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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 18:30:06 UTC

Update Date

2021-09-26 23:13:55 UTC

HMDB ID

HMDB0257498

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Sarizotan

Description

[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]({[5-(4-fluorophenyl)pyridin-3-yl]methyl})amine belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond. Based on a literature review very few articles have been published on [(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]({[5-(4-fluorophenyl)pyridin-3-yl]methyl})amine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Sarizotan is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Sarizotan is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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


  Mrv1652309112120302D          

 26 29  0  0  0  0            999 V2000
    0.7145   -0.4125    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    0.0000 F   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  2  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
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 23 26  1  0  0  0  0
M  END

HMDB0257498
     RDKit          3D
Sarizotan
 47 50  0  0  0  0  0  0  0  0999 V2000
    7.3940    2.9734    2.1750 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.4900    2.0541    1.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2035    2.4193    1.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3032    1.4778    0.9368 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7364    0.1731    0.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7719   -0.8116    0.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8411   -2.1121    0.6998 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9720   -3.0456    0.2670 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9909   -2.7085   -0.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8857   -1.4006   -1.0130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8085   -1.0318   -1.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3782   -0.6347   -1.2149 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4405   -0.2661   -2.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    0.1520   -1.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4921    1.4210   -0.6200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7971    1.8670   -0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6848    0.7481    0.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8600    1.0486    1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7064    0.0411    1.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4295   -1.2807    1.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2688   -1.5495    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3906   -0.5675    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2279   -0.8676   -0.6078 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7774   -0.4312   -0.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0293   -0.1719    1.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9327    0.7605    1.5789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9060    3.4438    1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2966    1.7452    0.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6161   -2.4133    1.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2709   -3.4222   -0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1423   -0.2541   -2.6413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5229   -1.9185   -2.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7341   -1.4465   -0.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0712    0.5859   -2.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6901   -1.0690   -2.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4437    0.3970   -2.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6965    1.2799    0.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451    2.1996   -1.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5682    2.4660    0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3746    2.5223   -0.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0882    2.0894    1.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6203    0.3174    2.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0693   -2.0928    1.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9819   -2.5786    0.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041    0.6077   -0.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3174   -1.1988    0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9360    0.4831    1.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  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  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 10 24  2  0
  5 25  1  0
 25 26  2  0
 26  2  1  0
 24  6  1  0
 23 14  1  0
 22 17  1  0
  3 27  1  0
  4 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 24 45  1  0
 25 46  1  0
 26 47  1  0
M  END


  Mrv1652309112120302D          

 26 29  0  0  0  0            999 V2000
    0.7145   -0.4125    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    0.0000 F   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  2  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
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 23 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0257498

> <DATABASE_NAME>
hmdb

> <SMILES>
FC1=CC=C(C=C1)C1=CC(CNCC2CCC3=CC=CC=C3O2)=CN=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H21FN2O/c23-20-8-5-17(6-9-20)19-11-16(12-24-14-19)13-25-15-21-10-7-18-3-1-2-4-22(18)26-21/h1-6,8-9,11-12,14,21,25H,7,10,13,15H2

> <INCHI_KEY>
HKFMQJUJWSFOLY-UHFFFAOYSA-N

> <FORMULA>
C22H21FN2O

> <MOLECULAR_WEIGHT>
348.421

> <EXACT_MASS>
348.163791467

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
38.19128624582909

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]({[5-(4-fluorophenyl)pyridin-3-yl]methyl})amine

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
4.2921233653333335

> <ALOGPS_LOGS>
-5.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.861549743635274

> <JCHEM_POLAR_SURFACE_AREA>
34.15

> <JCHEM_REFRACTIVITY>
100.63470000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.94e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sarizotan

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0257498
     RDKit          3D
Sarizotan
 47 50  0  0  0  0  0  0  0  0999 V2000
    7.3940    2.9734    2.1750 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.4900    2.0541    1.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2035    2.4193    1.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3032    1.4778    0.9368 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7364    0.1731    0.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7719   -0.8116    0.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8411   -2.1121    0.6998 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9720   -3.0456    0.2670 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9909   -2.7085   -0.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8857   -1.4006   -1.0130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8085   -1.0318   -1.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3782   -0.6347   -1.2149 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4405   -0.2661   -2.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    0.1520   -1.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4921    1.4210   -0.6200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7971    1.8670   -0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6848    0.7481    0.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8600    1.0486    1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7064    0.0411    1.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4295   -1.2807    1.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2688   -1.5495    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3906   -0.5675    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2279   -0.8676   -0.6078 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7774   -0.4312   -0.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0293   -0.1719    1.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9327    0.7605    1.5789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9060    3.4438    1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2966    1.7452    0.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6161   -2.4133    1.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2709   -3.4222   -0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1423   -0.2541   -2.6413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5229   -1.9185   -2.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7341   -1.4465   -0.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0712    0.5859   -2.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6901   -1.0690   -2.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4437    0.3970   -2.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6965    1.2799    0.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451    2.1996   -1.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5682    2.4660    0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3746    2.5223   -0.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0882    2.0894    1.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6203    0.3174    2.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0693   -2.0928    1.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9819   -2.5786    0.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041    0.6077   -0.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3174   -1.1988    0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9360    0.4831    1.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  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  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 10 24  2  0
  5 25  1  0
 25 26  2  0
 26  2  1  0
 24  6  1  0
 23 14  1  0
 22 17  1  0
  3 27  1  0
  4 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 24 45  1  0
 25 46  1  0
 26 47  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       0.000  -4.620   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       0.000  -9.240   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   26  F   UNK     0      -8.002 -12.320   0.000  0.00  0.00           F+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9    1   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26   23                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0257498
HETATM    1  F1  UNL     1       7.394   2.973   2.175  1.00  0.00           F  
HETATM    2  C1  UNL     1       6.490   2.054   1.713  1.00  0.00           C  
HETATM    3  C2  UNL     1       5.204   2.419   1.402  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.303   1.478   0.937  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.736   0.173   0.797  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.772  -0.812   0.304  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.841  -2.112   0.700  1.00  0.00           C  
HETATM    8  N1  UNL     1       2.972  -3.046   0.267  1.00  0.00           N  
HETATM    9  C7  UNL     1       1.991  -2.708  -0.587  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.886  -1.401  -1.013  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.809  -1.032  -1.951  1.00  0.00           C  
HETATM   12  N2  UNL     1      -0.378  -0.635  -1.215  1.00  0.00           N  
HETATM   13  C10 UNL     1      -1.440  -0.266  -2.131  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.690   0.152  -1.431  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.492   1.421  -0.620  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.797   1.867  -0.062  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.685   0.748   0.361  1.00  0.00           C  
HETATM   18  C15 UNL     1      -5.860   1.049   1.062  1.00  0.00           C  
HETATM   19  C16 UNL     1      -6.706   0.041   1.469  1.00  0.00           C  
HETATM   20  C17 UNL     1      -6.430  -1.281   1.204  1.00  0.00           C  
HETATM   21  C18 UNL     1      -5.269  -1.550   0.513  1.00  0.00           C  
HETATM   22  C19 UNL     1      -4.391  -0.567   0.086  1.00  0.00           C  
HETATM   23  O1  UNL     1      -3.228  -0.868  -0.608  1.00  0.00           O  
HETATM   24  C20 UNL     1       2.777  -0.431  -0.572  1.00  0.00           C  
HETATM   25  C21 UNL     1       6.029  -0.172   1.115  1.00  0.00           C  
HETATM   26  C22 UNL     1       6.933   0.760   1.579  1.00  0.00           C  
HETATM   27  H1  UNL     1       4.906   3.444   1.525  1.00  0.00           H  
HETATM   28  H2  UNL     1       3.297   1.745   0.690  1.00  0.00           H  
HETATM   29  H3  UNL     1       4.616  -2.413   1.384  1.00  0.00           H  
HETATM   30  H4  UNL     1       1.271  -3.422  -0.961  1.00  0.00           H  
HETATM   31  H5  UNL     1       1.142  -0.254  -2.641  1.00  0.00           H  
HETATM   32  H6  UNL     1       0.523  -1.918  -2.559  1.00  0.00           H  
HETATM   33  H7  UNL     1      -0.734  -1.447  -0.662  1.00  0.00           H  
HETATM   34  H8  UNL     1      -1.071   0.586  -2.722  1.00  0.00           H  
HETATM   35  H9  UNL     1      -1.690  -1.069  -2.837  1.00  0.00           H  
HETATM   36  H10 UNL     1      -3.444   0.397  -2.212  1.00  0.00           H  
HETATM   37  H11 UNL     1      -1.696   1.280   0.122  1.00  0.00           H  
HETATM   38  H12 UNL     1      -2.145   2.200  -1.340  1.00  0.00           H  
HETATM   39  H13 UNL     1      -3.568   2.466   0.868  1.00  0.00           H  
HETATM   40  H14 UNL     1      -4.375   2.522  -0.738  1.00  0.00           H  
HETATM   41  H15 UNL     1      -6.088   2.089   1.277  1.00  0.00           H  
HETATM   42  H16 UNL     1      -7.620   0.317   2.018  1.00  0.00           H  
HETATM   43  H17 UNL     1      -7.069  -2.093   1.507  1.00  0.00           H  
HETATM   44  H18 UNL     1      -4.982  -2.579   0.266  1.00  0.00           H  
HETATM   45  H19 UNL     1       2.704   0.608  -0.902  1.00  0.00           H  
HETATM   46  H20 UNL     1       6.317  -1.199   0.989  1.00  0.00           H  
HETATM   47  H21 UNL     1       7.936   0.483   1.823  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    3   26
CONECT    3    4   27
CONECT    4    5    5   28
CONECT    5    6   25
CONECT    6    7    7   24
CONECT    7    8   29
CONECT    8    9    9
CONECT    9   10   30
CONECT   10   11   24   24
CONECT   11   12   31   32
CONECT   12   13   33
CONECT   13   14   34   35
CONECT   14   15   23   36
CONECT   15   16   37   38
CONECT   16   17   39   40
CONECT   17   18   18   22
CONECT   18   19   41
CONECT   19   20   20   42
CONECT   20   21   43
CONECT   21   22   22   44
CONECT   22   23
CONECT   24   45
CONECT   25   26   26   46
CONECT   26   47
END

HMDB0257498
     RDKit          3D
Sarizotan
 47 50  0  0  0  0  0  0  0  0999 V2000
    7.3940    2.9734    2.1750 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.4900    2.0541    1.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2035    2.4193    1.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3032    1.4778    0.9368 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7364    0.1731    0.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7719   -0.8116    0.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8411   -2.1121    0.6998 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9720   -3.0456    0.2670 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9909   -2.7085   -0.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8857   -1.4006   -1.0130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8085   -1.0318   -1.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3782   -0.6347   -1.2149 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4405   -0.2661   -2.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    0.1520   -1.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4921    1.4210   -0.6200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7971    1.8670   -0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6848    0.7481    0.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8600    1.0486    1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7064    0.0411    1.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4295   -1.2807    1.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2688   -1.5495    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3906   -0.5675    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2279   -0.8676   -0.6078 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7774   -0.4312   -0.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0293   -0.1719    1.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9327    0.7605    1.5789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9060    3.4438    1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2966    1.7452    0.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6161   -2.4133    1.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2709   -3.4222   -0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1423   -0.2541   -2.6413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5229   -1.9185   -2.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7341   -1.4465   -0.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0712    0.5859   -2.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6901   -1.0690   -2.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4437    0.3970   -2.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6965    1.2799    0.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451    2.1996   -1.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5682    2.4660    0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3746    2.5223   -0.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0882    2.0894    1.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6203    0.3174    2.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0693   -2.0928    1.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9819   -2.5786    0.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041    0.6077   -0.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3174   -1.1988    0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9360    0.4831    1.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  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  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 10 24  2  0
  5 25  1  0
 25 26  2  0
 26  2  1  0
 24  6  1  0
 23 14  1  0
 22 17  1  0
  3 27  1  0
  4 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 24 45  1  0
 25 46  1  0
 26 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₂H₂₁FN₂O

Average Molecular Weight

348.421

Monoisotopic Molecular Weight

348.163791467

IUPAC Name

[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]({[5-(4-fluorophenyl)pyridin-3-yl]methyl})amine

Traditional Name

sarizotan

CAS Registry Number

Not Available

SMILES

FC1=CC=C(C=C1)C1=CC(CNCC2CCC3=CC=CC=C3O2)=CN=C1

InChI Identifier

InChI=1S/C22H21FN2O/c23-20-8-5-17(6-9-20)19-11-16(12-24-14-19)13-25-15-21-10-7-18-3-1-2-4-22(18)26-21/h1-6,8-9,11-12,14,21,25H,7,10,13,15H2

InChI Key

HKFMQJUJWSFOLY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Phenylpyridines

Direct Parent

Phenylpyridines

Alternative Parents

Substituents

3-phenylpyridine
Chromane
Benzopyran
1-benzopyran
Alkyl aryl ether
Fluorobenzene
Halobenzene
Aralkylamine
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Oxacycle
Ether
Secondary aliphatic amine
Azacycle
Secondary amine
Organonitrogen compound
Organofluoride
Organohalogen compound
Hydrocarbon derivative
Organic oxygen compound
Amine
Organooxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.41	ALOGPS
logP	4.29	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Basic)	8.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	34.15 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	100.63 m³·mol⁻¹	ChemAxon
Polarizability	38.19 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	186.23	30932474
DeepCCS	[M-H]-	183.872	30932474
DeepCCS	[M-2H]-	217.685	30932474
DeepCCS	[M+Na]+	193.006	30932474
AllCCS	[M+H]+	186.3	32859911
AllCCS	[M+H-H2O]+	183.4	32859911
AllCCS	[M+NH4]+	189.0	32859911
AllCCS	[M+Na]+	189.8	32859911
AllCCS	[M-H]-	187.5	32859911
AllCCS	[M+Na-2H]-	187.1	32859911
AllCCS	[M+HCOO]-	186.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sarizotan	FC1=CC=C(C=C1)C1=CC(CNCC2CCC3=CC=CC=C3O2)=CN=C1	4219.8	Standard polar	33892256
Sarizotan	FC1=CC=C(C=C1)C1=CC(CNCC2CCC3=CC=CC=C3O2)=CN=C1	2969.1	Standard non polar	33892256
Sarizotan	FC1=CC=C(C=C1)C1=CC(CNCC2CCC3=CC=CC=C3O2)=CN=C1	3111.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sarizotan,1TMS,isomer #1	C[Si](C)(C)N(CC1=CN=CC(C2=CC=C(F)C=C2)=C1)CC1CCC2=CC=CC=C2O1	3193.8	Semi standard non polar	33892256
Sarizotan,1TMS,isomer #1	C[Si](C)(C)N(CC1=CN=CC(C2=CC=C(F)C=C2)=C1)CC1CCC2=CC=CC=C2O1	3098.2	Standard non polar	33892256
Sarizotan,1TMS,isomer #1	C[Si](C)(C)N(CC1=CN=CC(C2=CC=C(F)C=C2)=C1)CC1CCC2=CC=CC=C2O1	3852.9	Standard polar	33892256
Sarizotan,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC1=CN=CC(C2=CC=C(F)C=C2)=C1)CC1CCC2=CC=CC=C2O1	3446.0	Semi standard non polar	33892256
Sarizotan,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC1=CN=CC(C2=CC=C(F)C=C2)=C1)CC1CCC2=CC=CC=C2O1	3306.4	Standard non polar	33892256
Sarizotan,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC1=CN=CC(C2=CC=C(F)C=C2)=C1)CC1CCC2=CC=CC=C2O1	3933.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sarizotan GC-MS (Non-derivatized) - 70eV, Positive	splash10-00li-0952000000-0faf9498bc01989893ad	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sarizotan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2319847

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3058747

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Sarizotan (HMDB0257498)

MOL for HMDB0257498 (Sarizotan)

3D MOL for HMDB0257498 (Sarizotan)

3D SDF for HMDB0257498 (Sarizotan)

3D-SDF for HMDB0257498 (Sarizotan)

PDB for HMDB0257498 (Sarizotan)

3D PDB for HMDB0257498 (Sarizotan)

SMILES for HMDB0257498 (Sarizotan)

INCHI for HMDB0257498 (Sarizotan)

Structure for HMDB0257498 (Sarizotan)

3D Structure for HMDB0257498 (Sarizotan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra