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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:51 UTC
HMDB IDHMDB0015077
Secondary Accession Numbers
  • HMDB15077
Metabolite Identification
Common NameCycrimine
DescriptionCycrimine is only found in individuals that have used or taken this drug. It is a drug used to reduce levels of acetylcholine to return a balance with dopamine in the treatment and management of Parkinson's disease. Cycrimine binds the muscarinic acetylcholine receptor M1, effectively inhibiting acetylcholine. This decrease in acetylcholine restores the normal dopamine-acetylcholine balance and relieves the symptoms of Parkinson's disease.
Structure
Data?1582753256
Synonyms
ValueSource
(+-)-CycrimineChEBI
alpha-Cyclopentyl-alpha-phenyl-1-piperidinepropanolChEBI
CicriminaChEBI
CycriminumChEBI
a-Cyclopentyl-a-phenyl-1-piperidinepropanolGenerator
Α-cyclopentyl-α-phenyl-1-piperidinepropanolGenerator
Cycrimine hydrochlorideHMDB
Chemical FormulaC19H29NO
Average Molecular Weight287.4397
Monoisotopic Molecular Weight287.224914555
IUPAC Name1-cyclopentyl-1-phenyl-3-(piperidin-1-yl)propan-1-ol
Traditional Namecycrimine
CAS Registry Number77-39-4
SMILES
OC(CCN1CCCCC1)(C1CCCC1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C19H29NO/c21-19(18-11-5-6-12-18,17-9-3-1-4-10-17)13-16-20-14-7-2-8-15-20/h1,3-4,9-10,18,21H,2,5-8,11-16H2
InChI KeySWRUZBWLEWHWRI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Monocyclic benzene moiety
  • Piperidine
  • Benzenoid
  • 1,3-aminoalcohol
  • Tertiary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organopnictogen compound
  • Aromatic alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility0.0091 g/LNot Available
LogP4Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0091 g/LALOGPS
logP4.15ALOGPS
logP3.79ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)13.84ChemAxon
pKa (Strongest Basic)9.32ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity88.6 m³·mol⁻¹ChemAxon
Polarizability34.78 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+165.88531661259
DarkChem[M-H]-163.07231661259
DeepCCS[M+H]+169.36530932474
DeepCCS[M-H]-167.00730932474
DeepCCS[M-2H]-199.89330932474
DeepCCS[M+Na]+175.45830932474
AllCCS[M+H]+171.832859911
AllCCS[M+H-H2O]+168.532859911
AllCCS[M+NH4]+174.832859911
AllCCS[M+Na]+175.732859911
AllCCS[M-H]-175.632859911
AllCCS[M+Na-2H]-175.832859911
AllCCS[M+HCOO]-176.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CycrimineOC(CCN1CCCCC1)(C1CCCC1)C1=CC=CC=C12502.4Standard polar33892256
CycrimineOC(CCN1CCCCC1)(C1CCCC1)C1=CC=CC=C12257.4Standard non polar33892256
CycrimineOC(CCN1CCCCC1)(C1CCCC1)C1=CC=CC=C12144.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cycrimine,1TMS,isomer #1C[Si](C)(C)OC(CCN1CCCCC1)(C1=CC=CC=C1)C1CCCC12294.9Semi standard non polar33892256
Cycrimine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(CCN1CCCCC1)(C1=CC=CC=C1)C1CCCC12527.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Cycrimine EI-B (Non-derivatized)splash10-0002-9000000000-43de7e4a24aa5556ad342017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cycrimine EI-B (Non-derivatized)splash10-0002-9000000000-43de7e4a24aa5556ad342018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cycrimine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ar1-9510000000-c092b5633c47762a06b72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cycrimine GC-MS (1 TMS) - 70eV, Positivesplash10-0095-9271000000-5eb5d8c1f3ea4beb52992017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cycrimine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cycrimine 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 - Cycrimine 10V, Positive-QTOFsplash10-00dr-0090000000-6f9526fe0f5d15d4532c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycrimine 20V, Positive-QTOFsplash10-0002-9240000000-299a379cecf027b96a432016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycrimine 40V, Positive-QTOFsplash10-05n4-9210000000-8dcfbc83609e96cd4b442016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycrimine 10V, Negative-QTOFsplash10-000i-0090000000-70c4a8394979876bee682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycrimine 20V, Negative-QTOFsplash10-00li-9280000000-fd557ec32c0107d272fb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycrimine 40V, Negative-QTOFsplash10-001i-9000000000-c9485c23a7ff0c78f6cf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycrimine 10V, Positive-QTOFsplash10-000i-2090000000-41ed81b26270a2b2ddb92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycrimine 20V, Positive-QTOFsplash10-000b-9170000000-c08538a237f0719b3b552021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycrimine 40V, Positive-QTOFsplash10-0002-9130000000-1a7b3611422cd43b31642021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycrimine 10V, Negative-QTOFsplash10-000i-0090000000-8ae387832bf542033b122021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycrimine 20V, Negative-QTOFsplash10-000i-0290000000-1e884590e7d00f776caf2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycrimine 40V, Negative-QTOFsplash10-001i-0190000000-9804f84996694e2cfc362021-10-11Wishart 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 DB00942 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00942 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00942
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2808
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCycrimine
METLIN IDNot Available
PubChem Compound2911
PDB IDNot Available
ChEBI ID59692
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. Vedasiromoni JR, Ganguly DK: Cycrimine on rat diaphragm. Arch Int Pharmacodyn Ther. 1976 Jan;219(1):64-9. [PubMed:1267542 ]

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. Vedasiromoni JR, Ganguly DK: Cycrimine on rat diaphragm. Arch Int Pharmacodyn Ther. 1976 Jan;219(1):64-9. [PubMed:1267542 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]