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Showing NP-Card for 1-Methylhistamine (NP0000517)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-06-29 00:46:37 UTC
NP-MRD IDNP0000517
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-Methylhistamine
Description1-Methylhistamine, also known as H137, belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group. 1-Methylhistamine exists in all living organisms, ranging from bacteria to humans. Within humans, 1-methylhistamine participates in a number of enzymatic reactions. In particular, S-adenosylhomocysteine and 1-methylhistamine can be biosynthesized from S-adenosylmethionine and histamine; which is mediated by the enzyme histamine N-methyltransferase. In addition, 1-methylhistamine can be converted into methylimidazole acetaldehyde through its interaction with the enzyme amine oxidase [flavin-containing] a. In humans, 1-methylhistamine is involved in histidine metabolism. 1-Methylhistamine is a potentially toxic compound.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000517 (1-Methylhistamine)


  Mrv1652305261923512D          

  9  9  0  0  0  0            999 V2000
    0.2425    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1820    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2425   -0.5569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8258    0.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1820   -0.5569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4735   -0.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6214    0.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2995   -1.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2048    1.2198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  7  9  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
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3D MOL for NP0000517 (1-Methylhistamine)

HMDB0000898
     RDKit          3D
1-Methylhistamine
 20 20  0  0  0  0  0  0  0  0999 V2000
    3.1329   -0.6104   -0.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9001   -0.0808   -0.0100 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7193    0.2096    1.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4604    0.6833    1.4701 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1699    0.6981    0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5694    1.1532    0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5472   -0.0041    0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2260   -1.0270   -0.7647 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7488    0.2166   -0.6286 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6059   -1.2435    0.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8450    0.1859   -0.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9038   -1.1825   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4562    0.0843    2.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6226    1.5226   -0.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8507    1.9855    0.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5680    0.3856    0.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5366   -0.4046    1.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6049   -0.7230   -1.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6535   -1.9417   -0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5762    0.0928   -1.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  5  9  2  0
  9  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  6 14  1  0
  6 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
  8 19  1  0
  9 20  1  0
M  END
Download

3D SDF for NP0000517 (1-Methylhistamine)


  Mrv1652305261923512D          

  9  9  0  0  0  0            999 V2000
    0.2425    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1820    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2425   -0.5569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8258    0.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1820   -0.5569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4735   -0.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6214    0.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2995   -1.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2048    1.2198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  7  9  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000517

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C=NC(CCN)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H11N3/c1-9-4-6(2-3-7)8-5-9/h4-5H,2-3,7H2,1H3

> <INCHI_KEY>
FHQDWPCFSJMNCT-UHFFFAOYSA-N

> <FORMULA>
C6H11N3

> <MOLECULAR_WEIGHT>
125.1716

> <EXACT_MASS>
125.095297367

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.241604820217898

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(1-methyl-1H-imidazol-4-yl)ethan-1-amine

> <ALOGPS_LOGP>
-0.57

> <JCHEM_LOGP>
-0.47729507866666643

> <ALOGPS_LOGS>
-1.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.57278986154642

> <JCHEM_POLAR_SURFACE_AREA>
43.84

> <JCHEM_REFRACTIVITY>
36.56009999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylhistamine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000517 (1-Methylhistamine)

HMDB0000898
     RDKit          3D
1-Methylhistamine
 20 20  0  0  0  0  0  0  0  0999 V2000
    3.1329   -0.6104   -0.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9001   -0.0808   -0.0100 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7193    0.2096    1.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4604    0.6833    1.4701 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1699    0.6981    0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5694    1.1532    0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5472   -0.0041    0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2260   -1.0270   -0.7647 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7488    0.2166   -0.6286 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6059   -1.2435    0.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8450    0.1859   -0.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9038   -1.1825   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4562    0.0843    2.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6226    1.5226   -0.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8507    1.9855    0.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5680    0.3856    0.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5366   -0.4046    1.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6049   -0.7230   -1.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6535   -1.9417   -0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5762    0.0928   -1.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  5  9  2  0
  9  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  6 14  1  0
  6 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
  8 19  1  0
  9 20  1  0
M  END
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PDB for NP0000517 (1-Methylhistamine)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       0.453   0.495   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.206   0.495   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       0.453  -1.040   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.541   1.584   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -2.206  -1.040   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -0.884  -1.810   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.027   1.188   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.292  -2.157   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.116   2.277   0.000  0.00  0.00           N+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7                                                       
CONECT    5    2    8    6                                                  
CONECT    6    3    5                                                       
CONECT    7    4    9                                                       
CONECT    8    5                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for NP0000517 (1-Methylhistamine)

COMPND    HMDB0000898
HETATM    1  C1  UNL     1       3.133  -0.610  -0.561  1.00  0.00           C  
HETATM    2  N1  UNL     1       1.900  -0.081  -0.010  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.719   0.210   1.293  1.00  0.00           C  
HETATM    4  N2  UNL     1       0.460   0.683   1.470  1.00  0.00           N  
HETATM    5  C3  UNL     1      -0.170   0.698   0.281  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.569   1.153   0.067  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.547  -0.004   0.219  1.00  0.00           C  
HETATM    8  N3  UNL     1      -2.226  -1.027  -0.765  1.00  0.00           N  
HETATM    9  C6  UNL     1       0.749   0.217  -0.629  1.00  0.00           C  
HETATM   10  H1  UNL     1       3.606  -1.243   0.219  1.00  0.00           H  
HETATM   11  H2  UNL     1       3.845   0.186  -0.811  1.00  0.00           H  
HETATM   12  H3  UNL     1       2.904  -1.183  -1.481  1.00  0.00           H  
HETATM   13  H4  UNL     1       2.456   0.084   2.063  1.00  0.00           H  
HETATM   14  H5  UNL     1      -1.623   1.523  -0.978  1.00  0.00           H  
HETATM   15  H6  UNL     1      -1.851   1.986   0.720  1.00  0.00           H  
HETATM   16  H7  UNL     1      -3.568   0.386   0.034  1.00  0.00           H  
HETATM   17  H8  UNL     1      -2.537  -0.405   1.242  1.00  0.00           H  
HETATM   18  H9  UNL     1      -2.605  -0.723  -1.700  1.00  0.00           H  
HETATM   19  H10 UNL     1      -2.653  -1.942  -0.531  1.00  0.00           H  
HETATM   20  H11 UNL     1       0.576   0.093  -1.689  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    9
CONECT    3    4    4   13
CONECT    4    5
CONECT    5    6    9    9
CONECT    6    7   14   15
CONECT    7    8   16   17
CONECT    8   18   19
CONECT    9   20
END
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SMILES for NP0000517 (1-Methylhistamine)

CN1C=NC(CCN)=C1
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INCHI for NP0000517 (1-Methylhistamine)

InChI=1S/C6H11N3/c1-9-4-6(2-3-7)8-5-9/h4-5H,2-3,7H2,1H3
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View in JSmol
Synonyms
ValueSource
1-Methyl-1H-imidazole-4-ethanamineChEBI
1-Methyl-4-(2-aminoethyl)imidazoleChEBI
3-MethylhistamineChEBI
4-(1-Aminoethyl)-1-methyl-1H-imidazoleChEBI
MethylhistamineChEBI
N-MethylhistamineChEBI
N(1)-MethylhistamineChEBI
Ntau-methylhistamineChEBI
tele-MethylhistamineChEBI
tele-Methylhistamine dihydrochlorideHMDB
1-Methyl-4-(beta-aminoethyl)imidazoleHMDB
1,4-MethylhistamineHMDB
N-tele MethylhistamineHMDB
1-Methyl-4-(b-aminoethyl)imidazoleHMDB
1-Methyl-4-histamineHMDB
2-(1-Methyl-1H-imidazol-4-yl)ethanamineHMDB
2-(1-Methyl-1H-imidazol-4-yl)ethylamineHMDB
4-(2-Aminoethyl)-1-methyl-imidazoleHMDB
4-(2-Aminoethyl)-1-methylimidazoleHMDB
H137HMDB
N( 1)-MethylhistamineHMDB
N(T)-MethylhistamineHMDB
N-tele-MethylhistamineHMDB
N-Telle-methylhistamineHMDB
N1-MethylhistamineHMDB
NT-MethylhistamineHMDB
Chemical FormulaC6H11N3
Average Mass125.1716 Da
Monoisotopic Mass125.09530 Da
IUPAC Name2-(1-methyl-1H-imidazol-4-yl)ethan-1-amine
Traditional Namemethylhistamine
CAS Registry Number501-75-7
SMILES
CN1C=NC(CCN)=C1
InChI Identifier
InChI=1S/C6H11N3/c1-9-4-6(2-3-7)8-5-9/h4-5H,2-3,7H2,1H3
InChI KeyFHQDWPCFSJMNCT-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
Casimiroa edulisKNApSAcK Database
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct Parent2-arylethylamines
Alternative Parents
Substituents
  • 2-arylethylamine
  • Aralkylamine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.12 g/LALOGPS
logP-0.57ALOGPS
logP-0.48ChemAxon
logS-1.4ALOGPS
pKa (Strongest Basic)9.57ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.84 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity36.56 m³·mol⁻¹ChemAxon
Polarizability14.24 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000898
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022306
KNApSAcK IDC00051904
Chemspider ID3488
KEGG Compound IDC05127
BioCyc IDN-METHYL-HISTAMINE
BiGG ID45171
Wikipedia LinkMethylhistamine
METLIN ID5854
PubChem Compound3614
PDB IDNot Available
ChEBI ID29009
Good Scents IDNot Available
References
General References
  1. Ito C: The role of the central histaminergic system on schizophrenia. Drug News Perspect. 2004 Jul-Aug;17(6):383-7. [PubMed:15334189 ]
  2. Khandelwal JK, Hough LB, Morrishow AM, Green JP: Measurement of tele-methylhistamine and histamine in human cerebrospinal fluid, urine, and plasma. Agents Actions. 1982 Dec;12(5-6):583-90. [PubMed:7164933 ]
  3. Winterkamp S, Weidenhiller M, Otte P, Stolper J, Schwab D, Hahn EG, Raithel M: Urinary excretion of N-methylhistamine as a marker of disease activity in inflammatory bowel disease. Am J Gastroenterol. 2002 Dec;97(12):3071-7. [PubMed:12492192 ]
  4. Elmore BO, Bollinger JA, Dooley DM: Human kidney diamine oxidase: heterologous expression, purification, and characterization. J Biol Inorg Chem. 2002 Jun;7(6):565-79. Epub 2002 Feb 13. [PubMed:12072962 ]
  5. Robbins IM, Barst RJ, Rubin LJ, Gaine SP, Price PV, Morrow JD, Christman BW: Increased levels of prostaglandin D(2) suggest macrophage activation in patients with primary pulmonary hypertension. Chest. 2001 Nov;120(5):1639-44. [PubMed:11713147 ]
  6. O'Sullivan S, Roquet A, Dahlen B, Dahlen S, Kumlin M: Urinary excretion of inflammatory mediators during allergen-induced early and late phase asthmatic reactions. Clin Exp Allergy. 1998 Nov;28(11):1332-9. [PubMed:9824404 ]
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