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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2021-09-14 14:57:38 UTC
HMDB IDHMDB0015555
Secondary Accession Numbers
  • HMDB15555
Metabolite Identification
Common NameMolindone
DescriptionAn indole derivative effective in schizophrenia and other psychoses and possibly useful in the treatment of the aggressive type of undersocialized conduct disorder. Molindone has much lower affinity for D2 receptors than most antipsychotic agents and has a relatively low affinity for D1 receptors. It has only low to moderate affinity for cholinergic and alpha-adrenergic receptors. Some electrophysiologic data from animals indicate that molindone has certain characteristics that resemble those of clozapine. (From AMA Drug Evaluations Annual, 1994, p283)
Structure
Data?1582753310
Synonyms
ValueSource
MobanHMDB
(+-)-MolindoneHMDB
endo Brand OF molindone hydrochlorideHMDB
Molindone hydrochlorideHMDB
Hydrochloride, molindoneHMDB
Molindone monohydrochlorideHMDB
Monohydrochloride, molindoneHMDB
Chemical FormulaC16H24N2O2
Average Molecular Weight276.374
Monoisotopic Molecular Weight276.183778022
IUPAC Name3-ethyl-2-methyl-5-(morpholin-4-ylmethyl)-4,5,6,7-tetrahydro-1H-indol-4-one
Traditional Namemolindone
CAS Registry Number7416-34-4
SMILES
CCC1=C(C)NC2=C1C(=O)C(CN1CCOCC1)CC2
InChI Identifier
InChI=1S/C16H24N2O2/c1-3-13-11(2)17-14-5-4-12(16(19)15(13)14)10-18-6-8-20-9-7-18/h12,17H,3-10H2,1-2H3
InChI KeyKLPWJLBORRMFGK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassNot Available
Direct ParentIndoles and derivatives
Alternative Parents
Substituents
  • Indole or derivatives
  • Aryl ketone
  • Aryl alkyl ketone
  • Aralkylamine
  • Morpholine
  • Oxazinane
  • Substituted pyrrole
  • Pyrrole
  • Heteroaromatic compound
  • Vinylogous amide
  • Ketone
  • Tertiary amine
  • Tertiary aliphatic amine
  • Ether
  • Dialkyl ether
  • Oxacycle
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point180.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.47 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.47 g/LALOGPS
logP2.09ALOGPS
logP2.04ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)15.34ChemAxon
pKa (Strongest Basic)6.65ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area45.33 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity81.06 m³·mol⁻¹ChemAxon
Polarizability32 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-7690000000-39a1949956d6f84592742017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0390000000-0fad419a5a8589ce686f2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0940000000-744eb27b9ac46d4750e82016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kml-6900000000-abd5f6ed2234c68e0ad22016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1090000000-f34c3352e69ca4aeb8c52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-3290000000-8f53dde449874fc02c8a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052o-9210000000-ae67eeb7ca5afa4f6bcc2016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-001j-7690000000-39a1949956d6f84592742021-09-05View Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01618 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01618 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01618
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID22342
KEGG Compound IDC07230
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMolindone
METLIN IDNot Available
PubChem Compound23897
PDB IDNot Available
ChEBI ID103799
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  2. Seeman P, Tallerico T: Antipsychotic drugs which elicit little or no parkinsonism bind more loosely than dopamine to brain D2 receptors, yet occupy high levels of these receptors. Mol Psychiatry. 1998 Mar;3(2):123-34. [PubMed:9577836 ]
  3. Lidow MS, Goldman-Rakic PS: Differential regulation of D2 and D4 dopamine receptor mRNAs in the primate cerebral cortex vs. neostriatum: effects of chronic treatment with typical and atypical antipsychotic drugs. J Pharmacol Exp Ther. 1997 Nov;283(2):939-46. [PubMed:9353417 ]
  4. Froimowitz M, Cody V: The incorporation of butyrophenones and related compounds into a pharmacophore for dopamine D2 antagonists. Drug Des Discov. 1997 Aug;15(2):63-81. [PubMed:9342550 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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
  1. Nguyen TV, Juorio AV: Down-regulation of tryptamine binding sites following chronic molindone administration. A comparison with responses of dopamine and 5-hydroxytryptamine receptors. Naunyn Schmiedebergs Arch Pharmacol. 1989 Oct;340(4):366-71. [PubMed:2586632 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular weight:
52602.6
References
  1. Nguyen TV, Juorio AV: Down-regulation of tryptamine binding sites following chronic molindone administration. A comparison with responses of dopamine and 5-hydroxytryptamine receptors. Naunyn Schmiedebergs Arch Pharmacol. 1989 Oct;340(4):366-71. [PubMed:2586632 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular weight:
51420.4
References
  1. Neeper R, Richelson E, Nelson A: Neuroleptic binding to muscarinic M2 receptors of normal human heart in vitro and comparison with binding to M1 and dopamine D2 receptors of brain. Neuropharmacology. 1991 May;30(5):527-9. [PubMed:1678146 ]