NP-MRD: Showing NP-Card for (2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}butanedioic acid (NP0196070)

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Record Information

Version

2.0

Created at

2022-09-04 14:04:20 UTC

Updated at

2022-09-04 14:04:20 UTC

NP-MRD ID

NP0196070

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}butanedioic acid

Description

Asp-Asp, also known as D-D or L-asp-L-asp, 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-Asp 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. (2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}butanedioic acid is found in Trypanosoma brucei. (2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}butanedioic acid was first documented in 2022 (PMID: 35938100). Based on a literature review a small amount of articles have been published on Asp-Asp (PMID: 35779611) (PMID: 35499031) (PMID: 35482820).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 28  0  0  0  0  0  0  0  0999 V2000
   -2.6463   -0.4949   -1.5444 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8303    0.3076   -0.6191 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6429    0.4442    0.6478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9083    1.1156    0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1648    1.4726   -0.8308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8260    1.3561    1.3337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5947   -0.4209   -0.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7306   -1.6629    0.3172 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5911    0.0184   -0.5358 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7657   -0.7526   -0.1872 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9556   -0.1723   -0.9194 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1488    1.2410   -0.5239 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4026    1.8018    0.2957 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1951    1.9463   -1.0916 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9845   -0.8114    1.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2335   -0.2556    2.0925 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0778   -1.5190    1.7566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2001   -0.3736   -2.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008   -1.5112   -1.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6562    1.2941   -1.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8189   -0.5792    1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0208    1.0196    1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2249    2.2892    1.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5302   -2.4655   -0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6126   -1.7774   -0.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8948   -0.7091   -0.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8130   -0.2709   -2.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1265    1.7798   -0.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4942   -2.3098    1.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  6  1  0
  4  5  2  0
  2  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 14  1  0
 12 13  2  0
 10 15  1  0
 15 17  1  0
 15 16  2  0
  1 18  1  0
  1 19  1  0
  2 20  1  6
  3 21  1  0
  3 22  1  0
  6 23  1  0
  8 24  1  0
 10 25  1  6
 11 26  1  0
 11 27  1  0
 14 28  1  0
 17 29  1  0
M  END


  Mrv1652309042216042D          

 17 16  0  0  1  0            999 V2000
    1.9520   -3.6020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -3.1895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5230   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -4.8395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -4.8395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.1270    0.0000 C   0  0  1  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
    1.2375    0.1105    0.0000 C   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
    1.9520    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.1270    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  4  0  0  0
  7  9  2  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0196070

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H12N2O7/c9-3(1-5(11)12)7(15)10-4(8(16)17)2-6(13)14/h3-4H,1-2,9H2,(H,10,15)(H,11,12)(H,13,14)(H,16,17)/t3-,4-/m0/s1

> <INCHI_KEY>
FRYULLIZUDQONW-IMJSIDKUSA-N

> <FORMULA>
C8H12N2O7

> <MOLECULAR_WEIGHT>
248.191

> <EXACT_MASS>
248.064450734

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
21.683848500381675

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2S)-2-amino-3-carboxy-1-hydroxypropylidene]amino}butanedioic acid

> <JCHEM_LOGP>
-4.082841527490248

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.405471806628166

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.644243738736109

> <JCHEM_PKA_STRONGEST_BASIC>
9.70232495693674

> <JCHEM_POLAR_SURFACE_AREA>
170.51

> <JCHEM_REFRACTIVITY>
50.38720000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S)-2-amino-3-carboxy-1-hydroxypropylidene]amino}butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  N   UNK     0       3.644  -6.724   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.310  -5.954   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.976  -6.724   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.976  -8.264   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.357  -9.034   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       2.310  -9.034   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.310  -4.414   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.976  -3.644   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       3.644  -3.644   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.644  -2.104   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  C   UNK     0       2.310   0.206   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.976   0.976   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       3.644   0.976   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.977  -1.334   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.977   0.206   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.311  -2.104   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   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

View in JSmol

Synonyms

Value	Source
D-D	ChEBI
DD	ChEBI
L-Asp-L-asp	ChEBI
Aspartyl-aspartic acid	MeSH
beta-L-Aspartyl-L-aspartic acid	MeSH

Chemical Formula

C₈H₁₂N₂O₇

Average Mass

248.1910 Da

Monoisotopic Mass

248.06445 Da

IUPAC Name

(2S)-2-{[(2S)-2-amino-3-carboxy-1-hydroxypropylidene]amino}butanedioic acid

Traditional Name

(2S)-2-{[(2S)-2-amino-3-carboxy-1-hydroxypropylidene]amino}butanedioic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H12N2O7/c9-3(1-5(11)12)7(15)10-4(8(16)17)2-6(13)14/h3-4H,1-2,9H2,(H,10,15)(H,11,12)(H,13,14)(H,16,17)/t3-,4-/m0/s1

InChI Key

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:73446 )

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	-4.1	ChemAxon
pKa (Strongest Acidic)	2.64	ChemAxon
pKa (Strongest Basic)	9.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	170.51 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	50.39 m³·mol⁻¹	ChemAxon
Polarizability	21.68 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

414197

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

471583

PDB ID

Not Available

ChEBI ID

73446

Good Scents ID

Not Available

References

General References

Suo SK, Zheng SL, Chi CF, Luo HY, Wang B: Novel angiotensin-converting enzyme inhibitory peptides from tuna byproducts-milts: Preparation, characterization, molecular docking study, and antioxidant function on H(2)O(2)-damaged human umbilical vein endothelial cells. Front Nutr. 2022 Jul 22;9:957778. doi: 10.3389/fnut.2022.957778. eCollection 2022. [PubMed:35938100 ]
Onder S, Biberoglu K, Tacal O, Schopfer LM: Chlorpyrifos oxon crosslinking of amyloid beta 42 peptides is a new route for generation of self-aggregating amyloidogenic oligomers that promote Alzheimer's disease. Chem Biol Interact. 2022 Aug 25;363:110029. doi: 10.1016/j.cbi.2022.110029. Epub 2022 Jun 30. [PubMed:35779611 ]
Zhuang S, Bao Y, Zhang Y, Zhang H, Liu J, Liu H: Antibacterial mechanism of the Asp-Asp-Asp-Tyr peptide. Food Chem X. 2022 Jan 29;13:100229. doi: 10.1016/j.fochx.2022.100229. eCollection 2022 Mar 30. [PubMed:35499031 ]
Stevens LJ, Pruijssers AJ, Lee HW, Gordon CJ, Tchesnokov EP, Gribble J, George AS, Hughes TM, Lu X, Li J, Perry JK, Porter DP, Cihlar T, Sheahan TP, Baric RS, Gotte M, Denison MR: Mutations in the SARS-CoV-2 RNA-dependent RNA polymerase confer resistance to remdesivir by distinct mechanisms. Sci Transl Med. 2022 Aug 3;14(656):eabo0718. doi: 10.1126/scitranslmed.abo0718. Epub 2022 Aug 3. [PubMed:35482820 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}butanedioic acid (NP0196070)

MOL for NP0196070 ((2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}butanedioic acid)

3D MOL for NP0196070 ((2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}butanedioic acid)

3D SDF for NP0196070 ((2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}butanedioic acid)

3D-SDF for NP0196070 ((2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}butanedioic acid)

PDB for NP0196070 ((2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}butanedioic acid)

3D PDB for NP0196070 ((2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}butanedioic acid)

SMILES for NP0196070 ((2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}butanedioic acid)

INCHI for NP0196070 ((2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}butanedioic acid)

Structure for NP0196070 ((2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}butanedioic acid)

3D Structure for NP0196070 ((2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}butanedioic acid)