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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:28 UTC

Update Date

2022-03-07 02:52:13 UTC

HMDB ID

HMDB0029612

Secondary Accession Numbers

HMDB29612

Metabolite Identification

Common Name

Asparagusic acid syn-S-oxide

Description

Asparagusic acid syn-S-oxide belongs to the class of organic compounds known as 1,2-dithiolane-4-carboxylic acids. These are organic compounds containing a 1,2-dithiolane ring that bears a carboxylic acid group at the 4-position. Asparagusic acid syn-S-oxide has been detected, but not quantified in, asparagus (Asparagus officinalis). This could make asparagusic acid syn-S-oxide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Asparagusic acid syn-S-oxide.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Asparagusate syn-S-oxide	Generator
(4R)-1-oxo-1Λ⁴,2-dithiolane-4-carboxylate	HMDB

Chemical Formula

C₄H₆O₃S₂

Average Molecular Weight

166.219

Monoisotopic Molecular Weight

165.975835438

IUPAC Name

(4R)-1-oxo-1λ⁴,2-dithiolane-4-carboxylic acid

Traditional Name

(4R)-1-oxo-1λ⁴,2-dithiolane-4-carboxylic acid

CAS Registry Number

42258-87-7

SMILES

OC(=O)[C@@H]1CSS(=O)C1

InChI Identifier

InChI=1S/C4H6O3S2/c5-4(6)3-1-8-9(7)2-3/h3H,1-2H2,(H,5,6)/t3-,9?/m1/s1

InChI Key

WKCDMZVXQHXDPX-ZMQIUWNVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2-dithiolane-4-carboxylic acids. These are organic compounds containing a 1,2-dithiolane ring that bears a carboxylic acid group at the 4-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dithiolanes

Sub Class

Dithiolanecarboxylic acids

Direct Parent

1,2-dithiolane-4-carboxylic acids

Alternative Parents

Substituents

1,2-dithiolane-4-carboxylic acid
1,2-dithiolane
Thiosulfinic acid ester
Sulfinyl compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029612)
Cytoplasm (HMDB: HMDB0029612)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029612)

Source

Endogenous

Endogenous (HMDB: HMDB0029612)

Plant

Plant (HMDB: HMDB0029612)

Exogenous

Food

Food (HMDB: HMDB0029612)

Vegetable

Shoot vegetable

Asparagus (FooDB: FOOD00021)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0029612)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	118 - 120 °C	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	44.5 g/L	ALOGPS
logP	-0.93	ALOGPS
logP	0.088	ChemAxon
logS	-0.57	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.48 m³·mol⁻¹	ChemAxon
Polarizability	14.3 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]+	133.666	31661259
DarkChem	[M-H]-	129.131	31661259
DeepCCS	[M+H]+	132.984	30932474
DeepCCS	[M-H]-	129.937	30932474
DeepCCS	[M-2H]-	166.565	30932474
DeepCCS	[M+Na]+	142.103	30932474
AllCCS	[M+H]+	131.3	32859911
AllCCS	[M+H-H2O]+	127.1	32859911
AllCCS	[M+NH4]+	135.3	32859911
AllCCS	[M+Na]+	136.4	32859911
AllCCS	[M-H]-	131.7	32859911
AllCCS	[M+Na-2H]-	133.8	32859911
AllCCS	[M+HCOO]-	136.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.07 minutes	32390414
Predicted by Siyang on May 30, 2022	8.5108 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.14 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	204.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1064.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	322.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	69.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	208.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	56.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	238.2 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	267.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	542.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	576.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	61.0 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	835.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	206.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	215.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	531.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	283.5 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	259.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Asparagusic acid syn-S-oxide	OC(=O)[C@@H]1CSS(=O)C1	2839.4	Standard polar	33892256
Asparagusic acid syn-S-oxide	OC(=O)[C@@H]1CSS(=O)C1	1480.0	Standard non polar	33892256
Asparagusic acid syn-S-oxide	OC(=O)[C@@H]1CSS(=O)C1	1631.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Asparagusic acid syn-S-oxide,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CSS(=O)C1	1626.7	Semi standard non polar	33892256
Asparagusic acid syn-S-oxide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CSS(=O)C1	1869.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Asparagusic acid syn-S-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9200000000-f901efe803b911ad01b8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Asparagusic acid syn-S-oxide GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9500000000-18c716266397a0a299b8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Asparagusic acid syn-S-oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Asparagusic acid syn-S-oxide 10V, Positive-QTOF	splash10-01b9-0900000000-b9743ea3f5237af52ccc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asparagusic acid syn-S-oxide 20V, Positive-QTOF	splash10-00di-5900000000-d5fa4a65f42eefe09dd9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asparagusic acid syn-S-oxide 40V, Positive-QTOF	splash10-00di-5900000000-f30d9dc8ad1010ac11b5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asparagusic acid syn-S-oxide 10V, Negative-QTOF	splash10-0udi-2900000000-fe760fe9df12da2e7cec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asparagusic acid syn-S-oxide 20V, Negative-QTOF	splash10-03y0-8900000000-8d151e9f2287b24e5b9e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asparagusic acid syn-S-oxide 40V, Negative-QTOF	splash10-0udi-7900000000-c7268dae0fb91c69cf34	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asparagusic acid syn-S-oxide 10V, Negative-QTOF	splash10-03xr-0900000000-f6e6963c47bc2ad790a2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asparagusic acid syn-S-oxide 20V, Negative-QTOF	splash10-0300-8900000000-04dbebe7eaae9cfc764c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asparagusic acid syn-S-oxide 40V, Negative-QTOF	splash10-022a-9000000000-404b7941300e95dd18c1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asparagusic acid syn-S-oxide 10V, Positive-QTOF	splash10-014i-0900000000-d240e6e3b0b10af46dd4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asparagusic acid syn-S-oxide 20V, Positive-QTOF	splash10-0r09-9700000000-a6df372716d3611a2a23	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asparagusic acid syn-S-oxide 40V, Positive-QTOF	splash10-03dl-9000000000-9ca5149e9d41f98c8ab4	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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
Predicted 1D NMR	¹H 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

FDB000780

KNApSAcK ID

C00000302

Chemspider ID

4953976

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131750887

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 Asparagusic acid syn-S-oxide (HMDB0029612)

MOL for HMDB0029612 (Asparagusic acid syn-S-oxide)

3D MOL for HMDB0029612 (Asparagusic acid syn-S-oxide)

3D SDF for HMDB0029612 (Asparagusic acid syn-S-oxide)

3D-SDF for HMDB0029612 (Asparagusic acid syn-S-oxide)

PDB for HMDB0029612 (Asparagusic acid syn-S-oxide)

3D PDB for HMDB0029612 (Asparagusic acid syn-S-oxide)

SMILES for HMDB0029612 (Asparagusic acid syn-S-oxide)

INCHI for HMDB0029612 (Asparagusic acid syn-S-oxide)

Structure for HMDB0029612 (Asparagusic acid syn-S-oxide)

3D Structure for HMDB0029612 (Asparagusic acid syn-S-oxide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra