NP-MRD: Showing NP-Card for Histidylleucine (NP0136498)

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Record Information

Version

2.0

Created at

2022-05-12 15:16:04 UTC

Updated at

2022-05-12 15:16:04 UTC

NP-MRD ID

NP0136498

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Histidylleucine

Description

His-Leu, also known as histidylleucine or HL, 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. His-Leu is a very strong basic compound (based on its pKa). Histidylleucine is found in Apis cerana. A dipeptide formed from L-histidine and L-leucine residues.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
    4.4860   -0.2898   -0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9596   -0.4211    0.8680 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8346    0.4979    1.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5278   -0.0050    0.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837   -0.7750    0.0816 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2192   -0.3005    0.2043 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4617    0.1666   -0.9126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1272    0.1713   -2.0371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8516    0.6752   -0.9173 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2991    1.0891   -2.2219 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8468   -0.2643   -0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1810    0.3784   -0.3999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7620    1.1987    0.5621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9745    1.5918    0.1410 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1888    1.0466   -1.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0900    0.3090   -1.3858 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5571   -2.2145    0.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961   -2.7985    0.8044 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7054   -2.9660    0.3836 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9697   -1.0219   -1.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5736   -0.4364   -0.5848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2284    0.7397   -0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1550   -1.4334    1.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8707    0.0749    2.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8230    0.5467    1.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3818    1.4992    1.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4513    1.0757    0.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2025   -0.1104    2.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9362   -0.6946   -0.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2357   -0.3158    1.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8454    1.6037   -0.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0719    1.7790   -2.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6734    0.2582   -2.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9165   -1.2049   -0.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6138   -0.4912    0.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2978    1.4664    1.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6357    2.2059    0.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0475    1.1326   -1.7174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9045   -3.7629    0.9487 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
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
  5 17  1  0
 17 19  1  0
 17 18  2  0
 16 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  6
  6 30  1  0
  9 31  1  1
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 19 39  1  0
M  END


  Mrv1652304062013482D          

 19 19  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
10001.029610001.4397    0.0000 O   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
10003.8856 9999.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.172510001.0263    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
  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  2  0  0  0  0
 15 17  1  0  0  0  0
  6  7  1  0  0  0  0
  7 18  1  0  0  0  0
  7 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136498

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H20N4O3/c1-7(2)3-10(12(18)19)16-11(17)9(13)4-8-5-14-6-15-8/h5-7,9-10H,3-4,13H2,1-2H3,(H,14,15)(H,16,17)(H,18,19)/t9-,10-/m0/s1

> <INCHI_KEY>
MMFKFJORZBJVNF-UWVGGRQHSA-N

> <FORMULA>
C12H20N4O3

> <MOLECULAR_WEIGHT>
268.317

> <EXACT_MASS>
268.15354052

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.009881951801464

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.06

> <JCHEM_LOGP>
-2.498636186209124

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.958722912627046

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.608108026397121

> <JCHEM_PKA_STRONGEST_BASIC>
7.838540773626667

> <JCHEM_POLAR_SURFACE_AREA>
121.10000000000001

> <JCHEM_REFRACTIVITY>
68.46430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.35e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
His-Leu

> <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    8668.5898669.354   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    8671.2568669.351   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    8672.5898668.582   0.000  0.00  0.00           C+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   19                                                  
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                                                            
CONECT   19    7                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
Histidylleucine	ChEBI
HL	ChEBI
L-His-L-leu	ChEBI
N-L-Histidyl-L-leucine	ChEBI
N-L-Histidyl-L-leucin	Kegg
H-L dipeptide	HMDB
HL dipeptide	HMDB
His-Leu	HMDB
Histidine leucine dipeptide	HMDB
Histidine-leucine dipeptide	HMDB
Histidinyl-leucine	HMDB
Histidinylleucine	HMDB
Histidyl-leucine	HMDB
L-Histidinyl-L-leucine	HMDB
L-Histidyl-L-leucine	HMDB
N-Histidinylleucine	HMDB
N-Histidylleucine	HMDB
N-L-Histidinyl-L-leucine	HMDB

Chemical Formula

C₁₂H₂₀N₄O₃

Average Mass

268.3170 Da

Monoisotopic Mass

268.15354 Da

IUPAC Name

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

Traditional Name

His-Leu

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H20N4O3/c1-7(2)3-10(12(18)19)16-11(17)9(13)4-8-5-14-6-15-8/h5-7,9-10H,3-4,13H2,1-2H3,(H,14,15)(H,16,17)(H,18,19)/t9-,10-/m0/s1

InChI Key

MMFKFJORZBJVNF-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

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633

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
Leucine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
Aralkylamine
Fatty amide
Fatty acyl
Heteroaromatic compound
Imidazole
Azole
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Primary amine
Amine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:5729 )

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	-2.1	ALOGPS
logP	-2.5	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	3.61	ChemAxon
pKa (Strongest Basic)	7.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	121.1 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	68.46 m³·mol⁻¹	ChemAxon
Polarizability	28.01 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

HMDB0028889

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

164234

KEGG Compound ID

C05010

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

189008

PDB ID

Not Available

ChEBI ID

5729

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Histidylleucine (NP0136498)

MOL for NP0136498 (Histidylleucine)

3D MOL for NP0136498 (Histidylleucine)

3D SDF for NP0136498 (Histidylleucine)

3D-SDF for NP0136498 (Histidylleucine)

PDB for NP0136498 (Histidylleucine)

3D PDB for NP0136498 (Histidylleucine)

SMILES for NP0136498 (Histidylleucine)

INCHI for NP0136498 (Histidylleucine)

Structure for NP0136498 (Histidylleucine)

3D Structure for NP0136498 (Histidylleucine)