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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 10:40:47 UTC

Update Date

2021-09-26 23:05:26 UTC

HMDB ID

HMDB0252698

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Gepirone

Description

Gepirone 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. However, similarly to buspirone, gepirone metabolizes into 1-(2-pyrimidinyl)piperazine, which is known to act as a potent antagonist of the α2-adrenergic receptor. Gepirone is a very strong basic compound (based on its pKa). However, in 2012 it once again failed to convince the FDA of its qualities for treating anxiety and depression. Gepirone is an antidepressant and anxiolytic drug of the azapirone group that was synthesized by Bristol-Myers Squibb in 1986 and has been under development for the treatment of depression but has yet to be marketed. In December 2015, the FDA once again gave gepirone a negative review for depression due to concerns of efficacy. However, in March 2016, the FDA reversed course and ruled favorably on the efficacy of gepirone. Gepirone was originally developed by Bristol-Myers Squibb, but was out-licensed to Fabre-Kramer in 1993. Unlike its relative buspirone however, gepirone has greater efficacy in activating the 5-HT1A and has negligible affinity for the D2 receptor (30- to 50-fold lower in comparison to buspirone). Moreover, the pro-sexual effects appear to be independent of its antidepressant and anxiolytic effects. This compound has been identified in human blood as reported by (PMID: 31557052 ). Gepirone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Gepirone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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


  Mrv1652310201623332D          

 26 28  0  0  0  0            999 V2000
   -2.2414   -4.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7111   -3.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  2  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
  2 26  1  0  0  0  0
M  END

HMDB0252698
     RDKit          3D
Gepirone
 55 57  0  0  0  0  0  0  0  0999 V2000
    6.7022    1.5395    0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6436    0.4530   -0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4636   -0.7771   -0.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7748    0.9016   -1.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5603    1.6019   -0.9351 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1710    2.6601   -1.5044 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7852    1.0667    0.1403 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3994    1.3268    0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4419    0.4128   -0.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5153   -1.0270    0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5737   -1.7466   -0.7729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8491   -1.2258   -0.5077 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4517   -1.4044    0.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9296   -1.6802    0.7560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5823   -0.9305   -0.2891 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7203   -0.1404   -0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3308    0.6016   -0.9781 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4026    1.3525   -0.7461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9444    1.4012    0.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3337    0.6466    1.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2428   -0.0988    1.2000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0259   -1.0142   -1.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5766   -0.5872   -1.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4905    0.2551    1.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8713   -0.4324    1.9354 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9791    0.1504    1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4381    1.4346   -0.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2528    1.3386    0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684    2.5408   -0.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7690   -1.5732   -0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1792   -0.4929   -1.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0624   -1.1349    0.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.0045   -1.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3583    1.5432   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1226    2.3685    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1896    1.2585    1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5864    0.7647   -0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237    0.5050   -1.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2194   -1.1194    1.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5074   -1.4722   -0.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2957   -1.5777   -1.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4829   -2.8521   -0.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9474   -2.1915    1.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3113   -0.4511    1.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0769   -2.7572    0.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3143   -1.3859    1.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8960    1.9537   -1.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8242    1.9979    0.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7061    0.6359    2.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1000   -2.0781   -1.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5302   -0.3358   -2.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6066    0.5213   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0958   -0.6684   -2.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3958    0.8096    1.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2441   -0.8828    1.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  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  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15 22  1  0
 22 23  1  0
  7 24  1  0
 24 25  2  0
 24 26  1  0
 26  2  1  0
 23 12  1  0
 21 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 26 54  1  0
 26 55  1  0
M  END


  Mrv1652310201623332D          

 26 28  0  0  0  0            999 V2000
   -2.2414   -4.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7111   -3.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  2  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
  2 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252698

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)CC(=O)N(CCCCN2CCN(CC2)C2=NC=CC=N2)C(=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H29N5O2/c1-19(2)14-16(25)24(17(26)15-19)9-4-3-8-22-10-12-23(13-11-22)18-20-6-5-7-21-18/h5-7H,3-4,8-15H2,1-2H3

> <INCHI_KEY>
QOIGKGMMAGJZNZ-UHFFFAOYSA-N

> <FORMULA>
C19H29N5O2

> <MOLECULAR_WEIGHT>
359.474

> <EXACT_MASS>
359.232125194

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
40.93483528372011

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,4-dimethyl-1-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}piperidine-2,6-dione

> <ALOGPS_LOGP>
2.09

> <JCHEM_LOGP>
1.3513217683333338

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.620561412370311

> <JCHEM_POLAR_SURFACE_AREA>
69.64000000000001

> <JCHEM_REFRACTIVITY>
101.49080000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gepirone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0252698
     RDKit          3D
Gepirone
 55 57  0  0  0  0  0  0  0  0999 V2000
    6.7022    1.5395    0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6436    0.4530   -0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4636   -0.7771   -0.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7748    0.9016   -1.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5603    1.6019   -0.9351 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1710    2.6601   -1.5044 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7852    1.0667    0.1403 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3994    1.3268    0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4419    0.4128   -0.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5153   -1.0270    0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5737   -1.7466   -0.7729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8491   -1.2258   -0.5077 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4517   -1.4044    0.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9296   -1.6802    0.7560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5823   -0.9305   -0.2891 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7203   -0.1404   -0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3308    0.6016   -0.9781 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4026    1.3525   -0.7461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9444    1.4012    0.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3337    0.6466    1.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2428   -0.0988    1.2000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0259   -1.0142   -1.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5766   -0.5872   -1.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4905    0.2551    1.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8713   -0.4324    1.9354 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9791    0.1504    1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4381    1.4346   -0.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2528    1.3386    0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684    2.5408   -0.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7690   -1.5732   -0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1792   -0.4929   -1.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0624   -1.1349    0.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.0045   -1.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3583    1.5432   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1226    2.3685    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1896    1.2585    1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5864    0.7647   -0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237    0.5050   -1.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2194   -1.1194    1.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5074   -1.4722   -0.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2957   -1.5777   -1.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4829   -2.8521   -0.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9474   -2.1915    1.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3113   -0.4511    1.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0769   -2.7572    0.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3143   -1.3859    1.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8960    1.9537   -1.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8242    1.9979    0.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7061    0.6359    2.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1000   -2.0781   -1.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5302   -0.3358   -2.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6066    0.5213   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0958   -0.6684   -2.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3958    0.8096    1.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2441   -0.8828    1.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  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  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15 22  1  0
 22 23  1  0
  7 24  1  0
 24 25  2  0
 24 26  1  0
 26  2  1  0
 23 12  1  0
 21 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 26 54  1  0
 26 55  1  0
M  END

HEADER    PROTEIN                                 20-OCT-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-OCT-16         0                                  
HETATM    1  C   UNK     0      -4.184  -7.967   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       0.000  -9.240   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       6.668 -10.010   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       9.336 -11.550   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      12.003 -11.550   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      10.669 -13.860   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      -3.194  -6.253   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9   26                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    2                                                       
CONECT   10    6   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26    2                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0252698
HETATM    1  C1  UNL     1       6.702   1.539   0.034  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.644   0.453  -0.210  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.464  -0.777  -0.631  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.775   0.902  -1.334  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.560   1.602  -0.935  1.00  0.00           C  
HETATM    6  O1  UNL     1       3.171   2.660  -1.504  1.00  0.00           O  
HETATM    7  N1  UNL     1       2.785   1.067   0.140  1.00  0.00           N  
HETATM    8  C6  UNL     1       1.399   1.327   0.308  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.442   0.413  -0.359  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.515  -1.027   0.043  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.574  -1.747  -0.773  1.00  0.00           C  
HETATM   12  N2  UNL     1      -1.849  -1.226  -0.508  1.00  0.00           N  
HETATM   13  C10 UNL     1      -2.452  -1.404   0.739  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.930  -1.680   0.756  1.00  0.00           C  
HETATM   15  N3  UNL     1      -4.582  -0.931  -0.289  1.00  0.00           N  
HETATM   16  C12 UNL     1      -5.720  -0.140  -0.028  1.00  0.00           C  
HETATM   17  N4  UNL     1      -6.331   0.602  -0.978  1.00  0.00           N  
HETATM   18  C13 UNL     1      -7.403   1.353  -0.746  1.00  0.00           C  
HETATM   19  C14 UNL     1      -7.944   1.401   0.510  1.00  0.00           C  
HETATM   20  C15 UNL     1      -7.334   0.647   1.501  1.00  0.00           C  
HETATM   21  N5  UNL     1      -6.243  -0.099   1.200  1.00  0.00           N  
HETATM   22  C16 UNL     1      -4.026  -1.014  -1.622  1.00  0.00           C  
HETATM   23  C17 UNL     1      -2.577  -0.587  -1.518  1.00  0.00           C  
HETATM   24  C18 UNL     1       3.491   0.255   1.062  1.00  0.00           C  
HETATM   25  O2  UNL     1       2.871  -0.432   1.935  1.00  0.00           O  
HETATM   26  C19 UNL     1       4.979   0.150   1.075  1.00  0.00           C  
HETATM   27  H1  UNL     1       7.438   1.435  -0.789  1.00  0.00           H  
HETATM   28  H2  UNL     1       7.253   1.339   0.972  1.00  0.00           H  
HETATM   29  H3  UNL     1       6.268   2.541  -0.018  1.00  0.00           H  
HETATM   30  H4  UNL     1       5.769  -1.573  -0.917  1.00  0.00           H  
HETATM   31  H5  UNL     1       7.179  -0.493  -1.425  1.00  0.00           H  
HETATM   32  H6  UNL     1       7.062  -1.135   0.230  1.00  0.00           H  
HETATM   33  H7  UNL     1       4.508  -0.004  -1.944  1.00  0.00           H  
HETATM   34  H8  UNL     1       5.358   1.543  -2.052  1.00  0.00           H  
HETATM   35  H9  UNL     1       1.123   2.369   0.041  1.00  0.00           H  
HETATM   36  H10 UNL     1       1.190   1.259   1.418  1.00  0.00           H  
HETATM   37  H11 UNL     1      -0.586   0.765  -0.039  1.00  0.00           H  
HETATM   38  H12 UNL     1       0.424   0.505  -1.466  1.00  0.00           H  
HETATM   39  H13 UNL     1       0.219  -1.119   1.100  1.00  0.00           H  
HETATM   40  H14 UNL     1       1.507  -1.472  -0.179  1.00  0.00           H  
HETATM   41  H15 UNL     1      -0.296  -1.578  -1.832  1.00  0.00           H  
HETATM   42  H16 UNL     1      -0.483  -2.852  -0.617  1.00  0.00           H  
HETATM   43  H17 UNL     1      -1.947  -2.192   1.343  1.00  0.00           H  
HETATM   44  H18 UNL     1      -2.311  -0.451   1.332  1.00  0.00           H  
HETATM   45  H19 UNL     1      -4.077  -2.757   0.551  1.00  0.00           H  
HETATM   46  H20 UNL     1      -4.314  -1.386   1.758  1.00  0.00           H  
HETATM   47  H21 UNL     1      -7.896   1.954  -1.511  1.00  0.00           H  
HETATM   48  H22 UNL     1      -8.824   1.998   0.768  1.00  0.00           H  
HETATM   49  H23 UNL     1      -7.706   0.636   2.509  1.00  0.00           H  
HETATM   50  H24 UNL     1      -4.100  -2.078  -1.933  1.00  0.00           H  
HETATM   51  H25 UNL     1      -4.530  -0.336  -2.332  1.00  0.00           H  
HETATM   52  H26 UNL     1      -2.607   0.521  -1.299  1.00  0.00           H  
HETATM   53  H27 UNL     1      -2.096  -0.668  -2.506  1.00  0.00           H  
HETATM   54  H28 UNL     1       5.396   0.810   1.892  1.00  0.00           H  
HETATM   55  H29 UNL     1       5.244  -0.883   1.428  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3    4   26
CONECT    3   30   31   32
CONECT    4    5   33   34
CONECT    5    6    6    7
CONECT    7    8   24
CONECT    8    9   35   36
CONECT    9   10   37   38
CONECT   10   11   39   40
CONECT   11   12   41   42
CONECT   12   13   23
CONECT   13   14   43   44
CONECT   14   15   45   46
CONECT   15   16   22
CONECT   16   17   17   21
CONECT   17   18
CONECT   18   19   19   47
CONECT   19   20   48
CONECT   20   21   21   49
CONECT   22   23   50   51
CONECT   23   52   53
CONECT   24   25   25   26
CONECT   26   54   55
END

HMDB0252698
     RDKit          3D
Gepirone
 55 57  0  0  0  0  0  0  0  0999 V2000
    6.7022    1.5395    0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6436    0.4530   -0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4636   -0.7771   -0.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7748    0.9016   -1.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5603    1.6019   -0.9351 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1710    2.6601   -1.5044 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7852    1.0667    0.1403 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3994    1.3268    0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4419    0.4128   -0.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5153   -1.0270    0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5737   -1.7466   -0.7729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8491   -1.2258   -0.5077 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4517   -1.4044    0.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9296   -1.6802    0.7560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5823   -0.9305   -0.2891 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7203   -0.1404   -0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3308    0.6016   -0.9781 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4026    1.3525   -0.7461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9444    1.4012    0.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3337    0.6466    1.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2428   -0.0988    1.2000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0259   -1.0142   -1.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5766   -0.5872   -1.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4905    0.2551    1.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8713   -0.4324    1.9354 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9791    0.1504    1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4381    1.4346   -0.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2528    1.3386    0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684    2.5408   -0.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7690   -1.5732   -0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1792   -0.4929   -1.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0624   -1.1349    0.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.0045   -1.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3583    1.5432   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1226    2.3685    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1896    1.2585    1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5864    0.7647   -0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237    0.5050   -1.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2194   -1.1194    1.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5074   -1.4722   -0.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2957   -1.5777   -1.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4829   -2.8521   -0.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9474   -2.1915    1.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3113   -0.4511    1.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0769   -2.7572    0.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3143   -1.3859    1.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8960    1.9537   -1.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8242    1.9979    0.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7061    0.6359    2.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1000   -2.0781   -1.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5302   -0.3358   -2.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6066    0.5213   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0958   -0.6684   -2.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3958    0.8096    1.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2441   -0.8828    1.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  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  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15 22  1  0
 22 23  1  0
  7 24  1  0
 24 25  2  0
 24 26  1  0
 26  2  1  0
 23 12  1  0
 21 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 26 54  1  0
 26 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Gepirone monohydrochloride	MeSH
4,4-Dimethyl-1-(4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl)-2,6-piperidinedione	MeSH
BMY-13805gepirone	ChEMBL
Ariza	ChEMBL
ORG-13011variza	ChEMBL

Chemical Formula

C₁₉H₂₉N₅O₂

Average Molecular Weight

359.474

Monoisotopic Molecular Weight

359.232125194

IUPAC Name

4,4-dimethyl-1-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}piperidine-2,6-dione

Traditional Name

gepirone

CAS Registry Number

Not Available

SMILES

CC1(C)CC(=O)N(CCCCN2CCN(CC2)C2=NC=CC=N2)C(=O)C1

InChI Identifier

InChI=1S/C19H29N5O2/c1-19(2)14-16(25)24(17(26)15-19)9-4-3-8-22-10-12-23(13-11-22)18-20-6-5-7-21-18/h5-7H,3-4,8-15H2,1-2H3

InChI Key

QOIGKGMMAGJZNZ-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

N-arylpiperazine
Piperidinedione
Dialkylarylamine
Aminopyrimidine
Delta-lactam
Piperidinone
N-alkylpiperazine
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 nitrogen compound
Amine
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0252698)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.09	ALOGPS
logP	1.35	ChemAxon
logS	-2.5	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	101.49 m³·mol⁻¹	ChemAxon
Polarizability	40.93 Å³	ChemAxon
Number of Rings	3	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
DeepCCS	[M+H]+	188.915	30932474
DeepCCS	[M-H]-	186.461	30932474
DeepCCS	[M-2H]-	220.664	30932474
DeepCCS	[M+Na]+	196.183	30932474
AllCCS	[M+H]+	187.4	32859911
AllCCS	[M+H-H2O]+	184.7	32859911
AllCCS	[M+NH4]+	189.8	32859911
AllCCS	[M+Na]+	190.5	32859911
AllCCS	[M-H]-	185.6	32859911
AllCCS	[M+Na-2H]-	186.2	32859911
AllCCS	[M+HCOO]-	187.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.7543 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.17 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	741.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	158.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	164.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	148.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	66.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	282.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	356.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	359.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	736.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	69.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1161.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	245.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	262.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	355.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	347.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	73.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Gepirone	CC1(C)CC(=O)N(CCCCN2CCN(CC2)C2=NC=CC=N2)C(=O)C1	3064.2	Standard polar	33892256
Gepirone	CC1(C)CC(=O)N(CCCCN2CCN(CC2)C2=NC=CC=N2)C(=O)C1	2949.1	Standard non polar	33892256
Gepirone	CC1(C)CC(=O)N(CCCCN2CCN(CC2)C2=NC=CC=N2)C(=O)C1	2993.1	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 - Gepirone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0m9r-2910000000-65e5547be23e1a515df1	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gepirone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gepirone 10V, Positive-QTOF	splash10-03di-0119000000-de7074794efd4bed7c98	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gepirone 20V, Positive-QTOF	splash10-03di-1849000000-2fbcf6a293e322cce6ea	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gepirone 40V, Positive-QTOF	splash10-0a4l-6910000000-bfc19e3f25371e4a5cbd	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gepirone 10V, Negative-QTOF	splash10-0a4i-0309000000-becf30dc57a0817caa68	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gepirone 20V, Negative-QTOF	splash10-052f-0905000000-8b3c2cc81a46dd57ada9	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gepirone 40V, Negative-QTOF	splash10-0006-4910000000-4b1ae201d3a504fb083c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gepirone 10V, Positive-QTOF	splash10-03di-0029000000-93ace071bda0a59752df	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gepirone 20V, Positive-QTOF	splash10-014i-0093000000-fd70a466fd2ca6d9fac7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gepirone 40V, Positive-QTOF	splash10-00xr-1951000000-fb0dd0ddc57a7ac690eb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gepirone 10V, Negative-QTOF	splash10-0a4i-0009000000-4cc5c8ea4f5e4a9dbb3b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gepirone 20V, Negative-QTOF	splash10-0a4i-0019000000-a60c434ce652cfe0ddbe	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gepirone 40V, Negative-QTOF	splash10-090c-6921000000-af88b3e11a357b1edacc	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB12184

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Gepirone

METLIN ID

Not Available

PubChem Compound

55191

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Gepirone (HMDB0252698)

MOL for HMDB0252698 (Gepirone)

3D MOL for HMDB0252698 (Gepirone)

3D SDF for HMDB0252698 (Gepirone)

3D-SDF for HMDB0252698 (Gepirone)

PDB for HMDB0252698 (Gepirone)

3D PDB for HMDB0252698 (Gepirone)

SMILES for HMDB0252698 (Gepirone)

INCHI for HMDB0252698 (Gepirone)

Structure for HMDB0252698 (Gepirone)

3D Structure for HMDB0252698 (Gepirone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra