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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:48 UTC
HMDB IDHMDB0014942
Secondary Accession Numbers
  • HMDB14942
Metabolite Identification
Common NameDicyclomine
DescriptionDicyclomine is only found in individuals that have used or taken this drug. It is a muscarinic antagonist used as an antispasmodic and in urinary incontinence. It has little effect on glandular secretion or the cardiovascular system. It does have some local anesthetic properties and is used in gastrointestinal, biliary, and urinary tract spasms. [PubChem]Action is achieved via a dual mechanism: (1) a specific anticholinergic effect (antimuscarinic) at the acetylcholine-receptor sites and (2) a direct effect upon smooth muscle (musculotropic).
Structure
Data?1582753238
Synonyms
ValueSource
2-(Diethylamino)ethyl 1-cyclohexylcyclohexanecarboxylateChEBI
Bicyclohexyl-1-carboxylic acid 2-diethylamino-ethyl esterChEBI
DicicloverinaChEBI
DicycloverinChEBI
DicycloverineChEBI
DicycloverinumChEBI
DicymineKegg
2-(Diethylamino)ethyl 1-cyclohexylcyclohexanecarboxylic acidGenerator
Bicyclohexyl-1-carboxylate 2-diethylamino-ethyl esterGenerator
Atlantis brand OF dicyclomine hydrochlorideHMDB
Di cyclonexHMDB
Di spazHMDB
Di-cyclonexHMDB
DiclominHMDB
Dicyclomine hydrochlorideHMDB
BentylHMDB
BentylolHMDB
Di-spazHMDB
DibentHMDB
Hauck brand OF dicyclomine hydrochlorideHMDB
Hydrochloride, dicyclomineHMDB
Pasadena brand OF dicyclomine hydrochlorideHMDB
Aventis brand OF dicyclomine hydrochlorideHMDB
Florizel brand OF dicyclomine hydrochlorideHMDB
Hoechst brand OF dicyclomine hydrochlorideHMDB
LomineHMDB
MerbentylHMDB
Ortega brand OF dicyclomine hydrochlorideHMDB
Riva brand OF dicyclomine hydrochlorideHMDB
SpascolHMDB
Vangard brand OF dicyclomine hydrochlorideHMDB
Vortech brand OF dicyclomine hydrochlorideHMDB
Aventis behring brand OF dicyclomine hydrochlorideHMDB
OR tylHMDB
OR-tylHMDB
Sigma brand OF dicyclomine hydrochlorideHMDB
Chemical FormulaC19H35NO2
Average Molecular Weight309.4867
Monoisotopic Molecular Weight309.266779369
IUPAC Name2-(diethylamino)ethyl 1-cyclohexylcyclohexane-1-carboxylate
Traditional Namebentyl
CAS Registry Number77-19-0
SMILES
CCN(CC)CCOC(=O)C1(CCCCC1)C1CCCCC1
InChI Identifier
InChI=1S/C19H35NO2/c1-3-20(4-2)15-16-22-18(21)19(13-9-6-10-14-19)17-11-7-5-8-12-17/h17H,3-16H2,1-2H3
InChI KeyCURUTKGFNZGFSE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentCarboxylic acid esters
Alternative Parents
Substituents
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Amino acid or derivatives
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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 Solubility0.0033 g/LNot Available
LogP5.5Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available179.123http://allccs.zhulab.cn/database/detail?ID=AllCCS00001287
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0033 g/LALOGPS
logP5.82ALOGPS
logP4.93ChemAxon
logS-5ALOGPS
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity91.78 m³·mol⁻¹ChemAxon
Polarizability37.39 ųChemAxon
Number of Rings2ChemAxon
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]+175.26431661259
DarkChem[M-H]-168.34331661259
DeepCCS[M+H]+177.37930932474
DeepCCS[M-H]-175.02130932474
DeepCCS[M-2H]-208.13330932474
DeepCCS[M+Na]+183.47230932474
AllCCS[M+H]+178.332859911
AllCCS[M+H-H2O]+175.432859911
AllCCS[M+NH4]+180.932859911
AllCCS[M+Na]+181.732859911
AllCCS[M-H]-179.932859911
AllCCS[M+Na-2H]-180.832859911
AllCCS[M+HCOO]-181.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DicyclomineCCN(CC)CCOC(=O)C1(CCCCC1)C1CCCCC12474.8Standard polar33892256
DicyclomineCCN(CC)CCOC(=O)C1(CCCCC1)C1CCCCC12137.2Standard non polar33892256
DicyclomineCCN(CC)CCOC(=O)C1(CCCCC1)C1CCCCC12157.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dicyclomine GC-MS (Non-derivatized) - 70eV, Positivesplash10-05n0-9310000000-5c2288f0a906568b62f82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dicyclomine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Dicyclomine LC-ESI-qTof , Positive-QTOFsplash10-03di-0109000000-67a7b4058325a5b3b7b52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dicyclomine , positive-QTOFsplash10-03di-0109000000-67a7b4058325a5b3b7b52017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dicyclomine 10V, Positive-QTOFsplash10-0ik9-2927000000-d964d2634a4237e50ae22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dicyclomine 20V, Positive-QTOFsplash10-0udi-4921000000-656082e53fe18900baf72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dicyclomine 40V, Positive-QTOFsplash10-0udl-9610000000-44f8f338bbb1297652372016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dicyclomine 10V, Negative-QTOFsplash10-0a4i-3349000000-be955b3e233bfdfb7dd12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dicyclomine 20V, Negative-QTOFsplash10-0a4i-6955000000-ffd091e5dc7db72c04992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dicyclomine 40V, Negative-QTOFsplash10-00si-9510000000-917072813308870a80db2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dicyclomine 10V, Positive-QTOFsplash10-03di-0009000000-f12ce219dd71dbe073652021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dicyclomine 20V, Positive-QTOFsplash10-03yi-7927000000-b4463d53448be3397da42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dicyclomine 40V, Positive-QTOFsplash10-001i-9500000000-4ac1bf2578d6bdc29b332021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dicyclomine 10V, Negative-QTOFsplash10-0a4i-0196000000-f14b98485885ad0ed6af2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dicyclomine 20V, Negative-QTOFsplash10-0a4i-0090000000-a3ed7511586051eaaff72021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dicyclomine 40V, Negative-QTOFsplash10-0cfr-1920000000-054220e523266e73b6fd2021-10-11Wishart 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 DB00804 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00804 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00804
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2934
KEGG Compound IDC06951
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDicyclomine
METLIN IDNot Available
PubChem Compound3042
PDB IDNot Available
ChEBI ID4514
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 monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular weight:
58164.815
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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. Jin CH, Shin EJ, Park JB, Jang CG, Li Z, Kim MS, Koo KH, Yoon HJ, Park SJ, Choi WC, Yamada K, Nabeshima T, Kim HC: Fustin flavonoid attenuates beta-amyloid (1-42)-induced learning impairment. J Neurosci Res. 2009 Dec;87(16):3658-70. doi: 10.1002/jnr.22159. [PubMed:19533734 ]
  4. 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:
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. Pavia J, Munoz M, Jimenez E, Martos F, Gonzalez-Correa JA, De la Cruz JP, Garcia V, Sanchez de la Cuesta F: Pharmacological characterization and distribution of muscarinic receptors in human placental syncytiotrophoblast brush-border and basal plasma membranes. Eur J Pharmacol. 1997 Feb 12;320(2-3):209-14. [PubMed:9059856 ]