NP-MRD: Showing NP-Card for Threonylhydroxyproline (NP0136647)

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Record Information

Version

2.0

Created at

2022-05-12 15:19:55 UTC

Updated at

2022-05-12 15:19:55 UTC

NP-MRD ID

NP0136647

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Threonylhydroxyproline

Description

Threoninylhydroxyproline, also known as T-HP dipeptide or THR-hpro, 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. Threoninylhydroxyproline 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

     RDKit          3D

 32 32  0  0  0  0  0  0  0  0999 V2000
    3.0893    1.6188   -0.8361 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9891    0.5842   -0.9814 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4388   -0.4184   -1.8312 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6864    0.0246    0.4065 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9450   -0.5431    0.9148 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6625   -1.0113    0.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1109   -2.2233    0.2971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7227   -0.8424    0.1137 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6658   -1.9659   -0.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6324   -1.2733   -1.0451 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9069   -0.9085   -2.1865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8919   -0.0225   -0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4538    0.3871    0.1132 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4457    1.0760    1.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9351    0.5746    2.4383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0298    2.3254    1.5131 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9769    1.3636   -1.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6950    2.6002   -1.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4639    1.6998    0.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0938    1.0293   -1.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2488   -0.2349   -2.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3716    0.8386    1.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1780   -1.3980    0.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8607   -0.7363    1.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2353   -2.1775    0.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2002   -2.8322   -0.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5077   -1.8762   -1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4544   -0.2824   -2.7245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4405   -0.2802    0.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3970    0.7658   -0.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1211    1.0273   -0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7705    3.1111    0.9353 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
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
 13  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  6
  3 21  1  0
  4 22  1  1
  5 23  1  0
  5 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  6
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  6
 16 32  1  0
M  END


  Mrv1652304062014142D          

 16 16  0  0  0  0            999 V2000
10002.1009 9999.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8128 9999.2054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.100910000.4412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8095 9997.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7175 9999.7002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.0502 9999.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3051 9998.4306    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.1301 9998.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3850 9999.2152    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.717510000.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.432010000.9377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.574110000.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.288610000.5252    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.003110001.7627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.003110000.9377    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.2886 9999.7002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  7  4  1  1  0  0  0
  9  1  1  6  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  6  0  0  0
 10 15  1  0  0  0  0
 13 12  1  0  0  0  0
 13 16  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0136647

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)[C@H](N)C(=O)N1C[C@H](O)C[C@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H16N2O5/c1-4(12)7(10)8(14)11-3-5(13)2-6(11)9(15)16/h4-7,12-13H,2-3,10H2,1H3,(H,15,16)/t4-,5-,6+,7+/m1/s1

> <INCHI_KEY>
LARRWQRLUSYTHC-JWXFUTCRSA-N

> <FORMULA>
C9H16N2O5

> <MOLECULAR_WEIGHT>
232.236

> <EXACT_MASS>
232.105921623

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
22.123510243489594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4R)-1-[(2S,3R)-2-amino-3-hydroxybutanoyl]-4-hydroxypyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-3.06

> <JCHEM_LOGP>
-4.886396606193393

> <ALOGPS_LOGS>
-0.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.46080812658342

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.461500863634976

> <JCHEM_PKA_STRONGEST_BASIC>
7.914951168661986

> <JCHEM_POLAR_SURFACE_AREA>
124.09

> <JCHEM_REFRACTIVITY>
52.7642

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.54e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4R)-1-[(2S,3R)-2-amino-3-hydroxybutanoyl]-4-hydroxypyrrolidine-2-carboxylic 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    8670.5888665.953   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8671.9178665.183   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8670.5888667.490   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8666.3118662.504   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0    8668.0068666.107   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8666.7608665.202   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8667.2368663.737   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8668.7768663.737   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8669.2528665.202   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8668.0068667.647   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8669.3408668.417   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8664.0058668.417   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.3398667.647   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0    8666.6728669.957   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0    8666.6728668.417   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8665.3398666.107   0.000  0.00  0.00           O+0
CONECT    1    2    3    9                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    7                                                            
CONECT    5    6    9   10                                                  
CONECT    6    7    5                                                       
CONECT    7    6    8    4                                                  
CONECT    8    7    9                                                       
CONECT    9    8    5    1                                                  
CONECT   10    5   11   15                                                  
CONECT   11   10                                                            
CONECT   12   13                                                            
CONECT   13   15   12   16                                                  
CONECT   14   15                                                            
CONECT   15   13   14   10                                                  
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
L-Threoninyl-L-hydroxyproline	HMDB
T-HP Dipeptide	HMDB
THP Dipeptide	HMDB
THR-HPro	HMDB
Threonine hydroxyproline dipeptide	HMDB
Threonine-hydroxyproline dipeptide	HMDB
THR-Hyp	HMDB
L-THR-L-Hyp	HMDB
Threoninyl-hydroxyproline	HMDB
Threoninylhydroxyproline	HMDB
(2S,4R)-1-[(2S,3R)-2-Amino-3-hydroxybutanoyl]-4-hydroxypyrrolidine-2-carboxylate	Generator
L-Threonyl-L-hydroxyproline	HMDB
N-L-Threoninyl-L-hydroxyproline	HMDB
N-L-Threonyl-L-hydroxyproline	HMDB
N-Threoninylhydroxyproline	HMDB
N-Threonylhydroxyproline	HMDB
Threonyl-hydroxyproline	HMDB
Threonylhydroxyproline	HMDB

Chemical Formula

C₉H₁₆N₂O₅

Average Mass

232.2360 Da

Monoisotopic Mass

232.10592 Da

IUPAC Name

(2S,4R)-1-[(2S,3R)-2-amino-3-hydroxybutanoyl]-4-hydroxypyrrolidine-2-carboxylic acid

Traditional Name

(2S,4R)-1-[(2S,3R)-2-amino-3-hydroxybutanoyl]-4-hydroxypyrrolidine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](O)[C@H](N)C(=O)N1C[C@H](O)C[C@H]1C(O)=O

InChI Identifier

InChI=1S/C9H16N2O5/c1-4(12)7(10)8(14)11-3-5(13)2-6(11)9(15)16/h4-7,12-13H,2-3,10H2,1H3,(H,15,16)/t4-,5-,6+,7+/m1/s1

InChI Key

LARRWQRLUSYTHC-JWXFUTCRSA-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
Proline or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine carboxylic acid
Tertiary carboxylic acid amide
Pyrrolidine
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary alcohol
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Alcohol
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-3.1	ALOGPS
logP	-4.9	ChemAxon
logS	-0.39	ALOGPS
pKa (Strongest Acidic)	3.46	ChemAxon
pKa (Strongest Basic)	7.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.09 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	52.76 m³·mol⁻¹	ChemAxon
Polarizability	22.12 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

HMDB0029062

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

35032825

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

69041809

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Threonylhydroxyproline (NP0136647)

MOL for NP0136647 (Threonylhydroxyproline)

3D MOL for NP0136647 (Threonylhydroxyproline)

3D SDF for NP0136647 (Threonylhydroxyproline)

3D-SDF for NP0136647 (Threonylhydroxyproline)

PDB for NP0136647 (Threonylhydroxyproline)

3D PDB for NP0136647 (Threonylhydroxyproline)

SMILES for NP0136647 (Threonylhydroxyproline)

INCHI for NP0136647 (Threonylhydroxyproline)

Structure for NP0136647 (Threonylhydroxyproline)

3D Structure for NP0136647 (Threonylhydroxyproline)