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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:43:51 UTC
Update Date2022-03-07 02:54:36 UTC
HMDB IDHMDB0035716
Secondary Accession Numbers
  • HMDB35716
Metabolite Identification
Common NameDihydroasparagusic acid
DescriptionDihydroasparagusic acid belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Dihydroasparagusic acid has been detected, but not quantified in, asparagus (Asparagus officinalis) and green vegetables. This could make dihydroasparagusic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Dihydroasparagusic acid.
Structure
Data?1563862760
Synonyms
ValueSource
3-Mercapto-2-mercaptomethylpropanoateChEBI
3-Mercapto-2-mercaptomethylpropanoic acidGenerator
DihydroasparagusateGenerator
3-mercapto-2-(Mercaptomethyl)-propanoic acidHMDB
3-mercapto-2-[Mercaptomethyl]propionic acidHMDB
3-Sulfanyl-2-(sulfanylmethyl)propanoic acidHMDB
b,B'-dimercaptoisobutyric acidHMDB
Dihydroasparagusic acidMeSH
Chemical FormulaC4H8O2S2
Average Molecular Weight152.235
Monoisotopic Molecular Weight151.99657088
IUPAC Name3-sulfanyl-2-(sulfanylmethyl)propanoic acid
Traditional Name3-sulfanyl-2-(sulfanylmethyl)propanoic acid
CAS Registry Number7634-96-0
SMILES
OC(=O)C(CS)CS
InChI Identifier
InChI=1S/C4H8O2S2/c5-4(6)3(1-7)2-8/h3,7-8H,1-2H2,(H,5,6)
InChI KeyKRHAHEQEKNJCSD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Alkylthiol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point59.5 - 60.5 °CNot Available
Boiling Point305.50 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility32450 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.450 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.68 g/LALOGPS
logP0.63ALOGPS
logP0.96ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.56ChemAxon
pKa (Strongest Basic)-9.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity37.45 m³·mol⁻¹ChemAxon
Polarizability14.95 ųChemAxon
Number of Rings0ChemAxon
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]+132.08731661259
DarkChem[M-H]-126.28631661259
DeepCCS[M+H]+140.4630932474
DeepCCS[M-H]-137.98330932474
DeepCCS[M-2H]-173.8430932474
DeepCCS[M+Na]+149.11530932474
AllCCS[M+H]+133.132859911
AllCCS[M+H-H2O]+129.232859911
AllCCS[M+NH4]+136.832859911
AllCCS[M+Na]+137.832859911
AllCCS[M-H]-134.032859911
AllCCS[M+Na-2H]-137.432859911
AllCCS[M+HCOO]-141.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dihydroasparagusic acidOC(=O)C(CS)CS2995.9Standard polar33892256
Dihydroasparagusic acidOC(=O)C(CS)CS1325.6Standard non polar33892256
Dihydroasparagusic acidOC(=O)C(CS)CS1458.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydroasparagusic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C(CS)CS1437.1Semi standard non polar33892256
Dihydroasparagusic acid,1TMS,isomer #2C[Si](C)(C)SCC(CS)C(=O)O1534.1Semi standard non polar33892256
Dihydroasparagusic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(CS)CS[Si](C)(C)C1585.9Semi standard non polar33892256
Dihydroasparagusic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(CS)CS[Si](C)(C)C1585.2Standard non polar33892256
Dihydroasparagusic acid,2TMS,isomer #2C[Si](C)(C)SCC(CS[Si](C)(C)C)C(=O)O1725.1Semi standard non polar33892256
Dihydroasparagusic acid,2TMS,isomer #2C[Si](C)(C)SCC(CS[Si](C)(C)C)C(=O)O1751.7Standard non polar33892256
Dihydroasparagusic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(CS[Si](C)(C)C)CS[Si](C)(C)C1754.4Semi standard non polar33892256
Dihydroasparagusic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(CS[Si](C)(C)C)CS[Si](C)(C)C1751.7Standard non polar33892256
Dihydroasparagusic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(CS)CS1692.5Semi standard non polar33892256
Dihydroasparagusic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)SCC(CS)C(=O)O1799.3Semi standard non polar33892256
Dihydroasparagusic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(CS)CS[Si](C)(C)C(C)(C)C2096.3Semi standard non polar33892256
Dihydroasparagusic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(CS)CS[Si](C)(C)C(C)(C)C2050.8Standard non polar33892256
Dihydroasparagusic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)SCC(CS[Si](C)(C)C(C)(C)C)C(=O)O2231.4Semi standard non polar33892256
Dihydroasparagusic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)SCC(CS[Si](C)(C)C(C)(C)C)C(=O)O2202.5Standard non polar33892256
Dihydroasparagusic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(CS[Si](C)(C)C(C)(C)C)CS[Si](C)(C)C(C)(C)C2460.0Semi standard non polar33892256
Dihydroasparagusic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(CS[Si](C)(C)C(C)(C)C)CS[Si](C)(C)C(C)(C)C2451.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroasparagusic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4900000000-c270d89929e9b2dab5772017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroasparagusic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-8900000000-614bcbbb6630eaf26c0e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroasparagusic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroasparagusic 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 - Dihydroasparagusic acid 10V, Positive-QTOFsplash10-0udi-0900000000-f42f38d5ef4ea5f7708e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroasparagusic acid 20V, Positive-QTOFsplash10-107i-2900000000-dae5abca84b1f2de91472016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroasparagusic acid 40V, Positive-QTOFsplash10-00di-9300000000-043131f81d0b719137522016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroasparagusic acid 10V, Negative-QTOFsplash10-0gb9-1900000000-5938fcc2f632c623fc632016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroasparagusic acid 20V, Negative-QTOFsplash10-0zfr-3900000000-1b8778cfdeec8e1677df2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroasparagusic acid 40V, Negative-QTOFsplash10-001i-9300000000-0bb1b0c8f55488c3a09b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroasparagusic acid 10V, Negative-QTOFsplash10-0f89-9600000000-5a24d2c4f7adeab2ed7d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroasparagusic acid 20V, Negative-QTOFsplash10-001i-9000000000-942ac689538269d6ca7b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroasparagusic acid 40V, Negative-QTOFsplash10-001i-9000000000-942ac689538269d6ca7b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroasparagusic acid 10V, Positive-QTOFsplash10-0udi-0900000000-71d685f6c846bbc9a2202021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroasparagusic acid 20V, Positive-QTOFsplash10-0fyk-8900000000-c222a327dc55e3ad32722021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroasparagusic acid 40V, Positive-QTOFsplash10-006t-9000000000-ac4538e3d22f38b90a342021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart 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 IDFDB014440
KNApSAcK IDC00000305
Chemspider ID389286
KEGG Compound IDC04371
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440312
PDB IDNot Available
ChEBI ID17919
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1631731
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.. .