NP-MRD: Showing NP-Card for Lysylproline (NP0136562)

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Record Information

Version

2.0

Created at

2022-05-12 15:17:44 UTC

Updated at

2022-05-12 15:17:45 UTC

NP-MRD ID

NP0136562

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lysylproline

Description

Lys-Pro, also known as lysyl-proline or KP, 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. Lys-Pro is a very strong basic compound (based on its pKa). A dipeptide formed from L-lysine and L-proline residues.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 38  0  0  0  0  0  0  0  0999 V2000
    5.5521   -0.3455    1.6705 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4158   -0.4304    0.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8464    0.9460    0.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6812    0.9280   -0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5702    0.0589    0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4080    0.0818   -0.8725 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0644    1.3989   -1.0436 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739   -0.7653   -0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3983   -1.9827   -0.0721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9751   -0.3121    0.0055 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4596    1.0420   -0.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9085    1.0465    0.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0840   -0.2005    1.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0224   -1.1367    0.5627 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5555   -2.0576   -0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4796   -2.8548   -0.1603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0266   -2.0202   -1.7458 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2004   -0.3842    2.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1094   -1.2346    1.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6695   -1.0642    1.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6854   -0.9228   -0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6452    1.6152    0.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5147    1.3713    1.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349    1.9679   -0.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0336    0.5006   -1.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528   -0.9832    0.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2526    0.4390    1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7976   -0.3983   -1.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1791    1.7274   -2.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3175    2.1116   -0.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8903    1.7535    0.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4204    1.3195   -1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5812    1.0839   -0.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0996    1.9815    0.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0944   -0.6479    0.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9189    0.0062    2.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5865   -1.6934    1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5688   -1.9456   -2.5897 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  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 17  1  0
 15 16  2  0
 14 10  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  6
  7 29  1  0
  7 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  1
 17 38  1  0
M  END

      
  Mrv1652304062014002D          

 17 17  0  0  0  0            999 V2000
10001.0931 9999.6070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.378610000.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6633 9999.6070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.949310000.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2353 9999.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.519210000.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8050 9999.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.089010000.0195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6633 9998.7821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.378610000.8450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.1794 9998.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.9863 9998.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.3988 9999.3294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8468 9999.9424    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.018310000.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.405310001.3015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.803010001.0043    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  0  0  0  0
  2 10  2  0  0  0  0
  3  4  1  0  0  0  0
  3  9  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  1 11  1  0  0  0  0
  1 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136562

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCCC[C@H](N)C(=O)N1CCC[C@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H21N3O3/c12-6-2-1-4-8(13)10(15)14-7-3-5-9(14)11(16)17/h8-9H,1-7,12-13H2,(H,16,17)/t8-,9-/m0/s1

> <INCHI_KEY>
AIXUQKMMBQJZCU-IUCAKERBSA-N

> <FORMULA>
C11H21N3O3

> <MOLECULAR_WEIGHT>
243.307

> <EXACT_MASS>
243.158291548

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.059026720535066

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-[(2S)-2,6-diaminohexanoyl]pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-3.10

> <JCHEM_LOGP>
-3.3585842295490793

> <ALOGPS_LOGS>
-1.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6801513796941574

> <JCHEM_PKA_STRONGEST_BASIC>
10.212734160831241

> <JCHEM_POLAR_SURFACE_AREA>
109.64999999999999

> <JCHEM_REFRACTIVITY>
62.79600000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.07e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[(2S)-2,6-diaminohexanoyl]pyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  N   UNK     0    8668.7078665.933   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0    8667.3738666.703   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8666.0388665.933   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8664.7058666.703   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8663.3738665.933   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8662.0368666.703   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8660.7038665.933   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0    8659.3668666.703   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0    8666.0388664.393   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0    8667.3738668.244   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8668.8688664.401   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8670.3748664.081   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8671.1448665.415   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8670.1148666.559   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8670.4348668.066   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8669.2908669.096   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    8671.8998668.541   0.000  0.00  0.00           O+0
CONECT    1    2   11   14                                                  
CONECT    2    1    3   10                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    3                                                            
CONECT   10    2                                                            
CONECT   11   12    1                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    1   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
KP	ChEBI
L-Lys-L-pro	ChEBI
Lysyl-proline	ChEBI
Lysylproline	ChEBI
K-P dipeptide	HMDB
KP dipeptide	HMDB
L-Lysyl-L-proline	HMDB
Lys-Pro	HMDB
Lysine proline dipeptide	HMDB
Lysine-proline dipeptide	HMDB
N-L-Lysyl-L-proline	HMDB
N-Lysylproline	HMDB

Chemical Formula

C₁₁H₂₁N₃O₃

Average Mass

243.3070 Da

Monoisotopic Mass

243.15829 Da

IUPAC Name

(2S)-1-[(2S)-2,6-diaminohexanoyl]pyrrolidine-2-carboxylic acid

Traditional Name

(2S)-1-[(2S)-2,6-diaminohexanoyl]pyrrolidine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

NCCCC[C@H](N)C(=O)N1CCC[C@H]1C(O)=O

InChI Identifier

InChI=1S/C11H21N3O3/c12-6-2-1-4-8(13)10(15)14-7-3-5-9(14)11(16)17/h8-9H,1-7,12-13H2,(H,16,17)/t8-,9-/m0/s1

InChI Key

AIXUQKMMBQJZCU-IUCAKERBSA-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
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Primary aliphatic amine
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organonitrogen compound
Organooxygen compound
Primary amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:74567 )

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	-3.4	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.65 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	62.8 m³·mol⁻¹	ChemAxon
Polarizability	26.06 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

HMDB0028959

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

149672

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

171204

PDB ID

Not Available

ChEBI ID

74567

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Lysylproline (NP0136562)

MOL for NP0136562 (Lysylproline)

3D MOL for NP0136562 (Lysylproline)

3D SDF for NP0136562 (Lysylproline)

3D-SDF for NP0136562 (Lysylproline)

PDB for NP0136562 (Lysylproline)

3D PDB for NP0136562 (Lysylproline)

SMILES for NP0136562 (Lysylproline)

INCHI for NP0136562 (Lysylproline)

Structure for NP0136562 (Lysylproline)

3D Structure for NP0136562 (Lysylproline)