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Showing metabocard for Betahistine (HMDB0015644)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2023-02-21 17:18:32 UTC
HMDB IDHMDB0015644
Secondary Accession Numbers
  • HMDB15644
Metabolite Identification
Common NameBetahistine
DescriptionBetahistine is only found in individuals that have used or taken this drug. It is an antivertigo drug first used for treating vertigo assosicated with Meniere's disease. It is also commonly used for patients with balance disorders.Betahistine primarily acts as a histamine H1-agonist with 0.07 times the activity of histamine. Stimulating the H1-receptors in the inner ear causes a vasodilatory effect and increased permeability in the blood vessels which results in reduced endolymphatic pressure. Betahistine is believed to act by reducing the asymmetrical functioning of sensory vestibular organs as well as by increasing vestibulocochlear blood flow. Doing so aids in decreasing symptoms of vertigo and balance disorders. Betahistine also acts as a histamine H3-receptor antagonist which causes an increased output of histamine from histaminergic nerve endings which can further increase the direct H1-agonist activity. Furthermore, H3-receptor antagonism increases the levels of neurotransmitters such as serotonin in the brainstem, which inhibits the activity of vestibular nuclei, helping to restore proper balance and decrease in vertigo symptoms.
Structure
Data?1676999912
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0015644 (Betahistine)

  Mrv1652303202019012D          

 10 10  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
M  END
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3D MOL for HMDB0015644 (Betahistine)

HMDB0015644
     RDKit          3D
Betahistine
 22 22  0  0  0  0  0  0  0  0999 V2000
   -3.1470    0.0113    1.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8878   -0.4660    0.5320 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6271    0.1055   -0.7956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3141   -0.3921   -1.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8274   -0.0355   -0.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0873   -0.4502   -0.9069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2218   -0.1712   -0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0929    0.5360    0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8461    0.9412    1.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7749    0.6417    0.6504 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8047    0.2102    0.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0417    1.0180    1.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5956   -0.7216    1.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9290   -1.5064    0.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4333   -0.2181   -1.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6382    1.2027   -0.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2165    0.0012   -2.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3340   -1.4974   -1.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1978   -1.0101   -1.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2176   -0.4974   -0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9623    0.7875    1.6103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7411    1.5106    2.3392 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  6 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
M  END
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3D SDF for HMDB0015644 (Betahistine)

  Mrv1652303202019012D          

 10 10  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015644

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCCC1=CC=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C8H12N2/c1-9-7-5-8-4-2-3-6-10-8/h2-4,6,9H,5,7H2,1H3

> <INCHI_KEY>
UUQMNUMQCIQDMZ-UHFFFAOYSA-N

> <FORMULA>
C8H12N2

> <MOLECULAR_WEIGHT>
136.1943

> <EXACT_MASS>
136.100048394

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
15.847728326464626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl[2-(pyridin-2-yl)ethyl]amine

> <ALOGPS_LOGP>
0.59

> <JCHEM_LOGP>
0.6324068453333336

> <ALOGPS_LOGS>
-0.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.769621036671913

> <JCHEM_POLAR_SURFACE_AREA>
24.92

> <JCHEM_REFRACTIVITY>
41.326299999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.93e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
betahistine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0015644 (Betahistine)

HMDB0015644
     RDKit          3D
Betahistine
 22 22  0  0  0  0  0  0  0  0999 V2000
   -3.1470    0.0113    1.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8878   -0.4660    0.5320 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6271    0.1055   -0.7956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3141   -0.3921   -1.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8274   -0.0355   -0.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0873   -0.4502   -0.9069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2218   -0.1712   -0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0929    0.5360    0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8461    0.9412    1.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7749    0.6417    0.6504 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8047    0.2102    0.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0417    1.0180    1.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5956   -0.7216    1.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9290   -1.5064    0.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4333   -0.2181   -1.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6382    1.2027   -0.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2165    0.0012   -2.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3340   -1.4974   -1.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1978   -1.0101   -1.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2176   -0.4974   -0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9623    0.7875    1.6103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7411    1.5106    2.3392 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  6 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
M  END
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PDB for HMDB0015644 (Betahistine)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.000   6.160   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0015644 (Betahistine)

COMPND    HMDB0015644
HETATM    1  C1  UNL     1      -3.147   0.011   1.059  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.888  -0.466   0.532  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.627   0.106  -0.796  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.314  -0.392  -1.345  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.827  -0.036  -0.486  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.087  -0.450  -0.907  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.222  -0.171  -0.180  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.093   0.536   0.990  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.846   0.941   1.398  1.00  0.00           C  
HETATM   10  N2  UNL     1       0.775   0.642   0.650  1.00  0.00           N  
HETATM   11  H1  UNL     1      -3.805   0.210   0.165  1.00  0.00           H  
HETATM   12  H2  UNL     1      -3.042   1.018   1.554  1.00  0.00           H  
HETATM   13  H3  UNL     1      -3.596  -0.722   1.741  1.00  0.00           H  
HETATM   14  H4  UNL     1      -1.929  -1.506   0.449  1.00  0.00           H  
HETATM   15  H5  UNL     1      -2.433  -0.218  -1.484  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.638   1.203  -0.657  1.00  0.00           H  
HETATM   17  H7  UNL     1      -0.216   0.001  -2.378  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.334  -1.497  -1.424  1.00  0.00           H  
HETATM   19  H9  UNL     1       2.198  -1.010  -1.831  1.00  0.00           H  
HETATM   20  H10 UNL     1       4.218  -0.497  -0.511  1.00  0.00           H  
HETATM   21  H11 UNL     1       3.962   0.788   1.610  1.00  0.00           H  
HETATM   22  H12 UNL     1       1.741   1.511   2.339  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14
CONECT    3    4   15   16
CONECT    4    5   17   18
CONECT    5    6    6   10
CONECT    6    7   19
CONECT    7    8    8   20
CONECT    8    9   21
CONECT    9   10   10   22
END
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SMILES for HMDB0015644 (Betahistine)

CNCCC1=CC=CC=N1
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INCHI for HMDB0015644 (Betahistine)

InChI=1S/C8H12N2/c1-9-7-5-8-4-2-3-6-10-8/h2-4,6,9H,5,7H2,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC8H12N2
Average Molecular Weight136.1943
Monoisotopic Molecular Weight136.100048394
IUPAC Namemethyl[2-(pyridin-2-yl)ethyl]amine
Traditional Namebetahistine
CAS Registry Number5638-76-6
SMILES
CNCCC1=CC=CC=N1
InChI Identifier
InChI=1S/C8H12N2/c1-9-7-5-8-4-2-3-6-10-8/h2-4,6,9H,5,7H2,1H3
InChI KeyUUQMNUMQCIQDMZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Pyridine
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available126.022http://allccs.zhulab.cn/database/detail?ID=AllCCS00000705
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06698 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06698 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06698
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2276
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBetahistine
METLIN IDNot Available
PubChem Compound2366
PDB IDNot Available
ChEBI ID35677
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Health Canada [Link]

Enzymes

Enzyme Details
1. Histamine H3 receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The H3 subclass of histamine receptors could mediate the histamine signals in CNS and peripheral nervous system. Signals through the inhibition of adenylate cyclase and displays high constitutive activity (spontaneous activity in the absence of agonist). Agonist stimulation of isoform 3 niether modified adenylate cyclase activity nor induced intracellular calcium mobilization
Gene Name:
HRH3
Uniprot ID:
Q9Y5N1
Molecular weight:
48670.8
References
  1. Barak N: Betahistine: what's new on the agenda? Expert Opin Investig Drugs. 2008 May;17(5):795-804. doi: 10.1517/13543784.17.5.795 . [PubMed:18447604 ]
  2. Lacour M, Sterkers O: Histamine and betahistine in the treatment of vertigo: elucidation of mechanisms of action. CNS Drugs. 2001;15(11):853-70. [PubMed:11700150 ]
  3. Gbahou F, Davenas E, Morisset S, Arrang JM: Effects of betahistine at histamine H3 receptors: mixed inverse agonism/agonism in vitro and partial inverse agonism in vivo. J Pharmacol Exp Ther. 2010 Sep 1;334(3):945-54. doi: 10.1124/jpet.110.168633. Epub 2010 Jun 8. [PubMed:20530654 ]
Enzyme Details
2. Histamine H1 receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6
References
  1. Barak N: Betahistine: what's new on the agenda? Expert Opin Investig Drugs. 2008 May;17(5):795-804. doi: 10.1517/13543784.17.5.795 . [PubMed:18447604 ]
  2. Lacour M, Sterkers O: Histamine and betahistine in the treatment of vertigo: elucidation of mechanisms of action. CNS Drugs. 2001;15(11):853-70. [PubMed:11700150 ]