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BioAssay: AID 380506

Inhibition of CYP3A4

A 70% ethanol extract of California poppy (Eschscholzia californica) was able to bind to 5-HT(1A) and 5-HT(7) receptors at 100 mug/mL. The subsequent isolation procedure yielded the known alkaloids californidine (1), escholtzine (2), N-methyllaurotetanine (3), caryachine (4), and O-methylcaryachine (5), along with a new pavine alkaloid, 6S,12S-neocaryachine-7-O-methyl ether N-metho salt (7). The more ..
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 Tested Compounds
 Tested Compounds
All(5)
 
 
Active(1)
 
 
Unspecified(4)
 
 
 Tested Substances
 Tested Substances
All(6)
 
 
Active(1)
 
 
Unspecified(5)
 
 
 Related BioAssays
 Related BioAssays
AID: 380506
Data Source: ChEMBL (528535)
Depositor Category: Literature, Extracted
BioAssay Version:
Deposit Date: 2010-05-26
Modify Date: 2013-11-21

Data Table ( Complete ):           Active    All
BioActive Compound: 1
Description:
Title: Alkaloids from Eschscholzia californica and their capacity to inhibit binding of [3H]8-Hydroxy-2-(di-N-propylamino)tetralin to 5-HT1A receptors in Vitro.

Abstract: A 70% ethanol extract of California poppy (Eschscholzia californica) was able to bind to 5-HT(1A) and 5-HT(7) receptors at 100 mug/mL. The subsequent isolation procedure yielded the known alkaloids californidine (1), escholtzine (2), N-methyllaurotetanine (3), caryachine (4), and O-methylcaryachine (5), along with a new pavine alkaloid, 6S,12S-neocaryachine-7-O-methyl ether N-metho salt (7). The structure of 7 was determined by spectroscopic data interpretation, while the absolute stereochemistry was determined by means of circular dichroism. From the results obtained from the radioligand-binding assay of the pure compounds, including the commercially available protopine (6), it was evident that the activity on the 5-HT(1A) receptor was at least partly due to the presence of the aporphine alkaloid 3, which showed the highest inhibition of [(3)H]8-hydroxy-2-(di-N-propylamino)tetralin ([(3)H]8-OH-DPAT) binding with an EC(50) value of 155 nM and a K(i) of 85 nM.
(PMID: 16562853)
Comment
Compounds with activity <= 50uM or explicitly reported as active by ChEMBL are flagged as active in this PubChem assay presentation.

Putative Target:

ChEMBL Target ID: 17045
Target Type: SINGLE PROTEIN
Pref Name: Cytochrome P450 3A4
Synonyms: 1;8-cineole 2-exo-monooxygenase;Albendazole monooxygenase;Albendazole sulfoxidase;CYPIIIA3;CYPIIIA4;Cytochrome P450 3A3;Cytochrome P450 3A4;Cytochrome P450 HLp;Cytochrome P450 NF-25;Cytochrome P450-PCN1;Nifedipine oxidase;Quinine 3-monooxygenase;Taurochenodeoxycholate 6-alpha-hydroxylase;
Gene Name: CYP3A3;CYP3A4;
Protein Accession: P08684;
Protein GI: 116241312;
Organism: Homo sapiens
Tax ID: 9606
Target Classification: enzyme cytochrome p450 cyp_3 cyp_3a cyp_3a4
Confidence: Homologous single protein target assigned
Relationship Type: Homologous protein target assigned
Categorized Comment
ChEMBL Assay Type: ADMET

ChEMBL Assay Data Source: Scientific Literature

Result Definitions
TIDNameDescriptionHistogramTypeUnit
OutcomeThe BioAssay activity outcomeOutcome
1IC50*IC50 PubChem standard valueFloatμM
2IC50 activity commentIC50 activity commentString
3IC50 standard flagIC50 standard flagInteger
4IC50 qualifierIC50 qualifierString
5IC50 published valueIC50 published valueFloatμM
6IC50 standard valueIC50 standard valueFloatnM

* Activity Concentration.

Data Table (Concise)
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