You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2018-05-20 20:14:43 UTC
HMDB IDHMDB0015114
Secondary Accession Numbers
  • HMDB15114
Metabolite Identification
Common NameCyclopentolate
DescriptionCyclopentolate is only found in individuals that have used or taken this drug. It is a parasympatholytic anticholinergic used solely to obtain mydriasis or cycloplegia. [PubChem]By blocking muscarinic receptors, cyclopentolate produces dilatation of the pupil (mydriasis) and prevents the eye from accommodating for near vision (cycloplegia).
Structure
Thumb
Synonyms
ValueSource
(+-)-CyclopentolateChEBI
1-Hydroxy-alpha-phenylcyclopentaneacetic acid 2-(dimethylamino)ethyl esterChEBI
2-(dimethylamino)Ethyl 1-hydroxy-alpha-phenylcyclopentaneacetateChEBI
2-(dimethylamino)Ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetateChEBI
2-Phenyl-2-(1-hydroxycyclopentyl)ethanoic acid beta-(dimethylamino)ethyl esterChEBI
alpha-(1-Hydroxycyclopentyl)benzeneacetic acid 2-(dimethylamino)ethyl esterChEBI
beta-(dimethylamino)Ethyl (1-hydroxycyclopentyl)phenylacetateChEBI
beta-Dimethylaminoethyl (1-hydroxycyclopentyl)phenylacetateChEBI
CiclopentolatoChEBI
CyclopentolatumChEBI
(+-)-Cyclopentolic acidGenerator
Cyclopentolic acidGenerator
1-Hydroxy-a-phenylcyclopentaneacetate 2-(dimethylamino)ethyl esterGenerator
1-Hydroxy-a-phenylcyclopentaneacetic acid 2-(dimethylamino)ethyl esterGenerator
1-Hydroxy-alpha-phenylcyclopentaneacetate 2-(dimethylamino)ethyl esterGenerator
1-Hydroxy-α-phenylcyclopentaneacetate 2-(dimethylamino)ethyl esterGenerator
1-Hydroxy-α-phenylcyclopentaneacetic acid 2-(dimethylamino)ethyl esterGenerator
2-(dimethylamino)Ethyl 1-hydroxy-a-phenylcyclopentaneacetateGenerator
2-(dimethylamino)Ethyl 1-hydroxy-a-phenylcyclopentaneacetic acidGenerator
2-(dimethylamino)Ethyl 1-hydroxy-alpha-phenylcyclopentaneacetic acidGenerator
2-(dimethylamino)Ethyl 1-hydroxy-α-phenylcyclopentaneacetateGenerator
2-(dimethylamino)Ethyl 1-hydroxy-α-phenylcyclopentaneacetic acidGenerator
2-(dimethylamino)Ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetic acidGenerator
2-Phenyl-2-(1-hydroxycyclopentyl)ethanoate b-(dimethylamino)ethyl esterGenerator
2-Phenyl-2-(1-hydroxycyclopentyl)ethanoate beta-(dimethylamino)ethyl esterGenerator
2-Phenyl-2-(1-hydroxycyclopentyl)ethanoate β-(dimethylamino)ethyl esterGenerator
2-Phenyl-2-(1-hydroxycyclopentyl)ethanoic acid b-(dimethylamino)ethyl esterGenerator
2-Phenyl-2-(1-hydroxycyclopentyl)ethanoic acid β-(dimethylamino)ethyl esterGenerator
a-(1-Hydroxycyclopentyl)benzeneacetate 2-(dimethylamino)ethyl esterGenerator
a-(1-Hydroxycyclopentyl)benzeneacetic acid 2-(dimethylamino)ethyl esterGenerator
alpha-(1-Hydroxycyclopentyl)benzeneacetate 2-(dimethylamino)ethyl esterGenerator
α-(1-hydroxycyclopentyl)benzeneacetate 2-(dimethylamino)ethyl esterGenerator
α-(1-hydroxycyclopentyl)benzeneacetic acid 2-(dimethylamino)ethyl esterGenerator
b-(dimethylamino)Ethyl (1-hydroxycyclopentyl)phenylacetateGenerator
b-(dimethylamino)Ethyl (1-hydroxycyclopentyl)phenylacetic acidGenerator
beta-(dimethylamino)Ethyl (1-hydroxycyclopentyl)phenylacetic acidGenerator
β-(dimethylamino)ethyl (1-hydroxycyclopentyl)phenylacetateGenerator
β-(dimethylamino)ethyl (1-hydroxycyclopentyl)phenylacetic acidGenerator
b-Dimethylaminoethyl (1-hydroxycyclopentyl)phenylacetateGenerator
b-Dimethylaminoethyl (1-hydroxycyclopentyl)phenylacetic acidGenerator
beta-Dimethylaminoethyl (1-hydroxycyclopentyl)phenylacetic acidGenerator
β-dimethylaminoethyl (1-hydroxycyclopentyl)phenylacetateGenerator
β-dimethylaminoethyl (1-hydroxycyclopentyl)phenylacetic acidGenerator
CyclopentoiateHMDB
CyclopentylateHMDB
DiopentolateHMDB
CyclogylMeSH
Chemical FormulaC17H25NO3
Average Molecular Weight291.3853
Monoisotopic Molecular Weight291.183443671
IUPAC Name2-(dimethylamino)ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetate
Traditional Namecyclopentolate
CAS Registry Number512-15-2
SMILES
CN(C)CCOC(=O)C(C1=CC=CC=C1)C1(O)CCCC1
InChI Identifier
InChI=1S/C17H25NO3/c1-18(2)12-13-21-16(19)15(14-8-4-3-5-9-14)17(20)10-6-7-11-17/h3-5,8-9,15,20H,6-7,10-13H2,1-2H3
InChI KeySKYSRIRYMSLOIN-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Cyclopentanol
  • Cyclic alcohol
  • Tertiary alcohol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point139 °C (hydrochloride salt)Not Available
Boiling PointNot AvailableNot Available
Water Solubility1.5 g/LNot Available
LogP2.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.5 g/LALOGPS
logP2.09ALOGPS
logP2.32ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)14.19ChemAxon
pKa (Strongest Basic)8.42ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.77 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity82.81 m³·mol⁻¹ChemAxon
Polarizability32.51 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-0f0d4362f3985858a9e0View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-0f0d4362f3985858a9e0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9310000000-1b840cdae4d0a8b51c1cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4j-9160000000-9def24a4ea67412da486View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-5290000000-7db0b218f03ba755d12cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9240000000-de729816cbf8bd6c1f4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rl-9200000000-f9603efdb4791c613d6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-2190000000-a63273dff0bd060cba13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-7980000000-2381615fef81f1f71dd9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004r-9200000000-4ae6271cc9d0bc0f9449View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00979 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00979 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00979
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2802
KEGG Compound IDC06932
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCyclopentolate
METLIN IDNot Available
PubChem Compound2905
PDB IDNot Available
ChEBI ID4024
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. MedlinePlus [Link]

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575
References
  1. Demayo AP, Reidenberg MM: Grand mal seizure in a child 30 minutes after Cyclogyl (cyclopentolate hydrochloride) and 10% Neo-Synephrine (phenylephrine hydrochloride) eye drops were instilled. Pediatrics. 2004 May;113(5):e499-500. [PubMed:15121994 ]
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 ]