<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3119</id>
  <title>T3D3077</title>
  <common-name>Delphinine</common-name>
  <description>Delphinine 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. (L1234)</description>
  <cas>561-07-9</cas>
  <pubchem-id>441726</pubchem-id>
  <chemical-formula>C33H45NO9</chemical-formula>
  <weight>599.7117</weight>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral (ingestion) (L1817) ; dermal (L1817)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Delphinine acts as an allosteric modulator of voltage-gated sodium channels. (L1234)</mechanism-of-toxicity>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Delphinine 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. (L1234)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Delphinine is cardiotoxic. (L1234)</health-effects>
  <symptoms>Delphinine causes hypotension, bradycardia and cardiac arrythmia. (L1234)</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-23T18:26:05Z</created-at>
  <updated-at type="dateTime">2026-04-04T19:30:21Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C08677</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Delphinine</stitch-id>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-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</moldb-smiles>
  <moldb-formula>C33H45NO9</moldb-formula>
  <moldb-inchi>InChI=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</moldb-inchi>
  <moldb-inchikey>REVYTWNGZDPRKE-UWZYQZSNSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">599.7117</moldb-average-mass>
  <moldb-mono-mass type="decimal">599.309432043</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id>390329</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002415</chemdb-id>
  <dsstox-id>DTXSID50971478</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00043291</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>112.99000000000002</moldb-polar-surface-area>
  <moldb-refractivity>154.4871</moldb-refractivity>
  <moldb-polarizability>64.07455082472418</moldb-polarizability>
  <moldb-rotatable-bond-count>10</moldb-rotatable-bond-count>
  <moldb-acceptor-count>8</moldb-acceptor-count>
  <moldb-donor-count>1</moldb-donor-count>
  <moldb-pka-strongest-acidic>12.863595191645889</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>10.198317290800727</moldb-pka-strongest-basic>
  <moldb-physiological-charge>1</moldb-physiological-charge>
  <moldb-number-of-rings>7</moldb-number-of-rings>
  <moldb-alogps-logp>2.42</moldb-alogps-logp>
  <moldb-alogps-logs>-4.44</moldb-alogps-logs>
  <moldb-alogps-solubility>2.18e-02 g/l</moldb-alogps-solubility>
</compound>
