QUINOVIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C36H56O9
Molecular Weight	632.8244
Optical Activity	UNSPECIFIED
Defined Stereocenters	15 / 15
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H]1CC[C@@]2(CC[C@]3(C(O)=O)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@H](C)[C@@H](O)[C@H](O)[C@H]6O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2[C@H]1C)C(O)=O

InChI

InChIKey=PUOQHFWXBKTHST-DLCGLXBKSA-N

InChI=1S/C36H56O9/c1-18-10-15-35(30(40)41)16-17-36(31(42)43)21(25(35)19(18)2)8-9-23-33(6)13-12-24(32(4,5)22(33)11-14-34(23,36)7)45-29-28(39)27(38)26(37)20(3)44-29/h8,18-20,22-29,37-39H,9-17H2,1-7H3,(H,40,41)(H,42,43)/t18-,19+,20-,22+,23-,24+,25+,26-,27+,28-,29+,33+,34-,35+,36-/m1/s1

HIDE SMILES / InChI

Description
Sources: http://onlinelibrary.wiley.com/doi/10.1002/jlac.19636670117/abstract
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12135095 | https://www.ncbi.nlm.nih.gov/pubmed/12462343

Quinovin is a glucoside isolated from bark of Cortex chinae and Mitragyna stipulosa. Quinovin is a mixture of three glycosides, 60% A (Quinovic acid b-D-quinovoside), 5% B (Cincholic acid b-D-quinovoside) and 30% C (Quinovic acid b-D-glucoside). Quinovine was shown to inhibit PDE1 from snake venom in submillimolar concentrations.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Phosphodiesterase 1 12 Target ID: CHEMBL2095150 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12462343	Inhibitor 8504		166.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Structure-activity relationship of triterpenoids isolated from Mitragyna stipulosa on cytotoxicity.	2002-06	12135095

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Activity against snake venom phosphodiesterase I (Sigma P 4631) (EC 3.1.4.1) was assayed. 33mM tris-HCl buffer pH 8.8 containing 30mM Mg(C2H3O2)2 4H2O with 0.000742 U/well final concentration was prepared using microtiter plate, and 0.33mM bis-( p-nitrophenyl) phosphate was used as a substrate. Quinovine was added, and after 30 min incubation the enzyme activity was monitored spectrophotometrically at 37C on a microtitre plate reader by following the release of p-nitrophenol from p-nitrophenyl phosphate at 410 nm.

Name

Type

Language

QUINOVIN

Common Name

English

3-O-(.BETA.-D-QUINOVOPYRANOSYL)QUINOVIC ACID

Preferred Name

English

CHINOVIN

Common Name

English

QUINOVIN [MI]

Common Name

English

URS-12-ENE-27,28-DIOIC ACID, 3-((6-DEOXY-.BETA.-D-GLUCOPYRANOSYL)OXY)-, (3.BETA.)-

Systematic Name

English

QUINOVA-BITTER

Common Name

English

Code System Code Type Description

CAS

53516-73-7