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Showing NP-Card for 3-Methylhistamine (NP0000201)

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Record Information
Version1.0
Created at2006-02-22 11:40:36 UTC
Updated at2021-06-29 00:47:14 UTC
NP-MRD IDNP0000201
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Methylhistamine
DescriptionN tau-methylhistamine is one of the histamine metabolites. N tau-methylhistamine in plasma and urine is a good parameter for histamine release, and the determination of this histamine metabolite is generally less hampered by possible artifacts (due to basophil disrupture, a very short half-life time or bacterial production) than determinations of histamine itself (PMID 2409780 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000201 (3-Methylhistamine)


  Mrv1652305261923582D          

  9  9  0  0  0  0            999 V2000
   19.3441   -4.0816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4944   -4.6088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0819   -3.3392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5595   -3.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9464   -4.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4944   -5.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1618   -4.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8270   -4.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9069   -3.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3  8  2  0  0  0  0
  3  9  1  0  0  0  0
  4  5  1  0  0  0  0
  5  7  1  0  0  0  0
  7  9  2  0  0  0  0
M  END
Download

3D MOL for NP0000201 (3-Methylhistamine)

HMDB0001861
     RDKit          3D
3-Methylhistamine
 20 20  0  0  0  0  0  0  0  0999 V2000
   -1.7928   -1.2132    0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5251    0.2012    0.2448 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3223    1.1911    0.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7268    2.3646    0.3867 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5496    2.0762   -0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4014    0.7076   -0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7446   -0.0420   -0.9158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7618   -0.2974    0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8724   -1.0152   -0.3427 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3685   -1.6505    1.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8908   -1.3477    0.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4480   -1.7929   -0.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2992    1.1081    1.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2057    2.7623   -0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2018    0.5653   -1.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4073   -1.0183   -1.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1233    0.6529    0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2638   -0.8449    1.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0282   -1.9531    0.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7157   -0.4542   -0.5025 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  6  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  5 14  1  0
  7 15  1  0
  7 16  1  0
  8 17  1  0
  8 18  1  0
  9 19  1  0
  9 20  1  0
M  END
Download

3D SDF for NP0000201 (3-Methylhistamine)


  Mrv1652305261923582D          

  9  9  0  0  0  0            999 V2000
   19.3441   -4.0816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4944   -4.6088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0819   -3.3392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5595   -3.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9464   -4.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4944   -5.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1618   -4.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8270   -4.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9069   -3.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3  8  2  0  0  0  0
  3  9  1  0  0  0  0
  4  5  1  0  0  0  0
  5  7  1  0  0  0  0
  7  9  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000201

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C=NC=C1CCN

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

> <INCHI_KEY>
CPAGZVLINCPJEH-UHFFFAOYSA-N

> <FORMULA>
C6H11N3

> <MOLECULAR_WEIGHT>
125.1716

> <EXACT_MASS>
125.095297367

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
13.917294955909469

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(1-methyl-1H-imidazol-5-yl)ethan-1-amine

> <ALOGPS_LOGP>
-0.83

> <JCHEM_LOGP>
-0.8158188426666664

> <ALOGPS_LOGS>
-1.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
9.779748590476665

> <JCHEM_POLAR_SURFACE_AREA>
43.84

> <JCHEM_REFRACTIVITY>
37.125800000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.85e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methylhistamine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000201 (3-Methylhistamine)

HMDB0001861
     RDKit          3D
3-Methylhistamine
 20 20  0  0  0  0  0  0  0  0999 V2000
   -1.7928   -1.2132    0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5251    0.2012    0.2448 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3223    1.1911    0.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7268    2.3646    0.3867 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5496    2.0762   -0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4014    0.7076   -0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7446   -0.0420   -0.9158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7618   -0.2974    0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8724   -1.0152   -0.3427 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3685   -1.6505    1.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8908   -1.3477    0.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4480   -1.7929   -0.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2992    1.1081    1.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2057    2.7623   -0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2018    0.5653   -1.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4073   -1.0183   -1.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1233    0.6529    0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2638   -0.8449    1.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0282   -1.9531    0.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7157   -0.4542   -0.5025 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  6  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  5 14  1  0
  7 15  1  0
  7 16  1  0
  8 17  1  0
  8 18  1  0
  9 19  1  0
  9 20  1  0
M  END
Download

PDB for NP0000201 (3-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  N   UNK     0      36.109  -7.619   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0      30.790  -8.603   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      30.020  -6.233   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      34.644  -7.143   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      33.500  -8.174   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.790 -10.143   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.035  -7.698   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.544  -7.698   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.560  -6.233   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2    6    7    8                                                  
CONECT    3    8    9                                                       
CONECT    4    1    5                                                       
CONECT    5    4    7                                                       
CONECT    6    2                                                            
CONECT    7    2    5    9                                                  
CONECT    8    2    3                                                       
CONECT    9    3    7                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for NP0000201 (3-Methylhistamine)

COMPND    HMDB0001861
HETATM    1  C1  UNL     1      -1.793  -1.213   0.356  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.525   0.201   0.245  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.322   1.191   0.669  1.00  0.00           C  
HETATM    4  N2  UNL     1      -1.727   2.365   0.387  1.00  0.00           N  
HETATM    5  C3  UNL     1      -0.550   2.076  -0.218  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.401   0.708  -0.318  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.745  -0.042  -0.916  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.762  -0.297   0.201  1.00  0.00           C  
HETATM    9  N3  UNL     1       2.872  -1.015  -0.343  1.00  0.00           N  
HETATM   10  H1  UNL     1      -1.368  -1.650   1.293  1.00  0.00           H  
HETATM   11  H2  UNL     1      -2.891  -1.348   0.424  1.00  0.00           H  
HETATM   12  H3  UNL     1      -1.448  -1.793  -0.525  1.00  0.00           H  
HETATM   13  H4  UNL     1      -3.299   1.108   1.165  1.00  0.00           H  
HETATM   14  H5  UNL     1       0.206   2.762  -0.590  1.00  0.00           H  
HETATM   15  H6  UNL     1       1.202   0.565  -1.706  1.00  0.00           H  
HETATM   16  H7  UNL     1       0.407  -1.018  -1.315  1.00  0.00           H  
HETATM   17  H8  UNL     1       2.123   0.653   0.625  1.00  0.00           H  
HETATM   18  H9  UNL     1       1.264  -0.845   1.028  1.00  0.00           H  
HETATM   19  H10 UNL     1       3.028  -1.953   0.043  1.00  0.00           H  
HETATM   20  H11 UNL     1       3.716  -0.454  -0.502  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    6
CONECT    3    4    4   13
CONECT    4    5
CONECT    5    6    6   14
CONECT    6    7
CONECT    7    8   15   16
CONECT    8    9   17   18
CONECT    9   19   20
END
Download

SMILES for NP0000201 (3-Methylhistamine)

CN1C=NC=C1CCN
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INCHI for NP0000201 (3-Methylhistamine)

InChI=1S/C6H11N3/c1-9-5-8-4-6(9)2-3-7/h4-5H,2-3,7H2,1H3
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View in JSmol
Synonyms
ValueSource
L-Histamine deriv. 1HMDB
N(T)-MethylhistamineHMDB
N(Tau)-methylhistamineHMDB
N-Tau-methylhistamineHMDB
Tau-methylhistamineHMDB
3-Methylhistamine dihydrochlorideHMDB
3-MethylhistamineMeSH
Chemical FormulaC6H11N3
Average Mass125.1716 Da
Monoisotopic Mass125.09530 Da
IUPAC Name2-(1-methyl-1H-imidazol-5-yl)ethan-1-amine
Traditional Name3-methylhistamine
CAS Registry Number644-42-8
SMILES
CN1C=NC=C1CCN
InChI Identifier
InChI=1S/C6H11N3/c1-9-5-8-4-6(9)2-3-7/h4-5H,2-3,7H2,1H3
InChI KeyCPAGZVLINCPJEH-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
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
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 DescriptorsNot Available
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 Solubility4.85 g/LALOGPS
logP-0.83ALOGPS
logP-0.82ChemAxon
logS-1.4ALOGPS
pKa (Strongest Basic)9.78ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.84 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.13 m³·mol⁻¹ChemAxon
Polarizability13.92 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001861
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022715
KNApSAcK IDNot Available
Chemspider ID62725
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethylhistamine
METLIN ID6355
PubChem Compound69520
PDB IDNot Available
ChEBI ID114444
Good Scents IDNot Available
References
General References
  1. Keyzer JJ, Breukelman H, Wolthers BG, Richardson FJ, de Monchy JG: Measurement of N tau-methylhistamine concentrations in plasma and urine as a parameter for histamine release during anaphylactoid reactions. Agents Actions. 1985 Apr;16(3-4):76-9. [PubMed:2409780 ]
  2. Murray S, Wellings R, Taylor IK, Fuller RW, Taylor GW: Gas chromatographic-mass spectrometric assay to measure urinary N tau-methylhistamine excretion in man. J Chromatogr. 1991 Jul 5;567(2):289-98. [PubMed:1939463 ]
  3. Mita H, Yasueda H, Shida T: Simultaneous determination of histamine and N tau-methylhistamine in human plasma and urine by gas chromatography--mass spectrometry. J Chromatogr. 1980 Nov 14;221(1):1-7. [PubMed:7451611 ]
  4. Gill EL, Koelmel JP, Meke L, Yost RA, Garrett TJ, Okun MS, Flores C, Vedam-Mai V: Ultrahigh-Performance Liquid Chromatography-High-Resolution Mass Spectrometry Metabolomics and Lipidomics Study of Stool from Transgenic Parkinson's Disease Mice Following Immunotherapy. J Proteome Res. 2020 Jan 3;19(1):424-431. doi: 10.1021/acs.jproteome.9b00605. Epub 2019 Nov 22. [PubMed:31713431 ]
  5. Puthongkham P, Lee ST, Venton BJ: Mechanism of Histamine Oxidation and Electropolymerization at Carbon Electrodes. Anal Chem. 2019 Jul 2;91(13):8366-8373. doi: 10.1021/acs.analchem.9b01178. Epub 2019 Jun 13. [PubMed:31194511 ]
  6. Liu YT, Jia HM, Chang X, Ding G, Zhang HW, Zou ZM: The metabolic disturbances of isoproterenol induced myocardial infarction in rats based on a tissue targeted metabonomics. Mol Biosyst. 2013 Nov;9(11):2823-34. doi: 10.1039/c3mb70222g. [PubMed:24057015 ]
  7. Kim NH, Park Y, Jeong ES, Kim CS, Jeoung MK, Kim KS, Hong SH, Son JK, Hong JT, Park IY, Moon DC: A liquid chromatographic method for the determination of histamine in immunoglobulin preparation using solid phase extraction and pre-column derivatization. Arch Pharm Res. 2007 Oct;30(10):1350-7. doi: 10.1007/BF02980277. [PubMed:18038915 ]
  8. Nishiga M, Kamei C: Ameliorative effects of histamine on 7-chlorokynurenic acid-induced spatial memory deficits in rats. Psychopharmacology (Berl). 2003 Apr;166(4):360-5. doi: 10.1007/s00213-003-1402-5. Epub 2003 Feb 25. [PubMed:12601505 ]