Details of the Drug

General Information of Drug (ID: DMFOZ60)

Drug Name
aconitine
Synonyms
aconitine; 302-27-2; CHEBI:2430; Acetylbenzoylaconine; NSC56464; 20-ethyl-3alpha,13,15alpha-trihydroxy-1alpha,6alpha,16beta-trimethoxy-4-(methoxymethyl)aconitane-8,14alpha-diyl 8-acetate 14-benzoate; 16-Ethyl-1alpha,6alpha,19beta-trimethoxy-4-(methoxymethyl)-aconitane-3alpha,8,10alpha,11,18alpha-pentol, 8-acetate 10-benzoate; NCGC00163146-01; CAS-302-27-2; DSSTox_RID_81535; DSSTox_CID_26319; SCHEMBL73323; DSSTox_GSID_46319; GTPL2617; DTXSID4046319; CHEMBL1979562; MolPort-002-527-310; Tox21_112015; NSC-56464; AKOS032428256
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 645.7
Logarithm of the Partition Coefficient (xlogp) 0.3
Rotatable Bond Count (rotbonds) 11
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 12
Chemical Identifiers
Formula
C34H47NO11
IUPAC Name
[(1S,2R,3R,4R,5R,6S,7S,8R,9R,13R,14R,16S,17S,18R)-8-acetyloxy-11-ethyl-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate
Canonical SMILES
CCN1C[C@@]2([C@@H](C[C@@H]([C@@]34[C@@H]2[C@H]([C@@H](C31)[C@@]5([C@@H]6[C@H]4C[C@@]([C@@H]6OC(=O)C7=CC=CC=C7)([C@H]([C@@H]5O)OC)O)OC(=O)C)OC)OC)O)COC
InChI
InChI=1S/C34H47NO11/c1-7-35-15-31(16-41-3)20(37)13-21(42-4)33-19-14-32(40)28(45-30(39)18-11-9-8-10-12-18)22(19)34(46-17(2)36,27(38)29(32)44-6)23(26(33)35)24(43-5)25(31)33/h8-12,19-29,37-38,40H,7,13-16H2,1-6H3/t19-,20-,21+,22-,23+,24+,25-,26?,27+,28-,29+,31+,32-,33+,34-/m1/s1
InChIKey
XFSBVAOIAHNAPC-XTHSEXKGSA-N
Cross-matching ID
PubChem CID
245005
ChEBI ID
CHEMBL2430
CAS Number
302-27-2
TTD ID
D0A1MW
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Voltage-gated sodium channel alpha Nav1.2 (SCN2A) TTLJTUF SCN2A_HUMAN Activator [2]
Voltage-gated sodium channel alpha Nav1.5 (SCN5A) TTZOVE0 SCN5A_HUMAN Activator [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Drug Response [4]
Casein kinase II subunit alpha (CSNK2A1) OT9T8WQM CSK21_HUMAN Gene/Protein Processing [5]
Dynamin-1-like protein (DNM1L) OTXK1Q1G DNM1L_HUMAN Post-Translational Modifications [6]
Dynamin-like 120 kDa protein, mitochondrial (OPA1) OTJGNWPW OPA1_HUMAN Gene/Protein Processing [6]
Mitochondrial fission factor (MFF) OTEVIXOM MFF_HUMAN Post-Translational Modifications [6]
Mitofusin-1 (MFN1) OTCBXQZF MFN1_HUMAN Gene/Protein Processing [6]
Myc proto-oncogene protein (MYC) OTPV5LUK MYC_HUMAN Gene/Protein Processing [5]
Neurogenic locus notch homolog protein 1 (NOTCH1) OTI1WADQ NOTC1_HUMAN Gene/Protein Processing [5]
Nuclear receptor subfamily 1 group I member 2 (NR1I2) OTC5U0N5 NR1I2_HUMAN Gene/Protein Processing [7]
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 (HCN4) OTPH3RRX HCN4_HUMAN Gene/Protein Processing [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2617).
2 Binding of batrachotoxinin A 20-alpha-benzoate to a receptor site associated with sodium channels in synaptic nerve ending particles. J Biol Chem. 1981 Sep 10;256(17):8922-7.
3 Properties of aconitine-modified sodium channels in single cells of mouse ventricular myocardium. Gen Physiol Biophys. 1986 Oct;5(5):473-84.
4 Transcellular transport of aconitine across human intestinal Caco-2 cells. Food Chem Toxicol. 2013 Jul;57:195-200. doi: 10.1016/j.fct.2013.03.033. Epub 2013 Apr 2.
5 Notch1-mediated histone demethylation of HCN4 contributes to aconitine-induced ventricular myocardial dysrhythmia. Toxicol Lett. 2020 Jul 1;327:19-31. doi: 10.1016/j.toxlet.2020.03.017. Epub 2020 Mar 28.
6 Aconitine induces mitochondrial energy metabolism dysfunction through inhibition of AMPK signaling and interference with mitochondrial dynamics in SH-SY5Y cells. Toxicol Lett. 2021 Sep 1;347:36-44. doi: 10.1016/j.toxlet.2021.04.020. Epub 2021 May 1.
7 Human PXR-mediated transcriptional activation of CYP3A4 by 'Fuzi' extracts. Toxicol Mech Methods. 2019 Mar;29(3):155-164.