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Natural Product (NP) Details

General Information of the NP (ID: NP0873)
Name
Gentiopicroside
Synonyms
Gentiopicroside; Gentiopicrin; 20831-76-9; UNII-0WE09Z21RC; 0WE09Z21RC; CHEBI:5321; Gentiopicroside, >=98% (HPLC); (5R,6S)-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-vinyl-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one; 1H,3H-Pyrano[3,4-c]pyran-1-one, 5-ethenyl-6-(beta-D-glucopyranosyloxy)-5,6-dihydro-, (5R,6S)-; Gentiopicrin,(S); (3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one; (5R,6S)-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-5-vinyl-5,6-dihydropyrano[3,4-c]pyran-1(3H)-one; MLS002473254; SCHEMBL154304; CHEMBL508320; MEGxp0_000872; POLYPROPYLENEGLYCOL4000; ACon1_001284; DTXSID40878043; HMS2198G10; HY-N0494; ZINC4098340; EINECS 244-070-2; MFCD00075700; s3777; ZB1867; AKOS015896721; CCG-268110; LMPR0102070009; NSC 606402; NCGC00180669-01; 1H,3H-Pyrano(3,4-c)pyran-1-one, 5-ethenyl-6-(beta-D-glucopyranosyloxy)-5,6-dihydro-, (5R-trans)-; AC-20248; AS-74360; O673; SMR001397341; CS-0009015; N1898; C09782; 831G769; BRD-K33131085-001-01-5; Q27106718; (5R,6S)-5-ethenyl-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,3H,5H,6H-pyrano[3,4-c]pyran-1-one; (5R,6S)-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-vinyl-5,6-dihydropyrano[3,4-c]pyran-1(3H)-one; (5R-trans)-6-(??-D-glucopyranosyloxy)-5,6-dihydro-5-vinyl-1H,3H-pyrano[3,4-c]pyran-1-one; (5R-trans)-6-(beta-D-Glucopyranosyloxy)-5,6-dihydro-5-vinyl-1H,3H-pyrano(3,4-c)pyran-1-one
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Species Origin Gentiana ...     Click to Show/Hide
Gentiana
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Gentianales
Family: Gentianaceae
Genus: Gentiana
Disease Chronic kidney disease [ICD-11: GB61] Investigative [1]
Structure
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2D MOL

3D MOL

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Formula
C16H20O9
PubChem CID
88708
Canonical SMILES
C=CC1C(OC=C2C1=CCOC2=O)OC3C(C(C(C(O3)CO)O)O)O
InChI
1S/C16H20O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2-3,6-7,10-13,15-20H,1,4-5H2/t7-,10-,11-,12+,13-,15+,16+/m1/s1
InChIKey
DUAGQYUORDTXOR-GPQRQXLASA-N
CAS Number
CAS 20831-76-9
ChEBI ID
CHEBI:5321
Herb ID
HBIN027510
SymMap ID
SMIT00064
TCMSP ID
MOL000636
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Adverse Effect can be Decreased by This NP
          Leflunomide + Methotrexate     Click to Show/Hide the Molecular Data of This Drug
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Down-regulation Expression IL1B  Molecule Info 
Pathway MAP
Down-regulation Expression IL6  Molecule Info 
Pathway MAP
Down-regulation Expression TNF  Molecule Info 
Pathway MAP
                    In-vivo Model SD rats (200 g +/- 20 g) were used in this study.
                    Experimental
                    Result(s)
Gentiopicroside (GPS) could exert hepatoprotective effects on leflunomide (LEF)- and/or methotrexate (MTX)-treated arthritic rats.
References
Reference 1 Gentiopicroside activates the bile acid receptor Gpbar1 (TGR5) to repress NF-kappaB pathway and ameliorate diabetic nephropathy. Pharmacol Res. 2020 Jan;151:104559.
Reference 2 Hepatoprotective effect of gentiopicroside in combination with leflunomide and/or methotrexate in arthritic rats. Life Sci. 2021 Jan 15;265:118689.
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Cite NPCDR
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Correspondence

X. N. Sun, Y. T. Zhang, Y. Zhou, X. C. Lian, L. L. Yan, T. Pan, T. Jin, H. Xie, Z. M. Liang, W. Q. Qiu, J. X. Wang, Z. R. Li, F. Zhu*, X. B. Sui*. NPCDR: natural product-based drug combination and its disease-specific molecular regulation. Nucleic Acids Research. 50(D1): 1324-1333 (2020). PMID: 34664659

Prof. Feng ZHU  (zhufeng@zju.edu.cn)

College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China


Prof. Xinbing SUI  (hzzju@hznu.edu.cn)

School of Pharmacy and Department of Medical Oncology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou, China