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Compound Detail

CHEMBL324842

ROSMARINIC ACID
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O=C(/C=C/c1ccc(O)c(O)c1)O[C@H](Cc1ccc(O)c(O)c1)C(=O)O

Basic Information

ChEMBL ID CHEMBL324842
Name ROSMARINIC ACID
Phase Preclinical
Structure Type MOL
InChI Key DOUMFZQKYFQNTF-WUTVXBCWSA-N
32
Targets
70
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

360.3
MW (Da)
1.76
ALogP
7
HBA
5
HBD
144.5
PSA (Ų)
0.30
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C18H16O8
MW 360.32
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 1.13

Activity Summary

IC50 57 meas. best 6.82
EC50 7 meas. best 5.1
Kd 3 meas. best 4.99
Ki 3 meas. best 7.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1
CHEMBL5925
Ki 7.57 7.57 26.9 1
Mus musculus
CHEMBL375
IC50 6.82 6.82 150.0 1
Alpha-synuclein
CHEMBL6152
IC50 6.68 6.68 210.0 1
Human immunodeficiency virus type 1 integrase
CHEMBL3471
IC50 6.26 5.192 550.0 5
HeLa
CHEMBL399
IC50 6.02 6.02 960.0 1
Tyrosine-protein kinase Fyn
CHEMBL1841
IC50 5.89 5.0813 1300.0 8
NON-PROTEIN TARGET
CHEMBL3879801
IC50 5.74 5.74 1810.0 1
Induced myeloid leukemia cell differentiation protein Mcl-1
CHEMBL4361
IC50 5.69 5.69 2025.7 1
MOLM-13
CHEMBL3706572
IC50 5.54 5.54 2900.0 1
17-beta-hydroxysteroid dehydrogenase type 2
CHEMBL2789
IC50 5.43 5.43 3720.0 1
Aldo-keto reductase family 1 member B1
CHEMBL2622
IC50 5.41 5.41 3890.4 1
Replicase polyprotein 1ab
CHEMBL4523582
IC50 5.41 5.41 3860.0 1
Aldo-keto reductase family 1 member B1
CHEMBL1900
IC50 5.41 5.41 3910.0 1
Interstitial collagenase
CHEMBL332
IC50 5.25 5.25 5600.0 1
MOLM-14
CHEMBL3706570
IC50 5.15 5.15 7100.0 1
Tyrosine-protein kinase Fyn
CHEMBL1841
Ki 5.12 5.055 7500.0 2
Radical scavenging activity
CHEMBL613712
EC50 5.1 5.1 8000.0 1
Transthyretin
CHEMBL3194
EC50 5.07 5.07 8600.0 1
Unchecked
CHEMBL612545
Kd 4.99 4.99 10200.0 1
No relevant target
CHEMBL2362975
IC50 4.96 4.96 11000.0 1
Transcription factor Jun
CHEMBL4977
IC50 4.79 4.79 16200.0 1
Amyloid-beta precursor protein
CHEMBL2487
EC50 4.69 4.3667 20300.0 3
Lysine-specific histone demethylase 1A
CHEMBL6136
IC50 4.68 4.68 20930.0 2
Molecular identity unknown
CHEMBL612546
IC50 4.66 4.375 21900.0 2
Tyrosine-protein kinase Lck
CHEMBL258
IC50 4.62 4.44 24000.0 2
Unchecked
CHEMBL612545
IC50 4.62 4.3917 24000.0 6
Proto-oncogene tyrosine-protein kinase Src
CHEMBL267
IC50 4.58 4.58 26000.0 1
72 kDa type IV collagenase
CHEMBL1075175
IC50 4.57 4.57 27200.0 1
Hepatitis B virus
CHEMBL613497
EC50 4.52 4.52 30000.0 1
RAW264.7
CHEMBL612557
IC50 4.47 4.47 34200.0 1
UDP-galactopyranose mutase
CHEMBL5169233
Kd 4.16 4.16 69000.0 1
Amyloid-beta precursor protein
CHEMBL2487
IC50 4.14 4.14 71900.0 1
HT-22
CHEMBL614316
EC50 4.07 4.07 86000.0 1
Bifunctional protein GlmU
CHEMBL1293297
IC50 4.07 4.07 84940.0 1
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
IC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1 Ki = 26.9 nM 7.57 Binding affinity to human ENPP1 assessed as inhibition constant 38432057
Mus musculus IC50 = 150.0 nM 6.82 Antihemorrhagic activity in ddY mouse assessed as inhibition of Protobothrops fl... 21388814
Alpha-synuclein IC50 = 210.0 nM 6.68 Inhibition of alpha-synuclein fibril formation (unknown origin) incubated for 24... 30743095
Human immunodeficiency virus type 1 integrase IC50 = 550.0 nM 6.26 Inhibition of HIV1 His6-tagged integrase-human GST tagged LEDGF/p75 (373-442 res... 23046280
HeLa IC50 = 960.0 nM 6.02 Cytotoxicity against human HeLa cells assessed as inhibition of cell growth and ... 36126331
Tyrosine-protein kinase Fyn IC50 = 1300.0 nM 5.89 Inhibition of human Fyn expressed in Sf9 cells after 20 mins by ELISA in presenc... 17315853
Tyrosine-protein kinase Fyn IC50 = 1300.0 nM 5.89 ADP-Glo Kinase Assay: The assay procedure determines the IC50 of each potential ... -
Tyrosine-protein kinase Fyn IC50 = 1300.0 nM 5.89 ADP-Glo™ Kinase Assay: The ADP-Glo™ Kinase Assay is specifically designed to qua... -
NON-PROTEIN TARGET IC50 = 1810.0 nM 5.74 Antioxidant activity against Cu2+-induced lipid peroxidation in human plasma LDL... 12027757
Induced myeloid leukemia cell differentiation protein Mcl-1 IC50 = 2025.72 nM 5.69 PUBCHEM_BIOASSAY: Dose Response Confirmation for Mcl-1/Noxa Interaction Inhibito... -
MOLM-13 IC50 = 2900.0 nM 5.54 Antiproliferative activity against human MOLM13 cells by Cell-Titer Glo assay 30370766
Tyrosine-protein kinase Fyn IC50 = 3600.0 nM 5.44 Inhibition of human Fyn expressed in Sf9 cells after 20 mins by ELISA in presenc... 17315853
17-beta-hydroxysteroid dehydrogenase type 2 IC50 = 3720.0 nM 5.43 Inhibition of human 17beta-HSD2 expressed in HEK293 cell lysates incubated for 1... 28319389
Aldo-keto reductase family 1 member B1 IC50 = 3890.45 nM 5.41 Inhibition of Rattus norvegicus (rat) lens aldose reductase -
Aldo-keto reductase family 1 member B1 IC50 = 3910.0 nM 5.41 Inhibition of aldose reductase 20071057
Replicase polyprotein 1ab IC50 = 3860.0 nM 5.41 SARS-CoV-2 3CL-Pro protease inhibition IC50 determined by FRET kind of response ... -
Human immunodeficiency virus type 1 integrase IC50 = 4000.0 nM 5.4 Inhibition of strand transfer activity of HIV-1 integrase 9301668
Interstitial collagenase IC50 = 5600.0 nM 5.25 Inhibition of human recombinant MMP1 catalytic domain using Dnp-Pro-beta-cyclohe... 23353736
MOLM-14 IC50 = 7100.0 nM 5.15 Antiproliferative activity against human MOLM14 cells by Cell-Titer Glo assay 30370766
Tyrosine-protein kinase Fyn Ki = 7500.0 nM 5.12 Inhibition of human Fyn expressed in Sf9 cells at 10 umol/L by ELISA 17315853

Literature References

PubMed DOI Target Context # Activities
9722482 10.1021/np980072s Rattus norvegicus 52
36322828 10.1021/acs.jnatprod.2c00767 Rattus norvegicus 19
29192771 10.1021/acs.jnatprod.7b00699 Unchecked 17
- 10.1007/s00044-011-9690-5 Rattus norvegicus 15
29477271 10.1016/j.bmcl.2018.02.025 Unchecked 14
2822857 10.1021/np50051a009 Unchecked 11
17576830 10.1128/aac.00041-07 Mus musculus 9
29477271 10.1016/j.bmcl.2018.02.025 Escherichia coli 8
17315853 10.1021/jm0607202 Tyrosine-protein kinase Fyn 8
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 5
37267066 10.1021/acs.jnatprod.3c00104 SARS-CoV-2 5
18351727 10.1021/jm7011134 Human immunodeficiency virus type 1 integrase 5
17576830 10.1128/aac.00041-07 BV-2 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
21041086 10.1016/j.bmcl.2010.10.040 Tyrosinase 4
35777270 10.1016/j.bmc.2022.116896 UDP-galactopyranose mutase 4
28759879 10.1016/j.ejmech.2017.07.026 Amyloid-beta precursor protein 4
17576830 10.1128/aac.00041-07 Japanese encephalitis virus 4
26517152 10.1021/acs.jnatprod.5b00508 Amyloid-beta precursor protein 3
7775983 10.1021/np50117a005 Unchecked 3

Data from ChEMBL 36 via Core Engine