ChemFOnt: Showing chemical card for Orlistat (CFc000009506)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:40 UTC

Chemfont ID

CFc000009506

Molecule Identification

Common Name

Orlistat

Definition

Orlistat is a drug designed to treat obesity. Its primary function is preventing the absorption of fats from the human diet, thereby reducing caloric intake. Orlistat works by inhibiting pancreatic lipase, an enzyme that breaks down triglycerides in the intestine. Without this enzyme, triglycerides from the diet are prevented from being hydrolyzed into absorbable free fatty acids and are excreted undigested.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Tetrahydrolipostatin	ChEBI
(2S)-2-Formamido-4-methylpentanoic acid [(2S)-1-[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]tridecan-2-yl] ester	ChEBI
Alli	ChEBI
N-Formyl-L-leucine (1S)-1-{[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl}dodecyl ester	ChEBI
Orlipastat	ChEBI
Orlistatum	ChEBI
Ro-18-0647	ChEBI
Xenical	ChEBI
(2S)-2-Formamido-4-methylpentanoate [(2S)-1-[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]tridecan-2-yl] ester	Generator
(-)-Tetrahydrolipstatin	HMDB
Tetrahydrolipstatin	HMDB
Roche brand OF orlistat	HMDB
THLP	HMDB
1-((3-Hexyl-4-oxo-2-oxetanyl)methyl)dodecyl-2-formamido-4-methylvalerate	HMDB
GlaxoSmithKline brand OF orlistat	HMDB
Hoffmann-la roche brand OF orlistat	HMDB
Tetrahydrolipastatin	HMDB

Chemical Formula

C₂₉H₅₃NO₅

Average Molecular Weight

495.7348

Monoisotopic Molecular Weight

495.392373811

IUPAC Name

(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S)-2-formamido-4-methylpentanoate

Traditional Name

orlistat

CAS Registry Number

96829-58-2

SMILES

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

InChI Identifier

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

InChI Key

AHLBNYSZXLDEJQ-FWEHEUNISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Leucine and derivatives

Alternative Parents

Substituents

Leucine or derivatives
Alpha-amino acid ester
N-formyl-alpha amino acid or derivatives
N-formyl-alpha-amino acid
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Beta_propiolactone
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Oxetane
Lactone
Oxacycle
Organoheterocyclic compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015215)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	9.2e-05 g/L	ALOGPS
logP	7.61	ALOGPS
logP	8.11	ChemAxon
logS	-6.7	ALOGPS
pKa (Strongest Acidic)	12.74	ChemAxon
pKa (Strongest Basic)	-0.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	81.7 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	139.94 m³·mol⁻¹	ChemAxon
Polarizability	61.12 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0015215

DrugBank ID

DB01083

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2298564

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Orlistat

METLIN ID

Not Available

PubChem Compound

3034010

PDB ID

Not Available

ChEBI ID

94686

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Orlistat (CFc000009506)

MOL for CFc000009506 (Orlistat)

3D MOL for CFc000009506 (Orlistat)

3D SDF for CFc000009506 (Orlistat)

3D-SDF for CFc000009506 (Orlistat)

PDB for CFc000009506 (Orlistat)

3D PDB for CFc000009506 (Orlistat)

SMILES for CFc000009506 (Orlistat)

INCHI for CFc000009506 (Orlistat)

Structure for CFc000009506 (Orlistat)

3D Structure for CFc000009506 (Orlistat)