1,3,5-trihydroxy benzene

ID: ALA473159

Chembl Id: CHEMBL473159

Cas Number: 108-73-6

PubChem CID: 359

Product Number: P104096

Max Phase: Approved

Molecular Formula: C6H6O3

Molecular Weight: 126.11

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Benezene-1,3,5-triol | Dilospan s | Phloroglucin | Phloroglucinol | Sym-trihydroxybenzene | NSC-1572 | phloroglucinol|108-73-6|Benzene-1,3,5-triol|1,3,5-trihydroxybenzene|Phloroglucin|1,3,5-benzenetriol|Phloroglucine|Spasfon-Lyoc|Dilospan S|sym-Trihydroxybenzene|s-Trihydroxybenzene|Benzene-s-triol|5-Hydroxyresorcinol|Benzene, trihydroxy|5-Oxyresorcinol|3,5-Dihydroxyphenol|Floroglucin|Floroglucinol|Phloroglucinol anhydrous|1,3,5-Triol|1,3,5-THB|5-Oxyresorcinolphloroglucin|1,3,5-TrihydroxycyclohexShow More

Trade Names(2): Spasfon | Spasfon-lyoc

Canonical SMILES:  Oc1cc(O)cc(O)c1

Standard InChI:  InChI=1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H

Standard InChI Key:  QCDYQQDYXPDABM-UHFFFAOYSA-N

Alternative Forms

  1. Parent:

Associated Targets(Human)

HT-1080 (3966 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MRC5 (9203 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HL-60 (67320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BACE1 Tchem Beta-secretase 1 (15641 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLK Tbio DNA polymerase kappa (8653 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TYR Tclin Tyrosinase (717 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC6 Tclin Histone deacetylase 6 (20808 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Crotalus adamanteus (3 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGS1 Cyclooxygenase-1 (5266 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RAW264.7 (28094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (378 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vero (26788 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (11336 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: YesAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 126.11Molecular Weight (Monoisotopic): 126.0317AlogP: 0.80#Rotatable Bonds:
Polar Surface Area: 60.69Molecular Species: NEUTRALHBA: 3HBD: 3
#RO5 Violations: HBA (Lipinski): 3HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 9.13CX Basic pKa: CX LogP: 1.06CX LogD: 1.05
Aromatic Rings: 1Heavy Atoms: 9QED Weighted: 0.48Np Likeness Score: 0.77

References

1. da Silva SL, Calgarotto AK, Maso V, Damico DC, Baldasso P, Veber CL, Villar JA, Oliveira AR, Comar M, Oliveira KM, Marangoni S..  (2009)  Molecular modeling and inhibition of phospholipase A2 by polyhydroxy phenolic compounds.,  44  (1): [PMID:18423943] [10.1016/j.ejmech.2008.02.043]
2. Bohr G, Gerhäuser C, Knauft J, Zapp J, Becker H..  (2005)  Anti-inflammatory acylphloroglucinol derivatives from Hops (Humulus lupulus).,  68  (10): [PMID:16252923] [10.1021/np050164z]
3. Ali MS, Tezuka Y, Awale S, Banskota AH, Kadota S..  (2001)  Six new diarylheptanoids from the seeds of Alpinia blepharocalyx.,  64  (3): [PMID:11277741] [10.1021/np000496y]
4. Li Y, Qian ZJ, Ryu B, Lee SH, Kim MM, Kim SK..  (2009)  Chemical components and its antioxidant properties in vitro: an edible marine brown alga, Ecklonia cava.,  17  (5): [PMID:19201199] [10.1016/j.bmc.2009.01.031]
5. Jung HA, Oh SH, Choi JS..  (2010)  Molecular docking studies of phlorotannins from Eisenia bicyclis with BACE1 inhibitory activity.,  20  (11): [PMID:20462757] [10.1016/j.bmcl.2010.04.093]
6. PubChem BioAssay data set, 
7. Stratford MR, Ramsden CA, Riley PA..  (2013)  Mechanistic studies of the inactivation of tyrosinase by resorcinol.,  21  (5): [PMID:23352755] [10.1016/j.bmc.2012.12.031]
8. Park JY, Kim JH, Kwon JM, Kwon HJ, Jeong HJ, Kim YM, Kim D, Lee WS, Ryu YB..  (2013)  Dieckol, a SARS-CoV 3CL(pro) inhibitor, isolated from the edible brown algae Ecklonia cava.,  21  (13): [PMID:23647823] [10.1016/j.bmc.2013.04.026]
9. WHO Anatomical Therapeutic Chemical Classification, 
10. British National Formulary (72nd edition), 
11. Unpublished dataset, 
12. 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]
13. Katie Heiser, Peter F. McLean, Chadwick T. Davis, Ben Fogelson, Hannah B. Gordon, Pamela Jacobson, Brett Hurst, Ben Miller, Ronald W. Alfa, Berton A. Earnshaw, Mason L. Victors, Yolanda T. Chong, Imran S. Haque, Adeline S. Low, Christopher C. Gibson.  (2020)  Identification of potential treatments for COVID-19 through artificial intelligence-enabled phenomic analysis of human cells infected with SARS-CoV-2,  [10.1101/2020.04.21.054387]
14. 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]
15. 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]
16. 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]