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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:55 UTC
HMDB IDHMDB0015279
Secondary Accession Numbers
  • HMDB15279
Metabolite Identification
Common NameFlavoxate
DescriptionFlavoxate, also known as flavoxatum or bladuril, belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Flavoxate is a drug which is used for symptomatic relief of dysuria, urgency, nocturia, suprapubic pain, frequency and incontinence as may occur in cystitis, prostatitis, urethritis, urethrocystitis/urethrotrigonitis. Flavoxate is a very strong basic compound (based on its pKa). A carboxylic ester resulting from the formal condensation of 3-methylflavone-8-carboxylic acid with 2-(1-piperidinyl)ethanol.
Structure
Data?1582753278
Synonyms
ValueSource
2-(1-Piperidinyl)ethyl 3-methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylateChEBI
2-Piperidinoethyl 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylateChEBI
2-Piperidinoethyl 3-methylflavone-8-carboxylateChEBI
beta-Piperidinoethyl 3-methylflavone-8-carboxylateChEBI
FlavoxatoChEBI
FlavoxatumChEBI
BladurilKegg
2-(1-Piperidinyl)ethyl 3-methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylic acidGenerator
2-Piperidinoethyl 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylic acidGenerator
2-Piperidinoethyl 3-methylflavone-8-carboxylic acidGenerator
b-Piperidinoethyl 3-methylflavone-8-carboxylateGenerator
b-Piperidinoethyl 3-methylflavone-8-carboxylic acidGenerator
beta-Piperidinoethyl 3-methylflavone-8-carboxylic acidGenerator
Β-piperidinoethyl 3-methylflavone-8-carboxylateGenerator
Β-piperidinoethyl 3-methylflavone-8-carboxylic acidGenerator
Flavoxic acidGenerator
Flavoxate hciHMDB
Ortho brand OF flavoxate hydrochlorideHMDB
UronidHMDB
Byk brand OF flavoxate hydrochlorideHMDB
Hydrochloride, flavoxateHMDB
Shire brand OF flavoxate hydrochlorideHMDB
Flavoxate hydrochlorideHMDB
Pierre fabre brand OF flavoxate hydrochlorideHMDB
Recordati brand OF flavoxate hydrochlorideHMDB
Cahill may roberts brand OF flavoxate hydrochlorideHMDB
Hoechst brand OF flavoxate hydrochlorideHMDB
Negma brand OF flavoxate hydrochlorideHMDB
SpasuretHMDB
UrispasHMDB
Chemical FormulaC24H25NO4
Average Molecular Weight391.4596
Monoisotopic Molecular Weight391.178358293
IUPAC Name2-(piperidin-1-yl)ethyl 3-methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylate
Traditional Nameflavoxate
CAS Registry Number15301-69-6
SMILES
CC1=C(OC2=C(C=CC=C2C(=O)OCCN2CCCCC2)C1=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C24H25NO4/c1-17-21(26)19-11-8-12-20(23(19)29-22(17)18-9-4-2-5-10-18)24(27)28-16-15-25-13-6-3-7-14-25/h2,4-5,8-12H,3,6-7,13-16H2,1H3
InChI KeySPIUTQOUKAMGCX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavones
Alternative Parents
Substituents
  • Flavone
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Pyranone
  • Monocyclic benzene moiety
  • Piperidine
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.015 g/LNot Available
LogP4.4Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.015 g/LALOGPS
logP3.65ALOGPS
logP4.24ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)7.29ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area55.84 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity113.51 m³·mol⁻¹ChemAxon
Polarizability43.39 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+189.99631661259
DarkChem[M-H]-188.13531661259
DeepCCS[M+H]+193.79930932474
DeepCCS[M-H]-191.44130932474
DeepCCS[M-2H]-225.56830932474
DeepCCS[M+Na]+200.79530932474
AllCCS[M+H]+195.732859911
AllCCS[M+H-H2O]+192.932859911
AllCCS[M+NH4]+198.232859911
AllCCS[M+Na]+199.032859911
AllCCS[M-H]-198.232859911
AllCCS[M+Na-2H]-198.432859911
AllCCS[M+HCOO]-198.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FlavoxateCC1=C(OC2=C(C=CC=C2C(=O)OCCN2CCCCC2)C1=O)C1=CC=CC=C14048.1Standard polar33892256
FlavoxateCC1=C(OC2=C(C=CC=C2C(=O)OCCN2CCCCC2)C1=O)C1=CC=CC=C13218.0Standard non polar33892256
FlavoxateCC1=C(OC2=C(C=CC=C2C(=O)OCCN2CCCCC2)C1=O)C1=CC=CC=C13517.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Flavoxate GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-9440000000-61df15b695a5a5f45ed32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Flavoxate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flavoxate 10V, Positive-QTOFsplash10-01ox-0549000000-120f63489486931b7e072016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flavoxate 20V, Positive-QTOFsplash10-03di-4985000000-83a666ed139f08bcbd882016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flavoxate 40V, Positive-QTOFsplash10-03du-9450000000-333e34520b27539a7dcb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flavoxate 10V, Negative-QTOFsplash10-0006-1279000000-07e90c379f3e210717a42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flavoxate 20V, Negative-QTOFsplash10-01pc-2194000000-713502a72cb4510c7e7e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flavoxate 40V, Negative-QTOFsplash10-001r-3490000000-d5de9d93a88df6343e692016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flavoxate 10V, Positive-QTOFsplash10-0006-0009000000-49ec7d7143d3c8cee3112021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flavoxate 20V, Positive-QTOFsplash10-0006-0009000000-49ec7d7143d3c8cee3112021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flavoxate 40V, Positive-QTOFsplash10-004l-0296000000-84da93dec3b4b52ebb1b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flavoxate 10V, Negative-QTOFsplash10-0006-0009000000-c5072b6146dc45950f0b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flavoxate 20V, Negative-QTOFsplash10-0006-0009000000-c5072b6146dc45950f0b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flavoxate 40V, Negative-QTOFsplash10-0ab9-0943000000-b898a47804be8af4d58c2021-10-11Wishart LabView 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 DB01148 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01148 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01148
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3237
KEGG Compound IDC07809
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFlavoxate
METLIN IDNot Available
PubChem Compound3354
PDB IDNot Available
ChEBI ID5088
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. 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 ]
  3. Abbiati GA, Ceserani R, Nardi D, Pietra C, Testa R: Receptor binding studies of the flavone, REC 15/2053, and other bladder spasmolytics. Pharm Res. 1988 Jul;5(7):430-3. [PubMed:3247311 ]
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 adenylate cyclase inhibition
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular weight:
51714.6
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. 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 ]
  3. Greco KA, McVary KT: The role of combination medical therapy in benign prostatic hyperplasia. Int J Impot Res. 2008 Dec;20 Suppl 3:S33-43. doi: 10.1038/ijir.2008.51. [PubMed:19002123 ]
  4. Uckert S, Stief CG, Odenthal KP, Truss MC, Lietz B, Jonas U: Responses of isolated normal human detrusor muscle to various spasmolytic drugs commonly used in the treatment of the overactive bladder. Arzneimittelforschung. 2000 May;50(5):456-60. [PubMed:10858873 ]
  5. Abbiati GA, Ceserani R, Nardi D, Pietra C, Testa R: Receptor binding studies of the flavone, REC 15/2053, and other bladder spasmolytics. Pharm Res. 1988 Jul;5(7):430-3. [PubMed:3247311 ]