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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-22 16:56:19 UTC

Update Date

2022-09-22 18:34:37 UTC

HMDB ID

HMDB0301759

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Alliin

Description

Alliin, also known as (S)-S-allyl-L-cysteine sulfoxide or (S)-3-(allylsulphinyl)-L-alanine, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. Alliin is soluble (in water) and a moderately acidic compound (based on its pKa). Alliin can be found in a number of food items such as red rice, mandarin orange (clementine, tangerine), ceylon cinnamon, and olive, which makes alliin a potential biomarker for the consumption of these food products. Garlic has been used since antiquity as a therapeutic remedy for certain conditions now associated with oxygen toxicity, and, when this was investigated, garlic did indeed show strong antioxidant and hydroxyl radical-scavenging properties, it is presumed owing to the alliin contained within. Alliin has also been found to affect immune responses in blood .

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2R)-2-Amino-3-(prop-2-ene-1-sulfinyl)propanoate	Generator
(2R)-2-Amino-3-(prop-2-ene-1-sulphinyl)propanoate	Generator
(2R)-2-Amino-3-(prop-2-ene-1-sulphinyl)propanoic acid	Generator
Alliin, (L-ala)-(R)-isomer	MeSH
Isoalliin	MeSH
Alliin, (L-ala)-(S)-isomer	MeSH
S-(2-Propenyl)cysteine sulfoxide	MeSH
PCSO	MeSH
S-Allylcysteine sulfoxide	MeSH
Alliin, (L-ala)-isomer	MeSH

Chemical Formula

C₆H₁₁NO₃S

Average Molecular Weight

177.221

Monoisotopic Molecular Weight

177.045963913

IUPAC Name

(2R)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid

Traditional Name

3-(allylsulfinyl)alanin

CAS Registry Number

556-27-4

SMILES

N[C@@H](CS(=O)CC=C)C(O)=O

InChI Identifier

InChI=1S/C6H11NO3S/c1-2-3-11(10)4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-,11?/m0/s1

InChI Key

XUHLIQGRKRUKPH-ITZCMCNPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Sulfoxide
Amino acid
Allyl sulfur compound
Sulfinyl compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carbonyl group
Amine
Hydrocarbon derivative
Organic nitrogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:2596 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-2.1	ALOGPS
logP	-3.7	ChemAxon
logS	-0.66	ALOGPS
pKa (Strongest Acidic)	1.84	ChemAxon
pKa (Strongest Basic)	8.45	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.39 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	43.72 m³·mol⁻¹	ChemAxon
Polarizability	17.46 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	139.872	32859911
AllCCS	[M+H-H2O]+	136.154	32859911
AllCCS	[M+Na]+	144.325	32859911
AllCCS	[M+NH4]+	143.329	32859911
AllCCS	[M-H]-	135.764	32859911
AllCCS	[M+Na-2H]-	137.753	32859911
AllCCS	[M+HCOO]-	139.991	32859911
DeepCCS	[M+H]+	133.159	30932474
DeepCCS	[M-H]-	129.331	30932474
DeepCCS	[M-2H]-	166.801	30932474
DeepCCS	[M+Na]+	142.34	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.6954 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.51 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	591.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	315.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	46.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	57.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	291.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	242.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	796.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	638.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	38.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	782.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	187.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	230.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	698.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	442.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	273.2 seconds	40023050

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Alliin,2TMS,isomer #1	C=CCS(=O)C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1600.0	Semi standard non polar	33892256
Alliin,2TMS,isomer #1	C=CCS(=O)C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1891.3	Standard non polar	33892256
Alliin,2TMS,isomer #1	C=CCS(=O)C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1944.8	Standard polar	33892256
Alliin,2TMS,isomer #2	C=CCS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1681.3	Semi standard non polar	33892256
Alliin,2TMS,isomer #2	C=CCS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1905.9	Standard non polar	33892256
Alliin,2TMS,isomer #2	C=CCS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2157.3	Standard polar	33892256
Alliin,3TMS,isomer #1	C=CCS(=O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1727.0	Semi standard non polar	33892256
Alliin,3TMS,isomer #1	C=CCS(=O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2012.8	Standard non polar	33892256
Alliin,3TMS,isomer #1	C=CCS(=O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1853.6	Standard polar	33892256
Alliin,2TBDMS,isomer #1	C=CCS(=O)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2052.7	Semi standard non polar	33892256
Alliin,2TBDMS,isomer #1	C=CCS(=O)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2429.2	Standard non polar	33892256
Alliin,2TBDMS,isomer #1	C=CCS(=O)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2181.0	Standard polar	33892256
Alliin,2TBDMS,isomer #2	C=CCS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2175.9	Semi standard non polar	33892256
Alliin,2TBDMS,isomer #2	C=CCS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2401.5	Standard non polar	33892256
Alliin,2TBDMS,isomer #2	C=CCS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2290.7	Standard polar	33892256
Alliin,3TBDMS,isomer #1	C=CCS(=O)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2452.4	Semi standard non polar	33892256
Alliin,3TBDMS,isomer #1	C=CCS(=O)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2722.4	Standard non polar	33892256
Alliin,3TBDMS,isomer #1	C=CCS(=O)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2220.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Alliin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-102d9a5a1f1fa625f97d	2017-07-27	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alliin 10V, Positive-QTOF	splash10-01si-2900000000-24acd7b523ee4a606a36	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alliin 20V, Positive-QTOF	splash10-000x-9700000000-e75bf2d8b03149e961c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alliin 40V, Positive-QTOF	splash10-0006-9000000000-f3eb54e254975ddaec90	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alliin 10V, Negative-QTOF	splash10-004r-2900000000-4945f8ea6edf677c1cd7	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alliin 20V, Negative-QTOF	splash10-000i-9500000000-78b8b7ac8907d004f235	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alliin 40V, Negative-QTOF	splash10-000j-9100000000-67dfec97d77e9d943fc5	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alliin 10V, Positive-QTOF	splash10-000f-9500000000-8ea3f234c3bfe3df2b0d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alliin 20V, Positive-QTOF	splash10-0006-9100000000-a5db6938dd6bc4d086ac	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alliin 40V, Positive-QTOF	splash10-006y-9000000000-5688c056fa4f9896d8fd	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alliin 10V, Negative-QTOF	splash10-000i-9000000000-4ac0c68cb3c192b2e052	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alliin 20V, Negative-QTOF	splash10-000i-9000000000-02c6e2c53f6107e27313	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alliin 40V, Negative-QTOF	splash10-0002-9000000000-93497b521a88141008ec	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1592041

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Alliin (HMDB0301759)

MOL for HMDB0301759 (Alliin)

3D MOL for HMDB0301759 (Alliin)

3D SDF for HMDB0301759 (Alliin)

3D-SDF for HMDB0301759 (Alliin)

PDB for HMDB0301759 (Alliin)

3D PDB for HMDB0301759 (Alliin)

SMILES for HMDB0301759 (Alliin)

INCHI for HMDB0301759 (Alliin)

Structure for HMDB0301759 (Alliin)

3D Structure for HMDB0301759 (Alliin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra