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CHEBI:9532 - thiamine(1+) diphosphate

ChEBI IDCHEBI:9532
ChEBI Namethiamine(1+) diphosphate
Stars
DefinitionA thiamine phosphate that is thiamine(1+) in which the hydroxy group has been replaced by a diphosphate group.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.
Last Modified19 July 2021
DownloadsMolfile
FormulaC12H19N4O7P2S
Net Charge+1
Average Mass425.320
Monoisotopic Mass425.04442
SMILESCc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1
InChIInChI=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
InChIKeyAYEKOFBPNLCAJY-UHFFFAOYSA-O
Wikipedia
Species of MetaboliteComponentSourceComments
Escherichia coli (ncbitaxon:562)
- PubMed (6284709)
- PubMed (21988831)
Arabidopsis thaliana (ncbitaxon:3702) - PubMed (17611796)
Saccharomyces cerevisiae (ncbitaxon:4932) - PubMed (16850348)
Homo sapiens (ncbitaxon:9606)
- PubMed (12111441)
blood (UBERON:0000178) PubMed (17642321)
cerebrospinal fluid (UBERON:0001359) PubMed (12111441)
Mus musculus (ncbitaxon:10090)
- PubMed (6121420)
- PubMed (19425150) Source: BioModels - MODEL1507180067
- MetaboLights (MTBLS225) From MetaboLights
- MetaboLights (MTBLS292) From MetaboLights
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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).
fundamental metabolite  Any metabolite produced by all living cells.
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.
Application:
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
thiamin diphosphateKEGG COMPOUND
thiamine diphosphateKEGG COMPOUND
thiamin pyrophosphateKEGG COMPOUND
TPPKEGG COMPOUND
ThPPKEGG COMPOUND
thiamine-pyrophosphateHMDB
Manual XrefsDatabases
C00068KEGG COMPOUND
C00019627KNApSAcK
TPPPDBeChem
ECMDB01372ECMDB
HMDB0001372HMDB
YMDB00381YMDB
Thiamine_pyrophosphateWikipedia
1100ChemSpider
FDB022584FooDB
Registry NumbersSources
Reaxys:3577792Reaxys
CAS:136-08-3ChemIDplus
Citations