NP-MRD: Showing NP-Card for Histidylmethionine (NP0136500)

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Record Information

Version

2.0

Created at

2022-05-12 15:16:08 UTC

Updated at

2022-05-12 15:16:08 UTC

NP-MRD ID

NP0136500

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Histidylmethionine

Description

His-Met, also known as HM or L-his-L-met, 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-Met is a very strong basic compound (based on its pKa). A dipeptide formed from L-histidine and L-methionine residues.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 37  0  0  0  0  0  0  0  0999 V2000
    5.3733    1.5096    0.7456 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6229    1.9639    0.7481 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8392    1.2310   -0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7333   -0.2448   -0.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9391   -0.8451    0.4189 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5667   -0.3917    0.4397 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5442   -1.2419    0.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437   -2.4860   -0.0116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9198   -0.6919    0.2586 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8503    0.7071    0.5218 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6653   -1.0436   -0.9918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0444   -0.4830   -0.9356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6410    0.2512    0.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8946    0.5496   -0.3104 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0775    0.0049   -1.5220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9589   -0.6246   -1.9102 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6386   -0.7186    1.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9758   -0.1979    2.6536 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9346   -1.1366    1.8574 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0109    2.3822    0.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7091    1.1602    1.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5246    0.7270   -0.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4715    1.5173   -1.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8784    1.7603   -0.8536 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3151   -0.6122   -1.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7739   -0.6616   -0.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8872   -1.9537    0.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3895    0.6161    0.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4375   -1.2119    1.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629    0.9682    1.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3621    1.2607   -0.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6934   -2.1408   -1.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1517   -0.6384   -1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1764    0.5442    0.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6204    1.1072    0.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0113    0.0742   -2.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3718   -1.0107    2.7613 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  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
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  6
  6 28  1  0
  9 29  1  1
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 19 37  1  0
M  END


  Mrv1652304062013492D          

 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
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 S   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
  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
  7 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136500

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H18N4O3S/c1-19-3-2-9(11(17)18)15-10(16)8(12)4-7-5-13-6-14-7/h5-6,8-9H,2-4,12H2,1H3,(H,13,14)(H,15,16)(H,17,18)/t8-,9-/m0/s1

> <INCHI_KEY>
AYIZHKDZYOSOGY-IUCAKERBSA-N

> <FORMULA>
C11H18N4O3S

> <MOLECULAR_WEIGHT>
286.35

> <EXACT_MASS>
286.10996163

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
29.465029283274013

> <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-(methylsulfanyl)butanoic acid

> <ALOGPS_LOGP>
-1.96

> <JCHEM_LOGP>
-3.1020186876159928

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.920393701130699

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.500519194891263

> <JCHEM_PKA_STRONGEST_BASIC>
7.838531187282672

> <JCHEM_POLAR_SURFACE_AREA>
121.10000000000002

> <JCHEM_REFRACTIVITY>
71.87939999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-4-(methylsulfanyl)butanoic 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  S   UNK     0    8673.9208666.271   0.000  0.00  0.00           S+0
HETATM   19  C   UNK     0    8675.2548667.039   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                                                       
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   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
Histidinyl-methionine	ChEBI
Histidylmethionine	ChEBI
HM	ChEBI
L-His-L-met	ChEBI
H-M dipeptide	HMDB
HM dipeptide	HMDB
His-Met	HMDB
Histidine methionine dipeptide	HMDB
Histidine-methionine dipeptide	HMDB
Histidinylmethionine	HMDB
Histidyl-methionine	HMDB
L-Histidinyl-L-methionine	HMDB
L-Histidyl-L-methionine	HMDB
N-Histidinylmethionine	HMDB
N-Histidylmethionine	HMDB
N-L-Histidinyl-L-methionine	HMDB
N-L-Histidyl-L-methionine	HMDB

Chemical Formula

C₁₁H₁₈N₄O₃S

Average Mass

286.3500 Da

Monoisotopic Mass

286.10996 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H18N4O3S/c1-19-3-2-9(11(17)18)15-10(16)8(12)4-7-5-13-6-14-7/h5-6,8-9H,2-4,12H2,1H3,(H,13,14)(H,15,16)(H,17,18)/t8-,9-/m0/s1

InChI Key

AYIZHKDZYOSOGY-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
Histidine or derivatives
Methionine 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
Aralkylamine
Thia fatty acid
Fatty amide
Fatty acyl
Azole
Imidazole
Heteroaromatic compound
Amino acid or derivatives
Carboxamide group
Carboxylic acid salt
Amino acid
Secondary carboxylic acid amide
Dialkylthioether
Sulfenyl compound
Thioether
Carboxylic acid
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Organic zwitterion
Organonitrogen compound
Primary aliphatic amine
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organooxygen compound
Amine
Organic oxygen compound
Carbonyl group
Organopnictogen compound
Organic salt
Organosulfur compound
Primary amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:74053 )

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	ALOGPS
logP	-3.1	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.5	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	8	ChemAxon
Refractivity	71.88 m³·mol⁻¹	ChemAxon
Polarizability	29.47 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

HMDB0028891

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5730867

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7408103

PDB ID

Not Available

ChEBI ID

74053

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Histidylmethionine (NP0136500)

MOL for NP0136500 (Histidylmethionine)

3D MOL for NP0136500 (Histidylmethionine)

3D SDF for NP0136500 (Histidylmethionine)

3D-SDF for NP0136500 (Histidylmethionine)

PDB for NP0136500 (Histidylmethionine)

3D PDB for NP0136500 (Histidylmethionine)

SMILES for NP0136500 (Histidylmethionine)

INCHI for NP0136500 (Histidylmethionine)

Structure for NP0136500 (Histidylmethionine)

3D Structure for NP0136500 (Histidylmethionine)