ChemFOnt: Showing chemical card for 2-(alpha-hydroxyethyl)thiamine diphosphate (CFc000283571)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:36:57 UTC

Chemfont ID

CFc000283571

Molecule Identification

Common Name

2-(alpha-hydroxyethyl)thiamine diphosphate

Definition

2-(alpha-hydroxyethyl)thiamine diphosphate, also known as 2-(α-hydroxyethyl)-tpp, is a member of the class of compounds known as thiamine phosphates. Thiamine phosphates are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group. 2-(alpha-hydroxyethyl)thiamine diphosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 2-(alpha-hydroxyethyl)thiamine diphosphate can be found in a number of food items such as amaranth, wild rice, date, and elliott's blueberry, which makes 2-(alpha-hydroxyethyl)thiamine diphosphate a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(1-Hydroxyethyl)thiamine diphosphate	ChEBI
2-(1-Hydroxyethyl)thiamine diphosphate dianion	ChEBI
2-(1-Hydroxyethyl)thiamine(1+) diphosphate(3-)	ChEBI
2-(1-Hydroxyethyl)thiamine diphosphoric acid	Generator
2-(1-Hydroxyethyl)thiamine diphosphoric acid dianion	Generator
2-(1-Hydroxyethyl)thiamine(1+) diphosphoric acid(3-)	Generator
2-(1-Hydroxyethyl)thiamine diphosphoric acid(2-)	Generator
2-(α-hydroxyethyl)thiamine diphosphoric acid	Generator
2-(Α-hydroxyethyl)thiamine diphosphoric acid	Generator

Chemical Formula

C₁₄H₂₀N₄O₈P₂S

Average Molecular Weight

466.34

Monoisotopic Molecular Weight

466.04880595

IUPAC Name

3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-(1-hydroxyethyl)-4-methyl-5-(2-{[(phosphonatooxy)phosphinato]oxy}ethyl)-1,3-thiazol-3-ium

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(O)C1=[N+](CC2=C(N)N=C(C)N=C2)C(C)=C(CCOP([O-])(=O)OP([O-])([O-])=O)S1

InChI Identifier

InChI=1S/C14H22N4O8P2S/c1-8-12(4-5-25-28(23,24)26-27(20,21)22)29-14(9(2)19)18(8)7-11-6-16-10(3)17-13(11)15/h6,9,19H,4-5,7H2,1-3H3,(H4-,15,16,17,20,21,22,23,24)/p-2

InChI Key

RRUVJGASJONMDY-UHFFFAOYSA-L

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
Organic pyrophosphate
2,4,5-trisubstituted 1,3-thiazole
Aminopyrimidine
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Imidolactam
Heteroaromatic compound
Azole
Thiazole
Secondary alcohol
Azacycle
Hydrocarbon derivative
Amine
Organic oxide
Primary amine
Alcohol
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Aromatic alcohol
Organic oxygen compound
Organic anion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organophosphate oxoanion (CHEBI:58939 )
a small molecule (2-ALPHA-HYDROXYETHYL-THPP )

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.27 g/L	ALOGPS
logP	-0.67	ALOGPS
logP	-6.9	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	1.78	ChemAxon
pKa (Strongest Basic)	5.53	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	197.69 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	113.21 m³·mol⁻¹	ChemAxon
Polarizability	41.33 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

External Links

HMDB ID

HMDB0304055

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030315

KNApSAcK ID

Not Available

Chemspider ID

21233048

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

58939

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 2-(alpha-hydroxyethyl)thiamine diphosphate (CFc000283571)

MOL for CFc000283571 (2-(alpha-hydroxyethyl)thiamine diphosphate)

3D MOL for CFc000283571 (2-(alpha-hydroxyethyl)thiamine diphosphate)

3D SDF for CFc000283571 (2-(alpha-hydroxyethyl)thiamine diphosphate)

3D-SDF for CFc000283571 (2-(alpha-hydroxyethyl)thiamine diphosphate)

PDB for CFc000283571 (2-(alpha-hydroxyethyl)thiamine diphosphate)

3D PDB for CFc000283571 (2-(alpha-hydroxyethyl)thiamine diphosphate)

SMILES for CFc000283571 (2-(alpha-hydroxyethyl)thiamine diphosphate)

INCHI for CFc000283571 (2-(alpha-hydroxyethyl)thiamine diphosphate)

Structure for CFc000283571 (2-(alpha-hydroxyethyl)thiamine diphosphate)

3D Structure for CFc000283571 (2-(alpha-hydroxyethyl)thiamine diphosphate)