Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 07:13:00 UTC
Update Date2021-09-26 23:01:34 UTC
HMDB IDHMDB0250233
Secondary Accession NumbersNone
Metabolite Identification
Common NameCicletanine
DescriptionCicletanine belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety. It appears to be more potent in salt-sensitive hypertension. Cicletanine is a very strong basic compound (based on its pKa). It can inhibit protein kinase C. Cicletanine is a furopyridine low-ceiling diuretic drug, usually used in the treatment of hypertension. The drug is manufactured by Ipsen and marketed by Recordati (in France) under the trade name Tenstaten. This compound has been identified in human blood as reported by (PMID: 31557052 ). Cicletanine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Cicletanine 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
Thumb
Synonyms
ValueSource
WIN 90ChEMBL
000(+/-)BN-1270cicletanineChEMBL
1,3-dihydro-6-Methyl-7-hydroxy-3-(4-chlorophenyl)furo(3,4-D)pyridineMeSH
JustarMeSH
CicletanideMeSH
Cicletanine hydrochlorideMeSH
TenstatenMeSH
CycletanideMeSH
Chemical FormulaC14H12ClNO2
Average Molecular Weight261.71
Monoisotopic Molecular Weight261.0556563
IUPAC Name3-(4-chlorophenyl)-6-methyl-1H,3H-furo[3,4-c]pyridin-7-ol
Traditional Namecicletanine
CAS Registry NumberNot Available
SMILES
CC1=C(O)C2=C(C=N1)C(OC2)C1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C14H12ClNO2/c1-8-13(17)12-7-18-14(11(12)6-16-8)9-2-4-10(15)5-3-9/h2-6,14,17H,7H2,1H3
InChI KeyCVKNDPRBJVBDSS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentChlorobenzenes
Alternative Parents
Substituents
  • Chlorobenzene
  • Methylpyridine
  • Hydroxypyridine
  • Aryl chloride
  • Aryl halide
  • Pyridine
  • Heteroaromatic compound
  • Dialkyl ether
  • Ether
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.8ALOGPS
logP2.6ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)8.57ChemAxon
pKa (Strongest Basic)5.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area42.35 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity69.68 m³·mol⁻¹ChemAxon
Polarizability26.49 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+160.56130932474
DeepCCS[M-H]-158.16530932474
DeepCCS[M-2H]-191.04930932474
DeepCCS[M+Na]+166.53930932474
AllCCS[M+H]+158.432859911
AllCCS[M+H-H2O]+154.432859911
AllCCS[M+NH4]+162.032859911
AllCCS[M+Na]+163.132859911
AllCCS[M-H]-159.832859911
AllCCS[M+Na-2H]-159.332859911
AllCCS[M+HCOO]-158.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CicletanineCC1=C(O)C2=C(C=N1)C(OC2)C1=CC=C(Cl)C=C13389.5Standard polar33892256
CicletanineCC1=C(O)C2=C(C=N1)C(OC2)C1=CC=C(Cl)C=C12203.2Standard non polar33892256
CicletanineCC1=C(O)C2=C(C=N1)C(OC2)C1=CC=C(Cl)C=C12221.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cicletanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-1930000000-290c32374109fc2d53082017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cicletanine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cicletanine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cicletanine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cicletanine 10V, Positive-QTOFsplash10-03di-0090000000-c2d8d50795734a82381b2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cicletanine 20V, Positive-QTOFsplash10-03di-0290000000-104c0008092324ad89f12017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cicletanine 40V, Positive-QTOFsplash10-00e9-7920000000-facfbaf27f3d6f5909462017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cicletanine 10V, Negative-QTOFsplash10-03di-0090000000-d52d8a345408bd8105662017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cicletanine 20V, Negative-QTOFsplash10-03di-0190000000-dda1f0abe3b349f45a282017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cicletanine 40V, Negative-QTOFsplash10-01po-5790000000-02fe05eeeef14de152f82017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cicletanine 10V, Positive-QTOFsplash10-03di-0090000000-e39fd00356e03fbb0a5c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cicletanine 20V, Positive-QTOFsplash10-03di-0290000000-7d4f43604ba3feb03c252021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cicletanine 40V, Positive-QTOFsplash10-0570-1930000000-f30eb525034fc1cf23dc2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cicletanine 10V, Negative-QTOFsplash10-03di-0090000000-5cbce30d17a0d1c5c9b92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cicletanine 20V, Negative-QTOFsplash10-01q9-0190000000-1dda8c1d2860783d740c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cicletanine 40V, Negative-QTOFsplash10-001i-7960000000-282cbb9a75503fe9519c2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12766
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCicletanine
METLIN IDNot Available
PubChem Compound54910
PDB IDNot Available
ChEBI IDNot Available
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 References
  1. 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 ]