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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:18 UTC

Update Date

2022-03-07 02:52:09 UTC

HMDB ID

HMDB0029417

Secondary Accession Numbers

HMDB29417

Metabolite Identification

Common Name

Cycloalliin

Description

Cycloalliin belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Cycloalliin has been detected, but not quantified in, several different foods, such as green onion, onion-family vegetables, garden onions (Allium cepa), red onion, and garden onion (var.). This could make cycloalliin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Cycloalliin.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Cycloallin	MeSH
3-Methyl-1,4-thiazane-5-carboxylic acid-1-oxide	MeSH
5-Methyl-3-thiomorpholinecarboxylic acid 1-oxide, 9ci	HMDB
5-Methyl-1-oxo-1λ⁴-thiomorpholine-3-carboxylate	Generator
Cycloalliin	MeSH

Chemical Formula

C₆H₁₁NO₃S

Average Molecular Weight

177.221

Monoisotopic Molecular Weight

177.045963913

IUPAC Name

5-methyl-1-oxo-1λ⁴-thiomorpholine-3-carboxylic acid

Traditional Name

5-methyl-1-oxo-1λ⁴-thiomorpholine-3-carboxylic acid

CAS Registry Number

455-41-4

SMILES

CC1CS(=O)CC(N1)C(O)=O

InChI Identifier

InChI=1S/C6H11NO3S/c1-4-2-11(10)3-5(7-4)6(8)9/h4-5,7H,2-3H2,1H3,(H,8,9)

InChI Key

JYMHODZXTIGVPA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Thiomorpholine-3-carboxylic acid
1,4-thiazinane
Sulfoxide
Amino acid
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Secondary amine
Sulfinyl compound
Organoheterocyclic compound
Azacycle
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Organic nitrogen compound
Amine
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

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
Water Solubility	52.3 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-4	ChemAxon
logS	-0.53	ALOGPS
pKa (Strongest Acidic)	1.26	ChemAxon
pKa (Strongest Basic)	7.79	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	41.89 m³·mol⁻¹	ChemAxon
Polarizability	17.07 Å³	ChemAxon
Number of Rings	1	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
DarkChem	[M+H]+	137.999	31661259
DarkChem	[M-H]-	133.233	31661259
DeepCCS	[M+H]+	131.306	30932474
DeepCCS	[M-H]-	127.475	30932474
DeepCCS	[M-2H]-	164.74	30932474
DeepCCS	[M+Na]+	139.993	30932474
AllCCS	[M+H]+	138.1	32859911
AllCCS	[M+H-H2O]+	133.9	32859911
AllCCS	[M+NH4]+	142.0	32859911
AllCCS	[M+Na]+	143.1	32859911
AllCCS	[M-H]-	133.3	32859911
AllCCS	[M+Na-2H]-	134.8	32859911
AllCCS	[M+HCOO]-	136.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cycloalliin	CC1CS(=O)CC(N1)C(O)=O	3058.4	Standard polar	33892256
Cycloalliin	CC1CS(=O)CC(N1)C(O)=O	1418.8	Standard non polar	33892256
Cycloalliin	CC1CS(=O)CC(N1)C(O)=O	1558.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cycloalliin,1TMS,isomer #1	CC1CS(=O)CC(C(=O)O[Si](C)(C)C)N1	1658.9	Semi standard non polar	33892256
Cycloalliin,1TMS,isomer #2	CC1CS(=O)CC(C(=O)O)N1[Si](C)(C)C	1700.9	Semi standard non polar	33892256
Cycloalliin,2TMS,isomer #1	CC1CS(=O)CC(C(=O)O[Si](C)(C)C)N1[Si](C)(C)C	1713.4	Semi standard non polar	33892256
Cycloalliin,2TMS,isomer #1	CC1CS(=O)CC(C(=O)O[Si](C)(C)C)N1[Si](C)(C)C	1789.8	Standard non polar	33892256
Cycloalliin,1TBDMS,isomer #1	CC1CS(=O)CC(C(=O)O[Si](C)(C)C(C)(C)C)N1	1914.4	Semi standard non polar	33892256
Cycloalliin,1TBDMS,isomer #2	CC1CS(=O)CC(C(=O)O)N1[Si](C)(C)C(C)(C)C	2001.4	Semi standard non polar	33892256
Cycloalliin,2TBDMS,isomer #1	CC1CS(=O)CC(C(=O)O[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C	2219.5	Semi standard non polar	33892256
Cycloalliin,2TBDMS,isomer #1	CC1CS(=O)CC(C(=O)O[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C	2341.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cycloalliin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-c19fb58b8de9b4610c82	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cycloalliin GC-MS (1 TMS) - 70eV, Positive	splash10-00el-9300000000-5b90c0be83f8decf8a0b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cycloalliin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cycloalliin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cycloalliin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cycloalliin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cycloalliin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - Cycloalliin 10V, Positive-QTOF	splash10-004i-0900000000-da896183c9bf8df450df	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloalliin 20V, Positive-QTOF	splash10-01sl-8900000000-682ada8684b8090f3276	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloalliin 40V, Positive-QTOF	splash10-0006-9200000000-1b42ba22c9af8fcd4eb4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloalliin 10V, Negative-QTOF	splash10-01t9-2900000000-fe357d631947ab91f41f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloalliin 20V, Negative-QTOF	splash10-0a4i-9200000000-efc045a11871e7c316e9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloalliin 40V, Negative-QTOF	splash10-0002-9300000000-7515b0068f427240f60f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloalliin 10V, Positive-QTOF	splash10-004i-0900000000-cb152457ebfe3e0f4d46	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloalliin 20V, Positive-QTOF	splash10-03n9-4900000000-f23b089a2c4aef2574dd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloalliin 40V, Positive-QTOF	splash10-03kc-9200000000-bdeea7b8047cc9c02662	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloalliin 10V, Negative-QTOF	splash10-004i-0900000000-74647462bbc23f49b635	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloalliin 20V, Negative-QTOF	splash10-03di-9500000000-2bb2019b64d2851923a6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloalliin 40V, Negative-QTOF	splash10-03el-9000000000-f4d852c7a488a1d50b37	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

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

FDB000512

KNApSAcK ID

C00055438

Chemspider ID

19100864

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3549960

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Cycloalliin (HMDB0029417)

MOL for HMDB0029417 (Cycloalliin)

3D MOL for HMDB0029417 (Cycloalliin)

3D SDF for HMDB0029417 (Cycloalliin)

3D-SDF for HMDB0029417 (Cycloalliin)

PDB for HMDB0029417 (Cycloalliin)

3D PDB for HMDB0029417 (Cycloalliin)

SMILES for HMDB0029417 (Cycloalliin)

INCHI for HMDB0029417 (Cycloalliin)

Structure for HMDB0029417 (Cycloalliin)

3D Structure for HMDB0029417 (Cycloalliin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra