4,4'-Dihydroxy-10,10'-dioxo-5,5'-bis-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-9,10,9',10'-tetrahydro-[9,9']bianthracenyl-2,2'-dicarboxylic acid

ID: ALA2368547

Cas Number: 8013-11-4

PubChem CID: 73111

Product Number: S426106, Order Now?

Max Phase: Preclinical

Molecular Formula: C42H38O20

Molecular Weight: 862.75

Molecule Type: Small molecule

In stock!

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: O=C(O)c1cc(O)c2c(c1)[C@H]([C@H]1c3cc(C(=O)O)cc(O)c3C(=O)c3c(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)cccc31)c1cccc(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c1C2=O

Standard InChI: InChI=1S/C42H38O20/c43-11-23-31(47)35(51)37(53)41(61-23)59-21-5-1-3-15-25(17-7-13(39(55)56)9-19(45)27(17)33(49)29(15)21)26-16-4-2-6-22(60-42-38(54)36(52)32(48)24(12-44)62-42)30(16)34(50)28-18(26)8-14(40(57)58)10-20(28)46/h1-10,23-26,31-32,35-38,41-48,51-54H,11-12H2,(H,55,56)(H,57,58)/t23-,24-,25-,26-,31-,32-,35+,36+,37-,38-,41-,42-/m1/s1

Standard InChI Key: IPQVTOJGNYVQEO-KGFNBKMBSA-N

Molfile:

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M  END

Associated Targets(Human)

ESR2 Tclin Estrogen receptor (3070 Activities)

Discover Target: ESR2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HCT-116 (91556 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HepG2 (196354 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

Discover Target: APEX1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CTRC Tchem Chymotrypsin (134 Activities)

Discover Target: CTRC

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

SARS-CoV-2 (38078 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

groL GroEL/GroES (1042 Activities)

Discover Target: groL

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (11336 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (207 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 862.75	Molecular Weight (Monoisotopic): 862.1956	AlogP: -1.10	#Rotatable Bonds: 9
Polar Surface Area: 347.96	Molecular Species: ACID	HBA: 18	HBD: 12
#RO5 Violations: 3	HBA (Lipinski): 20	HBD (Lipinski): 12	#RO5 Violations (Lipinski): 3
CX Acidic pKa: 3.23	CX Basic pKa: ┄	CX LogP: 1.19	CX LogD: -5.59
Aromatic Rings: 4	Heavy Atoms: 62	QED Weighted: 0.10	Np Likeness Score: 1.02

References

1. Matsuda H, Shimoda H, Morikawa T, Yoshikawa M.. (2001) Phytoestrogens from the roots of Polygonum cuspidatum (Polygonaceae): structure-requirement of hydroxyanthraquinones for estrogenic activity., 11 (14): [PMID:11459643] [10.1016/s0960-894x(01)00318-3]
2. Matsuda H, Shimoda H, Morikawa T, Yoshikawa M.. (2001) Phytoestrogens from the roots of Polygonum cuspidatum (Polygonaceae): structure-requirement of hydroxyanthraquinones for estrogenic activity., 11 (14): [PMID:11459643] [10.1016/s0960-894x(01)00318-3]
3. Cui XR, Tsukada M, Suzuki N, Shimamura T, Gao L, Koyanagi J, Komada F, Saito S.. (2008) Comparison of the cytotoxic activities of naturally occurring hydroxyanthraquinones and hydroxynaphthoquinones., 43 (6): [PMID:17949858] [10.1016/j.ejmech.2007.08.009]
4. 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]
5. PubChem BioAssay data set,
6. 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]
7. Stevens M, Abdeen S, Salim N, Ray AM, Washburn A, Chitre S, Sivinski J, Park Y, Hoang QQ, Chapman E, Johnson SM.. (2019) HSP60/10 chaperonin systems are inhibited by a variety of approved drugs, natural products, and known bioactive molecules., 29 (9): [PMID:30852084] [10.1016/j.bmcl.2019.02.028]
8. 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]
9. 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]

4,4'-Dihydroxy-10,10'-dioxo-5,5'-bis-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-9,10,9',10'-tetrahydro-[9,9']bianthracenyl-2,2'-dicarboxylic acid

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Associated Targets(non-human)

Molecule Features

Drug Indications

Mechanisms of Action

Calculated Properties

References

Source