Compound: orlistat
SMILES: O=C1O[C@@H](C[C@@H](OC(=O)[C@@H](NC=O)CC(C)C)CCCCCCCCCCC)[C@@H]1CCCCCC
InChIKey: AHLBNYSZXLDEJQ-FWEHEUNISA-N
Synonyms: orlistat, 96829-58-2, Tetrahydrolipstatin, Xenical, Orlipastat, Alli, (-)-Tetrahydrolipstatin, THLP, tetrahydrolipastatin, Ro 18-0647/002, orlistatum, Ro-18-0647/002, (2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S)-2-formamido-4-methylpentanoate, DTXSID8023395, [(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] (2S)-2-formamido-4-methylpentanoate, 95M8R751W8, NSC-758881, Ro-180647002, Ro-180647-002, CHEBI:94686, DTXCID40820067, L-Leucine, N-formyl-, 1-((3-hexyl-4-oxo-2-oxetanyl)methyl)dodecyl ester, (2S-(2alpha(R*),3beta))-, Beacita, ((2S)-1-((2S,3S)-3-hexyl-4-oxooxetan-2-yl)tridecan-2-yl) (2S)-2-formamido-4-methylpentanoate, (2S)-1-((2S,3S)-3-hexyl-4-oxooxetan-2-yl)tridecan-2-yl (2S)-2-formamido-4-methylpentanoate, RefChem:389166, A08AB01, Ro 18 0647, 639-755-1, Orlipastatum [INN-Latin], Orlistat (Alli, Xenical), MFCD05662360, N-Formyl-L-leucine (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester, Orlistat (Standard), L-Leucine, N-formyl-, (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester, Ro-18-0647, C29H53NO5, MLS002207022, N-Formyl-L-leucine, ester with (3S,4S)-3-hexyl-4-((2S)-2-hydroxytridecyl)-2-oxetanone, CHEMBL175247, Orlipastatum, SMR000466339, L-Leucine, N-formyl-, (1S)-1-(((2S,3S)-3-hexyl-4-oxo-2-oxetanyl)methyl)dodecyl ester, [(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate, Orlistat Powder, (S)-(S)-1-((2S,3S)-3-Hexyl-4-oxooxetan-2-yl)tridecan-2-yl 2-formamido-4-methylpentanoate, (2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl N-formyl-L-leucinate, Xenical (TN), CAS-96829-58-2, SR-01000759417, Orlistat [USAN:INN:BAN], UNII-95M8R751W8, HSDB 7556, N-formyl-L-leucine (1S)-1-{[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl}dodecyl ester, NCGC00095128-01, (-)-Tetrahydrolipstatin; Orlistat; Ro 18-0647/002; Tetrahydrolipstatin; Xenical; L-Leucine, N-formyl-, 1-[(3-hexyl-4-oxo-2-oxetanyl)methyl]dodecyl ester, [2S-[2alpha(R*),3beta]]-, KS-1183, Lipase Inhibitor, THL, ORLISTAT [HSDB], ORLISTAT [USAN], ORLISTAT [INN], ORLISTAT [JAN], ORLISTAT [MI], (-)-tetrahydrolipostatin, ORLISTAT [VANDF], R-212, ORLISTAT [MART.], ORLISTAT [USP-RS], ORLISTAT [WHO-DD], Orlistat (JAN/USP/INN), ORLISTAT [EMA EPAR], Orlistat, >=98%, solid, SCHEMBL16408, MLS000759448, MLS001423955, Orlistat - Bio-X trade mark, BIDD:GT0853, ORLISTAT [ORANGE BOOK], GTPL5277, orb1310386, ORLISTAT [USP MONOGRAPH], BDBM24567, HY-B0218R, AHLBNYSZXLDEJQ-FWEHEUNISA-N, Tetrahydrolipstatin;Ro-18-0647, GLXC-05010, HMS2051I08, HMS3413P06, HMS3677P06, (S)-((S)-1-((2S,3S)-3-hexyl-4-oxooxetan-2-yl)tridecan-2-yl) 2-formamido-4-methylpentanoate, HY-B0218, MSK10348, THL, Tox21_111437, EBC-11225, HB4009, s1629, AKOS015894875, Tox21_111437_1, CCG-100851, DB01083, FO26582, NC00101, NSC 758881, Ro18-0647, NCGC00165856-01, NCGC00165856-02, NCGC00165856-03, NCGC00165856-14, NCGC00165856-15, BO164179, R212, SY078600, CS-0694775, NS00004788, O0381, SW197481-2, Ro-18-0647-002, D04028, EN300-268136, AB00639987-09, AB00639987_10, Q424163, SR-01000759417-5, SR-01000759417-7, BRD-K63343048-001-12-2, BRD-K63343048-001-13-0, Z2379810072, Orlistat, United States Pharmacopeia (USP) Reference Standard, Orlistat, Pharmaceutical Secondary Standard; Certified Reference Material, N-formyl-L-leucine (S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester, N-formyl-L-leucine-(S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]-dodecyl ester, (2S)-2-formamido-4-methylpentanoic acid [(2S)-1-[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]tridecan-2-yl] ester, (S)-2-FORMYLAMINO-4-METHYL-PENTANOICACID(S)-1-[[(2S,3S)-3-HEXYL-4-OXO-2-OXETANYL]METHYL]-DODECYLESTER, [(2S)-1-[(2R,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] (2R)-2-formamido-4-methylpentanoate, 104872-04-0, L-LEUCINE, N-FORMYL-, 1-((3-HEXYL-4-OXO-2-OXETANYL)METHYL)DODECYL ESTER, (2S-(2.ALPHA.(R*),3.BETA.))-
Theoretical properties:
molecular_formula: C29H53NO5
molecular_weight: 495.7 g/mol
exact_mass: 495.39237379 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 23
heavy_atom_count: 35
topological_polar_surface_area: 81.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals
color: Crystals
melting_point: 40-50
solubility: Practically insoluble in water, freely soluble in chloroform, and very soluble in methanol and ethanol.
Descriptions:
{"pubchem": "Orlistat is a carboxylic ester resulting from the formal condensation of the carboxy group of N-formyl-L-leucine with the hydroxy group of (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one. A pancreatic lipase inhibitor, it is used as an anti-obesity drug. It has a role as an EC 3.1.1.3 (triacylglycerol lipase) inhibitor, an EC 2.3.1.85 (fatty acid synthase) inhibitor, an anti-obesity agent and a bacterial metabolite. It is a member of formamides, a L-leucine derivative, a carboxylic ester and a beta-lactone.", "chebi": "A carboxylic ester resulting from the formal condensation of the carboxy group of <em>N</em>-formyl-<small>L</small>-leucine with the hydroxy group of (3<i>S</i>,4<i>S</i>)-3-hexyl-4-[(2<i>S</i>)-2-hydroxytridecyl]oxetan-2-one. A pancreatic lipase inhibitor, it is used as an anti-obesity drug.", "chembl": "ORLISTAT is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Orlistat, sold under the brand name Xenical among others, is a medication used to treat obesity. Its primary function is preventing the absorption of fats from the human diet by acting as a lipase inhibitor, thereby reducing caloric intake. It is intended for use in conjunction with a healthcare provider-supervised reduced-calorie diet.\nOrlistat is the saturated derivative of lipstatin, a potent natural inhibitor of pancreatic lipases isolated from the bacterium Streptomyces toxytricini. However, due to its relative simplicity and stability, orlistat was chosen over lipstatin for development as an anti-obesity drug.\nThe effectiveness of orlistat in promoting weight loss is definite but modest. Pooled data from clinical trials suggest that people given orlistat in addition to lifestyle modifications, such as diet and exercise, lose about 2\u20133 kilograms (4\u20137 lb) more than those not taking the drug over the course of a year. Orlistat also modestly reduces blood pressure and appears to prevent the onset of type 2 diabetes, whether from the weight loss itself or other effects. It reduces the incidence of diabetes type II in people who are obese around the same amount that lifestyle changes do.\nBenefits aside, however, orlistat is noted for its gastrointestinal side effects (sometimes referred to as treatment effects), which can include steatorrhea (oily, loose stools). They decrease with time, however, and are the most frequently reported adverse effects of the drug. In Australia, the United States and the European Union, orlistat is available for sale without a prescription. Over-the-counter approval was controversial in the United States, with consumer advocacy group Public Citizen repeatedly opposing it on safety and efficacy grounds. Generic formulations of orlistat are available in some countries. In Australia it has been listed as an S3 medication, available from a pharmacist without a prescription, since 2000."}