NP-MRD: Showing NP-Card for Serylcysteine (NP0136624)

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Record Information

Version

2.0

Created at

2022-05-12 15:19:20 UTC

Updated at

2022-05-12 15:19:20 UTC

NP-MRD ID

NP0136624

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Serylcysteine

Description

Serylcysteine, also known as S-C dipeptide or L-ser-L-cys, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Serylcysteine is a very strong basic compound (based on its pKa). It is an incomplete breakdown product of protein digestion or protein catabolism.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304062014102D          

 13 12  0  0  0  0            999 V2000
 2497.7702 2498.9905    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2497.7702 2497.9831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2498.4847 2497.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.1991 2497.9831    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2499.9157 2497.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.6302 2497.9831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.1991 2498.8081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2498.4847 2496.7445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.0557 2499.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.3413 2498.9905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.0557 2500.2269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.4847 2499.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.4847 2500.2269    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  1  9  1  0  0  0  0
  1 12  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  1  0  0  0
  5  6  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136624

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CO)C(=O)N[C@@H](CS)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H12N2O4S/c7-3(1-9)5(10)8-4(2-13)6(11)12/h3-4,9,13H,1-2,7H2,(H,8,10)(H,11,12)/t3-,4-/m0/s1

> <INCHI_KEY>
FFOKMZOAVHEWET-IMJSIDKUSA-N

> <FORMULA>
C6H12N2O4S

> <MOLECULAR_WEIGHT>
208.23

> <EXACT_MASS>
208.051778048

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.502195443025876

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-sulfanylpropanoic acid

> <ALOGPS_LOGP>
-2.92

> <JCHEM_LOGP>
-4.379737257372703

> <ALOGPS_LOGS>
-1.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.051837297329211

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4635342591174694

> <JCHEM_PKA_STRONGEST_BASIC>
7.846590938266492

> <JCHEM_POLAR_SURFACE_AREA>
112.65

> <JCHEM_REFRACTIVITY>
47.0647

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.74e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-sulfanylpropanoic acid

> <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    4662.5044664.782   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4662.5044662.902   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4663.8384662.130   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4665.1724662.902   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4666.5094662.130   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    4667.8434662.902   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0    4665.1724664.442   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0    4663.8384660.590   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    4661.1714665.550   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    4659.8374664.782   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    4661.1714667.090   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    4663.8384665.550   0.000  0.00  0.00           C+0
HETATM   13  S   UNK     0    4663.8384667.090   0.000  0.00  0.00           S+0
CONECT    1    2    9   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4                                                            
CONECT    8    3                                                            
CONECT    9    1   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    1   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol

Synonyms

Value	Source
(2R)-2-{[(2S)-2-amino-1,3-dihydroxypropylidene]amino}-3-sulfanylpropanoate	HMDB
(2R)-2-{[(2S)-2-amino-1,3-dihydroxypropylidene]amino}-3-sulphanylpropanoate	HMDB
(2R)-2-{[(2S)-2-amino-1,3-dihydroxypropylidene]amino}-3-sulphanylpropanoic acid	HMDB
L-Ser-L-cys	HMDB
L-Seryl-L-cysteine	HMDB
N-L-Seryl-L-cysteine	HMDB
N-Serylcysteine	HMDB
S-C Dipeptide	HMDB
SC Dipeptide	HMDB
Ser-cys	HMDB
Serine cysteine dipeptide	HMDB
Serine-cysteine dipeptide	HMDB
Serinyl-cysteine	HMDB
Serinylcysteine	HMDB
Seryl-cysteine	HMDB

Chemical Formula

C₆H₁₂N₂O₄S

Average Mass

208.2300 Da

Monoisotopic Mass

208.05178 Da

IUPAC Name

(2R)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-sulfanylpropanoic acid

Traditional Name

(2R)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-sulfanylpropanoic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](CO)C(=O)N[C@@H](CS)C(O)=O

InChI Identifier

InChI=1S/C6H12N2O4S/c7-3(1-9)5(10)8-4(2-13)6(11)12/h3-4,9,13H,1-2,7H2,(H,8,10)(H,11,12)/t3-,4-/m0/s1

InChI Key

FFOKMZOAVHEWET-IMJSIDKUSA-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 dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
N-acyl-l-alpha-amino acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Serine or derivatives
Cysteine or derivatives
Alpha-amino acid or derivatives
Amino acid or derivatives
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Alkylthiol
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Primary alcohol
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
Carbonyl group
Organic oxide
Amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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	-2.9	ALOGPS
logP	-4.4	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	3.46	ChemAxon
pKa (Strongest Basic)	7.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	112.65 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	47.06 m³·mol⁻¹	ChemAxon
Polarizability	19.5 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

HMDB0029036

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

46937961

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Serylcysteine (NP0136624)

MOL for NP0136624 (Serylcysteine)

3D MOL for NP0136624 (Serylcysteine)

3D SDF for NP0136624 (Serylcysteine)

3D-SDF for NP0136624 (Serylcysteine)

PDB for NP0136624 (Serylcysteine)

3D PDB for NP0136624 (Serylcysteine)

SMILES for NP0136624 (Serylcysteine)

INCHI for NP0136624 (Serylcysteine)

Structure for NP0136624 (Serylcysteine)

3D Structure for NP0136624 (Serylcysteine)