Delphinine (CHEM002415)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (14)XML
Record Information
Version1.0
Creation Date2009-07-23 18:26:05 UTC
Update Date2016-11-09 01:08:46 UTC
Accession NumberCHEM002415
Identification
Common NameDelphinine
ClassSmall Molecule
DescriptionDelphinine is a plant toxin found in species of Larkspur (Delphinium family). It is related in structure and has similar effects to aconitine, acting as an allosteric modulator of voltage gated sodium channels, and producing hypotension, bradycardia and cardiac arrhythmia. It is highly poisonous, but in very small doses it has some uses in herbal medicine. (1)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amine
  • Ester
  • Ether
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC33H45NO9
Average Molecular Mass599.712 g/mol
Monoisotopic Mass599.309 g/mol
CAS Registry Number561-07-9
IUPAC Name(1S,2R,3R,4R,5S,6S,8R,9R,13S,16S,17R,18R)-8-(acetyloxy)-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate
Traditional Namedelphinine
SMILES[H][C@@]12C[C@@]3(O)[C@]([H])(OC(=O)C4=CC=CC=C4)[C@]1([H])[C@@](C[C@]3([H])OC)(OC(C)=O)[C@@]1([H])[C@]([H])(OC)[C@@]3([H])[C@]22C1([H])N(C)C[C@]3(COC)CC[C@]2([H])OC
InChI IdentifierInChI=1S/C33H45NO9/c1-18(35)43-32-15-22(40-5)31(37)14-20(23(32)28(31)42-29(36)19-10-8-7-9-11-19)33-21(39-4)12-13-30(17-38-3)16-34(2)27(33)24(32)25(41-6)26(30)33/h7-11,20-28,37H,12-17H2,1-6H3/t20-,21+,22+,23-,24+,25+,26-,27?,28-,30+,31+,32-,33+/m1/s1
InChI KeyREVYTWNGZDPRKE-UWZYQZSNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentAconitane-type diterpenoid alkaloids
Alternative Parents
Substituents
  • Aconitane-type diterpenoid alkaloid
  • Benzoate ester
  • Quinolidine
  • Benzoic acid or derivatives
  • Alkaloid or derivatives
  • Benzoyl
  • Azepane
  • Monocyclic benzene moiety
  • Benzenoid
  • Piperidine
  • Dicarboxylic acid or derivatives
  • Tertiary alcohol
  • Cyclic alcohol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Plasma Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
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 Solubility0.022 g/LALOGPS
logP2.42ALOGPS
logP1.09ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)12.86ChemAxon
pKa (Strongest Basic)10.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area112.99 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity154.49 m³·mol⁻¹ChemAxon
Polarizability64.07 ųChemAxon
Number of Rings7ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pvi-0200293000-7f08b6cb0ed01432a5f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0500290000-2f9aaf25bcdbf73fb31bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2900410000-37f88cd0b38caf020e9dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1100090000-cd959f2001cb47004777Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pkd-3100190000-ac4e9a53228352171a13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fu-9800470000-08c115ca35cc4064d019Spectrum
Toxicity Profile
Route of ExposureOral (ingestion) (2) ; dermal (2)
Mechanism of ToxicityDelphinine acts as an allosteric modulator of voltage-gated sodium channels. (1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesDelphinine is a plant toxin found in species of Larkspur (Delphinium family). It is highly poisonous, but in very small doses it has some uses in herbal medicine. (1)
Minimum Risk LevelNot Available
Health EffectsDelphinine is cardiotoxic. (1)
SymptomsDelphinine causes hypotension, bradycardia and cardiac arrythmia. (1)
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00001633
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDelphinine
Chemspider IDNot Available
ChEBI ID4384
PubChem Compound ID441726
Kegg Compound IDC08677
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available