Record Information
Version1.0
Creation date2010-04-08 22:08:04 UTC
Update date2018-05-28 23:18:30 UTC
Primary IDFDB008429
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAllithiamine
Descriptionobtained from garlic (Allium sativum). Imparts meaty flavour to foods. Has vitamin B1 activity. Investigated as a dietary supplement to enhance muscle performance in sports [DFC] Allithiamine (INN), or thiamine allyl disulfide (TAD), is a lipid-soluble form of vitamin B1 which occurs naturally in garlic. It is more bioavailable than the water-soluble form of vitamin B1, thiamine, and is the preferred form to be taken in case of a vitamin deficiency [Wikipedia]. Allithiamine is found in many foods, some of which are soft-necked garlic, wild leek, garlic, and onion-family vegetables.
CAS Number554-44-9
Structure
Thumb
Synonyms
SynonymSource
N-[(2E)-5-Hydroxy-3-(prop-2-en-1-yldisulphanyl)pent-2-en-2-yl]-N-[(6-imino-2-methyl-1,6-dihydropyrimidin-5-yl)methyl]formamideGenerator
N-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-N-[4-hydroxy-1-methyl-2-(2-propenyldithio)-1-butenyl]formamide, 9ciHMDB
TADHMDB
Thiamin-allyl-disulfidHMDB
Allithiamine hydrochlorideMeSH
AllithiamineMeSH
N-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-N-[4-hydroxy-1-methyl-2-(2-propenyldithio)-1-butenyl]formamide, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP1.59ALOGPS
logP0.15ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)15.9ChemAxon
pKa (Strongest Basic)6.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area92.34 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity102.34 m³·mol⁻¹ChemAxon
Polarizability37.76 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H22N4O2S2
IUPAC nameN-[(4-amino-2-methylpyrimidin-5-yl)methyl]-N-[(2E)-5-hydroxy-3-(prop-2-en-1-yldisulfanyl)pent-2-en-2-yl]formamide
InChI IdentifierInChI=1S/C15H22N4O2S2/c1-4-7-22-23-14(5-6-20)11(2)19(10-21)9-13-8-17-12(3)18-15(13)16/h4,8,10,20H,1,5-7,9H2,2-3H3,(H2,16,17,18)/b14-11+
InChI KeyWNCAVNGLACHSRZ-SDNWHVSQSA-N
Isomeric SMILESC\C(N(CC1=C(N)N=C(C)N=C1)C=O)=C(\CCO)SSCC=C
Average Molecular Weight354.491
Monoisotopic Molecular Weight354.118417348
Classification
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentAminopyrimidines and derivatives
Alternative Parents
Substituents
  • Aminopyrimidine
  • Imidolactam
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carboxamide group
  • Organic disulfide
  • Allyl sulfur compound
  • Azacycle
  • Sulfenyl compound
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Primary amine
  • Primary alcohol
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Amine
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 50.82%; H 6.26%; N 15.80%; O 9.03%; S 18.09%DFC
Melting PointMp 132-133° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider ID14116443
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID3037212
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB31758
CRC / DFC (Dictionary of Food Compounds) IDDKP23-C:DKP23-C
EAFUS IDNot Available
Dr. Duke IDALLITHIAMINE|ALLITHIAMIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAllithiamine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anti alcoholic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti Alzheimeran52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti anorectic50780 An agent which regulates the physiologic mechanisms that control the appetite and food intake.DUKE
anti backache52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti beriberi52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cardiospasmic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti colitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti decubiticDUKE
anti deliriant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antidote50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
anti encephalopathic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti fatigue52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti gastriticDUKE
anti heartburnDUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti migraine52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti myocarditic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti neuralgic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti neurasthenic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti neuritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti neuropathicDUKE
anti poliomyelitic22587 A substance that destroys or inhibits replication of viruses.DUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).