CHEBI:9532 - thiamine(1+) diphosphate

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ChEBI Name thiamine(1+) diphosphate
ChEBI ID CHEBI:9532
Definition A thiamine phosphate that is thiamine(1+) in which the hydroxy group has been replaced by a diphosphate group. It is the active form of vitamin B1 and an essential cofactor for enzymes in key metabolic pathways.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C12H19N4O7P2S
Net Charge +1
Average Mass 425.310
Monoisotopic Mass 425.04442
InChI InChI=1S/C12H18N4O7P2S/c1-8-11(3-4-22-25(20,21)23-24(17,18)19)26-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H4-,13,14,15,17,18,19,20,21)/p+1
InChIKey AYEKOFBPNLCAJY-UHFFFAOYSA-O
SMILES CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=C(N)N=C(C)N=C1
Metabolite of Species Details
Mus musculus (NCBI:txid10090) See: PubMed
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Mus musculus (NCBI:txid10090) From MetaboLights See: MetaboLights Study
Mus musculus (NCBI:txid10090) From MetaboLights See: MetaboLights Study
Arabidopsis thaliana (NCBI:txid3702) See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932) See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) See: PubMed
Homo sapiens (NCBI:txid9606) Found in cerebrospinal fluid (UBERON:0001359). See: PubMed
Homo sapiens (NCBI:txid9606) Found in blood (UBERON:0000178). See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): fundamental metabolite
Any metabolite produced by all living cells.
cofactor
An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).
water-soluble vitamin (role)
Any vitamin that dissolves in water and readily absorbed into tissues for immediate use. Unlike the fat-soluble vitamins, they are not stored in the body and need to be replenished regularly in the diet and will rarely accumulate to toxic levels since they are quickly excreted from the body via urine.
(via B vitamin )
Application(s): 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.
(via B vitamin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing thiamine(1+) diphosphate (CHEBI:9532) has role cofactor (CHEBI:23357)
thiamine(1+) diphosphate (CHEBI:9532) has role fundamental metabolite (CHEBI:78675)
thiamine(1+) diphosphate (CHEBI:9532) is a thiamine phosphate (CHEBI:26945)
thiamine(1+) diphosphate (CHEBI:9532) is a vitamin B1 (CHEBI:26948)
thiamine(1+) diphosphate (CHEBI:9532) is conjugate acid of thiamine(1+) diphosphate(1−) (CHEBI:45931)
Incoming thiamine(1+) diphosphate chloride (CHEBI:18290) has part thiamine(1+) diphosphate (CHEBI:9532)
thiamine(1+) diphosphate(1−) (CHEBI:45931) is conjugate base of thiamine(1+) diphosphate (CHEBI:9532)
IUPAC Name
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-[2-(diphosphooxy)ethyl]-4-methyl-1,3-thiazol-3-ium
Synonyms Sources
3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-(4,6,6-trihydroxy-4,6-dioxido-3,5-dioxa-4,6-diphosphahex-1-yl)thiazolium ChEBI
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium IUPAC
ThDP ChEBI
thiamin diphosphate KEGG COMPOUND
thiamin pyrophosphate KEGG COMPOUND
thiamine diphosphate KEGG COMPOUND
thiamine pyrophosphate PDBeChem
thiamine-pyrophosphate HMDB
ThPP KEGG COMPOUND
TPP KEGG COMPOUND
Manual Xrefs Databases
1100 ChemSpider
C00019627 KNApSAcK
C00068 KEGG COMPOUND
ECMDB01372 ECMDB
FDB022584 FooDB
HMDB0001372 HMDB
Thiamine_pyrophosphate Wikipedia
TPP PDBeChem
YMDB00381 YMDB
View more database links
Registry Numbers Types Sources
136-08-3 CAS Registry Number ChemIDplus
3577792 Beilstein Registry Number Beilstein
3577792 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
19 July 2021