NP-MRD: Showing NP-Card for N-Acetyl-S-(N-methylcarbamoyl)cysteine (NP0136264)

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Record Information

Version

2.0

Created at

2022-05-12 15:10:01 UTC

Updated at

2022-05-12 15:10:01 UTC

NP-MRD ID

NP0136264

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Acetyl-S-(N-methylcarbamoyl)cysteine

Description

N-Acetyl-S-(N-methylcarbamoyl)cysteine, also known as AMCC or S-(N-methylcarbamoyl)-N-acetylcysteine, belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetyl-S-(N-methylcarbamoyl)cysteine is a strong basic compound (based on its pKa). These are compounds containing an alpha amino acid which bears an acyl group at his terminal nitrogen atom.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304062013072D          

 15 14  0  0  0  0            999 V2000
   -0.1914    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2375   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  4  0  0  0
  5  3  1  0  0  0  0
  6  5  1  0  0  0  0
  8  2  1  4  0  0  0
  8  7  2  0  0  0  0
  9  4  2  0  0  0  0
  5  9  1  6  0  0  0
 10  4  1  0  0  0  0
 11  6  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 14  3  1  0  0  0  0
 14  7  1  0  0  0  0
  5 15  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0136264

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](CSC(O)=NC)(N=C(C)O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H12N2O4S/c1-4(10)9-5(6(11)12)3-14-7(13)8-2/h5H,3H2,1-2H3,(H,8,13)(H,9,10)(H,11,12)/t5-/m0/s1

> <INCHI_KEY>
MXRPNYMMDLFYDL-YFKPBYRVSA-N

> <FORMULA>
C7H12N2O4S

> <MOLECULAR_WEIGHT>
220.246

> <EXACT_MASS>
220.051777572

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
21.14874220037658

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(1-hydroxyethylidene)amino]-3-[(methyl-C-hydroxycarbonimidoyl)sulfanyl]propanoic acid

> <ALOGPS_LOGP>
-0.59

> <JCHEM_LOGP>
-0.5639569872305751

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.73731191944839

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.015367183234477

> <JCHEM_PKA_STRONGEST_BASIC>
4.907330948278605

> <JCHEM_POLAR_SURFACE_AREA>
102.48

> <JCHEM_REFRACTIVITY>
51.752

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.83e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
AMCC

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0      -0.357   4.414   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.978   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  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       7.645   1.334   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       0.976   2.104   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       2.310   4.414   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.644  -0.976   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.976  -0.976   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.311   3.644   0.000  0.00  0.00           O+0
HETATM   14  S   UNK     0       4.977   1.334   0.000  0.00  0.00           S+0
HETATM   15  H   UNK     0       3.644   0.564   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2    8                                                            
CONECT    3    5   14                                                       
CONECT    4    1    9   10                                                  
CONECT    5    3    6    9   15                                             
CONECT    6    5   11   12                                                  
CONECT    7    8   13   14                                                  
CONECT    8    2    7                                                       
CONECT    9    4    5                                                       
CONECT   10    4                                                            
CONECT   11    6                                                            
CONECT   12    6                                                            
CONECT   13    7                                                            
CONECT   14    3    7                                                       
CONECT   15    5                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
AMCC	HMDB
N-AMCC	HMDB
S-(N-Methylcarbamoyl)-N-acetylcysteine	HMDB
SNMCN-Acetylcysteine	HMDB
N-Acetyl-S-(N-methylcarbamoyl)cysteine	KEGG
(2R)-2-[(1-Hydroxyethylidene)amino]-3-[(methyl-C-hydroxycarbonimidoyl)sulfanyl]propanoate	Generator
(2R)-2-[(1-Hydroxyethylidene)amino]-3-[(methyl-C-hydroxycarbonimidoyl)sulphanyl]propanoate	Generator
(2R)-2-[(1-Hydroxyethylidene)amino]-3-[(methyl-C-hydroxycarbonimidoyl)sulphanyl]propanoic acid	Generator

Chemical Formula

C₇H₁₂N₂O₄S

Average Mass

220.2460 Da

Monoisotopic Mass

220.05178 Da

IUPAC Name

(2R)-2-[(1-hydroxyethylidene)amino]-3-[(methyl-C-hydroxycarbonimidoyl)sulfanyl]propanoic acid

Traditional Name

AMCC

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C7H12N2O4S/c1-4(10)9-5(6(11)12)3-14-7(13)8-2/h5H,3H2,1-2H3,(H,8,13)(H,9,10)(H,11,12)/t5-/m0/s1

InChI Key

MXRPNYMMDLFYDL-YFKPBYRVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen 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-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Cysteine or derivatives
Fatty acid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Sulfenyl compound
Carbonyl group
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Imine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-acyl-amino acid (CHEBI:2355 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	-0.59	ALOGPS
logP	-0.56	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	3.02	ChemAxon
pKa (Strongest Basic)	4.91	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	102.48 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	51.75 m³·mol⁻¹	ChemAxon
Polarizability	21.15 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

External Links

HMDB ID

HMDB0041942

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

97289

KEGG Compound ID

C11490

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

108218

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for N-Acetyl-S-(N-methylcarbamoyl)cysteine (NP0136264)

MOL for NP0136264 (N-Acetyl-S-(N-methylcarbamoyl)cysteine)

3D MOL for NP0136264 (N-Acetyl-S-(N-methylcarbamoyl)cysteine)

3D SDF for NP0136264 (N-Acetyl-S-(N-methylcarbamoyl)cysteine)

3D-SDF for NP0136264 (N-Acetyl-S-(N-methylcarbamoyl)cysteine)

PDB for NP0136264 (N-Acetyl-S-(N-methylcarbamoyl)cysteine)

3D PDB for NP0136264 (N-Acetyl-S-(N-methylcarbamoyl)cysteine)

SMILES for NP0136264 (N-Acetyl-S-(N-methylcarbamoyl)cysteine)

INCHI for NP0136264 (N-Acetyl-S-(N-methylcarbamoyl)cysteine)

Structure for NP0136264 (N-Acetyl-S-(N-methylcarbamoyl)cysteine)

3D Structure for NP0136264 (N-Acetyl-S-(N-methylcarbamoyl)cysteine)