bisogno T, Ligresti A, Morera E, Nalli M, Di Marzo V..  (2008)  Tetrahydrolipstatin analogues as modulators of endocannabinoid 2-arachidonoylglycerol metabolism.,  51  (21): [PMID:18831576] [10.1021/jm800978m]

2. Liu X, Wang Y, Duclos RI, O'Doherty GA..  (2018)  Stereochemical Structure Activity Relationship Studies (S-SAR) of Tetrahydrolipstatin.,  9  (3): [PMID:29541373] [10.1021/acsmedchemlett.8b00050]

3. Point V,Bénarouche A,Zarrillo J,Guy A,Magnez R,Fonseca L,Raux B,Leclaire J,Buono G,Fotiadu F,Durand T,Carrière F,Vaysse C,Couëdelo L,Cavalier JF.  (2016)  Slowing down fat digestion and absorption by an oxadiazolone inhibitor targeting selectively gastric lipolysis.,  123  [PMID:27543878] [10.1016/j.ejmech.2016.08.009]

Source

Source(1):

• Scientific Literature