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Compound Detail

CHEMBL221190

DIPHYLLIN
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COc1cc2c(O)c3c(c(-c4ccc5c(c4)OCO5)c2cc1OC)C(=O)OC3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL221190
Name DIPHYLLIN
Phase Preclinical
Structure Type MOL
InChI Key VMEJANRODATDOF-UHFFFAOYSA-N
31
Targets
52
Activities
2
Assay Types
6
PK Parameters
20
Publications
0
Known Names

Molecular Properties

380.4
MW (Da)
3.63
ALogP
7
HBA
1
HBD
83.5
PSA (Ų)
0.69
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C21H16O7
MW 380.35
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness 0.95

Activity Summary

IC50 47 meas. best 7.77
EC50 5 meas. best 5.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 7.77 5.9967 17.0 3
Panc02
CHEMBL4483283
 IC50 7.21 7.21 61.0 1
PaTu 8988t
CHEMBL4296488
 IC50 6.99 6.99 102.0 1
PC-3
CHEMBL390
 IC50 6.68 5.7467 210.0 3
CFPAC-1
CHEMBL613506
 IC50 6.68 6.68 208.0 1
ECa-109 cell line
CHEMBL614668
 IC50 6.68 6.68 210.0 1
MIA PaCa-2
CHEMBL614725
 IC50 6.57 6.57 271.0 1
TE-1
CHEMBL2366092
 IC50 6.55 6.55 280.0 1
DU-145
CHEMBL613508
 IC50 6.42 6.42 380.0 1
MCF7
CHEMBL387
 IC50 6.27 6.27 540.0 1
KB
CHEMBL398
 IC50 6.11 5.5425 780.0 4
A549
CHEMBL392
 IC50 6.05 5.2717 890.0 6
Ebolavirus
CHEMBL4434621
 EC50 5.96 5.96 1086.0 1
K562
CHEMBL385
 IC50 5.78 5.3433 1670.0 3
Unchecked
CHEMBL612545
 EC50 5.78 5.28 1648.0 3
Human immunodeficiency virus 1
CHEMBL378
 IC50 5.77 5.77 1710.0 1
SARS-CoV-2
CHEMBL4303835
 IC50 5.72 5.72 1920.0 1
ATP-dependent molecular chaperone HSP82
CHEMBL1293251
 EC50 5.66 5.66 2212.0 1
MDA-MB-231
CHEMBL400
 IC50 5.64 5.64 2270.0 1
A2058
CHEMBL613503
 IC50 5.58 5.58 2600.0 1
L02
CHEMBL4296457
 IC50 5.48 5.48 3322.0 1
SW480
CHEMBL612544
 IC50 5.47 5.47 3400.0 2
HCT-116
CHEMBL394
 IC50 5.45 4.88 3540.0 2
MONO-MAC-6
CHEMBL2366062
 IC50 5.41 5.41 3900.0 1
HT-29
CHEMBL384
 IC50 5.12 4.915 7600.0 2
LNCaP
CHEMBL612518
 IC50 4.94 4.94 11500.0 1
Leishmania
CHEMBL2366686
 IC50 4.84 4.84 14400.0 1
EBC-1
CHEMBL4296411
 IC50 4.83 4.83 14800.0 1
NCI-H838
CHEMBL1075547
 IC50 4.8 4.8 16000.0 1
HepG2
CHEMBL395
 IC50 4.67 4.67 21600.0 1
Calu-1
CHEMBL613505
 IC50 4.5 4.5 31800.0 1
ADMET
CHEMBL612558
 IC50 4.45 4.45 35200.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 31.6 mL.min-1.g-1 Homo sapiens
CL 13.2 mL.min-1.g-1 Homo sapiens
CL 277.3 mL.min-1.g-1 Mus musculus
CL 83.2 mL.min-1.g-1 Mus musculus
T1/2 0.73 hr Homo sapiens
T1/2 0.08333 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 17.0 nM 7.77 Inhibition of V-ATPase in bovine chromaffin granules incubated for 1 hrs by abso... 35489224
Panc02 IC50 = 61.0 nM 7.21 Antiproliferative activity against mouse Panc02 cells assessed as inhibition of ... 36122549
PaTu 8988t IC50 = 102.0 nM 6.99 Antiproliferative activity against human PaTu 8988t cells assessed as inhibition... 36122549
ECa-109 cell line IC50 = 210.0 nM 6.68 Antiproliferative activity against human Eca-109 cells measured after 2 days by ... 36857518
CFPAC-1 IC50 = 208.0 nM 6.68 Antiproliferative activity against human CFPAC-1 cells assessed as inhibition of... 36122549
PC-3 IC50 = 210.0 nM 6.68 Antiproliferative activity against human PC-3 cells assessed as inhibition of ce... 38336655
MIA PaCa-2 IC50 = 271.0 nM 6.57 Antiproliferative activity against human MIA PaCa-2 cells assessed as inhibition... 36122549
TE-1 IC50 = 280.0 nM 6.55 Antiproliferative activity against human TE-1 cells measured after 2 days by CCK... 36857518
DU-145 IC50 = 380.0 nM 6.42 Antiproliferative activity against human DU-145 cells assessed as inhibition of ... 38336655
MCF7 IC50 = 540.0 nM 6.27 Cytotoxicity against human MCF7 cells after 72 hrs by sulforhodamine B and MTT a... 22119124
KB IC50 = 780.0 nM 6.11 Cytotoxicity against human KB cells after 72 hrs by sulforhodamine B and MTT ass... 22119124
A549 IC50 = 890.0 nM 6.05 Antiproliferative activity against human A549 cells assessed as inhibition of ce... 38336655
Ebolavirus EC50 = 1086.0 nM 5.96 Antiviral activity against recombinant Ebola virus Mayinga expressing GFP infect... 38875806
K562 IC50 = 1670.0 nM 5.78 Cytotoxicity against human K562 cells after 72 hrs by sulforhodamine B and MTT a... 22119124
Unchecked EC50 = 1648.0 nM 5.78 PUBCHEM_BIOASSAY: Luminescence Cell-Based/Microorganism Dose Confirmation HTS to... -
Human immunodeficiency virus 1 IC50 = 1710.0 nM 5.77 Antiviral activity against HIV1 virions derived from HIV/VSG-G or HIV/HA virions... 28613071
SARS-CoV-2 IC50 = 1920.0 nM 5.72 Antiviral activity against SARS-COV2 infected in african green monkey Vero E6 ce... 36857518
A549 IC50 = 2020.0 nM 5.7 Cytotoxicity against human A549 cells incubated for 24 hrs by MTS assay 36857518
ATP-dependent molecular chaperone HSP82 EC50 = 2212.0 nM 5.66 PUBCHEM_BIOASSAY: Fluorescence Cell-Based Secondary Assay to Identify Inhibitors... -
Unchecked IC50 = 2310.0 nM 5.64 Cytotoxicity against human K/VP.5 cells after 72 hrs by CellTiter96 AQueous one ... 29656990

Literature References

PubMed DOI Target Context # Activities
36122549 10.1016/j.ejmech.2022.114708 CFPAC-1 20
19540764 10.1016/j.bmc.2009.05.054 Protective antigen 10
36122549 10.1016/j.ejmech.2022.114708 ADMET 8
36122549 10.1016/j.ejmech.2022.114708 Panc02 3
22119124 10.1016/j.ejmech.2011.11.011 KB 3
22119124 10.1016/j.ejmech.2011.11.011 K562 3
11908984 10.1021/np0101651 RAW264.7 3
36857518 10.1021/acs.jnatprod.2c00580 SARS-CoV-2 3
38452116 10.1021/acs.jmedchem.3c01574 Unchecked 3
36857518 10.1021/acs.jnatprod.2c00580 A549 3
29656990 10.1016/j.bmc.2018.03.033 Unchecked 2
36122549 10.1016/j.ejmech.2022.114708 PaTu 8988t 2
36122549 10.1016/j.ejmech.2022.114708 L02 2
36122549 10.1016/j.ejmech.2022.114708 MIA PaCa-2 2
- 10.6019/CHEMBL4513161 Pseudomonas aeruginosa 2
11908984 10.1021/np0101651 NON-PROTEIN TARGET 2
19540764 10.1016/j.bmc.2009.05.054 RAW264.7 2
19540764 10.1016/j.bmc.2009.05.054 CHO 2
26059594 10.1016/j.bmc.2015.05.033 Unchecked 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2

Data from ChEMBL 36 via Core Engine