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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2023-03-30 19:02:47 UTC

Update Date

2023-03-30 19:02:48 UTC

HMDB ID

HMDB0341494

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Acetyl-S-(2-hydroxypropyl)-L-cysteine

Description

2-[(1-hydroxyethylidene)amino]-3-[(2-hydroxypropyl)sulfanyl]propanoic acid 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. 2-[(1-hydroxyethylidene)amino]-3-[(2-hydroxypropyl)sulfanyl]propanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004231520292D          

 14 13  0  0  0  0            999 V2000
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    0.9059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    0.9059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341494

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(O)CSCC(NC(C)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H15NO4S/c1-5(10)3-14-4-7(8(12)13)9-6(2)11/h5,7,10H,3-4H2,1-2H3,(H,9,11)(H,12,13)

> <INCHI_KEY>
FGOZBZPHEMIBIQ-UHFFFAOYSA-N

> <FORMULA>
C8H15NO4S

> <MOLECULAR_WEIGHT>
221.27

> <EXACT_MASS>
221.072179141

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
22.54731119646779

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-acetamido-3-[(2-hydroxypropyl)sulfanyl]propanoic acid

> <ALOGPS_LOGP>
-0.59

> <JCHEM_LOGP>
-0.8575159440000004

> <ALOGPS_LOGS>
-1.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.86209955567126

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9041018562953047

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9963917941004703

> <JCHEM_POLAR_SURFACE_AREA>
86.63000000000001

> <JCHEM_REFRACTIVITY>
53.23270000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-acetamido-3-[(2-hydroxypropyl)sulfanyl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.930   2.461   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    5  S   UNK     0       9.597   4.001   0.000  0.00  0.00           S+0
HETATM    6  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      13.598   4.771   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      14.932   2.461   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.265   2.461   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      13.598   1.691   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      10.931   1.691   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-[(1-Hydroxyethylidene)amino]-3-[(2-hydroxypropyl)sulfanyl]propanoate	Generator
2-[(1-Hydroxyethylidene)amino]-3-[(2-hydroxypropyl)sulphanyl]propanoate	Generator
2-[(1-Hydroxyethylidene)amino]-3-[(2-hydroxypropyl)sulphanyl]propanoic acid	Generator

Chemical Formula

C₈H₁₅NO₄S

Average Molecular Weight

221.27

Monoisotopic Molecular Weight

221.072179141

IUPAC Name

2-acetamido-3-[(2-hydroxypropyl)sulfanyl]propanoic acid

Traditional Name

2-acetamido-3-[(2-hydroxypropyl)sulfanyl]propanoic acid

CAS Registry Number

Not Available

SMILES

CC(O)CSCC(NC(C)=O)C(O)=O

InChI Identifier

InChI=1S/C8H15NO4S/c1-5(10)3-14-4-7(8(12)13)9-6(2)11/h5,7,10H,3-4H2,1-2H3,(H,9,11)(H,12,13)

InChI Key

FGOZBZPHEMIBIQ-UHFFFAOYSA-N

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
Acetamide
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Dialkylthioether
Sulfenyl compound
Thioether
Monocarboxylic acid or derivatives
Carboxylic acid
Carbonyl group
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

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	-0.59	ALOGPS
logP	-0.86	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	3.9	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	53.23 m³·mol⁻¹	ChemAxon
Polarizability	22.55 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 Kovats Retention Indices

Not Available

Spectra

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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4183679

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-(2-hydroxypropyl)-L-cysteine (HMDB0341494)

MOL for HMDB0341494 (N-Acetyl-S-(2-hydroxypropyl)-L-cysteine)

3D MOL for HMDB0341494 (N-Acetyl-S-(2-hydroxypropyl)-L-cysteine)

3D SDF for HMDB0341494 (N-Acetyl-S-(2-hydroxypropyl)-L-cysteine)

3D-SDF for HMDB0341494 (N-Acetyl-S-(2-hydroxypropyl)-L-cysteine)

PDB for HMDB0341494 (N-Acetyl-S-(2-hydroxypropyl)-L-cysteine)

3D PDB for HMDB0341494 (N-Acetyl-S-(2-hydroxypropyl)-L-cysteine)

SMILES for HMDB0341494 (N-Acetyl-S-(2-hydroxypropyl)-L-cysteine)

INCHI for HMDB0341494 (N-Acetyl-S-(2-hydroxypropyl)-L-cysteine)

Structure for HMDB0341494 (N-Acetyl-S-(2-hydroxypropyl)-L-cysteine)

3D Structure for HMDB0341494 (N-Acetyl-S-(2-hydroxypropyl)-L-cysteine)

Predicted Kovats Retention Indices