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Showing metabocard for Xanomeline (HMDB0259915)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 22:54:00 UTC
Update Date2022-11-23 22:29:22 UTC
HMDB IDHMDB0259915
Secondary Accession NumbersNone
Metabolite Identification
Common NameXanomeline
Descriptionxanomeline, also known as ly 246708, belongs to the class of organic compounds known as alkyl aryl ethers. These are organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R' , where R is an alkyl group and R' is an aryl group. Based on a literature review a significant number of articles have been published on xanomeline. This compound has been identified in human blood as reported by (PMID: 31557052 ). Xanomeline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Xanomeline 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0259915 (Xanomeline)


  Mrv1533004261515222D          

 19 20  0  0  0  0            999 V2000
    3.5330   -2.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475   -1.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9620   -2.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6764   -1.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3909   -2.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1054   -1.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8198   -2.0617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5343   -1.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6206   -0.8287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4275   -0.6572    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.8400   -1.3716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2880   -1.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4595   -2.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2441   -3.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4157   -3.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8026   -4.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0180   -4.1507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8464   -3.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4049   -4.7027    0.0000 C   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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 17 19  1  0  0  0  0
M  END
Download

3D MOL for HMDB0259915 (Xanomeline)

HMDB0259915
     RDKit          3D
XANOMELINE
 42 43  0  0  0  0  0  0  0  0999 V2000
    5.3058   -1.2446    1.9828 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7003   -0.0666    1.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8050   -0.6139    0.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2048    0.5065   -0.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3805    1.3958    0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2186    0.8567    0.9392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2276    0.3337    0.2265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0453   -0.7002   -0.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8724   -1.6155   -0.9974 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0802   -2.6444   -2.0261 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4199   -1.9307   -2.0102 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2919   -0.8779   -1.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4638    0.0128   -0.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4672    1.0548   -0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7335    1.8206   -0.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9585    0.9629   -0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7537   -0.3666   -0.5290 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2563   -1.2756    0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7829   -0.2895   -1.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5791   -0.8515    2.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1629   -1.6536    1.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5658   -2.0588    2.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1040    0.5683    1.9346 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5122    0.5697    0.8449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0460   -1.2843    0.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3940   -1.2340   -0.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7666    0.1196   -1.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1217    1.1473   -0.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0575    1.8990    0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417    2.2983   -0.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6271    0.1076    1.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7562    1.6894    1.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6297    1.3904    0.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7106    2.3581    0.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8126    2.5454   -0.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7546    1.4281   -0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3909    0.8586    0.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5038   -0.7778    1.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7358   -2.0972   -0.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0963   -1.6798    1.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0469    0.5742   -2.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6757   -1.2352   -2.1499 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 12  8  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
M  END
Download

3D SDF for HMDB0259915 (Xanomeline)


  Mrv1533004261515222D          

 19 20  0  0  0  0            999 V2000
    3.5330   -2.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475   -1.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9620   -2.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6764   -1.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3909   -2.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1054   -1.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8198   -2.0617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5343   -1.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6206   -0.8287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4275   -0.6572    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.8400   -1.3716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2880   -1.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4595   -2.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2441   -3.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4157   -3.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8026   -4.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0180   -4.1507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8464   -3.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4049   -4.7027    0.0000 C   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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259915

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCOC1=NSN=C1C1=CCCN(C)C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H23N3OS/c1-3-4-5-6-10-18-14-13(15-19-16-14)12-8-7-9-17(2)11-12/h8H,3-7,9-11H2,1-2H3

> <INCHI_KEY>
JOLJIIDDOBNFHW-UHFFFAOYSA-N

> <FORMULA>
C14H23N3OS

> <MOLECULAR_WEIGHT>
281.42

> <EXACT_MASS>
281.156183547

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
32.55349452949281

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[4-(hexyloxy)-1,2,5-thiadiazol-3-yl]-1-methyl-1,2,3,6-tetrahydropyridine

> <ALOGPS_LOGP>
3.76

> <JCHEM_LOGP>
3.768544550666667

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
6.696646764982575

> <JCHEM_POLAR_SURFACE_AREA>
38.25000000000001

> <JCHEM_REFRACTIVITY>
81.7262

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.58e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
xanomeline

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0259915 (Xanomeline)

HMDB0259915
     RDKit          3D
XANOMELINE
 42 43  0  0  0  0  0  0  0  0999 V2000
    5.3058   -1.2446    1.9828 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7003   -0.0666    1.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8050   -0.6139    0.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2048    0.5065   -0.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3805    1.3958    0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2186    0.8567    0.9392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2276    0.3337    0.2265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0453   -0.7002   -0.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8724   -1.6155   -0.9974 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0802   -2.6444   -2.0261 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4199   -1.9307   -2.0102 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2919   -0.8779   -1.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4638    0.0128   -0.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4672    1.0548   -0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7335    1.8206   -0.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9585    0.9629   -0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7537   -0.3666   -0.5290 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2563   -1.2756    0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7829   -0.2895   -1.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5791   -0.8515    2.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1629   -1.6536    1.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5658   -2.0588    2.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1040    0.5683    1.9346 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5122    0.5697    0.8449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0460   -1.2843    0.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3940   -1.2340   -0.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7666    0.1196   -1.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1217    1.1473   -0.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0575    1.8990    0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417    2.2983   -0.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6271    0.1076    1.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7562    1.6894    1.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6297    1.3904    0.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7106    2.3581    0.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8126    2.5454   -0.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7546    1.4281   -0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3909    0.8586    0.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5038   -0.7778    1.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7358   -2.0972   -0.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0963   -1.6798    1.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0469    0.5742   -2.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6757   -1.2352   -2.1499 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 12  8  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
M  END
Download

PDB for HMDB0259915 (Xanomeline)

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       6.595  -3.848   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.929  -3.078   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.262  -3.848   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.596  -3.078   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.930  -3.848   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.263  -3.078   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      14.597  -3.848   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      15.931  -3.078   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      16.092  -1.547   0.000  0.00  0.00           N+0
HETATM   10  S   UNK     0      17.598  -1.227   0.000  0.00  0.00           S+0
HETATM   11  N   UNK     0      18.368  -2.560   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      17.338  -3.705   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.658  -5.211   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.122  -5.687   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.443  -7.193   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.298  -8.224   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      16.834  -7.748   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      16.513  -6.242   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.689  -8.778   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8   13                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END
Download

3D PDB for HMDB0259915 (Xanomeline)

COMPND    HMDB0259915
HETATM    1  C1  UNL     1       5.306  -1.245   1.983  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.700  -0.067   1.227  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.805  -0.614   0.155  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.205   0.506  -0.633  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.380   1.396   0.199  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.219   0.857   0.939  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.228   0.334   0.226  1.00  0.00           O  
HETATM    8  C7  UNL     1      -0.045  -0.700  -0.634  1.00  0.00           C  
HETATM    9  N1  UNL     1       0.872  -1.616  -0.997  1.00  0.00           N  
HETATM   10  S1  UNL     1       0.080  -2.644  -2.026  1.00  0.00           S  
HETATM   11  N2  UNL     1      -1.420  -1.931  -2.010  1.00  0.00           N  
HETATM   12  C8  UNL     1      -1.292  -0.878  -1.190  1.00  0.00           C  
HETATM   13  C9  UNL     1      -2.464   0.013  -0.932  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.467   1.055  -0.166  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.734   1.821  -0.032  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.959   0.963  -0.037  1.00  0.00           C  
HETATM   17  N3  UNL     1      -4.754  -0.367  -0.529  1.00  0.00           N  
HETATM   18  C13 UNL     1      -4.256  -1.276   0.481  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.783  -0.290  -1.604  1.00  0.00           C  
HETATM   20  H1  UNL     1       5.579  -0.852   2.985  1.00  0.00           H  
HETATM   21  H2  UNL     1       6.163  -1.654   1.427  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.566  -2.059   2.129  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.104   0.568   1.935  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.512   0.570   0.845  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.046  -1.284   0.621  1.00  0.00           H  
HETATM   26  H7  UNL     1       4.394  -1.234  -0.558  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.767   0.120  -1.563  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.122   1.147  -0.928  1.00  0.00           H  
HETATM   29  H10 UNL     1       3.058   1.899   0.956  1.00  0.00           H  
HETATM   30  H11 UNL     1       2.042   2.298  -0.444  1.00  0.00           H  
HETATM   31  H12 UNL     1       1.627   0.108   1.729  1.00  0.00           H  
HETATM   32  H13 UNL     1       0.756   1.689   1.602  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.630   1.390   0.364  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.711   2.358   0.928  1.00  0.00           H  
HETATM   35  H16 UNL     1      -3.813   2.545  -0.876  1.00  0.00           H  
HETATM   36  H17 UNL     1      -5.755   1.428  -0.668  1.00  0.00           H  
HETATM   37  H18 UNL     1      -5.391   0.859   0.997  1.00  0.00           H  
HETATM   38  H19 UNL     1      -3.504  -0.778   1.121  1.00  0.00           H  
HETATM   39  H20 UNL     1      -3.736  -2.097  -0.044  1.00  0.00           H  
HETATM   40  H21 UNL     1      -5.096  -1.680   1.087  1.00  0.00           H  
HETATM   41  H22 UNL     1      -4.047   0.574  -2.251  1.00  0.00           H  
HETATM   42  H23 UNL     1      -3.676  -1.235  -2.150  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8
CONECT    8    9    9   12
CONECT    9   10
CONECT   10   11
CONECT   11   12   12
CONECT   12   13
CONECT   13   14   14   19
CONECT   14   15   33
CONECT   15   16   34   35
CONECT   16   17   36   37
CONECT   17   18   19
CONECT   18   38   39   40
CONECT   19   41   42
END
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SMILES for HMDB0259915 (Xanomeline)

CCCCCCOC1=NSN=C1C1=CCCN(C)C1
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INCHI for HMDB0259915 (Xanomeline)

InChI=1S/C14H23N3OS/c1-3-4-5-6-10-18-14-13(15-19-16-14)12-8-7-9-17(2)11-12/h8H,3-7,9-11H2,1-2H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
LY 246708ChEBI
3-(3-O-Hexyl-1,2,5-thiadiazol-4-yl)-1,2,5,6-tetrahydro-1-methylpyridineMeSH
Xanomeline tartrateMeSH
(3-O-Hexyloxy)-TZTPMeSH
Chemical FormulaC14H23N3OS
Average Molecular Weight281.42
Monoisotopic Molecular Weight281.156183547
IUPAC Name5-[4-(hexyloxy)-1,2,5-thiadiazol-3-yl]-1-methyl-1,2,3,6-tetrahydropyridine
Traditional Namexanomeline
CAS Registry NumberNot Available
SMILES
CCCCCCOC1=NSN=C1C1=CCCN(C)C1
InChI Identifier
InChI=1S/C14H23N3OS/c1-3-4-5-6-10-18-14-13(15-19-16-14)12-8-7-9-17(2)11-12/h8H,3-7,9-11H2,1-2H3
InChI KeyJOLJIIDDOBNFHW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl aryl ethers. These are organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R' , where R is an alkyl group and R' is an aryl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassEthers
Direct ParentAlkyl aryl ethers
Alternative Parents
Substituents
  • Alkyl aryl ether
  • Hydropyridine
  • Heteroaromatic compound
  • Thiadiazole
  • Azole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological location
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP3.76ALOGPS
logP3.77ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.25 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity81.73 m³·mol⁻¹ChemAxon
Polarizability32.55 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+166.65632859911
AllCCS[M+H-H2O]+163.39132859911
AllCCS[M+Na]+170.55132859911
AllCCS[M+NH4]+169.68232859911
AllCCS[M-H]-169.7432859911
AllCCS[M+Na-2H]-170.2732859911
AllCCS[M+HCOO]-170.97232859911
DeepCCS[M+H]+169.08430932474
DeepCCS[M-H]-166.72630932474
DeepCCS[M-2H]-200.31330932474
DeepCCS[M+Na]+176.32530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
XANOMELINECCCCCCOC1=NSN=C1C1=CCCN(C)C12684.4Standard polar33892256
XANOMELINECCCCCCOC1=NSN=C1C1=CCCN(C)C12053.7Standard non polar33892256
XANOMELINECCCCCCOC1=NSN=C1C1=CCCN(C)C12073.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Xanomeline GC-MS (Non-derivatized) - 70eV, Positivesplash10-0l0m-9470000000-3bdb4b24e8abb06a4fa22021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanomeline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID54797
KEGG Compound IDC11767
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkXanomeline
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID10056
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. 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 ]