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17388-39-5 | 1H,3H-Pyrano[3,4-c]pyran-1-one, 5-ethenyl-6-(β-D-glucopyranosyloxy)-4,4a,5,6-tetrahydro-4a-hydroxy-, (4aR,5R,6S)-
CAS No: 17388-39-5 Catalog No: AG001Z98 MDL No:MFCD07783984
Product Description
Catalog Number:
AG001Z98
Chemical Name:
1H,3H-Pyrano[3,4-c]pyran-1-one, 5-ethenyl-6-(β-D-glucopyranosyloxy)-4,4a,5,6-tetrahydro-4a-hydroxy-, (4aR,5R,6S)-
CAS Number:
17388-39-5
Molecular Formula:
C16H22O10
Molecular Weight:
374.3399
MDL Number:
MFCD07783984
IUPAC Name:
(3S,4R,4aR)-4-ethenyl-4a-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,5,6-tetrahydropyrano[3,4-c]pyran-8-one
InChI:
InChI=1S/C16H22O10/c1-2-7-14(24-6-8-13(21)23-4-3-16(7,8)22)26-15-12(20)11(19)10(18)9(5-17)25-15/h2,6-7,9-12,14-15,17-20,22H,1,3-5H2/t7-,9+,10+,11-,12+,14-,15-,16+/m0/s1
InChI Key:
HEYZWPRKKUGDCR-QBXMEVCASA-N
SMILES:
C=C[C@H]1[C@@H](OC=C2[C@@]1(O)CCOC2=O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
UNII:
4038595T7Y
Properties
Complexity:
592
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
8
Defined Bond Stereocenter Count:
0
Exact Mass:
374.121g/mol
Formal Charge:
0
Heavy Atom Count:
26
Hydrogen Bond Acceptor Count:
10
Hydrogen Bond Donor Count:
5
Isotope Atom Count:
0
Molecular Weight:
374.342g/mol
Monoisotopic Mass:
374.121g/mol
Rotatable Bond Count:
4
Topological Polar Surface Area:
155A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-2
Literature
| Title | Journal |
|---|---|
| The anti-hyperplasia, anti-oxidative and anti-inflammatory properties of Qing Ye Dan and swertiamarin in testosterone-induced benign prostatic hyperplasia in rats. | Toxicology letters 20170104 |
| Beneficial effects of swertiamarin on dyslipidaemia in streptozotocin-induced type 2 diabetic rats. | Phytotherapy research : PTR 20120801 |
| Determination of the plasma pharmacokinetic and tissue distributions of swertiamarin in rats by liquid chromatography with tandem mass spectrometry. | Arzneimittel-Forschung 20120301 |
| Inhibitory effects of secoiridoids from the roots of Gentiana straminea on stimulus-induced superoxide generation, phosphorylation and translocation of cytosolic compounds to plasma membrane in human neutrophils. | Phytotherapy research : PTR 20120201 |
| Determination of novel nitrogen-containing metabolite after oral administration of swertiamarin to rats. | Journal of Asian natural products research 20120101 |
| Effects of Swertia japonica extract and its main compound swertiamarin on gastric emptying and gastrointestinal motility in mice. | Fitoterapia 20110901 |
| Development and validation of a LC-ESI-MS/MS method for the determination of swertiamarin in rat plasma and its application in pharmacokinetics. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20110601 |
| Hypoglycemic activity of C-glycosyl flavonoid from Enicostemma hyssopifolium. | Pharmaceutical biology 20110401 |
| Analysis of iridoids, secoiridoids and xanthones in Centaurium erythraea, Frasera caroliniensis and Gentiana lutea using LC-MS and RP-HPLC. | Journal of pharmaceutical and biomedical analysis 20110220 |
| A new HPTLC densitometric method for analysis of swertiamarin in Enicostemma littorale and commercial formulations. | Natural product research 20110101 |
| Introgression of Swertia mussotii gene into Bupleurum scorzonerifolium via somatic hybridization. | BMC plant biology 20110101 |
| Antioxidant and hepatoprotective effect of swertiamarin from Enicostemma axillare against D-galactosamine induced acute liver damage in rats. | Journal of ethnopharmacology 20100706 |
| Amelioration of STZ-induced type 1 diabetic nephropathy by aqueous extract of Enicostemma littorale Blume and swertiamarin in rats. | Molecular and cellular biochemistry 20100701 |
| Cloning and functional analysis of geraniol 10-hydroxylase, a cytochrome P450 from Swertia mussotii Franch. | Bioscience, biotechnology, and biochemistry 20100101 |
| Antihyperlipidaemic activity of swertiamarin, a secoiridoid glycoside in poloxamer-407-induced hyperlipidaemic rats. | Journal of natural medicines 20091001 |
| Swertiamarin: a lead from Enicostemma littorale Blume. for anti-hyperlipidaemic effect. | European journal of pharmacology 20090901 |
| [Determination of six active components in three species of genus Swertia by HPLC multiwavelength with detection]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090601 |
| Antinociceptive activity of swertiamarin isolated from Enicostemma axillare. | Phytomedicine : international journal of phytotherapy and phytopharmacology 20090301 |
| Antiedematogenic and free radical scavenging activity of swertiamarin isolated from Enicostemma axillare. | Planta medica 20090101 |
| Fagraldehyde, a secoiridoid isolated from Fagraea fragrans. | Journal of natural products 20081201 |
| [Chemical constituents from herbs of Swertia delavayi]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20080801 |
| Simultaneous determination of swertiamarin and its metabolites (5Z)-5-ethylidene-8-hydroxy-3,4,5,6,7,8-hexahydro-1H-pyrano[3,4-c]pyridin-1-one and erythrocentaurin in broth of Aspergillus niger by HPLC. | Biomedical chromatography : BMC 20080201 |
| [Determination of iridoids and triterpenes in herb of Swertia pseudochinesis by RP-HPLC]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20071201 |
| Simultaneous estimation of mangiferin and four secoiridoid glycosides in rat plasma using liquid chromatography tandem mass spectrometry and its application to pharmacokinetic study of herbal preparation. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20071015 |
| [Simultaneous determination of six main constituents in Swertia of Qinghai Province and Sichuan Province by HPLC]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20061201 |
| Microsphere-based protease assays and screening application for lethal factor and factor Xa. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501 |
| [HPLC fingerprinting of total glycosides of Swertia franchetiana]. | Yao xue xue bao = Acta pharmaceutica Sinica 20050501 |
| Variation of active constituents of an important Tibet folk medicine Swertia mussotii Franch. (Gentianaceae) between artificially cultivated and naturally distributed. | Journal of ethnopharmacology 20050408 |
| Separation and determination of gentiopicroside and swertiamarin in Tibetan medicines by micellar electrokinetic electrophoresis. | Biomedical chromatography : BMC 20040101 |
| Bioactivity of secoiridoid glycosides from Centaurium erythraea. | Phytomedicine : international journal of phytotherapy and phytopharmacology 20030501 |
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