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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-09 21:01:34 UTC

Update Date

2023-02-21 17:29:44 UTC

HMDB ID

HMDB0060176

Secondary Accession Numbers

HMDB60176

Metabolite Identification

Common Name

(S)-3-Sulfonatolactate

Description

(S)-3-Sulfonatolactate, also known as (2S)-3-sulpholactate or (2S)-3-sulfolactic acid, belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon (S)-3-Sulfonatolactate is an extremely weak basic (essentially neutral) compound (based on its pKa) (S)-3-Sulfonatolactate exists in all living organisms, ranging from bacteria to humans. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S)-3-Sulfolactate	Kegg
(2S)-3-Sulfolactic acid	Generator
(2S)-3-Sulpholactate	Generator
(2S)-3-Sulpholactic acid	Generator
(S)-3-Sulfonatolactic acid	Generator
(S)-3-Sulphonatolactate	Generator
(S)-3-Sulphonatolactic acid	Generator
(S)-3-Sulfolactate	HMDB
(S)-3-Sulpholactate	HMDB
(S)-3-Sulpholactic acid	HMDB

Chemical Formula

C₃H₆O₆S

Average Molecular Weight

170.141

Monoisotopic Molecular Weight

169.988508614

IUPAC Name

(2S)-2-hydroxy-3-sulfopropanoic acid

Traditional Name

(S)-3-sulfolactic acid

CAS Registry Number

Not Available

SMILES

O[C@H](CS(O)(=O)=O)C(O)=O

InChI Identifier

InChI=1S/C3H6O6S/c4-2(3(5)6)1-10(7,8)9/h2,4H,1H2,(H,5,6)(H,7,8,9)/t2-/m1/s1

InChI Key

CQQGIWJSICOUON-UWTATZPHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Alpha hydroxy acids and derivatives

Direct Parent

Alpha hydroxy acids and derivatives

Alternative Parents

Substituents

Alpha-hydroxy acid
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Alkanesulfonic acid
Sulfonyl
Organosulfonic acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Alcohol
Organosulfur compound
Organooxygen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

3-sulfolactic acid (CHEBI:16712 )

Ontology

Not Available

Exogenous (HMDB: HMDB0060176)

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	78.9 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-1.8	ChemAxon
logS	-0.33	ALOGPS
pKa (Strongest Acidic)	-1.6	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	28.78 m³·mol⁻¹	ChemAxon
Polarizability	13.16 Å³	ChemAxon
Number of Rings	0	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]+	136.478	31661259
DarkChem	[M-H]-	129.976	31661259
DeepCCS	[M+H]+	128.212	30932474
DeepCCS	[M-H]-	124.383	30932474
DeepCCS	[M-2H]-	161.962	30932474
DeepCCS	[M+Na]+	137.486	30932474
AllCCS	[M+H]+	137.3	32859911
AllCCS	[M+H-H2O]+	133.5	32859911
AllCCS	[M+NH4]+	141.0	32859911
AllCCS	[M+Na]+	142.0	32859911
AllCCS	[M-H]-	126.4	32859911
AllCCS	[M+Na-2H]-	128.7	32859911
AllCCS	[M+HCOO]-	131.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-3-Sulfonatolactate	O[C@H](CS(O)(=O)=O)C(O)=O	2584.8	Standard polar	33892256
(S)-3-Sulfonatolactate	O[C@H](CS(O)(=O)=O)C(O)=O	1047.9	Standard non polar	33892256
(S)-3-Sulfonatolactate	O[C@H](CS(O)(=O)=O)C(O)=O	1618.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(S)-3-Sulfonatolactate,1TMS,isomer #1	C[Si](C)(C)O[C@H](CS(=O)(=O)O)C(=O)O	1540.3	Semi standard non polar	33892256
(S)-3-Sulfonatolactate,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](O)CS(=O)(=O)O	1513.5	Semi standard non polar	33892256
(S)-3-Sulfonatolactate,1TMS,isomer #3	C[Si](C)(C)OS(=O)(=O)C[C@@H](O)C(=O)O	1549.6	Semi standard non polar	33892256
(S)-3-Sulfonatolactate,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](CS(=O)(=O)O)O[Si](C)(C)C	1621.3	Semi standard non polar	33892256
(S)-3-Sulfonatolactate,2TMS,isomer #2	C[Si](C)(C)O[C@H](CS(=O)(=O)O[Si](C)(C)C)C(=O)O	1678.3	Semi standard non polar	33892256
(S)-3-Sulfonatolactate,2TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](O)CS(=O)(=O)O[Si](C)(C)C	1642.5	Semi standard non polar	33892256
(S)-3-Sulfonatolactate,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](CS(=O)(=O)O[Si](C)(C)C)O[Si](C)(C)C	1757.8	Semi standard non polar	33892256
(S)-3-Sulfonatolactate,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](CS(=O)(=O)O[Si](C)(C)C)O[Si](C)(C)C	1853.3	Standard non polar	33892256
(S)-3-Sulfonatolactate,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](CS(=O)(=O)O[Si](C)(C)C)O[Si](C)(C)C	2058.8	Standard polar	33892256
(S)-3-Sulfonatolactate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H](CS(=O)(=O)O)C(=O)O	1787.9	Semi standard non polar	33892256
(S)-3-Sulfonatolactate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)CS(=O)(=O)O	1786.3	Semi standard non polar	33892256
(S)-3-Sulfonatolactate,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OS(=O)(=O)C[C@@H](O)C(=O)O	1822.2	Semi standard non polar	33892256
(S)-3-Sulfonatolactate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CS(=O)(=O)O)O[Si](C)(C)C(C)(C)C	2061.0	Semi standard non polar	33892256
(S)-3-Sulfonatolactate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H](CS(=O)(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2134.0	Semi standard non polar	33892256
(S)-3-Sulfonatolactate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)CS(=O)(=O)O[Si](C)(C)C(C)(C)C	2093.6	Semi standard non polar	33892256
(S)-3-Sulfonatolactate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CS(=O)(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2375.9	Semi standard non polar	33892256
(S)-3-Sulfonatolactate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CS(=O)(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2697.9	Standard non polar	33892256
(S)-3-Sulfonatolactate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CS(=O)(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2351.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-3-Sulfonatolactate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-ac5dfd8f0e9250dc3102	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-3-Sulfonatolactate GC-MS (2 TMS) - 70eV, Positive	splash10-0072-9450000000-dcb97013486b383cdecd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-3-Sulfonatolactate 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 - (S)-3-Sulfonatolactate 10V, Positive-QTOF	splash10-0uk9-0900000000-d6e8a3e86db3d677cfd5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Sulfonatolactate 20V, Positive-QTOF	splash10-00dr-9400000000-e2ea073d69910ee54245	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Sulfonatolactate 40V, Positive-QTOF	splash10-05fv-9500000000-34b231a76cf1ae0ef83a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Sulfonatolactate 10V, Negative-QTOF	splash10-001i-9300000000-61cf12226e84089a4497	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Sulfonatolactate 20V, Negative-QTOF	splash10-001i-9100000000-9f4242f429a7ee7ef2bf	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Sulfonatolactate 40V, Negative-QTOF	splash10-001i-9000000000-fef63dcc7cebb114eb30	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Sulfonatolactate 10V, Positive-QTOF	splash10-0uki-6900000000-97600a835f7d4be50cbe	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Sulfonatolactate 20V, Positive-QTOF	splash10-000y-9100000000-7e6b781b83d3e73adf5d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Sulfonatolactate 40V, Positive-QTOF	splash10-004i-9000000000-ce270c8270218035d062	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Sulfonatolactate 10V, Negative-QTOF	splash10-001i-9000000000-a6fb8cd4d3dc149be309	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Sulfonatolactate 20V, Negative-QTOF	splash10-001i-9000000000-a6fb8cd4d3dc149be309	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Sulfonatolactate 40V, Negative-QTOF	splash10-001i-9000000000-c5c98abbb0c088facff9	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

Not Available

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C11499

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443233

PDB ID

Not Available

ChEBI ID

16712

Food Biomarker Ontology

Not Available

VMH ID

SL_L

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]

Showing metabocard for (S)-3-Sulfonatolactate (HMDB0060176)

MOL for HMDB0060176 ((S)-3-Sulfonatolactate)

3D MOL for HMDB0060176 ((S)-3-Sulfonatolactate)

3D SDF for HMDB0060176 ((S)-3-Sulfonatolactate)

3D-SDF for HMDB0060176 ((S)-3-Sulfonatolactate)

PDB for HMDB0060176 ((S)-3-Sulfonatolactate)

3D PDB for HMDB0060176 ((S)-3-Sulfonatolactate)

SMILES for HMDB0060176 ((S)-3-Sulfonatolactate)

INCHI for HMDB0060176 ((S)-3-Sulfonatolactate)

Structure for HMDB0060176 ((S)-3-Sulfonatolactate)

3D Structure for HMDB0060176 ((S)-3-Sulfonatolactate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra