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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:27 UTC
Update Date2022-03-07 02:52:13 UTC
HMDB IDHMDB0029611
Secondary Accession Numbers
  • HMDB29611
Metabolite Identification
Common NameAsparagusic acid
DescriptionAsparagusic acid, also known as asparagusate, 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 exists in all living organisms, ranging from bacteria to humans. Asparagusic acid has been detected, but not quantified in, asparagus (Asparagus officinalis) and green vegetables. This could make asparagusic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Asparagusic acid.
Structure
Data?1600369497
Synonyms
ValueSource
AsparagusateChEBI
1,2-Dithiolane-4-carboxylateKegg
1,2-Dithiolane-4-carboxylic acidGenerator
1,2-Dithiacyclopentane-4-carboxylic acidHMDB
Asparagusic acidHMDB
Chemical FormulaC4H6O2S2
Average Molecular Weight150.219
Monoisotopic Molecular Weight149.980920816
IUPAC Name1,2-dithiolane-4-carboxylic acid
Traditional Nameasparagusic acid
CAS Registry Number2224-02-4
SMILES
OC(=O)C1CSSC1
InChI Identifier
InChI=1S/C4H6O2S2/c5-4(6)3-1-7-8-2-3/h3H,1-2H2,(H,5,6)
InChI KeyAYGMEFRECNWRJC-UHFFFAOYSA-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDithiolanes
Sub ClassDithiolanecarboxylic acids
Direct Parent1,2-dithiolane-4-carboxylic acids
Alternative Parents
Substituents
  • 1,2-dithiolane-4-carboxylic acid
  • 1,2-dithiolane
  • Organic disulfide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point75.7 - 76.5 °CNot Available
Boiling Point232.00 to 234.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility11230 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.480 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility16.3 g/LALOGPS
logP0.51ALOGPS
logP0.79ChemAxon
logS-0.96ALOGPS
pKa (Strongest Acidic)3.98ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.96 m³·mol⁻¹ChemAxon
Polarizability13.57 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.24131661259
DarkChem[M-H]-121.92231661259
DeepCCS[M+H]+130.80430932474
DeepCCS[M-H]-128.56830932474
DeepCCS[M-2H]-164.36530932474
DeepCCS[M+Na]+139.32130932474
AllCCS[M+H]+128.732859911
AllCCS[M+H-H2O]+124.232859911
AllCCS[M+NH4]+132.832859911
AllCCS[M+Na]+134.032859911
AllCCS[M-H]-129.032859911
AllCCS[M+Na-2H]-131.632859911
AllCCS[M+HCOO]-134.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Asparagusic acidOC(=O)C1CSSC12694.2Standard polar33892256
Asparagusic acidOC(=O)C1CSSC11336.7Standard non polar33892256
Asparagusic acidOC(=O)C1CSSC11445.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Asparagusic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1CSSC11538.5Semi standard non polar33892256
Asparagusic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1CSSC11776.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Asparagusic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6y-9700000000-fa3ab5cfd16223707d6a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Asparagusic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-9610000000-d18b399d9263840adae22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Asparagusic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Asparagusic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asparagusic acid 10V, Positive-QTOFsplash10-0ue9-0900000000-8328216b8a4ae814cbf32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asparagusic acid 20V, Positive-QTOFsplash10-0ue9-2900000000-c05f39b9b98ba14382a32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asparagusic acid 40V, Positive-QTOFsplash10-00di-9500000000-40853e90d1aaf9d03ef32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asparagusic acid 10V, Negative-QTOFsplash10-0udi-3900000000-55e81631466ad34ae53e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asparagusic acid 20V, Negative-QTOFsplash10-0wms-7900000000-3861c63829c12ac606fe2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asparagusic acid 40V, Negative-QTOFsplash10-0ue9-9400000000-2c0e39286992c94c2d882015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asparagusic acid 10V, Positive-QTOFsplash10-0udi-0900000000-02c2674a1528431c7f882021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asparagusic acid 20V, Positive-QTOFsplash10-0pc0-7900000000-564d21ee5ebcd97044b82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asparagusic acid 40V, Positive-QTOFsplash10-0005-9000000000-52813164e9d33f6c90ee2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asparagusic acid 10V, Negative-QTOFsplash10-01ot-0900000000-bfc3f8635b76b27dd7732021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asparagusic acid 20V, Negative-QTOFsplash10-001i-9400000000-b6f8b89f65409275ff4f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asparagusic acid 40V, Negative-QTOFsplash10-001i-9000000000-b54df5fd086565f234a12021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000778
KNApSAcK IDC00000304
Chemspider ID15819
KEGG Compound IDC01892
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAsparagusic acid
METLIN IDNot Available
PubChem Compound16682
PDB IDNot Available
ChEBI ID18091
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1387631
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .