3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-[2-(phosphonooxy)ethyl]thiazolium
Basic information
- CAS
10023-48-0- Standard SMILES
Cc1ncc(C[n+]2csc(CCOP(=O)(O)O)c2C)c(N)n1- InChIKey
HZSAJDVWZRBGIF-UHFFFAOYSA-O- Molecular formula
- C12H18N4O4PS+
- Average molar mass
- 345.34 g/mol
- Monoisotopic mass
- 345.07863824
Overview
Thiamine(1+) monophosphate is a thiamine phosphate that is thiamin(1+) in which the hydroxy group is replaced by a phosphate group. It has a role as an Arabidopsis thaliana metabolite, a mammalian metabolite, a mouse metabolite, a Saccharomyces cerevisiae metabolite, a plant metabolite, an Escherichia coli metabolite and a human metabolite. It is a thiamine phosphate and a vitamin B1. It is a conjugate acid of a thiamine(1+) monophosphate(1-).
Names & identifiers
- Preferred name
- 3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-[2-(phosphonooxy)ethyl]thiazolium
- IUPAC
- 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl dihydrogen phosphate
- English name
- 3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-[2-(phosphonooxy)ethyl]thiazolium
- Molecular formula
- C12H18N4O4PS+
- Molecular weight
- 345.33
Names & synonyms
3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-[2-(phosphonooxy)ethyl]thiazolium3-((4-Amino-2-methyl-5-pyrimidinyl)methyl)-4-methyl-5-(2-(phosphonooxy)ethyl)thiazoliumRefChem:488545thiamin phosphate10023-48-0thiamin monophosphateThMPPhosphothiaminumTiamina monofosfato3-((4-Amino-2-methylpyrimidin-5-yl)methyl)-4-methyl-5-(2-(phosphonooxy)ethyl)thiazol-3-ium2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl dihydrogen phosphateNCGC00164500-01
Show more names
Thiazolium,3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-[2-(phosphonooxy)ethyl]-2-{3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl}ethyl hydrogen phosphate
Aneurine monophosphateThiamin dihydrogenphosphatebmse000699SCHEMBL94444Aneurin-monophosphorsaeureesterCHEBI:9533GTPL4580CHEMBL1236378
Properties
Computed structural properties
- XLogP
- -0.1
- Topological polar surface area
- 151 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 6
- Heavy atoms
- 22
- Formal charge
- 1
- Complexity
- 413
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physical DescriptionSolid
Collision Cross Section
172.53 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
169.7 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
171 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
177.4 Ų [M+Na]+
Physicochemical properties
- Density
- 1.61 at · 1.61 at 20℃
- vapor pressure
- 0.001 · 0.001-0.007Pa at 20-50℃
- solubility
- Methanol (Slightly), Water (Slightly)
- form
- Solid
- LogP
- -3.1 · -3.1-0.39 at 20℃
- Surface tension
- 62.9 mN/m · 62.9mN/m at 999.6mg/L and 20℃
- Dissociation constant
- 0.92 · 0.92-6.22 at 25℃
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Regulatory InformationREACH registered substance: 2-{3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl}ethyl hydrogen phosphate (EC: 600-039-9)
Hazard Classes and CategoriesSkin Sens. 1 (100%)
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H317
- REACH Registrations
- Active
- Precautionary statements
- P261-P272-P280-P302+P352-P333+P313-P321-P363-P501
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Metabolite PathwaysThiamine Metabolism
Applications
UsesThiamine hydrochloride phosphate-d3 was used as a reagent in the redn. of cytochrome c in its reaction with thiamine and its structural analogs.
Additional notes
DefinitionChEBI: Thiamine(1+) monophosphate is a thiamine phosphate that is thiamin(1+) in which the hydroxy group is replaced by a phosphate group. It has a role as a plant metabolite, a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a mouse metabolite, an Arabidopsis thaliana metabolite and a mammalian metabolite. It is a vitamin B1 and a thiamine phosphate. It is a conjugate acid of a thiamine(1+) monophosphate(1-).
Related reactions
3 records
Compound notes
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