Record Information
Version1.0
Creation date2010-04-08 22:08:04 UTC
Update date2020-02-24 19:10:54 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
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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAllithiamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-8933000000-5863edf885acb6aa491dSpectrum
Predicted GC-MSAllithiamine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9738100000-988a1868bf948a98f819Spectrum
Predicted GC-MSAllithiamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05g1-4988000000-478fc1fca9712b55c99a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-6955000000-15f9fe0ab0f1565e606e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-4900000000-c3dba0a95a3c7199de862016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1139000000-0d86bae122907dbc2ce72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-5090000000-12bed19c4a0f0760784e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9320000000-6f8d2321e8baf30a6d302016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0198000000-93e54a05050e9d0407532021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fy6-1491000000-7f660b8e7968b1da3b392021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9710000000-21431b57ba2ccc9f0a192021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dr-1390000000-bd43d3fc6749b4a3a6572021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-cacf3688494c154d10432021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0229-9200000000-8bb76307a0b6cce5fefc2021-09-23View Spectrum
NMRNot Available
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
Food Biomarker OntologyNot Available
VMH 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 that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.DUKE
Anti-alcoholic52217 An agent that reduces alcohol cravings and withdrawal symptoms, commonly used in managing alcohol dependence and addiction, aiding in the treatment of alcohol use disorder by blocking the rewarding aspects of alcohol consumption.DUKE
Anti-Alzheimeran52217 An agent that inhibits the progression of Alzheimer's disease, reducing beta-amyloid plaque formation and neuroinflammation. Therapeutically, it improves cognitive function and memory, commonly used in managing mild to moderate Alzheimer's disease and other neurodegenerative disorders.DUKE
Anti-anorectic50780 An agent that stimulates appetite, used to treat conditions like cachexia and anorexia nervosa, promoting weight gain and improving nutritional status in patients with chronic diseases or eating disorders.DUKE
Anti backache52217 An agent that alleviates back pain, reducing inflammation and muscle spasms. Its biological role involves blocking pain pathways and relaxing muscles. Therapeutically, it's used to manage back pain, sciatica, and musculoskeletal disorders, providing relief and improving mobility. Key medical uses include treating acute and chronic back pain, and supporting rehabilitation.DUKE
Anti beriberi52217 A thiamine-based agent that prevents or treats beriberi, a disease caused by thiamine deficiency, reducing symptoms such as weakness, nerve damage, and heart problems, commonly used in managing malnutrition and related disorders.DUKE
Anti cardiospasmic38070 An agent that relaxes the muscles in the heart and surrounding blood vessels, reducing spasms. It is used therapeutically to treat conditions such as angina pectoris, coronary artery spasms, and esophageal spasms, providing relief from chest pain and discomfort.DUKE
Anti-colitic52217 An agent that reduces inflammation in the colon, commonly used to manage ulcerative colitis, Crohn's disease, and other inflammatory bowel diseases, promoting healing and relieving symptoms.DUKE
Anti decubiticAn agent that prevents or treats pressure ulcers (bed sores), promoting wound healing and tissue repair, commonly used in managing immobility-related skin injuries.DUKE
Anti deliriant52217 An agent that prevents or treats delirium, a serious disturbance in mental abilities. It plays a biological role in regulating neurotransmitters, and has therapeutic applications in managing confusion, agitation, and hallucinations. Key medical uses include treating delirium in ICU patients, post-operative delirium, and substance withdrawal-induced delirium.DUKE
Antidote50247 An agent that counteracts a poison or toxin, neutralizing its harmful effects. It plays a biological role in reversing toxicity, and has therapeutic applications in treating poisoning, overdose, and envenomation. Key medical uses include emergency treatment for snake bites, drug overdose, and chemical exposure.DUKE
Anti-encephalopathic52217 An agent that protects against encephalopathy, a brain disease or damage. It plays a biological role in reducing brain inflammation and oxidative stress. Therapeutically, it is used to manage conditions such as hepatic encephalopathy, traumatic brain injury, and stroke, helping to improve cognitive function and overall brain health.DUKE
Anti-fatigue52217 An agent that reduces physical and mental exhaustion, enhancing endurance and vitality. It plays a biological role in regulating energy metabolism and mitigating oxidative stress. Therapeutically, anti-fatigue agents are used to manage chronic fatigue syndrome, improve athletic performance, and alleviate symptoms of anemia and other debilitating conditions.DUKE
Anti-gastriticAn agent that reduces stomach inflammation, protecting the gastric lining and relieving symptoms of gastritis, commonly used in managing ulcers, acid reflux, and gastrointestinal disorders.DUKE
Anti heartburnAn agent that relieves symptoms of acid reflux, reducing esophageal irritation and discomfort, commonly used to manage gastroesophageal reflux disease (GERD) and heartburn.DUKE
Anti-herpetic22587 An agent that inhibits the replication of herpes viruses, reducing symptoms and severity of infections. Therapeutically, it is used to treat herpes simplex (HSV-1 and HSV-2) and varicella-zoster virus (VZV) infections, commonly used in managing genital herpes, cold sores, and shingles.DUKE
Anti-migraine52217 An agent that alleviates migraine symptoms, commonly used to treat and prevent migraine headaches by constricting blood vessels and blocking pain pathways, providing relief from severe headaches, nausea, and sensitivity to light and sound.DUKE
Anti-myocarditic38070 An agent that prevents or reduces myocarditis, inflammation of the heart muscle, by inhibiting immune responses or modulating inflammatory pathways. Therapeutically, it is used to manage myocarditis, pericarditis, and other cardiac inflammatory conditions, reducing the risk of heart failure and improving cardiac function.DUKE
Anti neuralgic52217 An agent that relieves nerve pain, reducing inflammation and discomfort. It plays a biological role in blocking pain pathways, and has therapeutic applications in managing conditions like trigeminal neuralgia, shingles, and diabetic neuropathy. Key medical uses include treating severe nerve pain, numbness, and tingling sensations.DUKE
Anti neurasthenic52217 An agent that alleviates symptoms of neurasthenia, a condition characterized by fatigue, anxiety, and depression. It plays a biological role in regulating neurotransmitter balance and stress response. Therapeutically, anti neurasthenics are used to manage chronic fatigue, anxiety disorders, and stress-related conditions, promoting overall mental well-being.DUKE
Anti neuritic52217 An agent that protects nerve tissue, reducing inflammation and promoting nerve regeneration. It plays a biological role in maintaining nerve health and has therapeutic applications in treating conditions such as neuritis, neuralgia, and neuropathy, with key medical uses including pain management and nerve damage repair.DUKE
Anti neuropathicAn agent that relieves symptoms such as pain, numbness, and tingling caused by damage or disease affecting the somatosensory nervous system, commonly used in managing conditions like diabetes, shingles, and nerve injuries.DUKE
Anti poliomyelitic22587 An agent that prevents or treats poliomyelitis, a highly infectious disease caused by the poliovirus. Its biological role is to neutralize or eliminate the virus, and its therapeutic applications include vaccination and immunization. Key medical uses include preventing polio outbreaks and treating infected individuals to reduce paralysis and other complications.DUKE
Insectifuge24852 A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.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).