Dicentrine (CHEM003052)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (2)XML
Record Information
Version1.0
Creation Date2014-08-29 05:07:05 UTC
Update Date2026-04-06 02:08:15 UTC
Accession NumberCHEM003052
Identification
Common NameDicentrine
ClassSmall Molecule
DescriptionDicentrine is an anticancer compound isolated from Lindera, a species of flowering plants.
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Amine
  • Ether
  • Food Toxin
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Dicentrine nitrate, (S)-isomerMeSH
Dicentrine, (R)-isomerMeSH
L-DicentrineMeSH
(R)-(-)-DicentrineMeSH
Chemical FormulaC20H21NO4
Average Molecular Mass339.385 g/mol
Monoisotopic Mass339.147 g/mol
CAS Registry Number517-66-8
IUPAC Name(12S)-16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaene
Traditional Namedicentrine
SMILES[H][C@]12CC3=CC(OC)=C(OC)C=C3C3=C1C(CCN2C)=CC1=C3OCO1
InChI IdentifierInChI=1S/C20H21NO4/c1-21-5-4-11-7-17-20(25-10-24-17)19-13-9-16(23-3)15(22-2)8-12(13)6-14(21)18(11)19/h7-9,14H,4-6,10H2,1-3H3/t14-/m0/s1
InChI KeyYJWBWQWUHVXPNC-AWEZNQCLSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAporphines
Sub ClassNot Available
Direct ParentAporphines
Alternative Parents
Substituents
  • Aporphine
  • Benzoquinoline
  • Phenanthrene
  • Naphthalene
  • Quinoline
  • Tetrahydroisoquinoline
  • Benzodioxole
  • Anisole
  • Aralkylamine
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Acetal
  • Ether
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Amine
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular matrix
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Cell cycleNot Availablemap04110
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.08 g/LALOGPS
logP2.76ALOGPS
logP3.01ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)7.06ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.16 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.72 m³·mol⁻¹ChemAxon
Polarizability37.12 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-a5de239393bfef9da0a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0029000000-4a28487f76316e86c9e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01r6-0090000000-deef7dd6d38cdcc8bc3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-6c8f5b7b70e9a8872976Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0019000000-0cd2b177006f7f79a807Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ki6-1092000000-e04c5d8a83d378fe1767Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityDicentrine was found to be a potent alpha 1-adrenoceptor blocking agent in rat thoracic aorta as revealed by its competitive antagonism of noradrenaline- (pA2 = 8.19 +/- 0.09) or phenylephrine (pA2 = 9.01 +/- 0.10)-induced vasoconstriction. These effects still persisted in denuded aorta. Dicentrine inhibited platelet aggregation and release reaction through the suppression of thromboxane formation and elevation of adenosine 3': S'-cyclic monophosphate. (1) d-Dicentrine significantly inhibits the growth of human hepatoma cell line HuH-7 by delaying its doubling time in tissue culture. An in vitro colony forming assay showed that d-dicentrine decreased the colony formation efficiency in both hepatoma cell lines, HuH-7 and MS-G2. An MTT assay in 21 tumor cell lines also revealed that d-dicentrine was most cytotoxic to esophageal carcinoma HCE-6, lymphoma cell lines Molt-4 and CESS, leukemia cell lines HL60 and K562, and hepatoma cell line MS-G2. (3) Dicentrine is also a selective α1-adrenoceptor antagonist with potent antiarrhythmic and antihypertensive activities. (2)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesDicentrine is an anticancer compound isolated from Lindera, a species of flowering plants.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00025658
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDicentrine
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID101300
Kegg Compound IDC17426
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available