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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6)transporters (1) Show 7 proteins XML

enzymes (6)transporters (1) Show 7 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014633

Secondary Accession Numbers

HMDB14633

Metabolite Identification

Common Name

Buspirone

Description

Buspirone is only found in individuals that have used or taken this drug. It is an anxiolytic agent and a serotonin receptor agonist belonging to the azaspirodecanedione class of compounds. Its structure is unrelated to those of the benzodiazepines, but it has an efficacy comparable to diazepam. [PubChem]Buspirone binds to 5-HT type 1A serotonin receptors on presynaptic neurons in the dorsal raphe and on postsynaptic neurons in the hippocampus, thus inhibiting the firing rate of 5-HT-containing neurons in the dorsal raphe. Buspirone also binds at dopamine type 2 (DA2) receptors, blocking presynaptic dopamine receptors. Buspirone increases firing in the locus ceruleus, an area of brain where norepinephrine cell bodies are found in high concentration. The net result of buspirone actions is that serotonergic activity is suppressed while noradrenergic and dopaminergic cell firing is enhanced.

Structure

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

490
  Mrv0541 02231214432D          

 28 31  0  0  0  0            999 V2000
    9.0752   -1.7862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0752    1.0717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0752   -0.3572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751    1.0717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    1.0717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    0.3572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    1.7862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7252   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2102   -1.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2102    0.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9948   -0.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9948    0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3127   -1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3127    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4877   -1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4877    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2502   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8377    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0127    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6001    1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3626    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3626    1.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5376    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5376    1.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    1.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  2  0  0  0  0
  2 16  2  0  0  0  0
  3 15  1  0  0  0  0
  3 16  1  0  0  0  0
  3 17  1  0  0  0  0
  4 20  1  0  0  0  0
  4 21  1  0  0  0  0
  4 22  1  0  0  0  0
  5 23  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  6 25  2  0  0  0  0
  6 26  1  0  0  0  0
  7 25  1  0  0  0  0
  7 27  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 12  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 26 28  2  0  0  0  0
 27 28  1  0  0  0  0
M  END

HMDB0014633
     RDKit          3D
Buspirone
 59 62  0  0  0  0  0  0  0  0999 V2000
   -2.6643   -1.4837    1.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3845   -0.4863    1.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8305   -0.6071    1.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5705    0.1280    0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0429    0.1659    0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7175    0.4834   -0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9978   -0.4360   -1.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6202   -0.6809   -0.9763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0967    1.5273    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6430    1.6893    0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1705    2.7925   -0.3438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7928    0.6620    0.5705 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3609    0.7497    0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8031    0.1874   -0.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6782    0.2809   -0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4211   -0.4338    0.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8362   -0.3469    0.1196 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3679   -1.0465   -1.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7810   -1.4896   -0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4896   -0.2627   -0.2650 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8572   -0.3623    0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4968   -1.5457    0.1628 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7846   -1.6595    0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5226   -0.5379    0.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8714    0.6754    0.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5711    0.7295    0.4278 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7686    0.9691   -0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4350    0.8986    0.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1175   -1.6745    1.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1614   -0.2889    2.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2779   -0.8562    1.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2234    0.9324    1.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4837    1.5475   -0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8081    0.2857   -0.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5119   -1.4100   -1.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9299   -0.0076   -2.5909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4326   -1.7414   -0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8192   -0.3308   -1.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4635    1.8641   -0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5605    2.2295    0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1045    1.8404    0.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9532    0.1494    1.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1316   -0.8904   -0.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475    0.6444   -1.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9905   -0.0859   -1.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9975    1.3478   -0.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1580   -1.5324    0.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0485   -0.0639    1.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3896   -0.4634   -1.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7911   -1.9914   -1.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6748   -2.0640    0.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2712   -2.0879   -1.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2798   -2.6159    0.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5607   -0.5902    1.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4372    1.5669    1.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4894    1.2375   -1.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3683    1.8301    0.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8428    1.7878    0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7410    0.8713    1.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  4  9  1  0
  9 10  1  0
 10 11  2  0
 10 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  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 20 27  1  0
 27 28  1  0
 12  2  1  0
 28 17  1  0
  8  4  1  0
 26 21  1  0
  3 29  1  0
  3 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 23 53  1  0
 24 54  1  0
 25 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  0
 28 59  1  0
M  END

490
  Mrv0541 02231214432D          

 28 31  0  0  0  0            999 V2000
    9.0752   -1.7862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0752    1.0717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0752   -0.3572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751    1.0717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    1.0717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    0.3572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    1.7862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7252   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2102   -1.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2102    0.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9948   -0.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9948    0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3127   -1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3127    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4877   -1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4877    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2502   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8377    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0127    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6001    1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3626    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3626    1.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5376    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5376    1.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    1.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  2  0  0  0  0
  2 16  2  0  0  0  0
  3 15  1  0  0  0  0
  3 16  1  0  0  0  0
  3 17  1  0  0  0  0
  4 20  1  0  0  0  0
  4 21  1  0  0  0  0
  4 22  1  0  0  0  0
  5 23  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  6 25  2  0  0  0  0
  6 26  1  0  0  0  0
  7 25  1  0  0  0  0
  7 27  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 12  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 26 28  2  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014633

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1CC2(CCCC2)CC(=O)N1CCCCN1CCN(CC1)C1=NC=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C21H31N5O2/c27-18-16-21(6-1-2-7-21)17-19(28)26(18)11-4-3-10-24-12-14-25(15-13-24)20-22-8-5-9-23-20/h5,8-9H,1-4,6-7,10-17H2

> <INCHI_KEY>
QWCRAEMEVRGPNT-UHFFFAOYSA-N

> <FORMULA>
C21H31N5O2

> <MOLECULAR_WEIGHT>
385.5031

> <EXACT_MASS>
385.247775261

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
44.11883665313514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}-8-azaspiro[4.5]decane-7,9-dione

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
1.7767331956666652

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.620561412370418

> <JCHEM_POLAR_SURFACE_AREA>
69.64000000000001

> <JCHEM_REFRACTIVITY>
108.89059999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
buspirone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014633
     RDKit          3D
Buspirone
 59 62  0  0  0  0  0  0  0  0999 V2000
   -2.6643   -1.4837    1.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3845   -0.4863    1.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8305   -0.6071    1.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5705    0.1280    0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0429    0.1659    0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7175    0.4834   -0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9978   -0.4360   -1.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6202   -0.6809   -0.9763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0967    1.5273    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6430    1.6893    0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1705    2.7925   -0.3438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7928    0.6620    0.5705 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3609    0.7497    0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8031    0.1874   -0.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6782    0.2809   -0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4211   -0.4338    0.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8362   -0.3469    0.1196 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3679   -1.0465   -1.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7810   -1.4896   -0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4896   -0.2627   -0.2650 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8572   -0.3623    0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4968   -1.5457    0.1628 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7846   -1.6595    0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5226   -0.5379    0.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8714    0.6754    0.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5711    0.7295    0.4278 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7686    0.9691   -0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4350    0.8986    0.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1175   -1.6745    1.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1614   -0.2889    2.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2779   -0.8562    1.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2234    0.9324    1.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4837    1.5475   -0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8081    0.2857   -0.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5119   -1.4100   -1.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9299   -0.0076   -2.5909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4326   -1.7414   -0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8192   -0.3308   -1.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4635    1.8641   -0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5605    2.2295    0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1045    1.8404    0.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9532    0.1494    1.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1316   -0.8904   -0.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475    0.6444   -1.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9905   -0.0859   -1.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9975    1.3478   -0.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1580   -1.5324    0.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0485   -0.0639    1.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3896   -0.4634   -1.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7911   -1.9914   -1.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6748   -2.0640    0.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2712   -2.0879   -1.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2798   -2.6159    0.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5607   -0.5902    1.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4372    1.5669    1.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4894    1.2375   -1.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3683    1.8301    0.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8428    1.7878    0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7410    0.8713    1.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  4  9  1  0
  9 10  1  0
 10 11  2  0
 10 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  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 20 27  1  0
 27 28  1  0
 12  2  1  0
 28 17  1  0
  8  4  1  0
 26 21  1  0
  3 29  1  0
  3 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 23 53  1  0
 24 54  1  0
 25 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  0
 28 59  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 490                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      16.940  -3.334   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      16.940   2.001   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      16.940  -0.667   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      10.780   2.001   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       7.700   2.001   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       5.390   0.667   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       5.390   3.334   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      20.020  -0.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.926  -1.913   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.926   0.579   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.390  -1.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.390   0.103   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.250  -2.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.250   0.667   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.710  -2.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.710   0.667   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.400  -0.667   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.630   0.667   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.090   0.667   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.320   2.001   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.010   0.667   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.010   3.334   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.470   0.667   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.470   3.334   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.160   2.001   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.850   0.667   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.850   3.334   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.080   2.001   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2   16                                                            
CONECT    3   15   16   17                                                  
CONECT    4   20   21   22                                                  
CONECT    5   23   24   25                                                  
CONECT    6   25   26                                                       
CONECT    7   25   27                                                       
CONECT    8    9   10   13   14                                             
CONECT    9    8   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   12                                                       
CONECT   12   10   11                                                       
CONECT   13    8   15                                                       
CONECT   14    8   16                                                       
CONECT   15    1    3   13                                                  
CONECT   16    2    3   14                                                  
CONECT   17    3   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20    4   19                                                       
CONECT   21    4   23                                                       
CONECT   22    4   24                                                       
CONECT   23    5   21                                                       
CONECT   24    5   22                                                       
CONECT   25    5    6    7                                                  
CONECT   26    6   28                                                       
CONECT   27    7   28                                                       
CONECT   28   26   27                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0014633
HETATM    1  O1  UNL     1      -2.664  -1.484   1.503  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.385  -0.486   1.147  1.00  0.00           C  
HETATM    3  C2  UNL     1      -4.830  -0.607   1.371  1.00  0.00           C  
HETATM    4  C3  UNL     1      -5.571   0.128   0.279  1.00  0.00           C  
HETATM    5  C4  UNL     1      -7.043   0.166   0.702  1.00  0.00           C  
HETATM    6  C5  UNL     1      -7.717   0.483  -0.614  1.00  0.00           C  
HETATM    7  C6  UNL     1      -6.998  -0.436  -1.575  1.00  0.00           C  
HETATM    8  C7  UNL     1      -5.620  -0.681  -0.976  1.00  0.00           C  
HETATM    9  C8  UNL     1      -5.097   1.527   0.091  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.643   1.689   0.096  1.00  0.00           C  
HETATM   11  O2  UNL     1      -3.171   2.793  -0.344  1.00  0.00           O  
HETATM   12  N1  UNL     1      -2.793   0.662   0.570  1.00  0.00           N  
HETATM   13  C10 UNL     1      -1.361   0.750   0.485  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.803   0.187  -0.780  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.678   0.281  -0.865  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.421  -0.434   0.208  1.00  0.00           C  
HETATM   17  N2  UNL     1       2.836  -0.347   0.120  1.00  0.00           N  
HETATM   18  C14 UNL     1       3.368  -1.046  -1.001  1.00  0.00           C  
HETATM   19  C15 UNL     1       4.781  -1.490  -0.599  1.00  0.00           C  
HETATM   20  N3  UNL     1       5.490  -0.263  -0.265  1.00  0.00           N  
HETATM   21  C16 UNL     1       6.857  -0.362   0.110  1.00  0.00           C  
HETATM   22  N4  UNL     1       7.497  -1.546   0.163  1.00  0.00           N  
HETATM   23  C17 UNL     1       8.785  -1.659   0.513  1.00  0.00           C  
HETATM   24  C18 UNL     1       9.523  -0.538   0.842  1.00  0.00           C  
HETATM   25  C19 UNL     1       8.871   0.675   0.788  1.00  0.00           C  
HETATM   26  N5  UNL     1       7.571   0.730   0.428  1.00  0.00           N  
HETATM   27  C20 UNL     1       4.769   0.969  -0.334  1.00  0.00           C  
HETATM   28  C21 UNL     1       3.435   0.899   0.423  1.00  0.00           C  
HETATM   29  H1  UNL     1      -5.118  -1.675   1.275  1.00  0.00           H  
HETATM   30  H2  UNL     1      -5.161  -0.289   2.378  1.00  0.00           H  
HETATM   31  H3  UNL     1      -7.278  -0.856   1.055  1.00  0.00           H  
HETATM   32  H4  UNL     1      -7.223   0.932   1.462  1.00  0.00           H  
HETATM   33  H5  UNL     1      -7.484   1.548  -0.854  1.00  0.00           H  
HETATM   34  H6  UNL     1      -8.808   0.286  -0.583  1.00  0.00           H  
HETATM   35  H7  UNL     1      -7.512  -1.410  -1.621  1.00  0.00           H  
HETATM   36  H8  UNL     1      -6.930  -0.008  -2.591  1.00  0.00           H  
HETATM   37  H9  UNL     1      -5.433  -1.741  -0.753  1.00  0.00           H  
HETATM   38  H10 UNL     1      -4.819  -0.331  -1.674  1.00  0.00           H  
HETATM   39  H11 UNL     1      -5.464   1.864  -0.922  1.00  0.00           H  
HETATM   40  H12 UNL     1      -5.560   2.230   0.834  1.00  0.00           H  
HETATM   41  H13 UNL     1      -1.104   1.840   0.618  1.00  0.00           H  
HETATM   42  H14 UNL     1      -0.953   0.149   1.332  1.00  0.00           H  
HETATM   43  H15 UNL     1      -1.132  -0.890  -0.815  1.00  0.00           H  
HETATM   44  H16 UNL     1      -1.248   0.644  -1.695  1.00  0.00           H  
HETATM   45  H17 UNL     1       0.990  -0.086  -1.883  1.00  0.00           H  
HETATM   46  H18 UNL     1       0.997   1.348  -0.847  1.00  0.00           H  
HETATM   47  H19 UNL     1       1.158  -1.532   0.213  1.00  0.00           H  
HETATM   48  H20 UNL     1       1.048  -0.064   1.197  1.00  0.00           H  
HETATM   49  H21 UNL     1       3.390  -0.463  -1.936  1.00  0.00           H  
HETATM   50  H22 UNL     1       2.791  -1.991  -1.128  1.00  0.00           H  
HETATM   51  H23 UNL     1       4.675  -2.064   0.340  1.00  0.00           H  
HETATM   52  H24 UNL     1       5.271  -2.088  -1.363  1.00  0.00           H  
HETATM   53  H25 UNL     1       9.280  -2.616   0.550  1.00  0.00           H  
HETATM   54  H26 UNL     1      10.561  -0.590   1.129  1.00  0.00           H  
HETATM   55  H27 UNL     1       9.437   1.567   1.044  1.00  0.00           H  
HETATM   56  H28 UNL     1       4.489   1.237  -1.386  1.00  0.00           H  
HETATM   57  H29 UNL     1       5.368   1.830   0.039  1.00  0.00           H  
HETATM   58  H30 UNL     1       2.843   1.788   0.202  1.00  0.00           H  
HETATM   59  H31 UNL     1       3.741   0.871   1.511  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4   29   30
CONECT    4    5    8    9
CONECT    5    6   31   32
CONECT    6    7   33   34
CONECT    7    8   35   36
CONECT    8   37   38
CONECT    9   10   39   40
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   14   41   42
CONECT   14   15   43   44
CONECT   15   16   45   46
CONECT   16   17   47   48
CONECT   17   18   28
CONECT   18   19   49   50
CONECT   19   20   51   52
CONECT   20   21   27
CONECT   21   22   22   26
CONECT   22   23
CONECT   23   24   24   53
CONECT   24   25   54
CONECT   25   26   26   55
CONECT   27   28   56   57
CONECT   28   58   59
END

HMDB0014633
     RDKit          3D
Buspirone
 59 62  0  0  0  0  0  0  0  0999 V2000
   -2.6643   -1.4837    1.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3845   -0.4863    1.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8305   -0.6071    1.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5705    0.1280    0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0429    0.1659    0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7175    0.4834   -0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9978   -0.4360   -1.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6202   -0.6809   -0.9763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0967    1.5273    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6430    1.6893    0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1705    2.7925   -0.3438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7928    0.6620    0.5705 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3609    0.7497    0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8031    0.1874   -0.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6782    0.2809   -0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4211   -0.4338    0.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8362   -0.3469    0.1196 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3679   -1.0465   -1.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7810   -1.4896   -0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4896   -0.2627   -0.2650 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8572   -0.3623    0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4968   -1.5457    0.1628 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7846   -1.6595    0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5226   -0.5379    0.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8714    0.6754    0.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5711    0.7295    0.4278 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7686    0.9691   -0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4350    0.8986    0.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1175   -1.6745    1.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1614   -0.2889    2.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2779   -0.8562    1.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2234    0.9324    1.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4837    1.5475   -0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8081    0.2857   -0.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5119   -1.4100   -1.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9299   -0.0076   -2.5909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4326   -1.7414   -0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8192   -0.3308   -1.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4635    1.8641   -0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5605    2.2295    0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1045    1.8404    0.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9532    0.1494    1.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1316   -0.8904   -0.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475    0.6444   -1.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9905   -0.0859   -1.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9975    1.3478   -0.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1580   -1.5324    0.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0485   -0.0639    1.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3896   -0.4634   -1.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7911   -1.9914   -1.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6748   -2.0640    0.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2712   -2.0879   -1.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2798   -2.6159    0.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5607   -0.5902    1.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4372    1.5669    1.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4894    1.2375   -1.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3683    1.8301    0.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8428    1.7878    0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7410    0.8713    1.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  4  9  1  0
  9 10  1  0
 10 11  2  0
 10 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  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 20 27  1  0
 27 28  1  0
 12  2  1  0
 28 17  1  0
  8  4  1  0
 26 21  1  0
  3 29  1  0
  3 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 23 53  1  0
 24 54  1  0
 25 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  0
 28 59  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8-(4-(4-(2-Pyrimidinyl)-1-piperizinyl)butyl)-8-azaspiro(4,5)decane-7,9-dione	ChEBI
Buspirona	ChEBI
Buspironum	ChEBI
Gen-buspirone	Kegg
Anxut	HMDB
Bespar	HMDB
Busp	HMDB
Gen buspirone	HMDB
Lin buspirone	HMDB
Linson pharma brand OF buspirone hydrochloride	HMDB
N-(4-(4-(2-Pyrimidinyl)-1-piperazinyl)butyl)-1-cyclopentanediacetamide	HMDB
Nu buspirone	HMDB
Ratio-buspirone	HMDB
Armstrong brand OF buspirone hydrochloride	HMDB
Bristol myers squibb brand OF buspirone hydrochloride	HMDB
Bristol-myers squibb brand OF buspirone hydrochloride	HMDB
Buspirone hydrochloride	HMDB
Hexal brand OF buspirone hydrochloride	HMDB
Neurosine	HMDB
Novo buspirone	HMDB
Novo-buspirone	HMDB
Nu pharm brand OF buspirone hydrochloride	HMDB
Apo buspirone	HMDB
Apo-buspirone	HMDB
Genpharm brand OF buspirone	HMDB
Novopharm brand OF buspirone hydrochloride	HMDB
Nu-pharm brand OF buspirone hydrochloride	HMDB
PMS Buspirone	HMDB
Ratiopharm brand OF buspirone hydrochloride	HMDB
Apotex brand OF buspirone hydrochloride	HMDB
Bristol myers brand OF buspirone hydrochloride	HMDB
Bristol-myers brand OF buspirone hydrochloride	HMDB
Buspar	HMDB
Eisai brand OF buspirone hydrochloride	HMDB
Hormosan brand OF buspirone hydrochloride	HMDB
Hydrochloride, buspirone	HMDB
Lin-buspirone	HMDB
Nu-buspirone	HMDB
PMS-Buspirone	HMDB
Pharmascience brand OF buspirone hydrochloride	HMDB
UPSA brand OF buspirone hydrochloride	HMDB
Ratio buspirone	HMDB

Chemical Formula

C₂₁H₃₁N₅O₂

Average Molecular Weight

385.5031

Monoisotopic Molecular Weight

385.247775261

IUPAC Name

8-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}-8-azaspiro[4.5]decane-7,9-dione

Traditional Name

buspirone

CAS Registry Number

36505-84-7

SMILES

O=C1CC2(CCCC2)CC(=O)N1CCCCN1CCN(CC1)C1=NC=CC=N1

InChI Identifier

InChI=1S/C21H31N5O2/c27-18-16-21(6-1-2-7-21)17-19(28)26(18)11-4-3-10-24-12-14-25(15-13-24)20-22-8-5-9-23-20/h5,8-9H,1-4,6-7,10-17H2

InChI Key

QWCRAEMEVRGPNT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazinanes

Sub Class

Piperazines

Direct Parent

N-arylpiperazines

Alternative Parents

Substituents

Azaspirodecanedione
N-arylpiperazine
Azaspirodecane
Piperidinedione
Dialkylarylamine
Aminopyrimidine
N-alkylpiperazine
Piperidinone
Delta-lactam
Pyrimidine
Piperidine
Carboxylic acid imide, n-substituted
Heteroaromatic compound
Carboxylic acid imide
Dicarboximide
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Lactam
Azacycle
Carboxylic acid derivative
Organic oxide
Organonitrogen compound
Organooxygen compound
Amine
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-arylpiperazine (CHEBI:3223 )
pyrimidines (CHEBI:3223 )
N-alkylpiperazine (CHEBI:3223 )
piperidones (CHEBI:3223 )
azaspiro compound (CHEBI:3223 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Process

Not Available

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	201.5 - 202.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.59 g/L	Not Available
LogP	2.3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	199.3	30932474
[M+H]+	Not Available	197.727	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001098

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.59 g/L	ALOGPS
logP	1.95	ALOGPS
logP	1.78	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	7.62	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.64 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	108.89 m³·mol⁻¹	ChemAxon
Polarizability	44.12 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	190.445	31661259
DarkChem	[M-H]-	184.756	31661259
DeepCCS	[M+H]+	186.412	30932474
DeepCCS	[M-H]-	184.054	30932474
DeepCCS	[M-2H]-	217.387	30932474
DeepCCS	[M+Na]+	192.666	30932474
AllCCS	[M+H]+	192.9	32859911
AllCCS	[M+H-H2O]+	190.7	32859911
AllCCS	[M+NH4]+	195.0	32859911
AllCCS	[M+Na]+	195.6	32859911
AllCCS	[M-H]-	188.9	32859911
AllCCS	[M+Na-2H]-	189.3	32859911
AllCCS	[M+HCOO]-	190.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Buspirone	O=C1CC2(CCCC2)CC(=O)N1CCCCN1CCN(CC1)C1=NC=CC=N1	3284.8	Standard polar	33892256
Buspirone	O=C1CC2(CCCC2)CC(=O)N1CCCCN1CCN(CC1)C1=NC=CC=N1	3175.1	Standard non polar	33892256
Buspirone	O=C1CC2(CCCC2)CC(=O)N1CCCCN1CCN(CC1)C1=NC=CC=N1	3335.7	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 - Buspirone GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-3930000000-f72780a741e10d32e14d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Buspirone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-6940000000-197b8ea9ac79cbda753b	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Buspirone LC-ESI-qTof , Positive-QTOF	splash10-000f-0930000000-081eac0a05abab8fc5fa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Buspirone LC-ESI-QTOF , positive-QTOF	splash10-000i-0009000000-429c277f63eb2ab52f57	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Buspirone LC-ESI-QTOF , positive-QTOF	splash10-000i-0009000000-170a03c9244dada2609b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Buspirone LC-ESI-QTOF , positive-QTOF	splash10-00di-0922000000-80c9aa9ae15b661116ad	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Buspirone LC-ESI-QTOF , positive-QTOF	splash10-00di-1900000000-fafa91d49f01314afdf1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Buspirone LC-ESI-QTOF , positive-QTOF	splash10-00dj-4900000000-460409b07d20201af414	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Buspirone , positive-QTOF	splash10-000f-0930000000-081eac0a05abab8fc5fa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Buspirone 60V, Positive-QTOF	splash10-00di-1900000000-1548c934ed4552c550c0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Buspirone 75V, Positive-QTOF	splash10-00di-4900000000-3f738f9b3afda733fdbb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Buspirone 30V, Positive-QTOF	splash10-00di-0923000000-0432dbe18a87c4f8aac9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Buspirone 90V, Positive-QTOF	splash10-00ea-9600000000-c19888c809dc5e1e4345	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Buspirone 90V, Positive-QTOF	splash10-00ea-9600000000-306c03950ac42645d650	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Buspirone 50V, Positive-QTOF	splash10-00dj-4900000000-460409b07d20201af414	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Buspirone 40V, Positive-QTOF	splash10-00di-1900000000-cd100d009ef3ee04589b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Buspirone 40V, Positive-QTOF	splash10-00di-1900000000-fafa91d49f01314afdf1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Buspirone 30V, Positive-QTOF	splash10-00di-0922000000-80c9aa9ae15b661116ad	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Buspirone 45V, Positive-QTOF	splash10-00di-0910000000-cf8501b071281e076ac4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Buspirone 15V, Positive-QTOF	splash10-000i-0009000000-f8f22927f54be6364e82	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Buspirone 50V, Positive-QTOF	splash10-00di-3900000000-1b0646e8d778da56bd8e	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Buspirone 10V, Positive-QTOF	splash10-000i-0029000000-e01810fdca67d6848abc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Buspirone 20V, Positive-QTOF	splash10-0079-5679000000-e3b3f87f2a5001651596	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Buspirone 40V, Positive-QTOF	splash10-0a4i-8940000000-0f2042c84fa52ff07a00	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Buspirone 10V, Negative-QTOF	splash10-001i-0309000000-0cb92cbc3313c049e2b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Buspirone 20V, Negative-QTOF	splash10-0159-0905000000-852ca5ee117750d57ba3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Buspirone 40V, Negative-QTOF	splash10-014i-4910000000-ae14188467b44ba1ea96	2016-08-03	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 DB00490	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00490	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00490

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2383

KEGG Compound ID

C06861

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Buspirone

METLIN ID

Not Available

PubChem Compound

2477

PDB ID

Not Available

ChEBI ID

3223

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

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

Zhu M, Zhao W, Jimenez H, Zhang D, Yeola S, Dai R, Vachharajani N, Mitroka J: Cytochrome P450 3A-mediated metabolism of buspirone in human liver microsomes. Drug Metab Dispos. 2005 Apr;33(4):500-7. Epub 2005 Jan 7. [PubMed:15640381 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

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

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Zhu M, Zhao W, Jimenez H, Zhang D, Yeola S, Dai R, Vachharajani N, Mitroka J: Cytochrome P450 3A-mediated metabolism of buspirone in human liver microsomes. Drug Metab Dispos. 2005 Apr;33(4):500-7. Epub 2005 Jan 7. [PubMed:15640381 ]

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

Zhu M, Zhao W, Jimenez H, Zhang D, Yeola S, Dai R, Vachharajani N, Mitroka J: Cytochrome P450 3A-mediated metabolism of buspirone in human liver microsomes. Drug Metab Dispos. 2005 Apr;33(4):500-7. Epub 2005 Jan 7. [PubMed:15640381 ]

Enzyme Details

4. Cytochrome P450 3A7

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:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

Enzyme Details

5. 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

Malt EA, Olafsson S, Aakvaag A, Lund A, Ursin H: Altered dopamine D2 receptor function in fibromyalgia patients: a neuroendocrine study with buspirone in women with fibromyalgia compared to female population based controls. J Affect Disord. 2003 Jun;75(1):77-82. [PubMed:12781354 ]
Boido A, Boido CC, Sparatore F: Synthesis and pharmacological evaluation of aryl/heteroaryl piperazinyl alkyl benzotriazoles as ligands for some serotonin and dopamine receptor subtypes. Farmaco. 2001 Apr;56(4):263-75. [PubMed:11421254 ]
Nader MA, Hannemann M: Interactions of buspirone or gepirone with nicotine on schedule-controlled behavior of pigeons. Behav Pharmacol. 1993 Jun;4(3):263-268. [PubMed:11224194 ]
Pache DM, Fernandez-Perez S, Sewell RD: Buspirone differentially modifies short-term memory function in a combined delayed matching/non-matching to position task. Eur J Pharmacol. 2003 Sep 23;477(3):205-11. [PubMed:14522358 ]
Fernandez-Perez S, Pache DM, Sewell RD: Co-administration of fluoxetine and WAY100635 improves short-term memory function. Eur J Pharmacol. 2005 Oct 17;522(1-3):78-83. Epub 2005 Oct 7. [PubMed:16214127 ]

Enzyme Details

6. 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

de Boer SF, Lesourd M, Mocaer E, Koolhaas JM: Selective antiaggressive effects of alnespirone in resident-intruder test are mediated via 5-hydroxytryptamine1A receptors: A comparative pharmacological study with 8-hydroxy-2-dipropylaminotetralin, ipsapirone, buspirone, eltoprazine, and WAY-100635. J Pharmacol Exp Ther. 1999 Mar;288(3):1125-33. [PubMed:10027850 ]
Rehman J, Kaynan A, Christ G, Valcic M, Maayani S, Melman A: Modification of sexual behavior of Long-Evans male rats by drugs acting on the 5-HT1A receptor. Brain Res. 1999 Mar 13;821(2):414-25. [PubMed:10064829 ]
Liang KC: Pre- or post-training injection of buspirone impaired retention in the inhibitory avoidance task: involvement of amygdala 5-HT1A receptors. Eur J Neurosci. 1999 May;11(5):1491-500. [PubMed:10215901 ]
Becker C, Hamon M, Benoliel JJ: Prevention by 5-HT1A receptor agonists of restraint stress- and yohimbine-induced release of cholecystokinin in the frontal cortex of the freely moving rat. Neuropharmacology. 1999 Apr;38(4):525-32. [PubMed:10221756 ]
Dupuis DS, Tardif S, Wurch T, Colpaert FC, Pauwels PJ: Modulation of 5-HT1A receptor signalling by point-mutation of cysteine351 in the rat Galpha(o) protein. Neuropharmacology. 1999 Jul;38(7):1035-41. [PubMed:10428422 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Osei-Owusu P, Scrogin KE: Buspirone raises blood pressure through activation of sympathetic nervous system and by direct activation of alpha1-adrenergic receptors after severe hemorrhage. J Pharmacol Exp Ther. 2004 Jun;309(3):1132-40. Epub 2004 Feb 9. [PubMed:14769835 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [PubMed:12438524 ]

Showing metabocard for Buspirone (HMDB0014633)

MOL for HMDB0014633 (Buspirone)

3D MOL for HMDB0014633 (Buspirone)

3D SDF for HMDB0014633 (Buspirone)

3D-SDF for HMDB0014633 (Buspirone)

PDB for HMDB0014633 (Buspirone)

3D PDB for HMDB0014633 (Buspirone)

SMILES for HMDB0014633 (Buspirone)

INCHI for HMDB0014633 (Buspirone)

Structure for HMDB0014633 (Buspirone)

3D Structure for HMDB0014633 (Buspirone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

Transporters

References