ContaminantDB: Bisibutiamine

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

Record Information

Version

1.0

Creation Date

2016-05-22 05:51:19 UTC

Update Date

2016-11-09 01:15:56 UTC

Accession Number

CHEM019143

Identification

Common Name

Bisibutiamine

Class

Small Molecule

Description

Sulbutiamine (brand name: Arcalion) is a synthetic derivative of thiamine (vitamin B1). In France, it is used to treat symptoms of weakness or fatigue. It is also sold as a dietary supplement. Sulbutiamine was discovered in Japan as part of an effort to develop useful thiamine derivatives.

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Youvitan	Kegg
Surmenalit	MeSH
Arcalion	MeSH
Bis(2-(isobutyryloxy)ethyl-1-N-((4-amino-2-methylpyrimidin-5-yl)methyl)formamido-2-propene-1-yl)disulfide	MeSH
Enerion	MeSH
2-Isobutyrylthiamine disulfide	MeSH
Sulbuthiamine	MeSH
Sulbutiamin	MeSH
Sulbutiamine	KEGG
[(Z)-4-[(4-amino-2-Methylpyrimidin-5-yl)methyl-formylamino]-3-[[(Z)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-(2-methylpropanoyloxy)pent-2-en-3-yl]disulfanyl]pent-3-enyl] 2-methylpropanoic acid	Generator
[(Z)-4-[(4-amino-2-Methylpyrimidin-5-yl)methyl-formylamino]-3-[[(Z)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-(2-methylpropanoyloxy)pent-2-en-3-yl]disulphanyl]pent-3-enyl] 2-methylpropanoate	Generator
[(Z)-4-[(4-amino-2-Methylpyrimidin-5-yl)methyl-formylamino]-3-[[(Z)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-(2-methylpropanoyloxy)pent-2-en-3-yl]disulphanyl]pent-3-enyl] 2-methylpropanoic acid	Generator
(3Z)-4-{N-[(6-imino-2-methyl-1,6-dihydropyrimidin-5-yl)methyl]formamido}-3-{[(2Z)-2-{n-[(6-imino-2-methyl-1,6-dihydropyrimidin-5-yl)methyl]formamido}-5-[(2-methylpropanoyl)oxy]pent-2-en-3-yl]disulfanyl}pent-3-en-1-yl 2-methylpropanoic acid	Generator
(3Z)-4-{N-[(6-imino-2-methyl-1,6-dihydropyrimidin-5-yl)methyl]formamido}-3-{[(2Z)-2-{n-[(6-imino-2-methyl-1,6-dihydropyrimidin-5-yl)methyl]formamido}-5-[(2-methylpropanoyl)oxy]pent-2-en-3-yl]disulphanyl}pent-3-en-1-yl 2-methylpropanoate	Generator
(3Z)-4-{N-[(6-imino-2-methyl-1,6-dihydropyrimidin-5-yl)methyl]formamido}-3-{[(2Z)-2-{n-[(6-imino-2-methyl-1,6-dihydropyrimidin-5-yl)methyl]formamido}-5-[(2-methylpropanoyl)oxy]pent-2-en-3-yl]disulphanyl}pent-3-en-1-yl 2-methylpropanoic acid	Generator

Chemical Formula

C₃₂H₄₆N₈O₆S₂

Average Molecular Mass

702.890 g/mol

Monoisotopic Mass

702.298 g/mol

CAS Registry Number

3286-46-2

IUPAC Name

(3Z)-4-{N-[(6-imino-2-methyl-1,6-dihydropyrimidin-5-yl)methyl]formamido}-3-{[(2Z)-2-{N-[(6-imino-2-methyl-1,6-dihydropyrimidin-5-yl)methyl]formamido}-5-[(2-methylpropanoyl)oxy]pent-2-en-3-yl]disulfanyl}pent-3-en-1-yl 2-methylpropanoate

Traditional Name

sulbutiamine

SMILES

CC(C)C(=O)OCC\C(SS\C(CCOC(=O)C(C)C)=C(\C)N(CC1=CN=C(C)NC1=N)C=O)=C(/C)N(CC1=CN=C(C)NC1=N)C=O

InChI Identifier

InChI=1S/C32H46N8O6S2/c1-19(2)31(43)45-11-9-27(21(5)39(17-41)15-25-13-35-23(7)37-29(25)33)47-48-28(10-12-46-32(44)20(3)4)22(6)40(18-42)16-26-14-36-24(8)38-30(26)34/h13-14,17-20H,9-12,15-16H2,1-8H3,(H2,33,35,37)(H2,34,36,38)/b27-21-,28-22-

InChI Key

CKHJPWQVLKHBIH-ZDSKVHJSSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aminopyrimidines and derivatives. These are organic compounds containing an amino group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Aminopyrimidines and derivatives

Alternative Parents

Substituents

Aminopyrimidine
Dicarboxylic acid or derivatives
Imidolactam
Heteroaromatic compound
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Carboxylic acid ester
Organic disulfide
Carboxylic acid derivative
Azacycle
Sulfenyl compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Amine
Organopnictogen compound
Carbonyl group
Organosulfur compound
Primary amine
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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	0.11 g/L	ALOGPS
logP	2.73	ALOGPS
logP	-0.082	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8.46	ChemAxon
pKa (Strongest Basic)	3.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	189.7 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	213.52 m³·mol⁻¹	ChemAxon
Polarizability	73.32 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0g4i-3904001300-8643326406a081dee375	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9700034000-45bc9bfcdc1c3c030cc9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-5900000000-f37b64ed4e400998c885	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-4103022900-140a4c48ac8bf03ef9aa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014r-6022391000-95a3dc9aa23cd75977e2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000l-9000110000-58d0175d05fd537fe1d1	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Sulbutiamine

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

20055424

Kegg Compound ID

C12750

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Bisibutiamine (CHEM019143)

Structure for CHEM019143: Bisibutiamine