NP-MRD: Showing NP-Card for (3s)-3-amino-3-(carboxymethyl-c-hydroxycarbonimidoyl)propanoic acid (NP0258115)

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Record Information

Version

2.0

Created at

2022-09-07 23:26:00 UTC

Updated at

2022-09-07 23:26:00 UTC

NP-MRD ID

NP0258115

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s)-3-amino-3-(carboxymethyl-c-hydroxycarbonimidoyl)propanoic acid

Description

Asp-Gly, also known as D-G or L-asp-gly, 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. Asp-Gly is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (3s)-3-amino-3-(carboxymethyl-c-hydroxycarbonimidoyl)propanoic acid is found in Trypanosoma brucei. (3s)-3-amino-3-(carboxymethyl-c-hydroxycarbonimidoyl)propanoic acid was first documented in 2022 (PMID: 35703476). Based on a literature review a small amount of articles have been published on Asp-Gly (PMID: 35603815) (PMID: 35437860) (PMID: 35185277).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082201262D          

 13 12  0  0  1  0            999 V2000
    0.8250    1.4289    0.0000 N   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
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  4  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0258115

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H10N2O5/c7-3(1-4(9)10)6(13)8-2-5(11)12/h3H,1-2,7H2,(H,8,13)(H,9,10)(H,11,12)/t3-/m0/s1

> <INCHI_KEY>
JHFNSBBHKSZXKB-VKHMYHEASA-N

> <FORMULA>
C6H10N2O5

> <MOLECULAR_WEIGHT>
190.155

> <EXACT_MASS>
190.05897143

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.082236155208935

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-amino-3-[(carboxymethyl)-C-hydroxycarbonimidoyl]propanoic acid

> <JCHEM_LOGP>
-4.0035997352820605

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.597794504722101

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.787864725185885

> <JCHEM_PKA_STRONGEST_BASIC>
9.702697367948762

> <JCHEM_POLAR_SURFACE_AREA>
133.21

> <JCHEM_REFRACTIVITY>
39.8579

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-amino-3-(carboxymethyl-C-hydroxycarbonimidoyl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  N   UNK     0       1.540   2.667   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.160   2.667   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.850   4.001   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.080  -2.667   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -3.080   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    2    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol

Synonyms

Value	Source
D-G	ChEBI
DG	ChEBI
L-Asp-gly	ChEBI
Aspartylglycine	MeSH
H-Asp(gly)-OH	MeSH

Chemical Formula

C₆H₁₀N₂O₅

Average Mass

190.1550 Da

Monoisotopic Mass

190.05897 Da

IUPAC Name

(3S)-3-amino-3-[(carboxymethyl)-C-hydroxycarbonimidoyl]propanoic acid

Traditional Name

(3S)-3-amino-3-(carboxymethyl-C-hydroxycarbonimidoyl)propanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C6H10N2O5/c7-3(1-4(9)10)6(13)8-2-5(11)12/h3H,1-2,7H2,(H,8,13)(H,9,10)(H,11,12)/t3-/m0/s1

InChI Key

JHFNSBBHKSZXKB-VKHMYHEASA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Trypanosoma brucei	LOTUS Database	35616633

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
Aspartic acid or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Fatty amide
N-acyl-amine
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Carboxylic acid
Organooxygen compound
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:73450 )

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	-4	ChemAxon
pKa (Strongest Acidic)	2.79	ChemAxon
pKa (Strongest Basic)	9.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	39.86 m³·mol⁻¹	ChemAxon
Polarizability	17.08 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

133220

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

151148

PDB ID

Not Available

ChEBI ID

73450

Good Scents ID

Not Available

References

General References

Song H, Yang Y, Li B: Tripeptide Hyp-Asp-Gly from collagen peptides inhibited platelet activation via regulation of PI3K/Akt-MAPK/ERK1/2 signaling pathway. J Food Sci. 2022 Jul;87(7):3279-3293. doi: 10.1111/1750-3841.16215. Epub 2022 Jun 15. [PubMed:35703476 ]
Xue W, Liu X, Zhao W, Yu Z: Identification and molecular mechanism of novel tyrosinase inhibitory peptides from collagen. J Food Sci. 2022 Jun;87(6):2744-2756. doi: 10.1111/1750-3841.16160. Epub 2022 May 23. [PubMed:35603815 ]
Sato A, Fukase T, Ebina K: Biotinylated peptides substituted with D-amino acids with high stability as anti-anaphylactic agents targeting platelet-activating factor. J Pept Sci. 2022 Oct;28(10):e3412. doi: 10.1002/psc.3412. Epub 2022 Apr 25. [PubMed:35437860 ]
Jha A, Moore E: Collagen-derived peptide, DGEA, inhibits pro-inflammatory macrophages in biofunctional hydrogels. J Mater Res. 2022;37(1):77-87. doi: 10.1557/s43578-021-00423-y. Epub 2021 Dec 2. [PubMed:35185277 ]
LOTUS database [Link]

Showing NP-Card for (3s)-3-amino-3-(carboxymethyl-c-hydroxycarbonimidoyl)propanoic acid (NP0258115)

MOL for NP0258115 ((3s)-3-amino-3-(carboxymethyl-c-hydroxycarbonimidoyl)propanoic acid)

3D MOL for NP0258115 ((3s)-3-amino-3-(carboxymethyl-c-hydroxycarbonimidoyl)propanoic acid)

3D SDF for NP0258115 ((3s)-3-amino-3-(carboxymethyl-c-hydroxycarbonimidoyl)propanoic acid)

3D-SDF for NP0258115 ((3s)-3-amino-3-(carboxymethyl-c-hydroxycarbonimidoyl)propanoic acid)

PDB for NP0258115 ((3s)-3-amino-3-(carboxymethyl-c-hydroxycarbonimidoyl)propanoic acid)

3D PDB for NP0258115 ((3s)-3-amino-3-(carboxymethyl-c-hydroxycarbonimidoyl)propanoic acid)

SMILES for NP0258115 ((3s)-3-amino-3-(carboxymethyl-c-hydroxycarbonimidoyl)propanoic acid)

INCHI for NP0258115 ((3s)-3-amino-3-(carboxymethyl-c-hydroxycarbonimidoyl)propanoic acid)

Structure for NP0258115 ((3s)-3-amino-3-(carboxymethyl-c-hydroxycarbonimidoyl)propanoic acid)

3D Structure for NP0258115 ((3s)-3-amino-3-(carboxymethyl-c-hydroxycarbonimidoyl)propanoic acid)