NP-MRD: Showing NP-Card for (2s,3r)-2-{[(2s,3r)-2-amino-1,3-dihydroxybutylidene]amino}-3-hydroxybutanoic acid (NP0315167)

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Record Information

Version

2.0

Created at

2022-09-11 13:39:52 UTC

Updated at

2022-09-11 13:39:53 UTC

NP-MRD ID

NP0315167

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r)-2-{[(2s,3r)-2-amino-1,3-dihydroxybutylidene]amino}-3-hydroxybutanoic acid

Description

Thr-Thr, also known as H-L-THR-L-THR-OH or T-T, 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. Thr-Thr 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,3r)-2-{[(2s,3r)-2-amino-1,3-dihydroxybutylidene]amino}-3-hydroxybutanoic acid is found in Trypanosoma brucei. (2s,3r)-2-{[(2s,3r)-2-amino-1,3-dihydroxybutylidene]amino}-3-hydroxybutanoic acid was first documented in 2022 (PMID: 35629879). Based on a literature review very few articles have been published on Thr-Thr.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 30  0  0  0  0  0  0  0  0999 V2000
   -2.6510    1.7679   -0.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6230    0.7801    0.8275 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9077    0.2252    0.9358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6664   -0.3488    0.6241 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3001    0.0393    0.4928 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6265   -0.8411    0.6505 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3085   -2.1595    0.9460 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0816   -0.5091    0.5283 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6073   -1.2555   -0.5974 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2791    0.9570    0.2053 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7684    1.1278   -0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5903    1.2476   -0.9549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1040   -1.1365   -0.5630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2870   -1.3584   -1.4829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4044   -1.6066   -0.6243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1758    2.6888    0.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3013    1.3904   -1.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6601    2.0514   -0.6810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4446    1.2904    1.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4184    0.3724    0.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7407   -1.0105    1.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6987   -2.8784    0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6240   -0.7976    1.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8672   -1.5103   -1.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2409   -2.0140   -0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0247    1.6227    1.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2892    1.6652    0.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9226    1.7437   -1.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2623    0.1536   -0.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0653    0.8563   -1.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5722   -2.5535   -0.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10 12  1  0
 10  8  1  0
  8  9  1  0
  8  6  1  0
  6  7  1  0
  6  5  2  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
  4 13  1  0
 13 15  1  0
 13 14  2  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 10 26  1  1
 12 30  1  0
  8 23  1  1
  9 24  1  0
  9 25  1  0
  7 22  1  0
  4 21  1  1
  2 19  1  1
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 20  1  0
 15 31  1  0
M  END


  Mrv1652309112215392D          

 15 14  0  0  1  0            999 V2000
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 N   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  2  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
    0.0000   -1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    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  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  4  0  0  0
  6  8  2  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0315167

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H16N2O5/c1-3(11)5(9)7(13)10-6(4(2)12)8(14)15/h3-6,11-12H,9H2,1-2H3,(H,10,13)(H,14,15)/t3-,4-,5+,6+/m1/s1

> <INCHI_KEY>
DSGIVWSDDRDJIO-ZXXMMSQZSA-N

> <FORMULA>
C8H16N2O5

> <MOLECULAR_WEIGHT>
220.225

> <EXACT_MASS>
220.105921623

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
21.099445190897164

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R)-2-{[(2S,3R)-2-amino-1,3-dihydroxybutylidene]amino}-3-hydroxybutanoic acid

> <JCHEM_LOGP>
-4.038165750293001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.042754511286104

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8979302679229146

> <JCHEM_PKA_STRONGEST_BASIC>
9.077940693692698

> <JCHEM_POLAR_SURFACE_AREA>
136.37

> <JCHEM_REFRACTIVITY>
50.2414

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-2-{[(2S,3R)-2-amino-1,3-dihydroxybutylidene]amino}-3-hydroxybutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.620   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.540   2.667   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.080  -2.667   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -3.080   0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.000  -2.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.770  -4.001   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.540  -2.667   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
H-L-THR-L-THR-OH	ChEBI
H-THR-THR-OH	ChEBI
L-THR-L-THR	ChEBI
T-T	ChEBI
Threoninyl-threonine	ChEBI
TT	ChEBI

Chemical Formula

C₈H₁₆N₂O₅

Average Mass

220.2250 Da

Monoisotopic Mass

220.10592 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H16N2O5/c1-3(11)5(9)7(13)10-6(4(2)12)8(14)15/h3-6,11-12H,9H2,1-2H3,(H,10,13)(H,14,15)/t3-,4-,5+,6+/m1/s1

InChI Key

DSGIVWSDDRDJIO-ZXXMMSQZSA-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
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
Beta-hydroxy acid
Short-chain hydroxy acid
Fatty amide
Hydroxy acid
N-acyl-amine
Fatty acid
Fatty acyl
Secondary carboxylic acid amide
Secondary alcohol
Amino acid or derivatives
Amino acid
Carboxamide group
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Primary aliphatic amine
Alcohol
Organic nitrogen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:73665 )

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

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

9496923

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11321969

PDB ID

Not Available

ChEBI ID

73665

Good Scents ID

Not Available

References

General References

Schwengber WK, Silveira VB, Hetzel GM, Robaina A, Ceolin L, Camelier MT, Goemann I, Dalla Corte RR, Scheffel RS, de Mello RGB, Maia AL, Dora JM: Type 2 Deiodinase Thr92Ala Polymorphism Is Not Associated with Cognitive Impairment in Older Adults: A Cross-Sectional Study. Metabolites. 2022 Apr 21;12(5):375. doi: 10.3390/metabo12050375. [PubMed:35629879 ]
LOTUS database [Link]

Showing NP-Card for (2s,3r)-2-{[(2s,3r)-2-amino-1,3-dihydroxybutylidene]amino}-3-hydroxybutanoic acid (NP0315167)

MOL for NP0315167 ((2s,3r)-2-{[(2s,3r)-2-amino-1,3-dihydroxybutylidene]amino}-3-hydroxybutanoic acid)

3D MOL for NP0315167 ((2s,3r)-2-{[(2s,3r)-2-amino-1,3-dihydroxybutylidene]amino}-3-hydroxybutanoic acid)

3D SDF for NP0315167 ((2s,3r)-2-{[(2s,3r)-2-amino-1,3-dihydroxybutylidene]amino}-3-hydroxybutanoic acid)

3D-SDF for NP0315167 ((2s,3r)-2-{[(2s,3r)-2-amino-1,3-dihydroxybutylidene]amino}-3-hydroxybutanoic acid)

PDB for NP0315167 ((2s,3r)-2-{[(2s,3r)-2-amino-1,3-dihydroxybutylidene]amino}-3-hydroxybutanoic acid)

3D PDB for NP0315167 ((2s,3r)-2-{[(2s,3r)-2-amino-1,3-dihydroxybutylidene]amino}-3-hydroxybutanoic acid)

SMILES for NP0315167 ((2s,3r)-2-{[(2s,3r)-2-amino-1,3-dihydroxybutylidene]amino}-3-hydroxybutanoic acid)

INCHI for NP0315167 ((2s,3r)-2-{[(2s,3r)-2-amino-1,3-dihydroxybutylidene]amino}-3-hydroxybutanoic acid)

Structure for NP0315167 ((2s,3r)-2-{[(2s,3r)-2-amino-1,3-dihydroxybutylidene]amino}-3-hydroxybutanoic acid)

3D Structure for NP0315167 ((2s,3r)-2-{[(2s,3r)-2-amino-1,3-dihydroxybutylidene]amino}-3-hydroxybutanoic acid)