5,6,7,8,4'-pentahydroxyflavone

ID: ALA234338

Chembl Id: CHEMBL234338

Cas Number: 577-26-4

PubChem CID: 96506

Max Phase: Preclinical

Molecular Formula: C15H10O7

Molecular Weight: 302.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 5,6,7,8,4'-Pentahydroxyflavone | Nortangeretin|5,6,7,8,4'-Pentahydroxyflavone|577-26-4|MLS000736839|4H-1-Benzopyran-4-one, 5,6,7,8-tetrahydroxy-2-(4-hydroxyphenyl)-|LMG443BS12|CHEBI:79553|NSC-76988|5,6,7,8-tetrahydroxy-2-(4-hydroxyphenyl)chromen-4-one|SMR000528344|2-(4-Hydroxyphenyl)-5,6,7,8-tetrahydroxy-4H-1-benzopyran-4-one|5,6,7,8-tetrahydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one|NSC 76988|DEMETHYLPONKANETIN|UNII-LMG443BS12|cid_96506|CHEMBL234338|SCHEMBL14053704|SCHEMBL21857630|BDBM61867Show More⌵

Canonical SMILES:  O=c1cc(-c2ccc(O)cc2)oc2c(O)c(O)c(O)c(O)c12

Standard InChI:  InChI=1S/C15H10O7/c16-7-3-1-6(2-4-7)9-5-8(17)10-11(18)12(19)13(20)14(21)15(10)22-9/h1-5,16,18-21H

Standard InChI Key:  SPZXXUUDYMHBSG-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA234338

   5,6,7,8,4'-Pentahydroxyflavone

Molecule Features

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: 302.24

Molecular Weight (Monoisotopic): 302.0427

AlogP: 1.99

#Rotatable Bonds: 1

Polar Surface Area: 131.36

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.33

CX Basic pKa: ┄

CX LogP: 2.10

CX LogD: 1.01

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.34

Np Likeness Score: 1.39

References

1. Karioti A, Protopappa A, Megoulas N, Skaltsa H..  (2007)  Identification of tyrosinase inhibitors from Marrubium velutinum and Marrubium cylleneum.,  15  (7): [PMID:17287127] [10.1016/j.bmc.2007.01.035]

2. PubChem BioAssay data set, 

3. Seiler CL, Richards KA, Jakubowski HV, McIntee EJ..  (2013)  Identification of new inhibitors for low molecular weight protein tyrosine phosphatase isoform B.,  23  (21): [PMID:24035092] [10.1016/j.bmcl.2013.08.079]

4. Brooke DG, van Dam EM, Watts CK, Khoury A, Dziadek MA, Brooks H, Graham LJ, Flanagan JU, Denny WA..  (2014)  Targeting the Warburg Effect in cancer; relationships for 2-arylpyridazinones as inhibitors of the key glycolytic enzyme 6-phosphofructo-2-kinase/2,6-bisphosphatase 3 (PFKFB3).,  22  (3): [PMID:24398380] [10.1016/j.bmc.2013.12.041]

5. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of NIH NCI Diversity Set V,  [10.6019/CHEMBL4296182]

6. Whitfield H, Hemmings AM, Mills SJ, Baker K, White G, Rushworth S, Riley AM, Potter BVL, Brearley CA..  (2021)  Allosteric Site on SHIP2 Identified Through Fluorescent Ligand Screening and Crystallography: A Potential New Target for Intervention.,  64  (7.0): [PMID:33724834] [10.1021/acs.jmedchem.0c01944]

7. Wang Y, Qu C, Liu T, Wang C..  (2020)  PFKFB3 inhibitors as potential anticancer agents: Mechanisms of action, current developments, and structure-activity relationships.,  203  [PMID:32679452] [10.1016/j.ejmech.2020.112612]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• CO-ADD antimicrobial screening data