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Compound Detail

CHEMBL866

MYCOPHENOLIC ACID
💊 Approved Drug
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💊 Approved Drug
COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)O)C(=O)OC2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL866
Name MYCOPHENOLIC ACID
Phase Approved
Structure Type MOL
InChI Key HPNSFSBZBAHARI-RUDMXATFSA-N
Therapeutic ✓ Yes

Known Names

68618 Acide mycophenolique Acido micofenolico Mycophenolate Mycophenolate mofetil impurity, mycophenolic acid- Mycophenolic acid NSC-129185 RS-61443 [AS MOFETIL]
54
Targets
169
Activities
4
Assay Types
30
PK Parameters
20
Publications
8
Known Names
19
Indications
1
Mechanisms

Molecular Properties

320.3
MW (Da)
2.73
ALogP
5
HBA
2
HBD
93.1
PSA (Ų)
0.62
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2004
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Year 1970

Extended Properties

Molecular Formula C17H20O6
MW 320.34
Aromatic Rings 1
Heavy Atoms 23
NP-Likeness 1.84

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Inosine-5'-monophosphate dehydrogenase (IMPDH) inhibitor INHIBITOR Inosine-5'-monophosphate dehydrogenase (IMPDH) ✓ ✓

Indications

Immune System Diseases Cytomegalovirus Infections Diabetes Mellitus, Type 1 Graft vs Host Disease Graft vs Host Disease Lupus Erythematosus, Systemic Lupus Nephritis Nephrotic Syndrome Sarcoidosis, Pulmonary Uveitis, Intermediate Crohn Disease Dry Eye Syndromes Leukemia Leukemia, Myeloid, Acute Lymphoma Renal Insufficiency, Chronic Myelodysplastic Syndromes Primary Myelofibrosis Scleroderma, Systemic

ATC Classification

L04AA06
mycophenolic acid
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: IMMUNOSUPPRESSANTS

Drug Warnings

Black Box Warning
carcinogenicity
Country: United States
Black Box Warning
immune system toxicity
Country: United States
Black Box Warning
teratogenicity
Country: United States
Black Box Warning
infectious disease
Country: United States

Activity Summary

IC50 94 meas. best 9.49
EC50 48 meas. best 10.22
Ki 26 meas. best 8.22
Kd 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
PBMC
CHEMBL613107
 EC50 10.22 10.22 0.1 1
Zika virus
CHEMBL4296612
 IC50 9.49 9.49 0.3 1
Inosine-5'-monophosphate dehydrogenase 2
CHEMBL2002
 Ki 8.22 8.0743 6.0 7
Unchecked
CHEMBL612545
 Ki 8.15 6.7867 7.0 3
Inosine-5'-monophosphate dehydrogenase 2
CHEMBL2002
 IC50 7.96 7.4776 11.0 17
Inosine-5'-monophosphate dehydrogenase 1
CHEMBL1822
 IC50 7.72 7.352 19.0 5
ADMET
CHEMBL612558
 IC50 7.7 7.09 20.0 4
Unchecked
CHEMBL612545
 EC50 7.52 6.0043 30.1 7
Inosine-5'-monophosphate dehydrogenase 1
CHEMBL1822
 Ki 7.48 7.4343 33.0 7
West Nile virus
CHEMBL613730
 EC50 7.4 6.625 40.0 2
BHK-21
CHEMBL614527
 EC50 7.4 7.4 40.0 1
PBMC
CHEMBL613107
 IC50 7.36 6.7225 44.0 4
Homo sapiens
CHEMBL372
 IC50 7.24 7.24 58.0 1
MOLT-4
CHEMBL614177
 IC50 7.12 7.12 75.0 1
K562
CHEMBL385
 IC50 7.1 5.71 80.0 6
Vero
CHEMBL391
 EC50 7.1 7.1 80.0 1
Chikungunya virus
CHEMBL4296563
 IC50 7.0 7.0 100.0 1
HUVEC
CHEMBL613979
 IC50 7.0 7.0 99.2 1
Inosine-5'-monophosphate dehydrogenase
CHEMBL4295605
 IC50 6.92 6.92 120.0 1
Jurkat
CHEMBL397
 IC50 6.89 5.5925 128.0 4
Unchecked
CHEMBL612545
 IC50 6.85 5.495 140.0 6
T-cell
CHEMBL614309
 IC50 6.55 6.55 280.0 1
K562
CHEMBL385
 Ki 6.52 6.52 300.0 1
Jurkat
CHEMBL397
 EC50 6.52 5.775 300.0 2
Chlamydia pneumoniae
CHEMBL612694
 IC50 6.51 6.51 310.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.5 6.25 320.0 2
CCRF-CEM
CHEMBL382
 IC50 6.47 6.3678 340.0 9
A549
CHEMBL392
 IC50 6.4 6.16 400.0 2
Human respirovirus 3
CHEMBL613126
 EC50 6.4 6.4 400.0 2
HT-29
CHEMBL384
 IC50 6.4 5.88 400.0 3
MCF7
CHEMBL387
 IC50 6.3 6.3 500.0 1
SH-SY5Y
CHEMBL614910
 IC50 6.25 6.25 560.0 1
MIN6
CHEMBL4483258
 EC50 6.22 6.22 600.0 1
Human orthopneumovirus
CHEMBL613127
 EC50 6.22 6.22 600.0 1
Respiratory syncytial virus
CHEMBL612679
 EC50 6.22 6.22 600.0 3
PSN1
CHEMBL614241
 IC50 6.16 6.16 700.0 1
dengue virus type 2
CHEMBL613966
 IC50 6.16 6.16 700.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 6.1 5.5283 800.0 6
Vaccinia virus
CHEMBL613493
 EC50 6.0 5.7978 1000.0 9
Plasmodium berghei
CHEMBL612653
 IC50 6.0 6.0 1000.0 1
Rattus norvegicus
CHEMBL376
 IC50 6.0 6.0 1000.0 1
Sindbis virus
CHEMBL613725
 EC50 5.85 5.625 1400.0 2
UDP-glucuronosyltransferase 2B7
CHEMBL4370
 Ki 5.82 5.76 1500.0 8
Mammalian orthoreovirus 1
CHEMBL612927
 EC50 5.75 5.46 1800.0 2
dengue virus type 2
CHEMBL613966
 EC50 5.72 5.48 1900.0 2
Human coronavirus OC43
CHEMBL5209665
 EC50 5.71 5.71 1950.0 1
L1210
CHEMBL386
 IC50 5.66 5.66 2180.0 1
Yellow fever virus
CHEMBL613731
 EC50 5.64 5.52 2300.0 2
DU-145
CHEMBL613508
 IC50 5.53 5.53 2940.0 1
Cowpox virus
CHEMBL612672
 IC50 5.5 5.5 3200.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 63900.0 ng.hr.mL-1 Homo sapiens
AUC 45000.0 ng.hr.mL-1 Homo sapiens
AUC 29000.0 ng.hr.mL-1 Homo sapiens
AUC 52900.0 ng.hr.mL-1 Homo sapiens
AUC 59900.0 ng.hr.mL-1 Homo sapiens
AUC 78600.0 ng.hr.mL-1 Homo sapiens
AUC 29800.0 ng.hr.mL-1 Homo sapiens
AUC 40800.0 ng.hr.mL-1 Homo sapiens
AUC 32900.0 ng.hr.mL-1 Homo sapiens
AUC 27300.0 ng.hr.mL-1 Homo sapiens
AUC 34000.0 ng.hr.mL-1 Homo sapiens
AUC 29200.0 ng.hr.mL-1 Homo sapiens
AUC 49300.0 ng.hr.mL-1 Homo sapiens
AUC 38400.0 ng.hr.mL-1 Homo sapiens
AUC 65300.0 ng.hr.mL-1 Homo sapiens
AUC 54100.0 ng.hr.mL-1 Homo sapiens
AUC 43300.0 ng.hr.mL-1 Homo sapiens
AUC 47400.0 ng.hr.mL-1 Homo sapiens
AUC 55800.0 ng.hr.mL-1 Homo sapiens
AUC 61000.0 ng.hr.mL-1 Homo sapiens
AUC 66800.0 ng.hr.mL-1 Homo sapiens
AUC 61900.0 ng.hr.mL-1 Homo sapiens
AUC 56700.0 ng.hr.mL-1 Homo sapiens
AUC 22500.0 ng.hr.mL-1 Homo sapiens
AUC 53600.0 ng.hr.mL-1 Homo sapiens
AUC 27400.0 ng.hr.mL-1 Homo sapiens
AUC 33200.0 ng.hr.mL-1 Homo sapiens
AUC 26300.0 ng.hr.mL-1 Homo sapiens
AUC 49700.0 ng.hr.mL-1 Homo sapiens
AUC 74300.0 ng.hr.mL-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
PBMC EC50 = 0.06 nM 10.22 Antiproliferative activity against human PBMC assessed as incorporation of [3H]t... 24121309
Zika virus IC50 = 0.32 nM 9.49 Antiviral activity against Zika virus 32786878
Inosine-5'-monophosphate dehydrogenase 2 Ki = 6.0 nM 8.22 Inhibitory activity against human Inosine-5'-monophosphate dehydrogenase 2 (IMPD... 9484510
Inosine-5'-monophosphate dehydrogenase 2 Ki = 7.0 nM 8.15 Inhibition of human IMPDH type 2 17958343
Inosine-5'-monophosphate dehydrogenase 2 Ki = 7.0 nM 8.15 Inhibition of human IMPDH2 by Spectrophotometer 21324702
Unchecked Ki = 7.0 nM 8.15 Inhibition of human IMPDH 24121309
Inosine-5'-monophosphate dehydrogenase 2 Ki = 10.0 nM 8.0 Inhibitory activity against human Inosine-5'-monophosphate dehydrogenase 2 (IMPD... 11806722
Inosine-5'-monophosphate dehydrogenase 2 Ki = 10.0 nM 8.0 Inhibition of human IMPDH 2 18038969
Inosine-5'-monophosphate dehydrogenase 2 Ki = 10.0 nM 8.0 Inhibition of human IMPDH2 18809333
Inosine-5'-monophosphate dehydrogenase 2 Ki = 10.0 nM 8.0 Inhibition of human IMP dehydrogenase 2 18583139
Unchecked Ki = 10.0 nM 8.0 Binding affinity to human IMPDH 24269162
Inosine-5'-monophosphate dehydrogenase 2 IC50 = 11.0 nM 7.96 Inhibition of human IMPDH2 16621550
Inosine-5'-monophosphate dehydrogenase 2 IC50 = 12.0 nM 7.92 Inhibition of human IMPDH2 expressed in Escherichia coli strain BL21(DE3) after ... 20934342
Inosine-5'-monophosphate dehydrogenase 2 IC50 = 14.0 nM 7.85 Inhibition of human inosine monophosphate dehydrogenase IMPDH II 12565968
Inosine-5'-monophosphate dehydrogenase 2 IC50 = 14.0 nM 7.85 Inhibition of human inosine-5'-monophosphate dehydrogenase 2 12014950
Inosine-5'-monophosphate dehydrogenase 2 IC50 = 14.0 nM 7.85 Inhibitory activity against inosine monophosphate dehydrogenase IMPDH II 12565969
Inosine-5'-monophosphate dehydrogenase 2 IC50 = 15.0 nM 7.82 Inhibitory concentration against Inosine-5'-monophosphate dehydrogenase 2 was de... 12392738
Inosine-5'-monophosphate dehydrogenase 2 IC50 = 15.0 nM 7.82 In vitro inhibition of Inosine-5'-monophosphate dehydrogenase 2. 12270177
Inosine-5'-monophosphate dehydrogenase 2 IC50 = 15.0 nM 7.82 Inhibitory activity tested against inosine-5'-monophosphate dehydrogenase 2 (IMP... 14505670
Inosine-5'-monophosphate dehydrogenase 2 IC50 = 15.0 nM 7.82 Inhibition of Inosine Monophosphate Dehydrogenase II (IMPDH II) 12372516

Literature References

PubMed DOI Target Context # Activities
- 10.1101/2024.03.28.586928 ADMET 100
21123165 10.1124/dmd.110.036608 UDP-glucuronosyltransferase 2B7 32
30322754 10.1016/j.bmc.2018.09.004 Inosine-5'-monophosphate dehydrogenase 19
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
17060520 10.1128/aac.00790-06 Vero 14
- 10.6019/CHEMBL4495565 SARS-CoV-2 12
22275465 10.1124/dmd.111.043984 UDP-glucuronosyltransferase 1A9 11
36538495 10.1021/acs.jmedchem.2c01790 Albumin 11
18426895 10.1128/aac.01618-07 Unchecked 9
22275465 10.1124/dmd.111.043984 ADMET 8
22275465 10.1124/dmd.111.043984 Liver microsome 8
1967654 10.1021/jm00164a057 Mus musculus 8
16640327 10.1021/jm051225t HUVEC 8
27979594 10.1016/j.bmcl.2016.12.010 NON-PROTEIN TARGET 7
20934342 10.1016/j.bmc.2010.09.004 K562 7
- 10.6019/CHEMBL4495565 ADMET 6
8863796 10.1021/jm9603633 Mus musculus 6
- 10.6019/CHEMBL4495565 Vero C1008 6
21282406 10.1124/dmd.110.037457 Nucleic Acid 5

Data from ChEMBL 36 via Core Engine