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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (15) Show 15 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:43 UTC

HMDB ID

HMDB0014708

Secondary Accession Numbers

HMDB14708

Metabolite Identification

Common Name

Cinnarizine

Description

Cinnarizine is an anti-histaminic drug which is mainly used for the control of vomiting due to motion sickness. Cinnarizine was first synthesized by Janssen Pharmaceutica in 1955. It acts by interfering with the signal transmission between vestibular apparatus of the inner ear and the vomiting centre of the hypothalamus. The disparity of signal processing between inner ear motion receptors and the visual senses is abolished, so that the confusion of brain whether the individual is moving or standing is reduced. Vomiting in motion sickness is actually a physiological compensatory mechanism of the brain to keep the individual from moving so that it can adjust to the signal perception. Cinnarizine could be also viewed as a nootropic drug because of its vasorelaxating abilities (due to calcium channel blockage), which happen mostly in brain. It is also effectively combined with other nootropics, primarily piracetam; in such combination each drug potentiate the other in boosting brain oxygen supply.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

568
  Mrv0541 02231214462D          

 28 31  0  0  0  0            999 V2000
    3.7935   -1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  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  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  2  0  0  0  0
  9 14  1  0  0  0  0
 10 13  2  0  0  0  0
 10 15  1  0  0  0  0
 11 20  2  3  0  0  0
 12 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 15 19  2  0  0  0  0
 16 21  2  0  0  0  0
 17 22  2  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  2  0  0  0  0
 26 28  2  0  0  0  0
 27 28  1  0  0  0  0
M  END

HMDB0014708
     RDKit          3D
Cinnarizine
 56 59  0  0  0  0  0  0  0  0999 V2000
    3.3892    0.2968    0.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5174   -0.0078    1.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8054    0.0669    0.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9891    0.4554   -0.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2723    0.5013   -1.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3861    0.1613   -0.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1788   -0.2315    0.8262 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9369   -0.2848    1.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1141    0.1943    1.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901   -0.7364    0.8593 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0007   -0.8166    1.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2683   -0.8947    0.8413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3588    0.0340   -0.1797 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5433    0.5026   -0.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3893   -0.4894   -1.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8255   -0.2305   -2.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6069   -1.0818   -3.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0157   -2.2738   -2.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6167   -2.5682   -1.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8141   -1.6867   -0.9441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3935    1.2991    0.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7423    1.0501    0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5853    1.7614    1.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0802    2.7237    1.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7307    2.9892    1.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8982    2.2686    1.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281    0.6496   -0.5764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9391   -0.4492   -0.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4469    0.6233   -0.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4949   -0.3370    2.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1673    0.7351   -1.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3993    0.8118   -2.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3883    0.1759   -0.8556 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0537   -0.5094    1.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8506   -0.6040    2.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3187   -0.0649    2.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6589    1.2278    1.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0125    0.0372    2.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0781   -1.7375    2.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2197   -1.9328    0.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0961   -0.8900    1.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2360    1.2513   -1.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5179    0.7001   -3.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8925   -0.7835   -4.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6402   -2.9297   -3.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9354   -3.5052   -1.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5320   -1.9484    0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1904    0.3101   -0.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6311    1.5508    1.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7234    3.2928    2.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3517    3.7586    2.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8488    2.5050    1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0970    1.4645    0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1818    1.0215   -1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8349   -0.1940   -1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5004   -1.3814   -0.9529 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  1  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 13 27  1  0
 27 28  1  0
  8  3  1  0
 28 10  1  0
 20 15  1  0
 26 21  1  0
  1 29  1  0
  2 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 14 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 22 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  0
 26 52  1  0
 27 53  1  0
 27 54  1  0
 28 55  1  0
 28 56  1  0
M  END

568
  Mrv0541 02231214462D          

 28 31  0  0  0  0            999 V2000
    3.7935   -1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  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  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  2  0  0  0  0
  9 14  1  0  0  0  0
 10 13  2  0  0  0  0
 10 15  1  0  0  0  0
 11 20  2  3  0  0  0
 12 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 15 19  2  0  0  0  0
 16 21  2  0  0  0  0
 17 22  2  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  2  0  0  0  0
 26 28  2  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014708

> <DATABASE_NAME>
hmdb

> <SMILES>
C(C=CC1=CC=CC=C1)N1CCN(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H28N2/c1-4-11-23(12-5-1)13-10-18-27-19-21-28(22-20-27)26(24-14-6-2-7-15-24)25-16-8-3-9-17-25/h1-17,26H,18-22H2

> <INCHI_KEY>
DERZBLKQOCDDDZ-UHFFFAOYSA-N

> <FORMULA>
C26H28N2

> <MOLECULAR_WEIGHT>
368.5139

> <EXACT_MASS>
368.225248906

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
43.96337681178743

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(diphenylmethyl)-4-(3-phenylprop-2-en-1-yl)piperazine

> <ALOGPS_LOGP>
5.19

> <JCHEM_LOGP>
5.88039114

> <ALOGPS_LOGS>
-5.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.398543592576612

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
119.86480000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.72e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cinnarizine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014708
     RDKit          3D
Cinnarizine
 56 59  0  0  0  0  0  0  0  0999 V2000
    3.3892    0.2968    0.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5174   -0.0078    1.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8054    0.0669    0.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9891    0.4554   -0.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2723    0.5013   -1.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3861    0.1613   -0.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1788   -0.2315    0.8262 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9369   -0.2848    1.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1141    0.1943    1.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901   -0.7364    0.8593 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0007   -0.8166    1.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2683   -0.8947    0.8413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3588    0.0340   -0.1797 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5433    0.5026   -0.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3893   -0.4894   -1.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8255   -0.2305   -2.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6069   -1.0818   -3.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0157   -2.2738   -2.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6167   -2.5682   -1.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8141   -1.6867   -0.9441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3935    1.2991    0.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7423    1.0501    0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5853    1.7614    1.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0802    2.7237    1.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7307    2.9892    1.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8982    2.2686    1.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281    0.6496   -0.5764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9391   -0.4492   -0.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4469    0.6233   -0.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4949   -0.3370    2.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1673    0.7351   -1.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3993    0.8118   -2.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3883    0.1759   -0.8556 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0537   -0.5094    1.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8506   -0.6040    2.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3187   -0.0649    2.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6589    1.2278    1.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0125    0.0372    2.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0781   -1.7375    2.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2197   -1.9328    0.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0961   -0.8900    1.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2360    1.2513   -1.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5179    0.7001   -3.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8925   -0.7835   -4.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6402   -2.9297   -3.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9354   -3.5052   -1.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5320   -1.9484    0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1904    0.3101   -0.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6311    1.5508    1.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7234    3.2928    2.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3517    3.7586    2.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8488    2.5050    1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0970    1.4645    0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1818    1.0215   -1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8349   -0.1940   -1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5004   -1.3814   -0.9529 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  1  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 13 27  1  0
 27 28  1  0
  8  3  1  0
 28 10  1  0
 20 15  1  0
 26 21  1  0
  1 29  1  0
  2 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 14 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 22 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  0
 26 52  1  0
 27 53  1  0
 27 54  1  0
 28 55  1  0
 28 56  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 568                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       7.081  -2.695   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       7.081   0.385   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.748  -1.925   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.415  -1.925   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.081  -4.235   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.748  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.415  -0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081   1.925   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415  -5.005   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748  -5.005   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415   2.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.748  -4.235   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748  -6.545   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415  -6.545   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -4.235   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.082  -5.005   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -7.315   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.748  -7.315   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.080  -5.005   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415   4.235   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.082  -6.545   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.080  -6.545   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.748   5.005   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.748   6.545   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.082   4.235   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.082   7.315   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.416   5.005   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.416   6.545   0.000  0.00  0.00           C+0
CONECT    1    3    4    5                                                  
CONECT    2    6    7    8                                                  
CONECT    3    1    6                                                       
CONECT    4    1    7                                                       
CONECT    5    1    9   10                                                  
CONECT    6    2    3                                                       
CONECT    7    2    4                                                       
CONECT    8    2   11                                                       
CONECT    9    5   12   14                                                  
CONECT   10    5   13   15                                                  
CONECT   11    8   20                                                       
CONECT   12    9   16                                                       
CONECT   13   10   17                                                       
CONECT   14    9   18                                                       
CONECT   15   10   19                                                       
CONECT   16   12   21                                                       
CONECT   17   13   22                                                       
CONECT   18   14   21                                                       
CONECT   19   15   22                                                       
CONECT   20   11   23                                                       
CONECT   21   16   18                                                       
CONECT   22   17   19                                                       
CONECT   23   20   24   25                                                  
CONECT   24   23   26                                                       
CONECT   25   23   27                                                       
CONECT   26   24   28                                                       
CONECT   27   25   28                                                       
CONECT   28   26   27                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0014708
HETATM    1  C1  UNL     1       3.389   0.297   0.704  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.517  -0.008   1.304  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.805   0.067   0.651  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.989   0.455  -0.639  1.00  0.00           C  
HETATM    5  C5  UNL     1       7.272   0.501  -1.201  1.00  0.00           C  
HETATM    6  C6  UNL     1       8.386   0.161  -0.485  1.00  0.00           C  
HETATM    7  C7  UNL     1       8.179  -0.231   0.826  1.00  0.00           C  
HETATM    8  C8  UNL     1       6.937  -0.285   1.398  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.114   0.194   1.440  1.00  0.00           C  
HETATM   10  N1  UNL     1       1.190  -0.736   0.859  1.00  0.00           N  
HETATM   11  C10 UNL     1      -0.001  -0.817   1.671  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.268  -0.895   0.841  1.00  0.00           C  
HETATM   13  N2  UNL     1      -1.359   0.034  -0.180  1.00  0.00           N  
HETATM   14  C12 UNL     1      -2.543   0.503  -0.738  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.389  -0.489  -1.466  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.826  -0.230  -2.775  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.607  -1.082  -3.491  1.00  0.00           C  
HETATM   18  C16 UNL     1      -5.016  -2.274  -2.940  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.617  -2.568  -1.671  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.814  -1.687  -0.944  1.00  0.00           C  
HETATM   21  C19 UNL     1      -3.394   1.299   0.202  1.00  0.00           C  
HETATM   22  C20 UNL     1      -4.742   1.050   0.247  1.00  0.00           C  
HETATM   23  C21 UNL     1      -5.585   1.761   1.107  1.00  0.00           C  
HETATM   24  C22 UNL     1      -5.080   2.724   1.923  1.00  0.00           C  
HETATM   25  C23 UNL     1      -3.731   2.989   1.893  1.00  0.00           C  
HETATM   26  C24 UNL     1      -2.898   2.269   1.027  1.00  0.00           C  
HETATM   27  C25 UNL     1      -0.128   0.650  -0.576  1.00  0.00           C  
HETATM   28  C26 UNL     1       0.939  -0.449  -0.503  1.00  0.00           C  
HETATM   29  H1  UNL     1       3.447   0.623  -0.316  1.00  0.00           H  
HETATM   30  H2  UNL     1       4.495  -0.337   2.355  1.00  0.00           H  
HETATM   31  H3  UNL     1       5.167   0.735  -1.258  1.00  0.00           H  
HETATM   32  H4  UNL     1       7.399   0.812  -2.225  1.00  0.00           H  
HETATM   33  H5  UNL     1       9.388   0.176  -0.856  1.00  0.00           H  
HETATM   34  H6  UNL     1       9.054  -0.509   1.421  1.00  0.00           H  
HETATM   35  H7  UNL     1       6.851  -0.604   2.438  1.00  0.00           H  
HETATM   36  H8  UNL     1       2.319  -0.065   2.513  1.00  0.00           H  
HETATM   37  H9  UNL     1       1.659   1.228   1.383  1.00  0.00           H  
HETATM   38  H10 UNL     1      -0.013   0.037   2.368  1.00  0.00           H  
HETATM   39  H11 UNL     1       0.078  -1.737   2.276  1.00  0.00           H  
HETATM   40  H12 UNL     1      -1.220  -1.933   0.390  1.00  0.00           H  
HETATM   41  H13 UNL     1      -2.096  -0.890   1.590  1.00  0.00           H  
HETATM   42  H14 UNL     1      -2.236   1.251  -1.543  1.00  0.00           H  
HETATM   43  H15 UNL     1      -3.518   0.700  -3.228  1.00  0.00           H  
HETATM   44  H16 UNL     1      -4.892  -0.784  -4.507  1.00  0.00           H  
HETATM   45  H17 UNL     1      -5.640  -2.930  -3.544  1.00  0.00           H  
HETATM   46  H18 UNL     1      -4.935  -3.505  -1.233  1.00  0.00           H  
HETATM   47  H19 UNL     1      -3.532  -1.948   0.048  1.00  0.00           H  
HETATM   48  H20 UNL     1      -5.190   0.310  -0.368  1.00  0.00           H  
HETATM   49  H21 UNL     1      -6.631   1.551   1.125  1.00  0.00           H  
HETATM   50  H22 UNL     1      -5.723   3.293   2.604  1.00  0.00           H  
HETATM   51  H23 UNL     1      -3.352   3.759   2.551  1.00  0.00           H  
HETATM   52  H24 UNL     1      -1.849   2.505   1.033  1.00  0.00           H  
HETATM   53  H25 UNL     1       0.097   1.465   0.133  1.00  0.00           H  
HETATM   54  H26 UNL     1      -0.182   1.021  -1.628  1.00  0.00           H  
HETATM   55  H27 UNL     1       1.835  -0.194  -1.054  1.00  0.00           H  
HETATM   56  H28 UNL     1       0.500  -1.381  -0.953  1.00  0.00           H  
CONECT    1    2    2    9   29
CONECT    2    3   30
CONECT    3    4    4    8
CONECT    4    5   31
CONECT    5    6    6   32
CONECT    6    7   33
CONECT    7    8    8   34
CONECT    8   35
CONECT    9   10   36   37
CONECT   10   11   28
CONECT   11   12   38   39
CONECT   12   13   40   41
CONECT   13   14   27
CONECT   14   15   21   42
CONECT   15   16   16   20
CONECT   16   17   43
CONECT   17   18   18   44
CONECT   18   19   45
CONECT   19   20   20   46
CONECT   20   47
CONECT   21   22   22   26
CONECT   22   23   48
CONECT   23   24   24   49
CONECT   24   25   50
CONECT   25   26   26   51
CONECT   26   52
CONECT   27   28   53   54
CONECT   28   55   56
END

HMDB0014708
     RDKit          3D
Cinnarizine
 56 59  0  0  0  0  0  0  0  0999 V2000
    3.3892    0.2968    0.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5174   -0.0078    1.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8054    0.0669    0.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9891    0.4554   -0.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2723    0.5013   -1.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3861    0.1613   -0.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1788   -0.2315    0.8262 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9369   -0.2848    1.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1141    0.1943    1.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901   -0.7364    0.8593 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0007   -0.8166    1.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2683   -0.8947    0.8413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3588    0.0340   -0.1797 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5433    0.5026   -0.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3893   -0.4894   -1.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8255   -0.2305   -2.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6069   -1.0818   -3.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0157   -2.2738   -2.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6167   -2.5682   -1.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8141   -1.6867   -0.9441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3935    1.2991    0.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7423    1.0501    0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5853    1.7614    1.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0802    2.7237    1.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7307    2.9892    1.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8982    2.2686    1.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281    0.6496   -0.5764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9391   -0.4492   -0.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4469    0.6233   -0.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4949   -0.3370    2.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1673    0.7351   -1.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3993    0.8118   -2.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3883    0.1759   -0.8556 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0537   -0.5094    1.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8506   -0.6040    2.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3187   -0.0649    2.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6589    1.2278    1.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0125    0.0372    2.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0781   -1.7375    2.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2197   -1.9328    0.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0961   -0.8900    1.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2360    1.2513   -1.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5179    0.7001   -3.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8925   -0.7835   -4.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6402   -2.9297   -3.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9354   -3.5052   -1.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5320   -1.9484    0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1904    0.3101   -0.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6311    1.5508    1.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7234    3.2928    2.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3517    3.7586    2.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8488    2.5050    1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0970    1.4645    0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1818    1.0215   -1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8349   -0.1940   -1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5004   -1.3814   -0.9529 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  1  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 13 27  1  0
 27 28  1  0
  8  3  1  0
 28 10  1  0
 20 15  1  0
 26 21  1  0
  1 29  1  0
  2 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 14 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 22 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  0
 26 52  1  0
 27 53  1  0
 27 54  1  0
 28 55  1  0
 28 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₆H₂₈N₂

Average Molecular Weight

368.5139

Monoisotopic Molecular Weight

368.225248906

IUPAC Name

1-(diphenylmethyl)-4-(3-phenylprop-2-en-1-yl)piperazine

Traditional Name

cinnarizine

CAS Registry Number

298-57-7

SMILES

C(C=CC1=CC=CC=C1)N1CCN(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C26H28N2/c1-4-11-23(12-5-1)13-10-18-27-19-21-28(22-20-27)26(24-14-6-2-7-15-24)25-16-8-3-9-17-25/h1-17,26H,18-22H2

InChI Key

DERZBLKQOCDDDZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Styrene
Aralkylamine
N-alkylpiperazine
1,4-diazinane
Piperazine
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014708)

Source

Exogenous

Exogenous (HMDB: HMDB0014708)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Cinnarizine H1-Antihistamine Action (PathBank: SMP0059110)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0017 g/L	Not Available
LogP	5.3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	206.2	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0017 g/L	ALOGPS
logP	5.19	ALOGPS
logP	5.88	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	8.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	119.86 m³·mol⁻¹	ChemAxon
Polarizability	43.96 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	188.369	31661259
DarkChem	[M-H]-	187.596	31661259
DeepCCS	[M+H]+	186.703	30932474
DeepCCS	[M-H]-	184.345	30932474
DeepCCS	[M-2H]-	218.556	30932474
DeepCCS	[M+Na]+	193.81	30932474
AllCCS	[M+H]+	196.1	32859911
AllCCS	[M+H-H2O]+	193.3	32859911
AllCCS	[M+NH4]+	198.7	32859911
AllCCS	[M+Na]+	199.4	32859911
AllCCS	[M-H]-	195.6	32859911
AllCCS	[M+Na-2H]-	195.0	32859911
AllCCS	[M+HCOO]-	194.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.7 minutes	32390414
Predicted by Siyang on May 30, 2022	12.9886 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.22 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	31.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1722.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	260.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	213.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	186.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	142.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	677.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	759.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	331.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1413.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	522.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1600.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	340.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	422.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	243.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	273.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cinnarizine	C(C=CC1=CC=CC=C1)N1CCN(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1	3807.0	Standard polar	33892256
Cinnarizine	C(C=CC1=CC=CC=C1)N1CCN(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1	3111.6	Standard non polar	33892256
Cinnarizine	C(C=CC1=CC=CC=C1)N1CCN(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1	3060.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cinnarizine GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-0970000000-46b22af17c83f41c0b79	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cinnarizine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnarizine 10V, Positive-QTOF	splash10-014i-0219000000-675f13add4c10c3ad62f	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnarizine 20V, Positive-QTOF	splash10-014i-1943000000-f6590cd5feec75a73b61	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnarizine 40V, Positive-QTOF	splash10-014i-1900000000-a9c864770658b441961c	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnarizine 10V, Negative-QTOF	splash10-014i-0009000000-deec46756ddbeb96cde8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnarizine 20V, Negative-QTOF	splash10-0gb9-0179000000-30d60e48e3225ac9d20e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnarizine 40V, Negative-QTOF	splash10-006x-7940000000-df85bd89cf9513a96383	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnarizine 10V, Positive-QTOF	splash10-014i-0908000000-1e4428111c90f6cb466f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnarizine 20V, Positive-QTOF	splash10-014i-0900000000-c692fb05e504a5da303a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnarizine 40V, Positive-QTOF	splash10-014i-0900000000-1ebe4db6c001bc488606	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnarizine 10V, Negative-QTOF	splash10-014i-0009000000-a018cfee1a374207513e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnarizine 20V, Negative-QTOF	splash10-014i-0009000000-a1fc57ee27e30862c1f5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnarizine 40V, Negative-QTOF	splash10-014i-3933000000-9a496f17754de7ad0ec0	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Cinnarizine H1-Antihistamine Action		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00568	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00568	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00568

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

1264793

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cinnarizine

METLIN ID

Not Available

PubChem Compound

1547484

PDB ID

Not Available

ChEBI ID

31403

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Only showing the first 10 proteins. There are 15 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Enzyme Details

2. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Enzyme Details

3. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Enzyme Details

4. Cytochrome P450 1A1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

References

Enzyme Details

5. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Enzyme Details

6. Cytochrome P450 2A6

General function:: Involved in monooxygenase activity
Specific function:: Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:: CYP2A6
Uniprot ID:: P11509
Molecular weight:: 56517.005

References

Enzyme Details

7. D(2) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD2
Uniprot ID:: P14416
Molecular weight:: 50618.9

References

Enzyme Details

8. Voltage-dependent L-type calcium channel subunit alpha-1D

General function:: Involved in ion channel activity
Specific function:: Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1D gives rise to L-type calcium currents. Long-lasting (L-type) calcium channels belong to the 'high-voltage activated' (HVA) group. They are blocked by dihydropyridines (DHP), phenylalkylamines, benzothiazepines, and by omega-agatoxin-IIIA (omega-Aga-IIIA). They are however insensitive to omega-conotoxin- GVIA (omega-CTx-GVIA) and omega-agatoxin-IVA (omega-Aga-IVA)
Gene Name:: CACNA1D
Uniprot ID:: Q01668
Molecular weight:: 245138.8

References

Enzyme Details

9. Voltage-dependent L-type calcium channel subunit alpha-1C

General function:: Involved in ion channel activity
Specific function:: Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1C gives rise to L-type calcium currents. Long-lasting (L-type) calcium channels belong to the 'high-voltage activated' (HVA) group. They are blocked by dihydropyridines (DHP), phenylalkylamines, benzothiazepines, and by omega-agatoxin-IIIA (omega-Aga-IIIA). They are however insensitive to omega-conotoxin- GVIA (omega-CTx-GVIA) and omega-agatoxin-IVA (omega-Aga-IVA). Calcium channels containing the alpha-1C subunit play an important role in excitation-contraction coupling in the heart. The various isoforms display marked differences in the sensitivity to DHP compounds. Binding of calmodulin or CABP1 at the same regulatory sites results in an opposit effects on the channel function
Gene Name:: CACNA1C
Uniprot ID:: Q13936
Molecular weight:: 248974.1

References

Enzyme Details

10. 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

Only showing the first 10 proteins. There are 15 proteins in total.

Show all enzymes and transporters

Showing metabocard for Cinnarizine (HMDB0014708)

MOL for HMDB0014708 (Cinnarizine)

3D MOL for HMDB0014708 (Cinnarizine)

3D SDF for HMDB0014708 (Cinnarizine)

3D-SDF for HMDB0014708 (Cinnarizine)

PDB for HMDB0014708 (Cinnarizine)

3D PDB for HMDB0014708 (Cinnarizine)

SMILES for HMDB0014708 (Cinnarizine)

INCHI for HMDB0014708 (Cinnarizine)

Structure for HMDB0014708 (Cinnarizine)

3D Structure for HMDB0014708 (Cinnarizine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References

References

References