NP-MRD: Showing NP-Card for Histidyllysine (NP0136499)

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Record Information

Version

2.0

Created at

2022-05-12 15:16:06 UTC

Updated at

2022-05-12 15:16:06 UTC

NP-MRD ID

NP0136499

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Histidyllysine

Description

His-Lys, also known as histidinyl-lysine or HK, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. His-Lys is a drug. His-Lys is a very strong basic compound (based on its pKa). A dipeptide formed from L-histidine and L-lysine residues.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 41  0  0  0  0  0  0  0  0999 V2000
    0.9729   -2.3423   -1.0546 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1607   -1.7829   -2.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4516   -0.4280   -2.4734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0077   -0.6935   -2.2042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8500    0.5572   -2.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4507    1.6001   -1.2607 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5510    1.1342    0.1006 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4978    1.1253    1.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6207    1.5694    0.6433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7202    0.6264    2.3983 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1239    0.2116    2.5089 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0892   -0.5611    2.7944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5385   -0.3951    2.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4130   -1.4144    3.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6614   -0.9473    2.9821 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6211    0.3213    2.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3298    0.6453    2.4597 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3026    2.7942   -1.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9946    3.2749   -0.5709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3081    3.3516   -2.7591 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867   -2.9580   -0.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0937   -2.9325   -1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2583   -1.6391   -2.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7726   -2.4624   -3.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5959    0.0185   -3.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8814    0.2602   -1.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3645   -1.3371   -3.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1544   -1.2654   -1.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7800    0.9398   -3.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9065    0.2430   -2.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3982    1.9078   -1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4833    0.7779    0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6311    1.4773    3.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3399   -0.0682    3.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2398   -0.6126    1.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1987   -0.8064    3.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2687   -1.4334    2.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1426   -2.4190    3.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5117   -1.5266    3.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4896    0.9720    2.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8197    4.2174   -2.9891 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
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
  6 18  1  0
 18 20  1  0
 18 19  2  0
 17 13  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  6
  7 32  1  0
 10 33  1  1
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 20 41  1  0
M  END


  Mrv1652304062013492D          

 20 20  0  0  0  0            999 V2000
 9998.880610000.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5954 9999.7892    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.309310000.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0248 9999.7892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.742510000.2013    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.4560 9999.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.171610000.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.309310001.0261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5954 9998.9638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.494910000.2836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8275 9999.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0824 9999.0140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9074 9999.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1623 9999.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.743510001.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.458510001.4379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.029610001.4397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.8856 9999.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.600510000.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.3145 9999.7863    0.0000 N   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  9  1  1  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
 13 14  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10 11  2  0  0  0  0
 10 14  1  0  0  0  0
  1 14  1  0  0  0  0
  5 15  1  6  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
  6  7  1  0  0  0  0
 19 20  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136499

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCCC[C@H](NC(=O)[C@@H](N)CC1=CNC=N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H21N5O3/c13-4-2-1-3-10(12(19)20)17-11(18)9(14)5-8-6-15-7-16-8/h6-7,9-10H,1-5,13-14H2,(H,15,16)(H,17,18)(H,19,20)/t9-,10-/m0/s1

> <INCHI_KEY>
CZVQSYNVUHAILZ-UWVGGRQHSA-N

> <FORMULA>
C12H21N5O3

> <MOLECULAR_WEIGHT>
283.332

> <EXACT_MASS>
283.164439556

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
29.84903607730932

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-6-amino-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]hexanoic acid

> <ALOGPS_LOGP>
-2.97

> <JCHEM_LOGP>
-3.9930869913234455

> <ALOGPS_LOGS>
-1.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.964532894053512

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.529047333775462

> <JCHEM_PKA_STRONGEST_BASIC>
10.206413513501248

> <JCHEM_POLAR_SURFACE_AREA>
147.12000000000003

> <JCHEM_REFRACTIVITY>
72.1029

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.29e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-6-amino-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]hexanoic 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    8664.5778667.042   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8665.9118666.273   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8667.2448667.042   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0    8668.5808666.273   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0    8669.9198667.042   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8671.2518666.273   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8672.5878667.042   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8667.2448668.582   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0    8665.9118664.732   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0    8661.9908667.196   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0    8660.7458666.291   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0    8661.2208664.826   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    8662.7608664.826   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.2368666.291   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8669.9218668.582   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8671.2568669.351   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    8668.5898669.354   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8673.9208666.271   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8675.2548667.039   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0    8676.5878666.268   0.000  0.00  0.00           N+0
CONECT    1    2   14                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6   18                                                       
CONECT    8    3                                                            
CONECT    9    2                                                            
CONECT   10   11   14                                                       
CONECT   11   12   10                                                       
CONECT   12   11   13                                                       
CONECT   13   14   12                                                       
CONECT   14   13   10    1                                                  
CONECT   15    5   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    7   19                                                       
CONECT   19   20   18                                                       
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
Histidinyl-lysine	ChEBI
Histidyllysine	ChEBI
HK	ChEBI
L-His-L-lys	ChEBI
N(2)-L-Histidyl-L-lysine	ChEBI
N(alpha)-L-Histidyl-L-lysine	ChEBI
N(a)-L-Histidyl-L-lysine	Generator
N(Α)-L-histidyl-L-lysine	Generator
H-K dipeptide	HMDB
HK dipeptide	HMDB
His-Lys	HMDB
Histidine lysine dipeptide	HMDB
Histidine-lysine dipeptide	HMDB
Histidinyllysine	HMDB
Histidyl-lysine	HMDB
L-Histidinyl-L-lysine	HMDB
L-Histidyl-L-lysine	HMDB
N2-Histidinyllysine	HMDB
N2-Histidyllysine	HMDB
N2-L-Histidinyl-L-lysine	HMDB
N2-L-Histidyl-L-lysine	HMDB

Chemical Formula

C₁₂H₂₁N₅O₃

Average Mass

283.3320 Da

Monoisotopic Mass

283.16444 Da

IUPAC Name

(2S)-6-amino-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]hexanoic acid

Traditional Name

(2S)-6-amino-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]hexanoic acid

CAS Registry Number

Not Available

SMILES

NCCCC[C@H](NC(=O)[C@@H](N)CC1=CNC=N1)C(O)=O

InChI Identifier

InChI=1S/C12H21N5O3/c13-4-2-1-3-10(12(19)20)17-11(18)9(14)5-8-6-15-7-16-8/h6-7,9-10H,1-5,13-14H2,(H,15,16)(H,17,18)(H,19,20)/t9-,10-/m0/s1

InChI Key

CZVQSYNVUHAILZ-UWVGGRQHSA-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 anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Anisole
Benzylamine
Dialkylarylamine
Methoxybenzene
Alkyl aryl ether
Aminopyrimidine
Monocyclic benzene moiety
Pyrimidine
Tetraalkylammonium salt
Heteroaromatic compound
Quaternary ammonium salt
Ether
Organoheterocyclic compound
Azacycle
Organic oxygen compound
Amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Organic salt
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	ALOGPS
logP	-4	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	147.12 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	72.1 m³·mol⁻¹	ChemAxon
Polarizability	29.85 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

HMDB0028890

DrugBank ID

DBMET01483

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

148224

PDB ID

Not Available

ChEBI ID

74052

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Histidyllysine (NP0136499)

MOL for NP0136499 (Histidyllysine)

3D MOL for NP0136499 (Histidyllysine)

3D SDF for NP0136499 (Histidyllysine)

3D-SDF for NP0136499 (Histidyllysine)

PDB for NP0136499 (Histidyllysine)

3D PDB for NP0136499 (Histidyllysine)

SMILES for NP0136499 (Histidyllysine)

INCHI for NP0136499 (Histidyllysine)

Structure for NP0136499 (Histidyllysine)

3D Structure for NP0136499 (Histidyllysine)