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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:16 UTC
Update Date2022-03-07 02:53:06 UTC
HMDB IDHMDB0031758
Secondary Accession Numbers
  • HMDB31758
Metabolite Identification
Common NameAllithiamine
DescriptionAllithiamine is found in chives as well as garlic (Allium sativum). It imparts a meaty flavour to foods. Allithiamine has vitamin B1 activity. It has been investigated as a dietary supplement to enhance muscle performance in sports. Allithiamine 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.[citation needed
Structure
Data?1563862166
Synonyms
ValueSource
Allithiamine hydrochlorideMeSH
N-[(4-amino-2-Methyl-5-pyrimidinyl)methyl]-N-[4-hydroxy-1-methyl-2-(2-propenyldithio)-1-butenyl]formamide, 9ciHMDB
TADHMDB
Thiamin-allyl-disulfidHMDB
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
AllithiamineMeSH
Chemical FormulaC15H22N4O2S2
Average Molecular Weight354.491
Monoisotopic Molecular Weight354.118417348
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
Traditional NameN-[(4-amino-2-methylpyrimidin-5-yl)methyl]-N-[(2E)-5-hydroxy-3-(prop-2-en-1-yldisulfanyl)pent-2-en-2-yl]formamide
CAS Registry Number554-44-9
SMILES
C\C(N(CC1=C(N)N=C(C)N=C1)C=O)=C(\CCO)SSCC=C
InChI Identifier
InChI=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
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.
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
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point132 - 133 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+183.53431661259
DarkChem[M-H]-182.631661259
DeepCCS[M+H]+181.28230932474
DeepCCS[M-H]-178.92430932474
DeepCCS[M-2H]-212.33130932474
DeepCCS[M+Na]+187.55930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AllithiamineC\C(N(CC1=C(N)N=C(C)N=C1)C=O)=C(\CCO)SSCC=C4284.9Standard polar33892256
AllithiamineC\C(N(CC1=C(N)N=C(C)N=C1)C=O)=C(\CCO)SSCC=C2938.0Standard non polar33892256
AllithiamineC\C(N(CC1=C(N)N=C(C)N=C1)C=O)=C(\CCO)SSCC=C3213.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Allithiamine,1TMS,isomer #1C=CCSS/C(CCO[Si](C)(C)C)=C(\C)N(C=O)CC1=CN=C(C)N=C1N3140.9Semi standard non polar33892256
Allithiamine,1TMS,isomer #2C=CCSS/C(CCO)=C(\C)N(C=O)CC1=CN=C(C)N=C1N[Si](C)(C)C3179.3Semi standard non polar33892256
Allithiamine,2TMS,isomer #1C=CCSS/C(CCO[Si](C)(C)C)=C(\C)N(C=O)CC1=CN=C(C)N=C1N[Si](C)(C)C3154.3Semi standard non polar33892256
Allithiamine,2TMS,isomer #1C=CCSS/C(CCO[Si](C)(C)C)=C(\C)N(C=O)CC1=CN=C(C)N=C1N[Si](C)(C)C2829.3Standard non polar33892256
Allithiamine,2TMS,isomer #2C=CCSS/C(CCO)=C(\C)N(C=O)CC1=CN=C(C)N=C1N([Si](C)(C)C)[Si](C)(C)C3052.8Semi standard non polar33892256
Allithiamine,2TMS,isomer #2C=CCSS/C(CCO)=C(\C)N(C=O)CC1=CN=C(C)N=C1N([Si](C)(C)C)[Si](C)(C)C2862.2Standard non polar33892256
Allithiamine,3TMS,isomer #1C=CCSS/C(CCO[Si](C)(C)C)=C(\C)N(C=O)CC1=CN=C(C)N=C1N([Si](C)(C)C)[Si](C)(C)C3059.8Semi standard non polar33892256
Allithiamine,3TMS,isomer #1C=CCSS/C(CCO[Si](C)(C)C)=C(\C)N(C=O)CC1=CN=C(C)N=C1N([Si](C)(C)C)[Si](C)(C)C2865.3Standard non polar33892256
Allithiamine,1TBDMS,isomer #1C=CCSS/C(CCO[Si](C)(C)C(C)(C)C)=C(\C)N(C=O)CC1=CN=C(C)N=C1N3332.1Semi standard non polar33892256
Allithiamine,1TBDMS,isomer #2C=CCSS/C(CCO)=C(\C)N(C=O)CC1=CN=C(C)N=C1N[Si](C)(C)C(C)(C)C3356.4Semi standard non polar33892256
Allithiamine,2TBDMS,isomer #1C=CCSS/C(CCO[Si](C)(C)C(C)(C)C)=C(\C)N(C=O)CC1=CN=C(C)N=C1N[Si](C)(C)C(C)(C)C3482.9Semi standard non polar33892256
Allithiamine,2TBDMS,isomer #1C=CCSS/C(CCO[Si](C)(C)C(C)(C)C)=C(\C)N(C=O)CC1=CN=C(C)N=C1N[Si](C)(C)C(C)(C)C3233.8Standard non polar33892256
Allithiamine,2TBDMS,isomer #2C=CCSS/C(CCO)=C(\C)N(C=O)CC1=CN=C(C)N=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3433.2Semi standard non polar33892256
Allithiamine,2TBDMS,isomer #2C=CCSS/C(CCO)=C(\C)N(C=O)CC1=CN=C(C)N=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3279.8Standard non polar33892256
Allithiamine,3TBDMS,isomer #1C=CCSS/C(CCO[Si](C)(C)C(C)(C)C)=C(\C)N(C=O)CC1=CN=C(C)N=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3584.2Semi standard non polar33892256
Allithiamine,3TBDMS,isomer #1C=CCSS/C(CCO[Si](C)(C)C(C)(C)C)=C(\C)N(C=O)CC1=CN=C(C)N=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3445.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Allithiamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-8933000000-5863edf885acb6aa491d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Allithiamine GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9738100000-988a1868bf948a98f8192017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Allithiamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allithiamine 10V, Positive-QTOFsplash10-05g1-4988000000-478fc1fca9712b55c99a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allithiamine 20V, Positive-QTOFsplash10-00dl-6955000000-15f9fe0ab0f1565e606e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allithiamine 40V, Positive-QTOFsplash10-00di-4900000000-c3dba0a95a3c7199de862016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allithiamine 10V, Negative-QTOFsplash10-0udi-1139000000-0d86bae122907dbc2ce72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allithiamine 20V, Negative-QTOFsplash10-00di-5090000000-12bed19c4a0f0760784e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allithiamine 40V, Negative-QTOFsplash10-0006-9320000000-6f8d2321e8baf30a6d302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allithiamine 10V, Positive-QTOFsplash10-03di-0198000000-93e54a05050e9d0407532021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allithiamine 20V, Positive-QTOFsplash10-0fy6-1491000000-7f660b8e7968b1da3b392021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allithiamine 40V, Positive-QTOFsplash10-00dl-9710000000-21431b57ba2ccc9f0a192021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allithiamine 10V, Negative-QTOFsplash10-03dr-1390000000-bd43d3fc6749b4a3a6572021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allithiamine 20V, Negative-QTOFsplash10-00di-9000000000-cacf3688494c154d10432021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allithiamine 40V, Negative-QTOFsplash10-0229-9200000000-8bb76307a0b6cce5fefc2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008429
KNApSAcK IDC00054938
Chemspider ID14116443
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAllithiamine
METLIN IDNot Available
PubChem Compound12358373
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .