NP-MRD: Showing NP-Card for Threonylhistidine (NP0136648)

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Record Information

Version

1.0

Created at

2022-05-12 15:19:56 UTC

Updated at

2022-05-12 15:19:56 UTC

NP-MRD ID

NP0136648

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Threonylhistidine

Description

Thr-His, also known as L-THR-L-his or T-H, 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-His is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 34  0  0  0  0  0  0  0  0999 V2000
    4.3212    0.9974   -0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2306    0.3489    0.4758 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3988    1.3605    0.9539 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4040   -0.5520   -0.4341 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9050    0.2389   -1.5035 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2554   -1.1375    0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4876   -1.8865    1.3125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0777   -0.8692   -0.0940 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2171   -1.3979    0.5722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1144   -0.3553    1.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6601    0.5934    0.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8243    0.5395   -0.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9196    1.6513   -1.3077 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8281    2.3712   -1.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630    1.7484   -0.1368 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0416   -2.2377   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6821   -2.3952   -1.5129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1857   -2.8432    0.1199 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9724    1.1402   -1.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2031    0.3051   -0.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6083    1.9866    0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6871   -0.2047    1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3253    2.0789    0.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786   -1.3448   -0.8272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3391    1.0341   -1.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5995   -0.2603   -2.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2190   -0.2542   -0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8440   -2.0292    1.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9752   -0.9115    1.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6158    0.1480    2.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5521   -0.2718   -0.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6059    3.3218   -1.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1565    2.1442    0.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2339   -3.0573    1.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
  9 16  1  0
 16 18  1  0
 16 17  2  0
 15 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  4 24  1  6
  5 25  1  0
  5 26  1  0
  8 27  1  0
  9 28  1  1
 10 29  1  0
 10 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
M  END


  Mrv1652304062014152D          

 18 18  0  0  0  0            999 V2000
10047.067410047.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10047.784510047.6501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10048.498810047.2383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10049.213110047.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10049.927610047.2383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10049.213110048.4748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10046.354110047.6501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10045.638710047.2383    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10044.925310047.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10045.638710046.4133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10046.354110048.4748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10047.067410046.4133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10048.498810046.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10049.214910045.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10049.301410045.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10050.110210045.0056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10050.523810045.7218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10049.970510046.3362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 12  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  6  0  0  0
  8  9  1  0  0  0  0
  3 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  8 10  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0136648

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)[C@H](N)C(=O)N[C@@H](CC1=CN=CN1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N4O4/c1-5(15)8(11)9(16)14-7(10(17)18)2-6-3-12-4-13-6/h3-5,7-8,15H,2,11H2,1H3,(H,12,13)(H,14,16)(H,17,18)/t5-,7+,8+/m1/s1

> <INCHI_KEY>
WXVIGTAUZBUDPZ-DTLFHODZSA-N

> <FORMULA>
C10H16N4O4

> <MOLECULAR_WEIGHT>
256.262

> <EXACT_MASS>
256.117155011

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
24.24516216896314

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]-3-(1H-imidazol-5-yl)propanoic acid

> <ALOGPS_LOGP>
-2.86

> <JCHEM_LOGP>
-4.541520837335837

> <ALOGPS_LOGS>
-1.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.672291085892738

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3322130177713767

> <JCHEM_PKA_STRONGEST_BASIC>
7.950446371190433

> <JCHEM_POLAR_SURFACE_AREA>
141.33

> <JCHEM_REFRACTIVITY>
61.3189

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.04e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]-3-(3H-imidazol-4-yl)propanoic 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    8754.5268754.845   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8755.8648755.614   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    8757.1988754.845   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8758.5318755.614   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8759.8658754.845   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8758.5318757.153   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8753.1948755.614   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8751.8598754.845   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8750.5278755.614   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8751.8598753.305   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0    8753.1948757.153   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0    8754.5268753.305   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8757.1988753.305   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8758.5348752.533   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8758.6968750.998   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0    8760.2068750.677   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0    8760.9788752.014   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0    8759.9458753.161   0.000  0.00  0.00           N+0
CONECT    1    2    7   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7                                                            
CONECT   12    1                                                            
CONECT   13    3   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   18   16                                                       
CONECT   18   17   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
L-THR-L-His	ChEBI
T-H	ChEBI
TH	ChEBI
L-Threoninyl-L-histidine	HMDB
L-Threonyl-L-histidine	HMDB
N-L-Threoninyl-L-histidine	HMDB
N-L-Threonyl-L-histidine	HMDB
N-Threoninylhistidine	HMDB
N-Threonylhistidine	HMDB
T-H dipeptide	HMDB
TH dipeptide	HMDB
Thr-His	HMDB
Threonine histidine dipeptide	HMDB
Threonine-histidine dipeptide	HMDB
Threoninyl-histidine	HMDB
Threoninylhistidine	HMDB
Threonyl-histidine	HMDB
Threonylhistidine	HMDB

Chemical Formula

C₁₀H₁₆N₄O₄

Average Mass

256.2620 Da

Monoisotopic Mass

256.11716 Da

IUPAC Name

(2S)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]-3-(1H-imidazol-5-yl)propanoic acid

Traditional Name

(2S)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]-3-(3H-imidazol-4-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](O)[C@H](N)C(=O)N[C@@H](CC1=CN=CN1)C(O)=O

InChI Identifier

InChI=1S/C10H16N4O4/c1-5(15)8(11)9(16)14-7(10(17)18)2-6-3-12-4-13-6/h3-5,7-8,15H,2,11H2,1H3,(H,12,13)(H,14,16)(H,17,18)/t5-,7+,8+/m1/s1

InChI Key

WXVIGTAUZBUDPZ-DTLFHODZSA-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
Histidine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
N-acyl-amine
Fatty acyl
Fatty amide
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Amino acid
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Primary amine
Organic oxygen compound
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Primary aliphatic amine
Amine
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:73663 )

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	-4.5	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.33	ChemAxon
pKa (Strongest Basic)	7.95	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	141.33 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	61.32 m³·mol⁻¹	ChemAxon
Polarizability	24.25 Å³	ChemAxon
Number of Rings	1	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

HMDB0029063

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8118661

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9943049

PDB ID

Not Available

ChEBI ID

73663

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Threonylhistidine (NP0136648)

MOL for NP0136648 (Threonylhistidine)

3D MOL for NP0136648 (Threonylhistidine)

3D SDF for NP0136648 (Threonylhistidine)

3D-SDF for NP0136648 (Threonylhistidine)

PDB for NP0136648 (Threonylhistidine)

3D PDB for NP0136648 (Threonylhistidine)

SMILES for NP0136648 (Threonylhistidine)

INCHI for NP0136648 (Threonylhistidine)

Structure for NP0136648 (Threonylhistidine)

3D Structure for NP0136648 (Threonylhistidine)