Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:08:04 UTC |
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Update date | 2020-02-24 19:10:54 UTC |
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Primary ID | FDB008429 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Allithiamine |
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Description | obtained 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. |
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CAS Number | 554-44-9 |
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Structure | |
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Synonyms | Synonym | Source |
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Allithiamine hydrochloride | MeSH | N-[(4-amino-2-Methyl-5-pyrimidinyl)methyl]-N-[4-hydroxy-1-methyl-2-(2-propenyldithio)-1-butenyl]formamide, 9ci | HMDB | TAD | HMDB | Thiamin-allyl-disulfid | HMDB | 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]formamide | Generator | Allithiamine | MeSH | N-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-N-[4-hydroxy-1-methyl-2-(2-propenyldithio)-1-butenyl]formamide, 9CI | db_source |
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Predicted Properties | |
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Chemical Formula | C15H22N4O2S2 |
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IUPAC name | N-[(4-amino-2-methylpyrimidin-5-yl)methyl]-N-[(2E)-5-hydroxy-3-(prop-2-en-1-yldisulfanyl)pent-2-en-2-yl]formamide |
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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+ |
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InChI Key | WNCAVNGLACHSRZ-SDNWHVSQSA-N |
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Isomeric SMILES | C\C(N(CC1=C(N)N=C(C)N=C1)C=O)=C(\CCO)SSCC=C |
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Average Molecular Weight | 354.491 |
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Monoisotopic Molecular Weight | 354.118417348 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Diazines |
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Sub Class | Pyrimidines and pyrimidine derivatives |
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Direct Parent | Aminopyrimidines and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 50.82%; H 6.26%; N 15.80%; O 9.03%; S 18.09% | DFC |
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Melting Point | Mp 132-133° dec. | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Allithiamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00dl-8933000000-5863edf885acb6aa491d | Spectrum | Predicted GC-MS | Allithiamine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9738100000-988a1868bf948a98f819 | Spectrum | Predicted GC-MS | Allithiamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-05g1-4988000000-478fc1fca9712b55c99a | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00dl-6955000000-15f9fe0ab0f1565e606e | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00di-4900000000-c3dba0a95a3c7199de86 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-1139000000-0d86bae122907dbc2ce7 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-5090000000-12bed19c4a0f0760784e | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9320000000-6f8d2321e8baf30a6d30 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0198000000-93e54a05050e9d040753 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0fy6-1491000000-7f660b8e7968b1da3b39 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00dl-9710000000-21431b57ba2ccc9f0a19 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03dr-1390000000-bd43d3fc6749b4a3a657 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-9000000000-cacf3688494c154d1043 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0229-9200000000-8bb76307a0b6cce5fefc | 2021-09-23 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 14116443 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 3037212 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB31758 |
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CRC / DFC (Dictionary of Food Compounds) ID | DKP23-C:DKP23-C |
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EAFUS ID | Not Available |
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Dr. Duke ID | ALLITHIAMINE|ALLITHIAMIN |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Allithiamine |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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analgesic | 35480 | 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 alcoholic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti Alzheimeran | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti anorectic | 50780 | An agent which regulates the physiologic mechanisms that control the appetite and food intake. | DUKE | anti backache | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti beriberi | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti cardiospasmic | 38070 | 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 colitic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti decubitic | | | DUKE | anti deliriant | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | antidote | 50247 | Any protective agent counteracting or neutralizing the action of poisons. | DUKE | anti encephalopathic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti fatigue | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti gastritic | | | DUKE | anti heartburn | | | DUKE | anti herpetic | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | anti migraine | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti myocarditic | 38070 | 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 neuralgic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti neurasthenic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti neuritic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti neuropathic | | | DUKE | anti poliomyelitic | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | insectifuge | 24852 | 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 | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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