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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:43:51 UTC

Update Date

2023-02-21 17:24:52 UTC

HMDB ID

HMDB0035716

Secondary Accession Numbers

HMDB35716

Metabolite Identification

Common Name

Dihydroasparagusic acid

Description

Dihydroasparagusic 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

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Mercapto-2-mercaptomethylpropanoate	ChEBI
3-Mercapto-2-mercaptomethylpropanoic acid	Generator
Dihydroasparagusate	Generator
3-mercapto-2-(Mercaptomethyl)-propanoic acid	HMDB
3-mercapto-2-[Mercaptomethyl]propionic acid	HMDB
3-Sulfanyl-2-(sulfanylmethyl)propanoic acid	HMDB
b,B'-dimercaptoisobutyric acid	HMDB
Dihydroasparagusic acid	MeSH

Chemical Formula

C₄H₈O₂S₂

Average Molecular Weight

152.235

Monoisotopic Molecular Weight

151.99657088

IUPAC Name

3-sulfanyl-2-(sulfanylmethyl)propanoic acid

Traditional Name

3-sulfanyl-2-(sulfanylmethyl)propanoic acid

CAS Registry Number

7634-96-0

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 Key

KRHAHEQEKNJCSD-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acids

Direct Parent

Carboxylic 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 Framework

Aliphatic acyclic compounds

External Descriptors

dithiol (CHEBI:17919 )
sulfur-containing carboxylic acid (CHEBI:17919 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0035716)
Cytoplasm (HMDB: HMDB0035716)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035716)

Source

Exogenous

Exogenous (HMDB: HMDB0035716)

Food

Food (HMDB: HMDB0035716)

Vegetable

Shoot vegetable

Asparagus (FooDB: FOOD00021)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0035716)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035716)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	59.5 - 60.5 °C	Not Available
Boiling Point	305.50 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	32450 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.450 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.68 g/L	ALOGPS
logP	0.63	ALOGPS
logP	0.96	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	4.56	ChemAxon
pKa (Strongest Basic)	-9.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	37.45 m³·mol⁻¹	ChemAxon
Polarizability	14.95 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	132.087	31661259
DarkChem	[M-H]-	126.286	31661259
DeepCCS	[M+H]+	140.46	30932474
DeepCCS	[M-H]-	137.983	30932474
DeepCCS	[M-2H]-	173.84	30932474
DeepCCS	[M+Na]+	149.115	30932474
AllCCS	[M+H]+	133.1	32859911
AllCCS	[M+H-H2O]+	129.2	32859911
AllCCS	[M+NH4]+	136.8	32859911
AllCCS	[M+Na]+	137.8	32859911
AllCCS	[M-H]-	134.0	32859911
AllCCS	[M+Na-2H]-	137.4	32859911
AllCCS	[M+HCOO]-	141.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydroasparagusic acid	OC(=O)C(CS)CS	2995.9	Standard polar	33892256
Dihydroasparagusic acid	OC(=O)C(CS)CS	1325.6	Standard non polar	33892256
Dihydroasparagusic acid	OC(=O)C(CS)CS	1458.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydroasparagusic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(CS)CS	1437.1	Semi standard non polar	33892256
Dihydroasparagusic acid,1TMS,isomer #2	C[Si](C)(C)SCC(CS)C(=O)O	1534.1	Semi standard non polar	33892256
Dihydroasparagusic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(CS)CS[Si](C)(C)C	1585.9	Semi standard non polar	33892256
Dihydroasparagusic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(CS)CS[Si](C)(C)C	1585.2	Standard non polar	33892256
Dihydroasparagusic acid,2TMS,isomer #2	C[Si](C)(C)SCC(CS[Si](C)(C)C)C(=O)O	1725.1	Semi standard non polar	33892256
Dihydroasparagusic acid,2TMS,isomer #2	C[Si](C)(C)SCC(CS[Si](C)(C)C)C(=O)O	1751.7	Standard non polar	33892256
Dihydroasparagusic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CS[Si](C)(C)C)CS[Si](C)(C)C	1754.4	Semi standard non polar	33892256
Dihydroasparagusic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CS[Si](C)(C)C)CS[Si](C)(C)C	1751.7	Standard non polar	33892256
Dihydroasparagusic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CS)CS	1692.5	Semi standard non polar	33892256
Dihydroasparagusic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)SCC(CS)C(=O)O	1799.3	Semi standard non polar	33892256
Dihydroasparagusic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CS)CS[Si](C)(C)C(C)(C)C	2096.3	Semi standard non polar	33892256
Dihydroasparagusic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CS)CS[Si](C)(C)C(C)(C)C	2050.8	Standard non polar	33892256
Dihydroasparagusic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)SCC(CS[Si](C)(C)C(C)(C)C)C(=O)O	2231.4	Semi standard non polar	33892256
Dihydroasparagusic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)SCC(CS[Si](C)(C)C(C)(C)C)C(=O)O	2202.5	Standard non polar	33892256
Dihydroasparagusic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CS[Si](C)(C)C(C)(C)C)CS[Si](C)(C)C(C)(C)C	2460.0	Semi standard non polar	33892256
Dihydroasparagusic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CS[Si](C)(C)C(C)(C)C)CS[Si](C)(C)C(C)(C)C	2451.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroasparagusic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-4900000000-c270d89929e9b2dab577	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroasparagusic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0ab9-8900000000-614bcbbb6630eaf26c0e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroasparagusic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroasparagusic acid 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 - Dihydroasparagusic acid 10V, Positive-QTOF	splash10-0udi-0900000000-f42f38d5ef4ea5f7708e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroasparagusic acid 20V, Positive-QTOF	splash10-107i-2900000000-dae5abca84b1f2de9147	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroasparagusic acid 40V, Positive-QTOF	splash10-00di-9300000000-043131f81d0b71913752	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroasparagusic acid 10V, Negative-QTOF	splash10-0gb9-1900000000-5938fcc2f632c623fc63	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroasparagusic acid 20V, Negative-QTOF	splash10-0zfr-3900000000-1b8778cfdeec8e1677df	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroasparagusic acid 40V, Negative-QTOF	splash10-001i-9300000000-0bb1b0c8f55488c3a09b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroasparagusic acid 10V, Negative-QTOF	splash10-0f89-9600000000-5a24d2c4f7adeab2ed7d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroasparagusic acid 20V, Negative-QTOF	splash10-001i-9000000000-942ac689538269d6ca7b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroasparagusic acid 40V, Negative-QTOF	splash10-001i-9000000000-942ac689538269d6ca7b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroasparagusic acid 10V, Positive-QTOF	splash10-0udi-0900000000-71d685f6c846bbc9a220	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroasparagusic acid 20V, Positive-QTOF	splash10-0fyk-8900000000-c222a327dc55e3ad3272	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroasparagusic acid 40V, Positive-QTOF	splash10-006t-9000000000-ac4538e3d22f38b90a34	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX 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

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

440312

PDB ID

Not Available

ChEBI ID

17919

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1631731

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 Dihydroasparagusic acid (HMDB0035716)

MOL for HMDB0035716 (Dihydroasparagusic acid)

3D MOL for HMDB0035716 (Dihydroasparagusic acid)

3D SDF for HMDB0035716 (Dihydroasparagusic acid)

3D-SDF for HMDB0035716 (Dihydroasparagusic acid)

PDB for HMDB0035716 (Dihydroasparagusic acid)

3D PDB for HMDB0035716 (Dihydroasparagusic acid)

SMILES for HMDB0035716 (Dihydroasparagusic acid)

INCHI for HMDB0035716 (Dihydroasparagusic acid)

Structure for HMDB0035716 (Dihydroasparagusic acid)

3D Structure for HMDB0035716 (Dihydroasparagusic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra