Compound: Triheptanoin
SMILES: O=C(OC(COC(=O)CCCCCC)COC(=O)CCCCCC)CCCCCC
InChIKey: PJHKBYALYHRYSK-UHFFFAOYSA-N
Synonyms: Triheptanoin, 620-67-7, Trioenanthoin, Trienanthoin, Triheptylin, Glycerol triheptanoate, Triheptanoic glyceride, Heptanoin, tri-, Dermofeel TC 7, GLYCERYL TRIHEPTANOATE, Dojolvi, 2,3-di(heptanoyloxy)propyl heptanoate, UX007, glyceroltriheptanoate, Dub thg, Dermofeel tc-7, Radiamuls 2375, Lanol 37 t, triheptanoina, triheptanoine, Heptanoic acid, 1,2,3-propanetriyl ester, 2P6O7CFW5K, UX-007, Heptanoic acid, 1,1',1''-(1,2,3-propanetriyl) ester, 1,3-bis(heptanoyloxy)propan-2-yl heptanoate, triheptanoinum, RefChem:57618, 210-647-2, Propane-1,2,3-triyl triheptanoate, Glycerol trienanthate, Triheptanoin [USAN], MFCD00042910, 1,2,3-propanetriyl triheptanoate, BRN 1807724, Lanol 37T, Glycerol-triheptanoate-, Propane-1,2,3-triyl trisheptanoate, EINECS 210-647-2, UNII-2P6O7CFW5K, 3-02-00-00769 (Beilstein Handbook Reference), Dojolvi (TN), Triheptanoin (Standard), TRIHEPTANOIN [MI], Triheptanoin (JAN/USAN), TRIHEPTANOIN [INN], EC 210-647-2, SCHEMBL525618, TRIHEPTANOIN [WHO-DD], Glycerol trienanthate, >=94%, orb1306942, CHEMBL4297585, SCHEMBL29026262, GTPL11431, DTXSID40862306, PJHKBYALYHRYSK-UHFFFAOYSA-N, Propane-1,2,3-triyltriheptanoate, GLXC-23231, HMS5087P05, TRIHEPTANOIN [ORANGE BOOK], HY-W013136R, EBC-27065, AKOS027320524, CS-W013852, DB11677, HY-W013136, IND106011; UX007, DA-78617, LS-15081, SY125872, NS00002549, A11580, D11465, EN300-19627495, F791276, Q414576, Propane-1,2,3-triyl triheptanoate; Glyceryl triheptanoate
Theoretical properties:
molecular_formula: C24H44O6
molecular_weight: 428.6 g/mol
exact_mass: 428.31378912 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 23
heavy_atom_count: 30
topological_polar_surface_area: 78.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chembl: TRIHEPTANOIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Triheptanoin, sold under the brand name Dojolvi, is a medication for the treatment of children and adults with molecularly confirmed long-chain fatty acid oxidation disorders (LC-FAOD).
The most common adverse reactions include abdominal pain, diarrhea, vomiting, and nausea.
Triheptanoin was approved for medical use in the United States in June 2020.
Triheptanoin is a triglyceride that is composed of three seven-carbon (C7:0) fatty acids. These odd-carbon fatty acids are able to provide anaplerotic substrates for the TCA cycle. Triheptanoin is used clinically in humans to treat inherited metabolic diseases, such as pyruvate carboxylase deficiency and carnitine palmitoyltransferase II deficiency. It also appears to increase the efficacy of the ketogenic diet as a treatment for epilepsy.
Since triheptanoin is composed of odd-carbon fatty acids, it can produce ketone bodies with five carbon atoms, as opposed to even-carbon fatty acids which are metabolized to ketone bodies with four carbon atoms. The five-carbon ketones produced from triheptanoin are beta-ketopentanoate and beta-hydroxypentanoate. Each of these ketone bodies easily crosses the blood–brain barrier and enters the brain.