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Compound Detail

CHEMBL458904

PATENTIFLORIN A
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COc1cc2c(O[C@@H]3O[C@H](C)[C@@H](O)[C@H](O)[C@H]3O)c3c(c(-c4ccc5c(c4)OCO5)c2cc1OC)C(=O)OC3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL458904
Name PATENTIFLORIN A
Phase Preclinical
Structure Type MOL
InChI Key NLWUWPJUIJTHAN-ZWQUELFCSA-N
6
Targets
24
Activities
2
Assay Types
2
PK Parameters
19
Publications
0
Known Names

Molecular Properties

526.5
MW (Da)
2.13
ALogP
11
HBA
3
HBD
142.4
PSA (Ų)
0.42
QED
2
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C27H26O11
MW 526.49
Aromatic Rings 3
Heavy Atoms 38
NP-Likeness 1.46

Activity Summary

IC50 22 meas. best 8.52
EC50 2 meas. best 7.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MCF7
CHEMBL387
 IC50 8.52 7.4267 3.0 3
KB
CHEMBL398
 IC50 8.4 7.2233 4.0 3
HCT-116
CHEMBL394
 IC50 7.92 6.96 12.0 2
Human immunodeficiency virus 1
CHEMBL378
 IC50 7.62 7.4317 24.0 12
Ebolavirus
CHEMBL4434621
 EC50 7.07 6.72 85.0 2
K562
CHEMBL385
 IC50 5.84 5.315 1430.0 2

Pharmacokinetic Data

Parameter Value Units Species
Cmax 101.0 nM Mus musculus
Tmax 0.25 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MCF7 IC50 = 3.0 nM 8.52 Cytotoxicity against doxorubicin-sensitive human MCF7 cells 15921419
KB IC50 = 4.0 nM 8.4 Cytotoxicity against human KB cells 15921419
HCT-116 IC50 = 12.0 nM 7.92 Cytotoxicity against human HCT116 cells 15921419
Human immunodeficiency virus 1 IC50 = 24.0 nM 7.62 Antiviral activity against HIV1 isolate LAV0.04 infected in PHA-stimulated human... 28613071
Human immunodeficiency virus 1 IC50 = 26.9 nM 7.57 Antiviral activity against HIV1 virions derived from HIV/VSG-G or HIV/HA virions... 28613071
Human immunodeficiency virus 1 IC50 = 30.0 nM 7.52 Antiviral activity against HIV1 isolate BAL infected in PHA-stimulated human PBM... 28613071
Human immunodeficiency virus 1 IC50 = 30.0 nM 7.52 Antiviral activity against HIV1 isolate SF162 infected in PHA-stimulated human P... 28613071
Human immunodeficiency virus 1 IC50 = 31.0 nM 7.51 Antiviral activity against HIV1 isolate 89.6 infected in PHA-stimulated human PB... 28613071
Human immunodeficiency virus 1 IC50 = 32.0 nM 7.5 Antiviral activity against HIV1 isolate BAL infected in PHA-stimulated human PBM... 28613071
Human immunodeficiency virus 1 IC50 = 32.0 nM 7.5 Antiviral activity against HIV1 isolate LAV0.04 infected in PHA-stimulated human... 28613071
Human immunodeficiency virus 1 IC50 = 32.0 nM 7.5 Antiviral activity against HIV1 isolate 89.6 infected in PHA-stimulated human PB... 28613071
Human immunodeficiency virus 1 IC50 = 37.0 nM 7.43 Antiviral activity against HIV1 isolate SF162 infected in PHA-stimulated human P... 28613071
MCF7 IC50 = 40.0 nM 7.4 Cytotoxicity against doxorubicin-resistant human MCF7 cells 15921419
Human immunodeficiency virus 1 IC50 = 47.0 nM 7.33 Antiviral activity against NNRTI-resistant HIV1 isolate N119 infected in PHA-sti... 28613071
Human immunodeficiency virus 1 IC50 = 61.0 nM 7.21 Antiviral activity against NRTI-resistant HIV1 isolate 1617-1 infected in PHA-st... 28613071
Ebolavirus EC50 = 85.0 nM 7.07 Antiviral activity against recombinant Ebola virus Mayinga expressing GFP infect... 38875806
KB IC50 = 93.0 nM 7.03 Cytotoxicity against human KB cells after 72 hrs by sulforhodamine B and MTT ass... 22119124
Human immunodeficiency virus 1 IC50 = 108.0 nM 6.97 Antiviral activity against HIV1 isolate LAV infected in PHA-stimulated human PBM... 28613071
Ebolavirus EC50 = 428.0 nM 6.37 Antiviral activity against recombinant Ebola virus Mayinga expressing GFP infect... 38875806
MCF7 IC50 = 440.0 nM 6.36 Cytotoxicity against human MCF7 cells after 72 hrs by sulforhodamine B and MTT a... 22119124

Literature References

PubMed DOI Target Context # Activities
28613071 10.1021/acs.jnatprod.7b00004 Human immunodeficiency virus 1 22
22119124 10.1016/j.ejmech.2011.11.011 HL-60 11
22119124 10.1016/j.ejmech.2011.11.011 HCT-116 7
15921419 10.1021/np050028u HCT-116 4
38875806 10.1016/j.ejmech.2024.116537 ADMET 4
22119124 10.1016/j.ejmech.2011.11.011 K562 3
22119124 10.1016/j.ejmech.2011.11.011 KB 3
15921419 10.1021/np050028u MCF7 3
15921419 10.1021/np050028u P388 2
28613071 10.1021/acs.jnatprod.7b00004 PBMC 2
38875806 10.1016/j.ejmech.2024.116537 Ebolavirus 2
22119124 10.1016/j.ejmech.2011.11.011 MCF7 1
15921419 10.1021/np050028u KB 1
22119124 10.1016/j.ejmech.2011.11.011 DNA topoisomerase 2-alpha 1
28613071 10.1021/acs.jnatprod.7b00004 HeLa 1
28613071 10.1021/acs.jnatprod.7b00004 A549 1
15921419 10.1021/np050028u Mus musculus 1
38875806 10.1016/j.ejmech.2024.116537 HEK293 1
38875806 10.1016/j.ejmech.2024.116537 Voltage-gated inwardly rectifying potassium channel KCNH2 1

Data from ChEMBL 36 via Core Engine