ChemFOnt: Showing chemical card for Thiamine monophosphate (CFc000001677)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:21 UTC

Chemfont ID

CFc000001677

Molecule Identification

Common Name

Thiamine monophosphate

Definition

Thiamine monophosphate, also known as thiamin phosphoric acid or TMP, 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. Thiamine monophosphate is a very strong basic compound (based on its pKa). Thiamine monophosphate is one of the five known natural thiamine phosphate derivatives. Thiamine (vitamin B1) is the transport form of the vitamin while the phosphorylated derivatives are the active forms.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
THIAMIN phosphATE	ChEBI
THIAMIN phosphoric acid	Generator
Thiamine monophosphoric acid	Generator
Aneurin-monophosphorsaeureester	HMDB
Aneurine monophosphate	HMDB
Monofosfotiamina	HMDB
monoPhosphoric ester OF thiamine	HMDB
Monophosphothiamine	HMDB
Monophosphothiaminum	HMDB
Phosphothiaminum	HMDB
Thiamin dihydrogenphosphate	HMDB
Thiamin monophosphate	HMDB
Thiamine monophosphate dihydrate	HMDB
Thiamine phosphate	HMDB
Tiamina monofosfato	HMDB
TMP	HMDB
monoPhosphate, thiamine	HMDB
Phosphoester, thiamine	HMDB
Thiamine phosphoester	HMDB

Chemical Formula

C₁₂H₁₇N₄O₄PS

Average Molecular Weight

344.327

Monoisotopic Molecular Weight

344.070812254

IUPAC Name

3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-[2-(hydrogen phosphonooxy)ethyl]-4-methyl-1,3-thiazol-3-ium

Traditional Name

3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-[2-(hydrogen phosphonooxy)ethyl]-4-methyl-1,3-thiazol-3-ium

CAS Registry Number

495-23-8

SMILES

CC1=C(CCOP(O)([O-])=O)SC=[N+]1CC1=CN=C(C)N=C1N

InChI Identifier

InChI=1S/C12H17N4O4PS/c1-8-11(3-4-20-21(17,18)19)22-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H3-,13,14,15,17,18,19)

InChI Key

HZSAJDVWZRBGIF-UHFFFAOYSA-N

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
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 zwitterion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

thiamine phosphate (CHEBI:37574 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0002666)

Non-excretory biofluid

Biofluid or Excreta

Cerebrospinal Fluid (CSF) (PMID: 12111441)
Cerebrospinal fluid (HMDB: HMDB0002666)

Source

Exogenous

Exogenous (HMDB: HMDB0002666)

Food

Animal origin

Poultry

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)

Endogenous

Endogenous (HMDB: HMDB0002666)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Thiamine Metabolism (HMDB: HMDB0002666)
Thiamine Metabolism (PathBank: SMP0063677)
Thiamin Diphosphate Biosynthesis (PathBank: SMP0122222)
Vitamin B1/Thiamine Metabolism (PathBank: SMP0002385)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0002666)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.089 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-5.7	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	1.66	ChemAxon
pKa (Strongest Basic)	5.51	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	125.27 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	83.15 m³·mol⁻¹	ChemAxon
Polarizability	31.96 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon