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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (17) Show 17 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2020-02-26 21:41:32 UTC

HMDB ID

HMDB0015396

Secondary Accession Numbers

HMDB15396

Metabolite Identification

Common Name

Paliperidone

Description

Paliperidone is the primary active metabolite of the older antipsychotic risperidone. While its specific mechanism of action is unknown, it is believed that paliperidone and risperidone act via similar if not the same pathways. It has been proposed that the drug's therapeutic activity in schizophrenia is mediated through a combination of central dopamine Type 2 (D2) and serotonin Type 2 (5HT2A) receptor antagonism. Paliperidone is also active as an antagonist at alpha 1 and alpha 2 adrenergic receptors and H1 histaminergic receptors, which may explain some of the other effects of the drug. Paliperidone was approved by the FDA for treatment of schizophrenia on December 20, 2006.

Structure

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

1267
  Mrv0541 02231215222D          

 31 35  0  0  1  0            999 V2000
    1.6500   -0.6622    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.9340   -2.4952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2647    2.2343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8223   -1.0943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9643   -0.2693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5367    0.1432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7359   -2.3226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8223    1.3808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5353   -1.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2498   -1.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5353   -0.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9643   -1.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2498    0.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6788    0.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8208   -1.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3932   -0.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1078    0.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2742   -0.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2742    1.4093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0218    0.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0218    0.9854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5367    0.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0719   -1.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8223   -0.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1078    0.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5209   -1.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8156   -0.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3932    1.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7136   -1.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0083   -0.2183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4573   -0.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 31  1  0  0  0  0
  2  7  1  0  0  0  0
  2 26  1  0  0  0  0
  3 19  1  0  0  0  0
  4 24  2  0  0  0  0
  5 12  1  0  0  0  0
  5 13  1  0  0  0  0
  5 14  1  0  0  0  0
  6 18  1  0  0  0  0
  6 22  1  0  0  0  0
  6 24  1  0  0  0  0
  7 15  2  0  0  0  0
  8 22  2  0  0  0  0
  8 25  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 15  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 14 16  1  0  0  0  0
 15 23  1  0  0  0  0
 16 17  1  0  0  0  0
 17 24  1  0  0  0  0
 17 25  2  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 20 21  1  0  0  0  0
 23 26  2  0  0  0  0
 23 27  1  0  0  0  0
 25 28  1  0  0  0  0
 26 29  1  0  0  0  0
 27 30  2  0  0  0  0
 29 31  2  0  0  0  0
 30 31  1  0  0  0  0
M  END

HMDB0243668
     RDKit          3D
(R)-Paliperidone
 58 62  0  0  0  0  0  0  0  0999 V2000
   -2.5020   -1.0474   -2.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2981   -0.3890   -1.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6162   -0.6839   -1.2513 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3939   -0.1056   -0.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8777    0.7564    0.5721 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5500    1.0467    0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0709    1.8611    1.3324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7084    0.4917   -0.4367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2743    0.7866   -0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4048   -0.3194    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0014   -0.0594   -0.0786 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5499   -0.0462   -1.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9449    0.5114   -1.4174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7114    0.2472   -0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1431    0.1535   -0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6766    0.1566   -1.7429 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9471    0.0526   -1.6627 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3635   -0.0254   -0.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6105   -0.1454    0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7254   -0.2034    1.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9538   -0.3216    2.1183 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.6041   -0.1423    2.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3709   -0.0228    1.7060 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2255    0.0367    0.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1818   -1.0658    0.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7213   -0.9651    0.7827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6827    1.3855    1.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1013    0.9568    1.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3010   -0.4686    1.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8343   -0.4768   -0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5575    0.4535   -1.0670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3171   -2.1036   -2.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6241   -0.4500   -2.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1020   -1.0649   -3.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0554    1.6756    0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9439    1.1151   -1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6098   -1.2309   -0.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6282   -0.4899    1.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6275   -1.0884   -1.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8905    0.5093   -2.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4744    0.1176   -2.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8423    1.6116   -1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4713    1.0587    0.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4824   -0.1933   -0.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6722   -0.1882    3.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4557    0.0312    2.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7287   -1.3100    1.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2615   -1.8798   -0.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392   -1.9679    0.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6492   -0.5520    1.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6533    2.4957    1.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2251    1.1741    2.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7263    1.6057    0.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4996    0.9903    2.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6916   -1.1960    1.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3875   -0.6761    1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9622   -1.4806   -0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9271    1.0789   -1.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  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  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 14 25  1  0
 25 26  1  0
  5 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
  8  2  2  0
 26 11  1  0
 30  4  1  0
 24 15  1  0
 24 18  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 19 44  1  0
 22 45  1  0
 23 46  1  0
 25 47  1  0
 25 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  1  0
 27 52  1  0
 28 53  1  0
 28 54  1  0
 29 55  1  0
 29 56  1  0
 30 57  1  0
 31 58  1  0
M  END

1267
  Mrv0541 02231215222D          

 31 35  0  0  1  0            999 V2000
    1.6500   -0.6622    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.9340   -2.4952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2647    2.2343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8223   -1.0943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9643   -0.2693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5367    0.1432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7359   -2.3226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8223    1.3808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5353   -1.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2498   -1.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5353   -0.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9643   -1.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2498    0.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6788    0.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8208   -1.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3932   -0.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1078    0.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2742   -0.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2742    1.4093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0218    0.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0218    0.9854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5367    0.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0719   -1.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8223   -0.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1078    0.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5209   -1.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8156   -0.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3932    1.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7136   -1.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0083   -0.2183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4573   -0.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 31  1  0  0  0  0
  2  7  1  0  0  0  0
  2 26  1  0  0  0  0
  3 19  1  0  0  0  0
  4 24  2  0  0  0  0
  5 12  1  0  0  0  0
  5 13  1  0  0  0  0
  5 14  1  0  0  0  0
  6 18  1  0  0  0  0
  6 22  1  0  0  0  0
  6 24  1  0  0  0  0
  7 15  2  0  0  0  0
  8 22  2  0  0  0  0
  8 25  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 15  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 14 16  1  0  0  0  0
 15 23  1  0  0  0  0
 16 17  1  0  0  0  0
 17 24  1  0  0  0  0
 17 25  2  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 20 21  1  0  0  0  0
 23 26  2  0  0  0  0
 23 27  1  0  0  0  0
 25 28  1  0  0  0  0
 26 29  1  0  0  0  0
 27 30  2  0  0  0  0
 29 31  2  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015396

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(CCN2CCC(CC2)C2=NOC3=C2C=CC(F)=C3)C(=O)N2CCCC(O)C2=N1

> <INCHI_IDENTIFIER>
InChI=1S/C23H27FN4O3/c1-14-17(23(30)28-9-2-3-19(29)22(28)25-14)8-12-27-10-6-15(7-11-27)21-18-5-4-16(24)13-20(18)31-26-21/h4-5,13,15,19,29H,2-3,6-12H2,1H3

> <INCHI_KEY>
PMXMIIMHBWHSKN-UHFFFAOYSA-N

> <FORMULA>
C23H27FN4O3

> <MOLECULAR_WEIGHT>
426.4839

> <EXACT_MASS>
426.206718955

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
45.94750072428491

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-9-hydroxy-2-methyl-4H,6H,7H,8H,9H-pyrido[1,2-a]pyrimidin-4-one

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
1.7565551636666674

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.742356596976887

> <JCHEM_PKA_STRONGEST_BASIC>
8.763162789831293

> <JCHEM_POLAR_SURFACE_AREA>
82.17

> <JCHEM_REFRACTIVITY>
116.04139999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.97e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
invega

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0243668
     RDKit          3D
(R)-Paliperidone
 58 62  0  0  0  0  0  0  0  0999 V2000
   -2.5020   -1.0474   -2.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2981   -0.3890   -1.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6162   -0.6839   -1.2513 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3939   -0.1056   -0.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8777    0.7564    0.5721 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5500    1.0467    0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0709    1.8611    1.3324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7084    0.4917   -0.4367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2743    0.7866   -0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4048   -0.3194    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0014   -0.0594   -0.0786 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5499   -0.0462   -1.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9449    0.5114   -1.4174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7114    0.2472   -0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1431    0.1535   -0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6766    0.1566   -1.7429 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9471    0.0526   -1.6627 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3635   -0.0254   -0.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6105   -0.1454    0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7254   -0.2034    1.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9538   -0.3216    2.1183 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.6041   -0.1423    2.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3709   -0.0228    1.7060 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2255    0.0367    0.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1818   -1.0658    0.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7213   -0.9651    0.7827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6827    1.3855    1.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1013    0.9568    1.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3010   -0.4686    1.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8343   -0.4768   -0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5575    0.4535   -1.0670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3171   -2.1036   -2.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6241   -0.4500   -2.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1020   -1.0649   -3.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0554    1.6756    0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9439    1.1151   -1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6098   -1.2309   -0.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6282   -0.4899    1.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6275   -1.0884   -1.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8905    0.5093   -2.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4744    0.1176   -2.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8423    1.6116   -1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4713    1.0587    0.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4824   -0.1933   -0.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6722   -0.1882    3.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4557    0.0312    2.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7287   -1.3100    1.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2615   -1.8798   -0.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392   -1.9679    0.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6492   -0.5520    1.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6533    2.4957    1.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2251    1.1741    2.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7263    1.6057    0.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4996    0.9903    2.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6916   -1.1960    1.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3875   -0.6761    1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9622   -1.4806   -0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9271    1.0789   -1.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  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  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 14 25  1  0
 25 26  1  0
  5 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
  8  2  2  0
 26 11  1  0
 30  4  1  0
 24 15  1  0
 24 18  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 19 44  1  0
 22 45  1  0
 23 46  1  0
 25 47  1  0
 25 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  1  0
 27 52  1  0
 28 53  1  0
 28 54  1  0
 29 55  1  0
 29 56  1  0
 30 57  1  0
 31 58  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1267                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       3.080  -1.236   0.000  0.00  0.00           F+0
HETATM    2  O   UNK     0       7.343  -4.658   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      21.027   4.171   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      18.335  -2.043   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      13.000  -0.503   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      19.669   0.267   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       8.840  -4.336   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      18.335   2.577   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      10.333  -2.043   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.666  -2.813   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.333  -0.503   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.000  -2.043   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.666   0.267   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.334   0.267   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.999  -2.813   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.667  -0.503   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.001   0.267   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.045  -0.556   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.045   2.631   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.441   0.235   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      22.441   1.839   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.669   1.807   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.601  -2.189   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.335  -0.503   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.001   1.807   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.572  -3.335   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.122  -0.725   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.667   2.577   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.065  -3.017   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.615  -0.407   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.587  -1.554   0.000  0.00  0.00           C+0
CONECT    1   31                                                            
CONECT    2    7   26                                                       
CONECT    3   19                                                            
CONECT    4   24                                                            
CONECT    5   12   13   14                                                  
CONECT    6   18   22   24                                                  
CONECT    7    2   15                                                       
CONECT    8   22   25                                                       
CONECT    9   10   11   15                                                  
CONECT   10    9   12                                                       
CONECT   11    9   13                                                       
CONECT   12    5   10                                                       
CONECT   13    5   11                                                       
CONECT   14    5   16                                                       
CONECT   15    7    9   23                                                  
CONECT   16   14   17                                                       
CONECT   17   16   24   25                                                  
CONECT   18    6   20                                                       
CONECT   19    3   21   22                                                  
CONECT   20   18   21                                                       
CONECT   21   19   20                                                       
CONECT   22    6    8   19                                                  
CONECT   23   15   26   27                                                  
CONECT   24    4    6   17                                                  
CONECT   25    8   17   28                                                  
CONECT   26    2   23   29                                                  
CONECT   27   23   30                                                       
CONECT   28   25                                                            
CONECT   29   26   31                                                       
CONECT   30   27   31                                                       
CONECT   31    1   29   30                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

COMPND    HMDB0243668
HETATM    1  C1  UNL     1      -2.502  -1.047  -2.370  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.298  -0.389  -1.313  1.00  0.00           C  
HETATM    3  N1  UNL     1      -4.616  -0.684  -1.251  1.00  0.00           N  
HETATM    4  C3  UNL     1      -5.394  -0.106  -0.305  1.00  0.00           C  
HETATM    5  N2  UNL     1      -4.878   0.756   0.572  1.00  0.00           N  
HETATM    6  C4  UNL     1      -3.550   1.047   0.501  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.071   1.861   1.332  1.00  0.00           O  
HETATM    8  C5  UNL     1      -2.708   0.492  -0.437  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.274   0.787  -0.535  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.405  -0.319   0.009  1.00  0.00           C  
HETATM   11  N3  UNL     1       1.001  -0.059  -0.079  1.00  0.00           N  
HETATM   12  C8  UNL     1       1.550  -0.046  -1.397  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.945   0.511  -1.417  1.00  0.00           C  
HETATM   14  C10 UNL     1       3.711   0.247  -0.126  1.00  0.00           C  
HETATM   15  C11 UNL     1       5.143   0.154  -0.488  1.00  0.00           C  
HETATM   16  N4  UNL     1       5.677   0.157  -1.743  1.00  0.00           N  
HETATM   17  O2  UNL     1       6.947   0.053  -1.663  1.00  0.00           O  
HETATM   18  C12 UNL     1       7.364  -0.025  -0.432  1.00  0.00           C  
HETATM   19  C13 UNL     1       8.611  -0.145   0.144  1.00  0.00           C  
HETATM   20  C14 UNL     1       8.725  -0.203   1.506  1.00  0.00           C  
HETATM   21  F1  UNL     1       9.954  -0.322   2.118  1.00  0.00           F  
HETATM   22  C15 UNL     1       7.604  -0.142   2.295  1.00  0.00           C  
HETATM   23  C16 UNL     1       6.371  -0.023   1.706  1.00  0.00           C  
HETATM   24  C17 UNL     1       6.226   0.037   0.359  1.00  0.00           C  
HETATM   25  C18 UNL     1       3.182  -1.066   0.409  1.00  0.00           C  
HETATM   26  C19 UNL     1       1.721  -0.965   0.783  1.00  0.00           C  
HETATM   27  C20 UNL     1      -5.683   1.386   1.580  1.00  0.00           C  
HETATM   28  C21 UNL     1      -7.101   0.957   1.626  1.00  0.00           C  
HETATM   29  C22 UNL     1      -7.301  -0.469   1.134  1.00  0.00           C  
HETATM   30  C23 UNL     1      -6.834  -0.477  -0.297  1.00  0.00           C  
HETATM   31  O3  UNL     1      -7.557   0.454  -1.067  1.00  0.00           O  
HETATM   32  H1  UNL     1      -2.317  -2.104  -2.140  1.00  0.00           H  
HETATM   33  H2  UNL     1      -1.624  -0.450  -2.603  1.00  0.00           H  
HETATM   34  H3  UNL     1      -3.102  -1.065  -3.331  1.00  0.00           H  
HETATM   35  H4  UNL     1      -1.055   1.676   0.137  1.00  0.00           H  
HETATM   36  H5  UNL     1      -0.944   1.115  -1.537  1.00  0.00           H  
HETATM   37  H6  UNL     1      -0.610  -1.231  -0.589  1.00  0.00           H  
HETATM   38  H7  UNL     1      -0.628  -0.490   1.096  1.00  0.00           H  
HETATM   39  H8  UNL     1       1.628  -1.088  -1.832  1.00  0.00           H  
HETATM   40  H9  UNL     1       0.890   0.509  -2.076  1.00  0.00           H  
HETATM   41  H10 UNL     1       3.474   0.118  -2.292  1.00  0.00           H  
HETATM   42  H11 UNL     1       2.842   1.612  -1.586  1.00  0.00           H  
HETATM   43  H12 UNL     1       3.471   1.059   0.561  1.00  0.00           H  
HETATM   44  H13 UNL     1       9.482  -0.193  -0.475  1.00  0.00           H  
HETATM   45  H14 UNL     1       7.672  -0.188   3.384  1.00  0.00           H  
HETATM   46  H15 UNL     1       5.456   0.031   2.296  1.00  0.00           H  
HETATM   47  H16 UNL     1       3.729  -1.310   1.341  1.00  0.00           H  
HETATM   48  H17 UNL     1       3.262  -1.880  -0.349  1.00  0.00           H  
HETATM   49  H18 UNL     1       1.239  -1.968   0.835  1.00  0.00           H  
HETATM   50  H19 UNL     1       1.649  -0.552   1.827  1.00  0.00           H  
HETATM   51  H20 UNL     1      -5.653   2.496   1.417  1.00  0.00           H  
HETATM   52  H21 UNL     1      -5.225   1.174   2.587  1.00  0.00           H  
HETATM   53  H22 UNL     1      -7.726   1.606   0.977  1.00  0.00           H  
HETATM   54  H23 UNL     1      -7.500   0.990   2.662  1.00  0.00           H  
HETATM   55  H24 UNL     1      -6.692  -1.196   1.701  1.00  0.00           H  
HETATM   56  H25 UNL     1      -8.388  -0.676   1.229  1.00  0.00           H  
HETATM   57  H26 UNL     1      -6.962  -1.481  -0.762  1.00  0.00           H  
HETATM   58  H27 UNL     1      -6.927   1.079  -1.521  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    8    8
CONECT    3    4    4
CONECT    4    5   30
CONECT    5    6   27
CONECT    6    7    7    8
CONECT    8    9
CONECT    9   10   35   36
CONECT   10   11   37   38
CONECT   11   12   26
CONECT   12   13   39   40
CONECT   13   14   41   42
CONECT   14   15   25   43
CONECT   15   16   16   24
CONECT   16   17
CONECT   17   18
CONECT   18   19   19   24
CONECT   19   20   44
CONECT   20   21   22   22
CONECT   22   23   45
CONECT   23   24   24   46
CONECT   25   26   47   48
CONECT   26   49   50
CONECT   27   28   51   52
CONECT   28   29   53   54
CONECT   29   30   55   56
CONECT   30   31   57
CONECT   31   58
END

HMDB0243668
     RDKit          3D
(R)-Paliperidone
 58 62  0  0  0  0  0  0  0  0999 V2000
   -2.5020   -1.0474   -2.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2981   -0.3890   -1.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6162   -0.6839   -1.2513 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3939   -0.1056   -0.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8777    0.7564    0.5721 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5500    1.0467    0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0709    1.8611    1.3324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7084    0.4917   -0.4367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2743    0.7866   -0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4048   -0.3194    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0014   -0.0594   -0.0786 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5499   -0.0462   -1.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9449    0.5114   -1.4174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7114    0.2472   -0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1431    0.1535   -0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6766    0.1566   -1.7429 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9471    0.0526   -1.6627 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3635   -0.0254   -0.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6105   -0.1454    0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7254   -0.2034    1.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9538   -0.3216    2.1183 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.6041   -0.1423    2.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3709   -0.0228    1.7060 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2255    0.0367    0.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1818   -1.0658    0.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7213   -0.9651    0.7827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6827    1.3855    1.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1013    0.9568    1.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3010   -0.4686    1.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8343   -0.4768   -0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5575    0.4535   -1.0670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3171   -2.1036   -2.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6241   -0.4500   -2.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1020   -1.0649   -3.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0554    1.6756    0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9439    1.1151   -1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6098   -1.2309   -0.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6282   -0.4899    1.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6275   -1.0884   -1.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8905    0.5093   -2.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4744    0.1176   -2.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8423    1.6116   -1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4713    1.0587    0.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4824   -0.1933   -0.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6722   -0.1882    3.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4557    0.0312    2.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7287   -1.3100    1.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2615   -1.8798   -0.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392   -1.9679    0.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6492   -0.5520    1.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6533    2.4957    1.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2251    1.1741    2.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7263    1.6057    0.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4996    0.9903    2.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6916   -1.1960    1.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3875   -0.6761    1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9622   -1.4806   -0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9271    1.0789   -1.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  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  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 14 25  1  0
 25 26  1  0
  5 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
  8  2  2  0
 26 11  1  0
 30  4  1  0
 24 15  1  0
 24 18  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 19 44  1  0
 22 45  1  0
 23 46  1  0
 25 47  1  0
 25 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  1  0
 27 52  1  0
 28 53  1  0
 28 54  1  0
 29 55  1  0
 29 56  1  0
 30 57  1  0
 31 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ro-76477invega	HMDB
9-Hydroxyrisperidone	HMDB
9 OH Risperidone	HMDB
Invega sustenna	HMDB
Sustenna, invega	HMDB
9 Hydroxy risperidone	HMDB
9-Hydroxy-risperidone	HMDB
Invega	HMDB
9 Hydroxyrisperidone	HMDB
Paliperidone palmitate	HMDB
3-(2-(4-(6-Fluoro-3-(1,2-benzisoxazolyl))-1-piperidinyl)ethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido(1,2-a)pyrimidin-4-one	HMDB
9-OH-Risperidone	HMDB
Palmitate, paliperidone	HMDB
Paliperidone	MeSH

Chemical Formula

C₂₃H₂₇FN₄O₃

Average Molecular Weight

426.4839

Monoisotopic Molecular Weight

426.206718955

IUPAC Name

3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-9-hydroxy-2-methyl-4H,6H,7H,8H,9H-pyrido[1,2-a]pyrimidin-4-one

Traditional Name

invega

CAS Registry Number

144598-75-4

SMILES

CC1=C(CCN2CCC(CC2)C2=NOC3=C2C=CC(F)=C3)C(=O)N2CCCC(O)C2=N1

InChI Identifier

InChI=1S/C23H27FN4O3/c1-14-17(23(30)28-9-2-3-19(29)22(28)25-14)8-12-27-10-6-15(7-11-27)21-18-5-4-16(24)13-20(18)31-26-21/h4-5,13,15,19,29H,2-3,6-12H2,1H3

InChI Key

PMXMIIMHBWHSKN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridopyrimidines. Pyridopyrimidines are compounds containing a pyridopyrimidine, which consists of a pyridine fused to a pyrimidine. Pyridine is 6-membered ring consisting of five carbon atoms and a nitrogen atom. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridopyrimidines

Sub Class

Not Available

Direct Parent

Pyridopyrimidines

Alternative Parents

Substituents

Pyridopyrimidine
Benzisoxazole
Pyrimidone
Aralkylamine
Aryl fluoride
Aryl halide
Benzenoid
Piperidine
Pyridine
Pyrimidine
Heteroaromatic compound
Azole
Isoxazole
Lactam
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Azacycle
Oxacycle
Organic oxide
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Organopnictogen compound
Amine
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organofluorine compound (CHEBI:83804 )
secondary alcohol (CHEBI:83804 )
pyridopyrimidine (CHEBI:83804 )
1,2-benzoxazoles (CHEBI:83804 )
heteroarylpiperidine (CHEBI:83804 )

Ontology

Not Available

Non-excretory biofluid

Blood (PMID: 31557052)

Process

Not Available

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	0.3 g/L	Not Available
LogP	1.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	2.3	ALOGPS
logP	1.76	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.74	ChemAxon
pKa (Strongest Basic)	8.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.17 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	116.04 m³·mol⁻¹	ChemAxon
Polarizability	45.95 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	203.459	30932474
DeepCCS	[M-H]-	201.101	30932474
DeepCCS	[M-2H]-	234.905	30932474
DeepCCS	[M+Na]+	210.134	30932474
AllCCS	[M+H]+	201.2	32859911
AllCCS	[M+H-H2O]+	198.9	32859911
AllCCS	[M+NH4]+	203.2	32859911
AllCCS	[M+Na]+	203.8	32859911
AllCCS	[M-H]-	197.5	32859911
AllCCS	[M+Na-2H]-	198.1	32859911
AllCCS	[M+HCOO]-	198.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Paliperidone	CC1=C(CCN2CCC(CC2)C2=NOC3=C2C=CC(F)=C3)C(=O)N2CCCC(O)C2=N1	3810.4	Standard polar	33892256
Paliperidone	CC1=C(CCN2CCC(CC2)C2=NOC3=C2C=CC(F)=C3)C(=O)N2CCCC(O)C2=N1	3520.0	Standard non polar	33892256
Paliperidone	CC1=C(CCN2CCC(CC2)C2=NOC3=C2C=CC(F)=C3)C(=O)N2CCCC(O)C2=N1	3699.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Paliperidone,1TMS,isomer #1	CC1=C(CCN2CCC(C3=NOC4=CC(F)=CC=C34)CC2)C(=O)N2CCCC(O[Si](C)(C)C)C2=N1	3604.5	Semi standard non polar	33892256
Paliperidone,1TBDMS,isomer #1	CC1=C(CCN2CCC(C3=NOC4=CC(F)=CC=C34)CC2)C(=O)N2CCCC(O[Si](C)(C)C(C)(C)C)C2=N1	3796.2	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 - Paliperidone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-5696500000-a1613a1582e63c496dad	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Paliperidone GC-MS (1 TMS) - 70eV, Positive	splash10-001i-8471900000-a149ff175555e0db24e9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Paliperidone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Paliperidone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Paliperidone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Paliperidone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paliperidone LC-ESI-QTOF , positive-QTOF	splash10-004i-0000900000-455daaf1442d16f7bdaa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paliperidone LC-ESI-QTOF , positive-QTOF	splash10-004i-0010900000-dfa5205279a00e3db1e5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paliperidone LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0090300000-40916890e9a9a7068fa9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paliperidone LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0090000000-e69a1027f43e06f96a84	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paliperidone LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0090000000-5a71379b6aa632f43ea0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paliperidone 50V, Positive-QTOF	splash10-0a4i-0090000000-103c0bd1983ff6c70791	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paliperidone 10V, Positive-QTOF	splash10-004i-0000900000-67897696e1ccd20be748	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paliperidone 20V, Positive-QTOF	splash10-004i-0010900000-3f0ac407b1be971eacce	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paliperidone 40V, Positive-QTOF	splash10-0a4i-0090000000-667604bf1f7b3eb44b05	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paliperidone 30V, Positive-QTOF	splash10-0a4i-0090300000-d85372a8c1c3760561b7	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paliperidone 10V, Positive-QTOF	splash10-056r-0010900000-4c04153687e330cf24f2	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paliperidone 20V, Positive-QTOF	splash10-0a4i-2190300000-49c57d85e07909de54b7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paliperidone 40V, Positive-QTOF	splash10-0553-1953000000-4d3870a4f5b6d29b2e93	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paliperidone 10V, Negative-QTOF	splash10-004i-0100900000-84585ac1690268aadeb8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paliperidone 20V, Negative-QTOF	splash10-00or-0762900000-06cb779681cd658cd019	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paliperidone 40V, Negative-QTOF	splash10-014i-3495000000-eae8a7bebdef7929728b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paliperidone 10V, Positive-QTOF	splash10-004i-0000900000-5841a1f00bf45590e4cb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paliperidone 20V, Positive-QTOF	splash10-056r-0021900000-f500c685d988a30e3b2b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paliperidone 40V, Positive-QTOF	splash10-0a4i-0291100000-4f2ff3ad6bd7637e3474	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paliperidone 10V, Negative-QTOF	splash10-004i-0001900000-2e23abd8cfea8f54e176	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paliperidone 20V, Negative-QTOF	splash10-004i-1220900000-423d3855930b6ff1c88b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paliperidone 40V, Negative-QTOF	splash10-000i-0693200000-e42a7777acb1ba6bfe15	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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 DB01267	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01267	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01267

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

103109

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Paliperidone

METLIN ID

Not Available

PubChem Compound

115237

PDB ID

Not Available

ChEBI ID

83804

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

Urichuk L, Prior TI, Dursun S, Baker G: Metabolism of atypical antipsychotics: involvement of cytochrome p450 enzymes and relevance for drug-drug interactions. Curr Drug Metab. 2008 Jun;9(5):410-8. [PubMed:18537577 ]
Jones MP, Nicholl D, Trakas K: Efficacy and tolerability of paliperidone ER and other oral atypical antipsychotics in schizophrenia. Int J Clin Pharmacol Ther. 2010 Jun;48(6):383-99. [PubMed:20497747 ]

Only showing the first 10 proteins. There are 17 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Gunes A, Spina E, Dahl ML, Scordo MG: ABCB1 polymorphisms influence steady-state plasma levels of 9-hydroxyrisperidone and risperidone active moiety. Ther Drug Monit. 2008 Oct;30(5):628-33. doi: 10.1097/FTD.0b013e3181858ca9. [PubMed:18708991 ]

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

Boerth JM, Caley CF, Goethe JW: Interpreting serum risperidone concentrations. Pharmacotherapy. 2005 Feb;25(2):299-302. [PubMed:15767244 ]

Enzyme Details

3. Cytochrome P450 3A5

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:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

Yasui-Furukori N, Hidestrand M, Spina E, Facciola G, Scordo MG, Tybring G: Different enantioselective 9-hydroxylation of risperidone by the two human CYP2D6 and CYP3A4 enzymes. Drug Metab Dispos. 2001 Oct;29(10):1263-8. [PubMed:11560868 ]

Enzyme Details

4. Alpha-2A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:: ADRA2A
Uniprot ID:: P08913
Molecular weight:: 48956.3

References

Richelson E, Souder T: Binding of antipsychotic drugs to human brain receptors focus on newer generation compounds. Life Sci. 2000 Nov 24;68(1):29-39. [PubMed:11132243 ]

Enzyme Details

5. Alpha-2B adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:: ADRA2B
Uniprot ID:: P18089
Molecular weight:: 49953.1

References

Richelson E, Souder T: Binding of antipsychotic drugs to human brain receptors focus on newer generation compounds. Life Sci. 2000 Nov 24;68(1):29-39. [PubMed:11132243 ]

Enzyme Details

6. 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

Cohen LJ: Risperidone. Pharmacotherapy. 1994 May-Jun;14(3):253-65. [PubMed:7524043 ]
Megens AA, Awouters FH, Schotte A, Meert TF, Dugovic C, Niemegeers CJ, Leysen JE: Survey on the pharmacodynamics of the new antipsychotic risperidone. Psychopharmacology (Berl). 1994 Feb;114(1):9-23. [PubMed:7531353 ]
Regenthal R, Kunstler U, Hesse S, Sabri O, Preiss R: D2 dopamine receptor occupancy, risperidone plasma level and extrapyramidal motor symptoms in previously drug-free schizophrenic patients. Int J Clin Pharmacol Ther. 2005 Aug;43(8):370-8. [PubMed:16119512 ]
Remington G, Mamo D, Labelle A, Reiss J, Shammi C, Mannaert E, Mann S, Kapur S: A PET study evaluating dopamine D2 receptor occupancy for long-acting injectable risperidone. Am J Psychiatry. 2006 Mar;163(3):396-401. [PubMed:16513859 ]
Richelson E, Souder T: Binding of antipsychotic drugs to human brain receptors focus on newer generation compounds. Life Sci. 2000 Nov 24;68(1):29-39. [PubMed:11132243 ]
Yamada Y, Ohno Y, Nakashima Y, Fukuda M, Takayanagi R, Sato H, Tsuchiya F, Sawada Y, Iga T: Prediction and assessment of extrapyramidal side effects induced by risperidone based on dopamine D(2) receptor occupancy. Synapse. 2002 Oct;46(1):32-7. [PubMed:12211096 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

7. D(4) 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:: DRD4
Uniprot ID:: P21917
Molecular weight:: 48359.9

References

Leysen JE, Janssen PM, Megens AA, Schotte A: Risperidone: a novel antipsychotic with balanced serotonin-dopamine antagonism, receptor occupancy profile, and pharmacologic activity. J Clin Psychiatry. 1994 May;55 Suppl:5-12. [PubMed:7520908 ]
Megens AA, Awouters FH, Schotte A, Meert TF, Dugovic C, Niemegeers CJ, Leysen JE: Survey on the pharmacodynamics of the new antipsychotic risperidone. Psychopharmacology (Berl). 1994 Feb;114(1):9-23. [PubMed:7531353 ]

Enzyme Details

8. 5-hydroxytryptamine receptor 1A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1A
Uniprot ID:: P08908
Molecular weight:: 46106.3

References

Richelson E, Souder T: Binding of antipsychotic drugs to human brain receptors focus on newer generation compounds. Life Sci. 2000 Nov 24;68(1):29-39. [PubMed:11132243 ]

Enzyme Details

9. 5-hydroxytryptamine receptor 2A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:: HTR2A
Uniprot ID:: P28223
Molecular weight:: 52602.6

References

Cohen LJ: Risperidone. Pharmacotherapy. 1994 May-Jun;14(3):253-65. [PubMed:7524043 ]
He H, Richardson JS: A pharmacological, pharmacokinetic and clinical overview of risperidone, a new antipsychotic that blocks serotonin 5-HT2 and dopamine D2 receptors. Int Clin Psychopharmacol. 1995 Mar;10(1):19-30. [PubMed:7542676 ]
Leysen JE, Janssen PM, Megens AA, Schotte A: Risperidone: a novel antipsychotic with balanced serotonin-dopamine antagonism, receptor occupancy profile, and pharmacologic activity. J Clin Psychiatry. 1994 May;55 Suppl:5-12. [PubMed:7520908 ]
Megens AA, Awouters FH, Schotte A, Meert TF, Dugovic C, Niemegeers CJ, Leysen JE: Survey on the pharmacodynamics of the new antipsychotic risperidone. Psychopharmacology (Berl). 1994 Feb;114(1):9-23. [PubMed:7531353 ]
Richelson E, Souder T: Binding of antipsychotic drugs to human brain receptors focus on newer generation compounds. Life Sci. 2000 Nov 24;68(1):29-39. [PubMed:11132243 ]
Yamada Y, Ohno Y, Nakashima Y, Fukuda M, Takayanagi R, Sato H, Tsuchiya F, Sawada Y, Iga T: Prediction and assessment of extrapyramidal side effects induced by risperidone based on dopamine D(2) receptor occupancy. Synapse. 2002 Oct;46(1):32-7. [PubMed:12211096 ]

Enzyme Details

10. 5-hydroxytryptamine receptor 2C

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:: HTR2C
Uniprot ID:: P28335
Molecular weight:: 51820.7

References

Richelson E, Souder T: Binding of antipsychotic drugs to human brain receptors focus on newer generation compounds. Life Sci. 2000 Nov 24;68(1):29-39. [PubMed:11132243 ]

Only showing the first 10 proteins. There are 17 proteins in total.

Show all enzymes and transporters

Showing metabocard for Paliperidone (HMDB0015396)

MOL for HMDB0015396 (Paliperidone)

3D MOL for HMDB0015396 (Paliperidone)

3D SDF for HMDB0015396 (Paliperidone)

3D-SDF for HMDB0015396 (Paliperidone)

PDB for HMDB0015396 (Paliperidone)

3D PDB for HMDB0015396 (Paliperidone)

SMILES for HMDB0015396 (Paliperidone)

INCHI for HMDB0015396 (Paliperidone)

Structure for HMDB0015396 (Paliperidone)

3D Structure for HMDB0015396 (Paliperidone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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