NP-MRD: Showing NP-Card for Threonyltryptophan (NP0136657)

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Record Information

Version

2.0

Created at

2022-05-12 15:20:10 UTC

Updated at

2022-05-12 15:20:10 UTC

NP-MRD ID

NP0136657

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Threonyltryptophan

Description

Thr-Trp 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-Trp is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
   -3.7815   -2.0915    0.8348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5900   -0.8370    0.5871 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8188   -0.9468    1.2795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8734    0.4150    1.0485 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7749    1.5657    0.7718 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6152    0.6943    0.3449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5913    1.7170   -0.4275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4302   -0.0282    0.4213 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024    0.3411   -0.3320 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7848    0.5561    0.7297 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1415    0.9264    0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5938    2.2551    0.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9019    2.2935    0.2801 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3654    1.0778   -0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5995    0.5463   -0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7441   -0.8027   -0.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6715   -1.6743   -0.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4453   -1.1230   -0.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2889    0.2226    0.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0342   -0.7886   -1.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6756   -1.8200   -1.2534 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0747   -0.7811   -2.1858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0390   -2.2038    0.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4344   -2.9995    0.7916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2455   -2.0628    1.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8111   -0.7755   -0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5538   -1.1532    0.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7524    0.4083    2.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2031    2.4578    0.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1336    1.5105   -0.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3624   -0.8700    1.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5315    1.2631   -0.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3323    1.3035    1.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7462   -0.3905    1.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0238    3.1371    0.8348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5291    3.1491    0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4421    1.2156   -0.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7217   -1.2229   -0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7185   -2.7363   -0.6103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5623   -1.7361    0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6987   -0.0123   -2.3243 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  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  9 20  1  0
 20 22  1  0
 20 21  2  0
 19 11  1  0
 19 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  6
  3 27  1  0
  4 28  1  1
  5 29  1  0
  5 30  1  0
  8 31  1  0
  9 32  1  6
 10 33  1  0
 10 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 22 41  1  0
M  END


  Mrv1652304062014162D          

 22 23  0  0  0  0            999 V2000
10000.516910000.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.232210001.1006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.945010000.6897    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.657810001.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.370410000.6897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.657810001.9235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.805110001.1006    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.091310000.6897    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.379610001.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0913 9999.8666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.805110001.9235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.5169 9999.8666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.9450 9999.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.6596 9999.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.7459 9998.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.5528 9998.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.9653 9999.1766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.4133 9999.7896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1937 9998.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.4484 9997.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2556 9997.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.8078 9997.6772    0.0000 C   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  1  0  0  0  0
 15 16  1  0  0  0  0
 14 18  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 15 19  2  0  0  0  0
 22 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 10  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0136657

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)[C@H](N)C(=O)N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H19N3O4/c1-8(19)13(16)14(20)18-12(15(21)22)6-9-7-17-11-5-3-2-4-10(9)11/h2-5,7-8,12-13,17,19H,6,16H2,1H3,(H,18,20)(H,21,22)/t8-,12+,13+/m1/s1

> <INCHI_KEY>
KAFKKRJQHOECGW-JCOFBHIZSA-N

> <FORMULA>
C15H19N3O4

> <MOLECULAR_WEIGHT>
305.334

> <EXACT_MASS>
305.137556104

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
30.510142067075353

> <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-indol-3-yl)propanoic acid

> <ALOGPS_LOGP>
-1.22

> <JCHEM_LOGP>
-2.25438824477311

> <ALOGPS_LOGS>
-2.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.472088202691715

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.783334237909041

> <JCHEM_PKA_STRONGEST_BASIC>
7.922179039227511

> <JCHEM_POLAR_SURFACE_AREA>
128.44

> <JCHEM_REFRACTIVITY>
79.46270000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]-3-(1H-indol-3-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    8667.6328667.954   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8668.9678668.721   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    8670.2978667.954   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8671.6288668.721   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8672.9588667.954   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8671.6288670.257   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8666.3038668.721   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8664.9708667.954   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8663.6428668.721   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8664.9708666.418   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0    8666.3038670.257   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0    8667.6328666.418   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8670.2978666.418   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8671.6318665.648   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8671.7928664.116   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8673.2998663.796   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0    8674.0698665.130   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0    8673.0388666.274   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8670.7628662.971   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8671.2378661.507   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8672.7448661.186   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8673.7758662.331   0.000  0.00  0.00           C+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   19                                                  
CONECT   16   15   22   17                                                  
CONECT   17   16   18                                                       
CONECT   18   14   17                                                       
CONECT   19   20   15                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
L-Thr-L-Trp	HMDB
L-Threoninyl-L-tryptophan	HMDB
L-Threonyl-L-tryptophan	HMDB
N-L-Threoninyl-L-tryptophan	HMDB
N-L-Threonyl-L-tryptophan	HMDB
N-Threoninyltryptophan	HMDB
N-Threonyltryptophan	HMDB
T-W dipeptide	HMDB
TW dipeptide	HMDB
Thr-Trp	HMDB
Threonine tryptophan dipeptide	HMDB
Threonine-tryptophan dipeptide	HMDB
Threoninyl-tryptophan	HMDB
Threoninyltryptophan	HMDB
Threonyl-tryptophan	HMDB
Threonyltryptophan	HMDB

Chemical Formula

C₁₅H₁₉N₃O₄

Average Mass

305.3340 Da

Monoisotopic Mass

305.13756 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

C[C@@H](O)[C@H](N)C(=O)N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O

InChI Identifier

InChI=1S/C15H19N3O4/c1-8(19)13(16)14(20)18-12(15(21)22)6-9-7-17-11-5-3-2-4-10(9)11/h2-5,7-8,12-13,17,19H,6,16H2,1H3,(H,18,20)(H,21,22)/t8-,12+,13+/m1/s1

InChI Key

KAFKKRJQHOECGW-JCOFBHIZSA-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
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Indolyl carboxylic acid derivative
Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Fatty amide
N-acyl-amine
Substituted pyrrole
Benzenoid
Fatty acyl
Pyrrole
Heteroaromatic compound
Secondary carboxylic acid amide
Secondary alcohol
Amino acid or derivatives
Carboxamide group
Amino acid
Organoheterocyclic compound
Azacycle
Carboxylic acid
Monocarboxylic acid or derivatives
Primary amine
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organonitrogen compound
Amine
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dipeptide (CHEBI:73666 )

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	-1.2	ALOGPS
logP	-2.3	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.78	ChemAxon
pKa (Strongest Basic)	7.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	128.44 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	79.46 m³·mol⁻¹	ChemAxon
Polarizability	30.51 Å³	ChemAxon
Number of Rings	2	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

HMDB0029072

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29368070

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71728368

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Threonyltryptophan (NP0136657)

MOL for NP0136657 (Threonyltryptophan)

3D MOL for NP0136657 (Threonyltryptophan)

3D SDF for NP0136657 (Threonyltryptophan)

3D-SDF for NP0136657 (Threonyltryptophan)

PDB for NP0136657 (Threonyltryptophan)

3D PDB for NP0136657 (Threonyltryptophan)

SMILES for NP0136657 (Threonyltryptophan)

INCHI for NP0136657 (Threonyltryptophan)

Structure for NP0136657 (Threonyltryptophan)

3D Structure for NP0136657 (Threonyltryptophan)