(2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-2,3,4,4a-tetrahydropyrano[3,2-c]isochromen-6(10bH)-one

ID: ALA273019

Cas Number: 477-90-7

PubChem CID: 66065

Product Number: B111464, Order Now?

Max Phase: Unknown

Molecular Formula: C14H16O9

Molecular Weight: 328.27

Molecule Type: Small molecule

Associated Items:

Bioactivity Summary Target Summary Assay Summary

This product is currently unavailable

Names and Identifiers

Canonical SMILES: COc1c(O)cc2c(c1O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1OC2=O

Standard InChI: InChI=1S/C14H16O9/c1-21-11-5(16)2-4-7(9(11)18)12-13(23-14(4)20)10(19)8(17)6(3-15)22-12/h2,6,8,10,12-13,15-19H,3H2,1H3/t6-,8-,10+,12+,13-/m1/s1

Standard InChI Key: YWJXCIXBAKGUKZ-HJJNZUOJSA-N

Molfile:

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    6.6646  -12.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6635  -13.4262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3783  -13.8390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3765  -12.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0918  -12.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0906  -13.4237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8036  -13.8366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5221  -13.4257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8059  -12.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5191  -12.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2348  -12.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2435  -11.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5302  -10.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8083  -11.3547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5375  -10.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2554   -9.7162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9617  -10.9606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9454  -12.6121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8012  -14.6616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3740  -11.3612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9502  -12.1866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9500  -11.3616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9488  -13.8381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0868  -11.7657    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2283  -13.0114    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  2  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  1  2  2  0
 13 15  1  6
  5  9  1  0
 15 16  1  0
  6  7  1  0
 12 17  1  1
  7  8  1  0
 11 18  1  6
  8 10  1  0
  7 19  2  0
  9 10  1  0
  4 20  1  0
  5  4  2  0
  1 21  1  0
  4  1  1  0
 21 22  1  0
  5  6  1  0
  2 23  1  0
  9 24  1  1
  2  3  1  0
 10 25  1  6
M  END

Associated Targets(Human)

BGC-823 (3035 Activities)

Natural Product: Yes	Oral: No	Chemical Probe: No	Parenteral: No
Molecule Type: Small molecule	Topical: No	First In Class: No	Black Box: No
Chirality: Yes	Availability: No	Prodrug: No

Molecular Weight: 328.27	Molecular Weight (Monoisotopic): 328.0794	AlogP: -1.20	#Rotatable Bonds: 2
Polar Surface Area: 145.91	Molecular Species: NEUTRAL	HBA: 9	HBD: 5
#RO5 Violations: ┄	HBA (Lipinski): 9	HBD (Lipinski): 5	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: 8.62	CX Basic pKa: ┄	CX LogP: -1.23	CX LogD: -1.25
Aromatic Rings: 1	Heavy Atoms: 23	QED Weighted: 0.42	Np Likeness Score: 2.63

1. Chen Z, Liu YM, Yang S, Song BA, Xu GF, Bhadury PS, Jin LH, Hu DY, Liu F, Xue W, Zhou X.. (2008) Studies on the chemical constituents and anticancer activity of Saxifraga stolonifera (L) Meeb., 16 (3): [PMID:17997321] [10.1016/j.bmc.2007.10.072]
2. Han LK, Ninomiya H, Taniguchi M, Baba K, Kimura Y, Okuda H.. (1998) Norepinephrine-augmenting lipolytic effectors from Astilbe thunbergii rhizomes., 61 (8): [PMID:9722485] [10.1021/np980107o]
3. Piacente S, Pizza C, De Tommasi N, Mahmood N.. (1996) Constituents of Ardisia japonica and their in vitro anti-HIV activity., 59 (6): [PMID:8786362] [10.1021/np960074h]
4. Nazir N, Koul S, Qurishi MA, Najar MH, Zargar MI.. (2011) Evaluation of antioxidant and antimicrobial activities of Bergenin and its derivatives obtained by chemoenzymatic synthesis., 46 (6): [PMID:21474216] [10.1016/j.ejmech.2011.03.025]
5. Vijaya Kumar T, Tiwari AK, Robinson A, Suresh Babu K, Sateesh Chandra Kumar R, Anand Kumar D, Zehra A, Madhusudna Rao J.. (2011) Synthesis and antiglycation potentials of bergenin derivatives., 21 (16): [PMID:21752643] [10.1016/j.bmcl.2011.04.131]
6. de Oliveira CM, Nonato FR, de Lima FO, Couto RD, David JP, David JM, Soares MB, Villarreal CF.. (2011) Antinociceptive properties of bergenin., 74 (10): [PMID:21939182] [10.1021/np200232s]
7. PubChem BioAssay data set,
8. Shah MR, Arfan M, Amin H, Hussain Z, Qadir MI, Choudhary MI, VanDerveer D, Mesaik MA, Soomro S, Jabeen A, Khan IU.. (2012) Synthesis of new bergenin derivatives as potent inhibitors of inflammatory mediators NO and TNF-α., 22 (8): [PMID:22437110] [10.1016/j.bmcl.2012.02.096]
9. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date,
10. Brunhofer G, Fallarero A, Karlsson D, Batista-Gonzalez A, Shinde P, Gopi Mohan C, Vuorela P.. (2012) Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine., 20 (22): [PMID:23062825] [10.1016/j.bmc.2012.09.040]
11. Arfan M, Amin H, Khan I, Shah MR, Shah H, Khan AZ, Halimi SMA, Khan N, Kaleem WA, Qayum M, Shahidullah A, Khan MA. (2012) Molecular simulations of bergenin as a new urease inhibitor, 21 (9): [10.1007/s00044-011-9762-6]
12. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP.. (2013) Structure-based identification of OATP1B1/3 inhibitors., 83 (6): [PMID:23571415] [10.1124/mol.112.084152]
13. Kashima Y, Miyazawa M.. (2013) Synthesis, antioxidant capacity, and structure-activity relationships of tri-O-methylnorbergenin analogues on tyrosinase inhibition., 23 (24): [PMID:24268551] [10.1016/j.bmcl.2013.10.066]
14. Jain SK, Singh S, Khajuria A, Guru SK, Joshi P, Meena S, Nadkarni JR, Singh A, Bharate SS, Bhushan S, Bharate SB, Vishwakarma RA.. (2014) Pyrano-isochromanones as IL-6 inhibitors: synthesis, in vitro and in vivo antiarthritic activity., 57 (16): [PMID:25111439] [10.1021/jm500901e]
15. Li YJ, Xu CT, Lin DD, Qin JK, Ye GJ, Deng QH.. (2016) Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata., 26 (15): [PMID:27374242] [10.1016/j.bmcl.2016.06.054]
16. Singh R, Kumar V, Bharate SS, Vishwakarma RA.. (2017) Synthesis, pH dependent, plasma and enzymatic stability of bergenin prodrugs for potential use against rheumatoid arthritis., 25 (20): [PMID:28843845] [10.1016/j.bmc.2017.08.011]
17. Liang C, Pei S, Ju W, Jia M, Tian D, Tang Y, Mao G.. (2017) Synthesis and in vitro and in vivo antitumour activity study of 11-hydroxyl esterified bergenin/cinnamic acid hybrids., 133 [PMID:28395218] [10.1016/j.ejmech.2017.03.053]
18. Franck Touret, Magali Gilles, Karine Barral, Antoine Nougairède, Etienne Decroly, Xavier de Lamballerie, Bruno Coutard. (2020) In vitro screening of a FDA approved chemical library reveals potential inhibitors of SARS-CoV-2 replication, [10.1101/2020.04.03.023846]
19. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek. (2020) Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection, [10.21203/rs.3.rs-23951/v1]
20. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani. (2020) Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen, [10.6019/CHEMBL4495564]
21. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani. (2020) Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen, [10.6019/CHEMBL4495564]
22. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen. (2020) Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort, [10.6019/CHEMBL4495565]
23. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen. (2020) Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort, [10.6019/CHEMBL4495565]
24. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius. (2021) HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators, [10.6019/CHEMBL4808148]
25. Deng L, Song C, Niu Y, Li Q, Wang M, Wu YF, Ye XS.. (2021) Synthesis and biological evaluation of bergenin derivatives as new immunosuppressants., 12 (11.0): [PMID:34825192] [10.1039/D1MD00210D]
26. Puhl AC, Fernandes RS, Godoy AS, Gil LHVG, Oliva G, Ekins S.. (2023) The protein disulfide isomerase inhibitor 3-methyltoxoflavin inhibits Chikungunya virus., 83 [PMID:36940609] [10.1016/j.bmc.2023.117239]

(2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-2,3,4,4a-tetrahydropyrano[3,2-c]isochromen-6(10bH)-one

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Associated Targets(non-human)

Molecule Features

Drug Indications

Mechanisms of Action

Calculated Properties

References

Source