BENZOYLACONINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H45NO10
Molecular Weight	603.7004
Optical Activity	UNSPECIFIED
Defined Stereocenters	15 / 15
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12[C@H]3C[C@@](O)([C@@H]1OC(=O)C4=CC=CC=C4)[C@@H](OC)[C@H](O)[C@]2(O)[C@H]5[C@H](OC)[C@@]6([H])[C@]37C5N(CC)C[C@]6(COC)[C@H](O)C[C@@H]7OC

InChI

InChIKey=DHJXZSFKLJCHLH-BMTFSNIDSA-N

InChI=1S/C32H45NO10/c1-6-33-14-29(15-39-2)18(34)12-19(40-3)31-17-13-30(37)26(43-28(36)16-10-8-7-9-11-16)20(17)32(38,25(35)27(30)42-5)21(24(31)33)22(41-4)23(29)31/h7-11,17-27,34-35,37-38H,6,12-15H2,1-5H3/t17-,18-,19+,20-,21+,22+,23-,24-,25+,26-,27+,29+,30-,31+,32-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C32H45NO10
Molecular Weight	603.7004
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	12 / 15
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27761113 | https://www.ncbi.nlm.nih.gov/pubmed/27139035
Curator's Comment: Description was created based on several sources, including https://www.medchemexpress.com/DataSheet/Benzoylaconine.html

Benzoylaconine (Isaconitine; Pikraconitin) is an alkaloid in the Chinese traditional medicine Radix Aconiti Lateralis Preparata (Fuzi). Benzoylaconine is a metabolite of aconitine. Benzoylaconine increased P-gp expression in LS174T and Caco-2 cells, it also increased the P-gp transport activity. Benzoylaconine has being shown to stimulate dynorphin A expression in cultured primary spinal microglia.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
P-glycoprotein 1 54 Target ID: CHEMBL4302 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27139035	Activator 1430
Proenkephalin B 1 Target ID: CHEMBL2227 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27761113	Activator 1430		3.0 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Determination of the dermal penetration of esterom components using microdialysis sampling.	2003 Nov	14661928
Biological activities and pharmacokinetics of aconitine, benzoylaconine, and aconine after oral administration in rats.	2016 Aug	26360128
Induction of P-glycoprotein expression and activity by Aconitum alkaloids: Implication for clinical drug-drug interactions.	2016 May 3	27139035

Patents

Sample Use Guides

In Vivo Use Guide

Rats received a single intrathecal bolus injection of benzolyaconine (100, 200, and 400 ug)

Route of Administration: Other

In Vitro Use Guide

Benzolyaconine concentration-dependently increased prodynorphin gene expression, with the EC50 value of 3 uM

Substance Class	Chemical Created by `admin` on `Fri Dec 15 20:13:23 GMT 2023` Edited by `admin` on `Fri Dec 15 20:13:23 GMT 2023`
Record UNII	369U7A6HXD
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BENZOYLACONINE

Common Name

English

BENZACONINE

Common Name

English

ISACONITINE

Common Name

English

PICRACONITINE

Common Name

English

ACONITANE-3,8,13,14,15-PENTOL, 20-ETHYL-1,6,16-TRIMETHOXY-4-(METHOXYMETHYL)-, 14-BENZOATE, (1.ALPHA.,3.ALPHA.,6.ALPHA.,14.ALPHA.,15.ALPHA.,16.BETA.)-

Common Name

English

PIKRACONITIN

Common Name

English

ACONINE 14-BENZOATE

Common Name

English

Code System Code Type Description

CHEBI

132633