NP-MRD: Showing NP-Card for Lysylhistidine (NP0136556)

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Record Information

Version

1.0

Created at

2022-05-12 15:17:36 UTC

Updated at

2022-05-12 15:17:36 UTC

NP-MRD ID

NP0136556

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lysylhistidine

Description

L-Histidine,L-lysyl- 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. L-Histidine,L-lysyl- is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 41  0  0  0  0  0  0  0  0999 V2000
    2.0752    2.0315   -0.1608 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5342    1.1023   -1.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2469   -0.0959   -0.7098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6754   -1.1615    0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1827   -1.0126    1.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0256   -0.2244    1.8821 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9638   -0.4189    3.3867 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2844   -0.7295    1.4279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1445   -1.1888    2.2307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5890   -0.6988    0.0455 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8622   -1.1799   -0.4806 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4346   -0.2559   -1.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7403    1.1080   -0.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6430    1.6385    0.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0262    2.9236    0.1945 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3658    3.2315   -1.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1896    2.1196   -1.7862 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6151   -2.5144   -1.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4743   -2.9939   -1.1850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7163   -3.1308   -1.7233 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7398    2.0920    0.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8763    2.9680   -0.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2461    1.7070   -1.8181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6876    0.8996   -1.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1852    0.2651   -0.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7879   -0.5622   -1.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9538   -1.8153   -0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5457   -1.9401    0.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0721   -0.5799    2.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1234   -2.0486    1.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0327    0.8522    1.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9120   -0.2441    3.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7445   -1.4301    3.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0856   -0.3315   -0.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5783   -1.3691    0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4318   -0.6602   -1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7822   -0.1128   -2.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3362    1.1783    1.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7142    4.1858   -1.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3731    2.0560   -2.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3952   -3.6597   -1.1812 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  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 11 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  1
  7 32  1  0
  7 33  1  0
 10 34  1  0
 11 35  1  1
 12 36  1  0
 12 37  1  0
 14 38  1  0
 16 39  1  0
 17 40  1  0
 20 41  1  0
M  END

      
  Mrv1652304062013592D          

 20 20  0  0  0  0            999 V2000
10002.474810000.6868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.760510000.2743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.045910000.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.330610000.2743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.616610000.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.902510000.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.186410000.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.472110000.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.756110000.6868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.3306 9999.4493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.045910001.5124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.760510001.9252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.189510001.9252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.474810001.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.189510000.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.903910000.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.657710000.3513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10005.209710000.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.797210001.6789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.990210001.5073    0.0000 C   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
  3  4  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  1  0  0  0  0
  4 10  1  1  0  0  0
  5  6  1  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
 14 12  2  0  0  0  0
 14 13  1  0  0  0  0
  1 14  1  6  0  0  0
  1 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 20  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136556

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H21N5O3/c13-4-2-1-3-9(14)11(18)17-10(12(19)20)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>
IGRMTQMIDNDFAA-UWVGGRQHSA-N

> <FORMULA>
C12H21N5O3

> <MOLECULAR_WEIGHT>
283.332

> <EXACT_MASS>
283.164439556

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
29.106740244448225

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2,6-diaminohexanamido]-3-(1H-imidazol-5-yl)propanoic acid

> <ALOGPS_LOGP>
-3.01

> <JCHEM_LOGP>
-4.401394275724775

> <ALOGPS_LOGS>
-1.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
12.80101002246639

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4007905533175267

> <JCHEM_PKA_STRONGEST_BASIC>
10.211637113734097

> <JCHEM_POLAR_SURFACE_AREA>
147.12

> <JCHEM_REFRACTIVITY>
72.66859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2,6-diaminohexanamido]-3-(3H-imidazol-4-yl)propanoic 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  C   UNK     0    8671.2868667.949   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8669.9538667.179   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    8668.6198667.949   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8667.2848667.179   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8665.9518667.949   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8664.6188667.179   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.2818667.949   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8661.9488667.179   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0    8660.6118667.949   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0    8667.2848665.639   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0    8668.6198669.490   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8669.9538670.260   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8672.6208670.260   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8671.2868669.490   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8672.6208667.179   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8673.9548667.949   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0    8675.3618667.322   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0    8676.3918668.467   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0    8675.6218669.801   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0    8674.1158669.480   0.000  0.00  0.00           C+0
CONECT    1    2   14   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    4                                                            
CONECT   11    3                                                            
CONECT   12   14                                                            
CONECT   13   14                                                            
CONECT   14   12   13    1                                                  
CONECT   15    1   16                                                       
CONECT   16   15   20   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   20   18                                                       
CONECT   20   16   19                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
K-H dipeptide	HMDB
KH dipeptide	HMDB
L-Lys-L-His	HMDB
L-Lysyl-L-histidine	HMDB
Lys-His	HMDB
Lysine histidine dipeptide	HMDB
Lysine-histidine dipeptide	HMDB
Lysyl-histidine	HMDB
Lysylhistidine	HMDB
N-L-Lysyl-L-histidine	HMDB
N-Lysylhistidine	HMDB

Chemical Formula

C₁₂H₂₁N₅O₃

Average Mass

283.3320 Da

Monoisotopic Mass

283.16444 Da

IUPAC Name

(2S)-2-[(2S)-2,6-diaminohexanamido]-3-(1H-imidazol-5-yl)propanoic acid

Traditional Name

(2S)-2-[(2S)-2,6-diaminohexanamido]-3-(3H-imidazol-4-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H21N5O3/c13-4-2-1-3-9(14)11(18)17-10(12(19)20)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

IGRMTQMIDNDFAA-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 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-l-alpha-amino acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
Fatty amide
N-acyl-amine
Fatty acyl
Azole
Imidazole
Heteroaromatic compound
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Organoheterocyclic compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Organooxygen compound
Organic oxygen compound
Organic oxide
Primary aliphatic amine
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Amine
Primary amine
Organonitrogen compound
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	-4.4	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.4	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	147.12 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	72.67 m³·mol⁻¹	ChemAxon
Polarizability	29.11 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

HMDB0028953

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8032710

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9857010

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Lysylhistidine (NP0136556)

MOL for NP0136556 (Lysylhistidine)

3D MOL for NP0136556 (Lysylhistidine)

3D SDF for NP0136556 (Lysylhistidine)

3D-SDF for NP0136556 (Lysylhistidine)

PDB for NP0136556 (Lysylhistidine)

3D PDB for NP0136556 (Lysylhistidine)

SMILES for NP0136556 (Lysylhistidine)

INCHI for NP0136556 (Lysylhistidine)

Structure for NP0136556 (Lysylhistidine)

3D Structure for NP0136556 (Lysylhistidine)