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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 15:17:32 UTC

Update Date

2021-09-23 15:17:32 UTC

HMDB ID

HMDB0302178

Secondary Accession Numbers

None

Metabolite Identification

Common Name

S-Butylcysteine sulfoxide

Description

S-butylcysteine sulfoxide is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. S-butylcysteine sulfoxide is soluble (in water) and a moderately acidic compound (based on its pKa). S-butylcysteine sulfoxide can be found in soft-necked garlic, which makes S-butylcysteine sulfoxide a potential biomarker for the consumption of this food product.

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       8.621   3.017   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.287   3.787   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0       5.954   3.017   0.000  0.00  0.00           S+0
HETATM    4  O   UNK     0       5.954   1.477   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.620   3.787   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.286   3.017   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.953   3.787   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.955   3.787   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.288   3.017   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       9.955   5.327   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       8.621   1.477   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       0.619   3.017   0.000  0.00  0.00           C+0
CONECT    1    2    8   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6   12                                                       
CONECT    8    1    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    1                                                            
CONECT   12    7                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

COMPND    HMDB0302178
HETATM    1  C1  UNL     1      -4.628   0.828  -0.300  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.429   0.111   0.284  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.187   0.419  -0.523  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.024  -0.315   0.097  1.00  0.00           C  
HETATM    5  S1  UNL     1       0.509   0.013  -0.830  1.00  0.00           S  
HETATM    6  O1  UNL     1       0.771   1.521  -0.623  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.797  -0.888  -0.025  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.159  -0.789  -0.598  1.00  0.00           C  
HETATM    9  N1  UNL     1       4.014  -1.630   0.263  1.00  0.00           N  
HETATM   10  C7  UNL     1       3.753   0.538  -0.687  1.00  0.00           C  
HETATM   11  O2  UNL     1       4.806   0.812  -0.033  1.00  0.00           O  
HETATM   12  O3  UNL     1       3.240   1.567  -1.460  1.00  0.00           O  
HETATM   13  H1  UNL     1      -5.313   1.137   0.509  1.00  0.00           H  
HETATM   14  H2  UNL     1      -4.237   1.720  -0.827  1.00  0.00           H  
HETATM   15  H3  UNL     1      -5.146   0.179  -1.024  1.00  0.00           H  
HETATM   16  H4  UNL     1      -3.668  -0.973   0.293  1.00  0.00           H  
HETATM   17  H5  UNL     1      -3.322   0.476   1.339  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.374  -0.008  -1.545  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.059   1.501  -0.570  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.927   0.006   1.152  1.00  0.00           H  
HETATM   21  H9  UNL     1      -1.265  -1.393   0.103  1.00  0.00           H  
HETATM   22  H10 UNL     1       1.805  -0.626   1.061  1.00  0.00           H  
HETATM   23  H11 UNL     1       1.514  -1.980  -0.045  1.00  0.00           H  
HETATM   24  H12 UNL     1       3.204  -1.310  -1.599  1.00  0.00           H  
HETATM   25  H13 UNL     1       4.281  -1.019   1.075  1.00  0.00           H  
HETATM   26  H14 UNL     1       3.441  -2.407   0.684  1.00  0.00           H  
HETATM   27  H15 UNL     1       3.286   2.512  -1.103  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16   17
CONECT    3    4   18   19
CONECT    4    5   20   21
CONECT    5    6    6    7
CONECT    7    8   22   23
CONECT    8    9   10   24
CONECT    9   25   26
CONECT   10   11   11   12
CONECT   12   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
S-Butylcysteine sulphoxide	Generator

Chemical Formula

C₇H₁₅NO₃S

Average Molecular Weight

193.264

Monoisotopic Molecular Weight

193.077264041

IUPAC Name

(2R)-2-amino-3-(butane-1-sulfinyl)propanoic acid

Traditional Name

(2R)-2-amino-3-(butane-1-sulfinyl)propanoic acid

CAS Registry Number

Not Available

SMILES

CCCCS(=O)C[C@H](N)C(O)=O

InChI Identifier

InChI=1S/C7H15NO3S/c1-2-3-4-12(11)5-6(8)7(9)10/h6H,2-5,8H2,1H3,(H,9,10)/t6-,12?/m0/s1

InChI Key

CBFHOPPJBYHALQ-RLWMBFFFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Sulfoxide
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Sulfinyl compound
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302178)

Food

Herb and spice

Herb

Soft-necked garlic (FooDB: FOOD00850)

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
logP	-1.6	ALOGPS
logP	-3.1	ChemAxon
logS	-0.92	ALOGPS
pKa (Strongest Acidic)	2.03	ChemAxon
pKa (Strongest Basic)	8.45	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.39 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	48.43 m³·mol⁻¹	ChemAxon
Polarizability	20.35 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
AllCCS	[M+H]+	143.093	32859911
AllCCS	[M+H-H2O]+	139.518	32859911
AllCCS	[M+Na]+	147.369	32859911
AllCCS	[M+NH4]+	146.414	32859911
AllCCS	[M-H]-	140.953	32859911
AllCCS	[M+Na-2H]-	142.627	32859911
AllCCS	[M+HCOO]-	144.533	32859911
DeepCCS	[M+H]+	144.312	30932474
DeepCCS	[M-H]-	140.483	30932474
DeepCCS	[M-2H]-	177.807	30932474
DeepCCS	[M+Na]+	153.471	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
S-Butylcysteine sulfoxide,2TMS,isomer #1	CCCCS(=O)C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1726.5	Semi standard non polar	33892256
S-Butylcysteine sulfoxide,2TMS,isomer #1	CCCCS(=O)C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2137.3	Standard non polar	33892256
S-Butylcysteine sulfoxide,2TMS,isomer #1	CCCCS(=O)C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2032.8	Standard polar	33892256
S-Butylcysteine sulfoxide,2TMS,isomer #2	CCCCS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1808.2	Semi standard non polar	33892256
S-Butylcysteine sulfoxide,2TMS,isomer #2	CCCCS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2033.3	Standard non polar	33892256
S-Butylcysteine sulfoxide,2TMS,isomer #2	CCCCS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2210.5	Standard polar	33892256
S-Butylcysteine sulfoxide,3TMS,isomer #1	CCCCS(=O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1834.3	Semi standard non polar	33892256
S-Butylcysteine sulfoxide,3TMS,isomer #1	CCCCS(=O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2158.8	Standard non polar	33892256
S-Butylcysteine sulfoxide,3TMS,isomer #1	CCCCS(=O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1944.4	Standard polar	33892256
S-Butylcysteine sulfoxide,2TBDMS,isomer #1	CCCCS(=O)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2164.1	Semi standard non polar	33892256
S-Butylcysteine sulfoxide,2TBDMS,isomer #1	CCCCS(=O)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2687.7	Standard non polar	33892256
S-Butylcysteine sulfoxide,2TBDMS,isomer #1	CCCCS(=O)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2258.5	Standard polar	33892256
S-Butylcysteine sulfoxide,2TBDMS,isomer #2	CCCCS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2268.8	Semi standard non polar	33892256
S-Butylcysteine sulfoxide,2TBDMS,isomer #2	CCCCS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2518.7	Standard non polar	33892256
S-Butylcysteine sulfoxide,2TBDMS,isomer #2	CCCCS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2351.0	Standard polar	33892256
S-Butylcysteine sulfoxide,3TBDMS,isomer #1	CCCCS(=O)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2535.6	Semi standard non polar	33892256
S-Butylcysteine sulfoxide,3TBDMS,isomer #1	CCCCS(=O)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2862.5	Standard non polar	33892256
S-Butylcysteine sulfoxide,3TBDMS,isomer #1	CCCCS(=O)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2313.8	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Butylcysteine sulfoxide 10V, Positive-QTOF	splash10-002e-1900000000-8d8dea22afe27830dead	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Butylcysteine sulfoxide 20V, Positive-QTOF	splash10-0a4m-9800000000-8097ac693fd2e248eb96	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Butylcysteine sulfoxide 40V, Positive-QTOF	splash10-0a4l-9000000000-520dd479ff2c01cc15ca	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Butylcysteine sulfoxide 10V, Negative-QTOF	splash10-0006-1900000000-48a9a6724fd8efc87656	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Butylcysteine sulfoxide 20V, Negative-QTOF	splash10-052r-7900000000-7e03a667226a8cebda19	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Butylcysteine sulfoxide 40V, Negative-QTOF	splash10-00ks-9200000000-b40a91c1fe8cb1ffd2b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Butylcysteine sulfoxide 10V, Positive-QTOF	splash10-0a4u-9700000000-4752b8f889bd93102b2e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Butylcysteine sulfoxide 20V, Positive-QTOF	splash10-0a4l-9100000000-0f2f84d37d467f56ae22	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Butylcysteine sulfoxide 40V, Positive-QTOF	splash10-052f-9000000000-ac831a82369f9a681005	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Butylcysteine sulfoxide 10V, Negative-QTOF	splash10-0a4i-0900000000-96cc2a0c239d15096ccb	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Butylcysteine sulfoxide 20V, Negative-QTOF	splash10-0zg0-7900000000-9df4fb46a184843795af	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Butylcysteine sulfoxide 40V, Negative-QTOF	splash10-000j-9000000000-d03716011cf68330b979	2021-10-21	Wishart 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

FDB003553

KNApSAcK ID

Not Available

Chemspider ID

10196996

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

636439

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

Not Available

Showing metabocard for S-Butylcysteine sulfoxide (HMDB0302178)

MOL for HMDB0302178 (S-Butylcysteine sulfoxide)

3D MOL for HMDB0302178 (S-Butylcysteine sulfoxide)

3D SDF for HMDB0302178 (S-Butylcysteine sulfoxide)

3D-SDF for HMDB0302178 (S-Butylcysteine sulfoxide)

PDB for HMDB0302178 (S-Butylcysteine sulfoxide)

3D PDB for HMDB0302178 (S-Butylcysteine sulfoxide)

SMILES for HMDB0302178 (S-Butylcysteine sulfoxide)

INCHI for HMDB0302178 (S-Butylcysteine sulfoxide)

Structure for HMDB0302178 (S-Butylcysteine sulfoxide)

3D Structure for HMDB0302178 (S-Butylcysteine sulfoxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra