MiMeDB: Showing metabocard for N-Acetylmethionine sulfoxide (MMDBc0000746)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:54:04 UTC

Update Date

2024-04-30 19:33:36 UTC

Metabolite ID

MMDBc0000746

Metabolite Identification

Common Name

N-Acetylmethionine sulfoxide

Description

N-Acetylmethionine sulfoxide (CAS: 3054-51-1), also known as N-ACMSO or 2-(acetylamino)-4-(methylsulfinyl)butanoic acid, 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. N-Acetylmethionine sulfoxide has been identified in the human placenta (PMID: 32033212 ).

Structure

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


  Mrv1652311141922232D          

 13 12  0  0  0  0            999 V2000
 9992.2282 9991.9348    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9991.5146 9992.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.8001 9991.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.0857 9992.3473    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9989.3670 9991.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.0857 9993.1723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.2282 9991.1108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9439 9990.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6576 9991.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9439 9989.8722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9439 9992.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6576 9991.9348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9439 9993.1723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  1  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000746

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=O)N[C@@H](CCS(C)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H13NO4S/c1-5(9)8-6(7(10)11)3-4-13(2)12/h6H,3-4H2,1-2H3,(H,8,9)(H,10,11)/t6-,13?/m0/s1

> <INCHI_KEY>
NPIMMZJBURSMON-YLTHGKPTSA-N

> <FORMULA>
C7H13NO4S

> <MOLECULAR_WEIGHT>
207.24

> <EXACT_MASS>
207.056529077

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
20.13034442603751

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-acetamido-4-methanesulfinylbutanoic acid

> <ALOGPS_LOGP>
-0.96

> <JCHEM_LOGP>
-2.4839143003333333

> <ALOGPS_LOGS>
-0.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.169773016336855

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4502696397505304

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8007818606917136

> <JCHEM_POLAR_SURFACE_AREA>
83.47

> <JCHEM_REFRACTIVITY>
48.78650000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.15e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-acetamido-4-methanesulfinylbutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-NOV-19         0                                  
HETATM    1  C   UNK     0    8652.1598651.612   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8650.8278652.382   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8649.4938651.612   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0    8648.1608652.382   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0    8646.8188651.612   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8648.1608653.922   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0    8652.1598650.073   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0    8653.4958649.302   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8654.8288650.073   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8653.4958647.762   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8653.4958652.382   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8654.8288651.612   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8653.4958653.922   0.000  0.00  0.00           O+0
CONECT    1    2    7   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    1   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

Synonyms

Value	Source
(2S)-2-[(1-Hydroxyethylidene)amino]-4-methanesulfinylbutanoate	Generator
(2S)-2-[(1-Hydroxyethylidene)amino]-4-methanesulphinylbutanoate	Generator
(2S)-2-[(1-Hydroxyethylidene)amino]-4-methanesulphinylbutanoic acid	Generator
N-ACMSO	MeSH
N-Acetylmethionine sulfoxide	MeSH
(2S)-2-(Acetylamino)-4-(methylsulfinyl)butanoic acid	HMDB
(2S)-2-Acetamido-4-(methylsulfinyl)butanoic acid	HMDB
(2S)-2-Acetamido-4-methanesulfinylbutanoic acid	HMDB
(2S)-2-Acetamido-4-methylsulfinylbutanoic acid	HMDB
2-(Acetylamino)-4-(methylsulfinyl)butanoic acid	HMDB
N-Acetyl-L-methionine sulfoxide	HMDB

Molecular Formula

C₇H₁₃NO₄S

Average Mass

207.24

Monoisotopic Mass

207.056529077

IUPAC Name

(2S)-2-acetamido-4-methanesulfinylbutanoic acid

Traditional Name

(2S)-2-acetamido-4-methanesulfinylbutanoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)N[C@@H](CCS(C)=O)C(O)=O

InChI Identifier

InChI=1S/C7H13NO4S/c1-5(9)8-6(7(10)11)3-4-13(2)12/h6H,3-4H2,1-2H3,(H,8,9)(H,10,11)/t6-,13?/m0/s1

InChI Key

NPIMMZJBURSMON-YLTHGKPTSA-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
Thia fatty acid
Fatty acid
Fatty acyl
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Sulfoxide
Sulfinyl compound
Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Carbonyl group
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	21.5 g/L	ALOGPS
logP	-0.96	ALOGPS
logP	-2.5	ChemAxon
logS	-0.98	ALOGPS
pKa (Strongest Acidic)	3.45	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.47 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	48.79 m³·mol⁻¹	ChemAxon
Polarizability	20.13 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0910000000-93ffaabee484f7cd67a4	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f6t-7900000000-0ea877575dff1139e961	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9100000000-7b0e97a852e51236a59b	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-7950000000-3b5c400fe303c2551109	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-9400000000-3b4399cf013a7bb28812	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ox-9000000000-87fb4d29772a0579d39c	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces
Placenta

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	5	Human stool; Human ; Human feces; Human saliva; Human urine; Human sputum; Human subgingival plaque; Human vaginal fluid; Human supragingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0240343

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

19354090

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for N-Acetylmethionine sulfoxide (MMDBc0000746)

MOL for #<Metabolite:0x000055e8c571cd30>

3D MOL for #<Metabolite:0x000055e8c571cd30>

3D SDF for #<Metabolite:0x000055e8c571cd30>

3D-SDF for #<Metabolite:0x000055e8c571cd30>

PDB for #<Metabolite:0x000055e8c571cd30>

3D PDB for #<Metabolite:0x000055e8c571cd30>

SMILES for #<Metabolite:0x000055e8c571cd30>

INCHI for #<Metabolite:0x000055e8c571cd30>

Structure for #<Metabolite:0x000055e8c571cd30>

3D Structure for #<Metabolite:0x000055e8c571cd30>