ChemFOnt: Showing chemical card for Thiamine triphosphate (CFc000001165)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:44 UTC

Chemfont ID

CFc000001165

Molecule Identification

Common Name

Thiamine triphosphate

Definition

Thiamine triphosphate is the triphosphate ester of thiamine. Thiamine triphosphate (ThTP) was previously considered to be a specific neuroactive form of thiamine. However, it was recently shown that ThTP exists in bacteria, fungi, plants and animals suggesting a much more general cellular role. In particular, it seems to play a role in response to amino acid starvation. In mammals, ThTP is hydrolyzed by a specific thiamine triphosphatase. In Leigh's disease, this compound is present in decreased amounts in the brain due to a metabolic block in its formation.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-(4,6,8,8-trihydroxy-4,6,8-trioxido-3,5,7-trioxa-4,6,8-triphosphaoct-1-yl)-thiazolium	ChEBI
3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-5-{2-[(hydroxy{[hydroxy(phosphonooxy)phosphoryl]oxy}phosphoryl)oxy]ethyl}-4-methyl-1,3-thiazol-3-ium	ChEBI
Thiamin triphosphate	ChEBI
Thiamine triphosphoric acid ester	ChEBI
THTP	ChEBI
TTP	ChEBI
Thiamin triphosphoric acid	Generator
Thiamine triphosphate ester	Generator
Thiamine triphosphoric acid	Generator
Triphosphate, thiamin	MeSH, HMDB
Triphosphate, thiamine	MeSH, HMDB

Chemical Formula

C₁₂H₂₀N₄O₁₀P₃S

Average Molecular Weight

505.294

Monoisotopic Molecular Weight

505.011298106

IUPAC Name

3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy({[hydroxy(phosphonooxy)phosphoryl]oxy})phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium

Traditional Name

thiamin triphosphate

CAS Registry Number

3475-65-8

SMILES

CC1=C(CCOP(O)(=O)OP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=C(N)N=C(C)N=C1

InChI Identifier

InChI=1S/C12H19N4O10P3S/c1-8-11(30-7-16(8)6-10-5-14-9(2)15-12(10)13)3-4-24-28(20,21)26-29(22,23)25-27(17,18)19/h5,7H,3-4,6H2,1-2H3,(H5-,13,14,15,17,18,19,20,21,22,23)/p+1

InChI Key

IWLROWZYZPNOFC-UHFFFAOYSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Thiamine phosphates

Alternative Parents

Substituents

Thiamine-phosphate
4,5-disubstituted 1,3-thiazole
Aminopyrimidine
Monoalkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Imidolactam
Azole
Thiazole
Heteroaromatic compound
Azacycle
Amine
Hydrocarbon derivative
Primary amine
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1,3-thiazolium cation (CHEBI:9534 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0001512)

Source

Endogenous

Endogenous (HMDB: HMDB0001512)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Thiamine Metabolism (HMDB: HMDB0001512)
Thiamine Metabolism (PathBank: SMP0063677)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.37 g/L	ALOGPS
logP	-0.49	ALOGPS
logP	-6.8	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	0.9	ChemAxon
pKa (Strongest Basic)	5.53	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	215.5 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	106.02 m³·mol⁻¹	ChemAxon
Polarizability	41.52 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon