ContaminantDB: Benfotiamine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 05:09:14 UTC

Update Date

2016-11-09 01:15:46 UTC

Accession Number

CHEM018316

Identification

Common Name

Benfotiamine

Class

Small Molecule

Description

A thioester that is a synthetic analogue of thiamine obtained by acylative cleavage of the thiazole ring and O-phospohorylation.

Contaminant Sources

STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Benfotiamina	ChEBI
Benfotiaminum	ChEBI
Benphothiamine	ChEBI
Benzoylthiamine monophosphate	ChEBI
Benzoylthiamine O-monophosphate	ChEBI
N-((4-Amino-2-methyl-5-pyrimidinyl)methyl)-N-(4-hydroxy-2-mercapto-1-methyl-1-butenyl)formamide S-benzoate O-phosphate	ChEBI
S-Benzoylthiamine monophosphate	ChEBI
S-Benzoylthiamine O-monophosphate	ChEBI
Benzoylthiamine monophosphoric acid	Generator
Benzoylthiamine O-monophosphoric acid	Generator
N-((4-Amino-2-methyl-5-pyrimidinyl)methyl)-N-(4-hydroxy-2-mercapto-1-methyl-1-butenyl)formamide S-benzoic acid O-phosphoric acid	Generator
S-Benzoylthiamine monophosphoric acid	Generator
S-Benzoylthiamine O-monophosphoric acid	Generator
BTMP-Benfo	MeSH
Neurostop	MeSH
Benfothiamine	MeSH
Milgamma	MeSH

Chemical Formula

C₁₉H₂₃N₄O₆PS

Average Molecular Mass

466.450 g/mol

Monoisotopic Mass

466.108 g/mol

CAS Registry Number

22457-89-2

IUPAC Name

{[3-(benzoylsulfanyl)-4-{N-[(6-imino-2-methyl-1,6-dihydropyrimidin-5-yl)methyl]formamido}pent-3-en-1-yl]oxy}phosphonic acid

Traditional Name

[3-(benzoylsulfanyl)-4-{N-[(4-imino-2-methyl-3H-pyrimidin-5-yl)methyl]formamido}pent-3-en-1-yl]oxyphosphonic acid

SMILES

CC(N(CC1=CN=C(C)NC1=N)C=O)=C(CCOP(O)(O)=O)SC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C19H23N4O6PS/c1-13(23(12-24)11-16-10-21-14(2)22-18(16)20)17(8-9-29-30(26,27)28)31-19(25)15-6-4-3-5-7-15/h3-7,10,12H,8-9,11H2,1-2H3,(H2,20,21,22)(H2,26,27,28)

InChI Key

BTNNPSLJPBRMLZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzoic acids and derivatives. These are organic compounds containing a carboxylic acid substituent attached to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acids and derivatives

Alternative Parents

Substituents

Benzoic acid or derivatives
Thiobenzoic acid or derivatives
Benzoyl
Aminopyrimidine
Monoalkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Imidolactam
Heteroaromatic compound
Tertiary carboxylic acid amide
Thiocarboxylic acid ester
Amino acid or derivatives
Carbothioic s-ester
Carboxamide group
Sulfenyl compound
Azacycle
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Organosulfur compound
Hydrocarbon derivative
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Primary amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

thioester (CHEBI:41039 )
aminopyrimidine (CHEBI:41039 )
formamides (CHEBI:41039 )
organic phosphate (CHEBI:41039 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.039 g/L	ALOGPS
logP	0.95	ALOGPS
logP	-0.58	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	1.66	ChemAxon
pKa (Strongest Basic)	2.91	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	152.38 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	130.32 m³·mol⁻¹	ChemAxon
Polarizability	45.13 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052b-5902000000-eef1fb578efea4856082	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01b9-0819600000-f83de1cf3a67b419c198	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xr-1926000000-669575172de9ec3034f9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-2910000000-6297bd0e72aa5c82736e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03fr-7209300000-53c9b7a14421df34d35b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9011000000-baa459c55802adb04433	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-98917e5bfc9b005b0cfd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0100900000-9469dc9c77e37a9af145	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xr-2925500000-d4a96d31948bf5f7d202	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00e9-4922000000-e8ea330c6095a3ce5c65	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004j-9010100000-c7f77ffa9289fae934c2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-15030017c51fd2fb76a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-2c0e23e32e082d7e1719	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum