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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2019-10-11 16:08:09 UTC

Update Date

2022-03-07 03:18:18 UTC

HMDB ID

HMDB0240544

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Acetyl-S-methylcysteine

Description

N-Acetyl-S-methylcysteine belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. Based on a literature review very few articles have been published on N-Acetyl-S-methylcysteine.

Structure

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

HEADER    PROTEIN                                 11-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-OCT-19         0                                  
HETATM    1  C   UNK     0      -0.357   4.414   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.976   3.644   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.310  -0.206   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.976   2.104   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       2.310   4.414   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.644  -0.976   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.976  -0.976   0.000  0.00  0.00           O+0
HETATM   11  S   UNK     0       4.977   1.334   0.000  0.00  0.00           S+0
HETATM   12  H   UNK     0       3.644   0.564   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2   11                                                            
CONECT    3    5   11                                                       
CONECT    4    1    7    8                                                  
CONECT    5    3    6    7   12                                             
CONECT    6    5    9   10                                                  
CONECT    7    4    5                                                       
CONECT    8    4                                                            
CONECT    9    6                                                            
CONECT   10    6                                                            
CONECT   11    2    3                                                       
CONECT   12    5                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2R)-2-[(1-Hydroxyethylidene)amino]-3-(methylsulfanyl)propanoate	HMDB
(2R)-2-[(1-Hydroxyethylidene)amino]-3-(methylsulphanyl)propanoate	HMDB
(2R)-2-[(1-Hydroxyethylidene)amino]-3-(methylsulphanyl)propanoic acid	HMDB

Chemical Formula

C₆H₁₁NO₃S

Average Molecular Weight

177.22

Monoisotopic Molecular Weight

177.045964392

IUPAC Name

(2R)-2-[(1-hydroxyethylidene)amino]-3-(methylsulfanyl)propanoic acid

Traditional Name

(2R)-2-[(1-hydroxyethylidene)amino]-3-(methylsulfanyl)propanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C6H11NO3S/c1-4(8)7-5(3-11-2)6(9)10/h5H,3H2,1-2H3,(H,7,8)(H,9,10)/t5-/m0/s1

InChI Key

RYGLCORNOFFGTB-YFKPBYRVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated 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

N-acyl-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Cysteine or derivatives
Fatty acid
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Dialkylthioether
Sulfenyl compound
Thioether
Carbonyl group
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0240544)

Food

Herb and spice

Herb

Garlic (HMDB: HMDB0240544)

Vegetable

Onion-family vegetable

Onion family vegetables (HMDB: HMDB0240544)

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	-0.07	ALOGPS
logP	0.5	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	3.95	ChemAxon
pKa (Strongest Basic)	1.13	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.89 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	42.84 m³·mol⁻¹	ChemAxon
Polarizability	17.6 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DeepCCS	[M+H]+	133.639	30932474
DeepCCS	[M-H]-	131.021	30932474
DeepCCS	[M-2H]-	167.162	30932474
DeepCCS	[M+Na]+	141.765	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.52 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8627 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.08 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	999.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	308.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	70.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	72.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	259.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	341.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	148.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	665.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	213.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	816.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	202.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	208.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	439.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	303.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	115.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-S-methylcysteine	[H][C@@](CSC)(N=C(C)O)C(O)=O	2573.0	Standard polar	33892256
N-Acetyl-S-methylcysteine	[H][C@@](CSC)(N=C(C)O)C(O)=O	1537.4	Standard non polar	33892256
N-Acetyl-S-methylcysteine	[H][C@@](CSC)(N=C(C)O)C(O)=O	1605.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-S-methylcysteine,1TMS,isomer #1	CSC[C@H](N=C(C)O[Si](C)(C)C)C(=O)O	1566.8	Semi standard non polar	33892256
N-Acetyl-S-methylcysteine,1TMS,isomer #2	CSC[C@H](N=C(C)O)C(=O)O[Si](C)(C)C	1515.2	Semi standard non polar	33892256
N-Acetyl-S-methylcysteine,2TMS,isomer #1	CSC[C@H](N=C(C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1605.4	Semi standard non polar	33892256
N-Acetyl-S-methylcysteine,1TBDMS,isomer #1	CSC[C@H](N=C(C)O[Si](C)(C)C(C)(C)C)C(=O)O	1804.4	Semi standard non polar	33892256
N-Acetyl-S-methylcysteine,1TBDMS,isomer #2	CSC[C@H](N=C(C)O)C(=O)O[Si](C)(C)C(C)(C)C	1738.5	Semi standard non polar	33892256
N-Acetyl-S-methylcysteine,2TBDMS,isomer #1	CSC[C@H](N=C(C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2043.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-S-methylcysteine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-S-methylcysteine 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 - N-Acetyl-S-methylcysteine 10V, Negative-QTOF	splash10-001i-8900000000-3225e6c7b083a90fd06b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-S-methylcysteine 20V, Negative-QTOF	splash10-0002-9000000000-0580f553f538d9b6946a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-S-methylcysteine 40V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-S-methylcysteine 10V, Positive-QTOF	splash10-001i-1900000000-ef4e95b1da38005d5ed0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-S-methylcysteine 20V, Positive-QTOF	splash10-00sr-9300000000-9b2829060a72cbce5ace	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-S-methylcysteine 40V, Positive-QTOF	splash10-0005-9000000000-e4bdee128b55c12bdc41	2021-09-24	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

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

FDB093739

KNApSAcK ID

Not Available

Chemspider ID

23977237

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13893975

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 N-Acetyl-S-methylcysteine (HMDB0240544)

MOL for HMDB0240544 (N-Acetyl-S-methylcysteine)

3D MOL for HMDB0240544 (N-Acetyl-S-methylcysteine)

3D SDF for HMDB0240544 (N-Acetyl-S-methylcysteine)

3D-SDF for HMDB0240544 (N-Acetyl-S-methylcysteine)

PDB for HMDB0240544 (N-Acetyl-S-methylcysteine)

3D PDB for HMDB0240544 (N-Acetyl-S-methylcysteine)

SMILES for HMDB0240544 (N-Acetyl-S-methylcysteine)

INCHI for HMDB0240544 (N-Acetyl-S-methylcysteine)

Structure for HMDB0240544 (N-Acetyl-S-methylcysteine)

3D Structure for HMDB0240544 (N-Acetyl-S-methylcysteine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra