NP-MRD: Showing NP-Card for Asparaginylcysteine (NP0136367)

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Record Information

Version

2.0

Created at

2022-05-12 15:12:44 UTC

Updated at

2022-05-12 15:12:44 UTC

NP-MRD ID

NP0136367

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Asparaginylcysteine

Description

Asparaginylcysteine, also known as N-C dipeptide or asn-cys, belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. Asparaginylcysteine 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


  Mrv1652304062013252D          

 15 14  0  0  0  0            999 V2000
 2506.6750 2505.2454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2505.9581 2505.6572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2505.2433 2505.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2504.5285 2505.6572    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2503.8137 2505.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.0988 2505.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.3840 2505.2454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2503.0988 2506.4826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2504.5285 2506.4826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2505.2433 2504.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2507.3899 2505.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2508.1047 2505.2454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2507.3899 2506.4826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2506.6750 2504.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2507.3899 2504.0061    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 11  1  0  0  0  0
  1 14  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 10  2  0  0  0  0
  4  5  1  0  0  0  0
  4  9  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136367

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H13N3O4S/c8-3(1-5(9)11)6(12)10-4(2-15)7(13)14/h3-4,15H,1-2,8H2,(H2,9,11)(H,10,12)(H,13,14)/t3-,4-/m0/s1

> <INCHI_KEY>
TWXZVVXRRRRSLT-IMJSIDKUSA-N

> <FORMULA>
C7H13N3O4S

> <MOLECULAR_WEIGHT>
235.26

> <EXACT_MASS>
235.062677085

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.940565693724473

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.96

> <JCHEM_LOGP>
-4.7798985198729165

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.049972093768316

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.441200481297454

> <JCHEM_PKA_STRONGEST_BASIC>
7.3458742126431575

> <JCHEM_POLAR_SURFACE_AREA>
135.51000000000002

> <JCHEM_REFRACTIVITY>
53.378600000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(2S)-2-amino-3-carbamoylpropanamido]-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    4679.1274676.458   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4677.7884677.227   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4676.4544676.458   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4675.1204677.227   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4673.7864676.458   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4672.4514677.227   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    4671.1174676.458   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0    4672.4514678.768   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0    4675.1204678.768   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0    4676.4544674.917   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    4680.4614677.227   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    4681.7954676.458   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    4680.4614678.768   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    4679.1274674.917   0.000  0.00  0.00           C+0
HETATM   15  S   UNK     0    4680.4614674.145   0.000  0.00  0.00           S+0
CONECT    1    2   11   14                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4                                                            
CONECT   10    3                                                            
CONECT   11    1   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    1   15                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
(2R)-2-{[(2S)-2-amino-1-hydroxy-3-(C-hydroxycarbonimidoyl)propylidene]amino}-3-sulfanylpropanoate	HMDB
(2R)-2-{[(2S)-2-amino-1-hydroxy-3-(C-hydroxycarbonimidoyl)propylidene]amino}-3-sulphanylpropanoate	HMDB
(2R)-2-{[(2S)-2-amino-1-hydroxy-3-(C-hydroxycarbonimidoyl)propylidene]amino}-3-sulphanylpropanoic acid	HMDB
Asn-cys	HMDB
Asparagine cysteine dipeptide	HMDB
Asparagine-cysteine dipeptide	HMDB
Asparaginyl-cysteine	HMDB
L-Asn-L-cys	HMDB
L-Asparaginyl-L-cysteine	HMDB
N-Asparaginylcysteine	HMDB
N-C Dipeptide	HMDB
N-L-Asparaginyl-L-cysteine	HMDB
NC Dipeptide	HMDB

Chemical Formula

C₇H₁₃N₃O₄S

Average Mass

235.2600 Da

Monoisotopic Mass

235.06268 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C7H13N3O4S/c8-3(1-5(9)11)6(12)10-4(2-15)7(13)14/h3-4,15H,1-2,8H2,(H2,9,11)(H,10,12)(H,13,14)/t3-,4-/m0/s1

InChI Key

TWXZVVXRRRRSLT-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 peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Cysteine or derivatives
Alpha-amino acid or derivatives
Amino acid or derivatives
Amino acid
Alkylthiol
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary aliphatic amine
Amine
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Hydrocarbon derivative
Primary amine
Carbonyl group
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	-3	ALOGPS
logP	-4.8	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.44	ChemAxon
pKa (Strongest Basic)	7.35	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	135.51 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	53.38 m³·mol⁻¹	ChemAxon
Polarizability	21.94 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

HMDB0028728

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

54338059

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Asparaginylcysteine (NP0136367)

MOL for NP0136367 (Asparaginylcysteine)

3D MOL for NP0136367 (Asparaginylcysteine)

3D SDF for NP0136367 (Asparaginylcysteine)

3D-SDF for NP0136367 (Asparaginylcysteine)

PDB for NP0136367 (Asparaginylcysteine)

3D PDB for NP0136367 (Asparaginylcysteine)

SMILES for NP0136367 (Asparaginylcysteine)

INCHI for NP0136367 (Asparaginylcysteine)

Structure for NP0136367 (Asparaginylcysteine)

3D Structure for NP0136367 (Asparaginylcysteine)