CHEBI:41039 - benfotiamine

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ChEBI Name benfotiamine
ChEBI ID CHEBI:41039
Definition A thioester that is a synthetic analogue of thiamine obtained by acylative cleavage of the thiazole ring and O-phospohorylation.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:31259
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Formula C19H23N4O6PS
Net Charge 0
Average Mass 466.44800
Monoisotopic Mass 466.10759
InChI InChI=1S/C19H23N4O6PS/c1-13(23(12-24)11-16-10-21-14(2)22-18(16)20)17(8-9-29-30(26,27)28)31-19(25)15-6-4-3-5-7-15/h3-7,10,12H,8-9,11H2,1-2H3,(H2,20,21,22)(H2,26,27,28)
InChIKey BTNNPSLJPBRMLZ-UHFFFAOYSA-N
SMILES [H]C(=O)N(Cc1cnc(C)nc1N)C(C)=C(CCOP(O)(O)=O)SC(=O)c1ccccc1
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): immunological adjuvant
A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.
provitamin B1
A provitamin that can be converted into vitamin B1 by enzymes from animal tissues.
Application(s): immunological adjuvant
A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.
nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
protective agent
Synthetic or natural substance which is given to prevent a disease or disorder or are used in the process of treating a disease or injury due to a poisonous agent.
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ChEBI Ontology
Outgoing benfotiamine (CHEBI:41039) has functional parent thiamine(1+) (CHEBI:18385)
benfotiamine (CHEBI:41039) has role antioxidant (CHEBI:22586)
benfotiamine (CHEBI:41039) has role immunological adjuvant (CHEBI:50847)
benfotiamine (CHEBI:41039) has role nutraceutical (CHEBI:50733)
benfotiamine (CHEBI:41039) has role protective agent (CHEBI:50267)
benfotiamine (CHEBI:41039) has role provitamin B1 (CHEBI:72470)
benfotiamine (CHEBI:41039) is a aminopyrimidine (CHEBI:38338)
benfotiamine (CHEBI:41039) is a formamides (CHEBI:24079)
benfotiamine (CHEBI:41039) is a organic phosphate (CHEBI:25703)
benfotiamine (CHEBI:41039) is a thioester (CHEBI:51277)
IUPAC Name
S-[2-{[(4-amino-2-methylpyrimidin-5-yl)methyl](formyl)amino}-5-(phosphonooxy)pent-2-en-3-yl] benzenecarbothioate
INNs Sources
benfotiamina ChemIDplus
benfotiamine KEGG DRUG
benfotiamine WHO MedNet
benfotiaminum ChemIDplus
Synonyms Sources
Benphothiamine ChemIDplus
Benzoylthiamine monophosphate ChemIDplus
Benzoylthiamine O-monophosphate ChemIDplus
N-((4-Amino-2-methyl-5-pyrimidinyl)methyl)-N-(4-hydroxy-2-mercapto-1-methyl-1-butenyl)formamide S-benzoate O-phosphate ChemIDplus
S-Benzoylthiamine monophosphate ChemIDplus
S-Benzoylthiamine O-monophosphate ChemIDplus
Manual Xrefs Databases
Benfotiamine Wikipedia
BFT PDBeChem
D01255 KEGG DRUG
LSM-5213 LINCS
US2006045896 Patent
View more database links
Registry Numbers Types Sources
22457-89-2 CAS Registry Number ChemIDplus
771326 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017