Compound Detail

CHEMBL241405

METHYL ROSMARINATE

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COC(=O)[C@@H](Cc1ccc(O)c(O)c1)OC(=O)/C=C/c1ccc(O)c(O)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL241405
Name	METHYL ROSMARINATE
Phase	Preclinical
Structure Type	MOL
InChI Key	XHALVRQBZGZHFE-BBOMDTFKSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

374.4

MW (Da)

1.85

ALogP

HBA

HBD

133.5

PSA (Å²)

0.34

QED

Ro5 Violations

Rot. Bonds

Natural Product First in Class Prodrug

IC50 12 meas. best 6.21

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Matrix metalloproteinase-9 CHEMBL321	IC50	6.21	6.21	610.0	1
Macrophage metalloelastase CHEMBL4393	IC50	5.56	5.56	2750.0	1
72 kDa type IV collagenase CHEMBL333	IC50	5.45	5.45	3580.0	1
MOLM-13 CHEMBL3706572	IC50	5.08	5.08	8400.0	1
RAW264.7 CHEMBL612557	IC50	4.95	4.95	11300.0	1
Interstitial collagenase CHEMBL332	IC50	4.83	4.83	14700.0	2
Stromelysin-1 CHEMBL283	IC50	4.55	4.55	28260.0	1
Collagenase 3 CHEMBL280	IC50	4.54	4.54	29030.0	1
SARS-CoV-2 CHEMBL4303835	IC50	4.24	4.145	57000.0	2
Unchecked CHEMBL612545	IC50	4.1	4.1	80000.0	1

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Matrix metalloproteinase-9	IC50	=	610.0	nM	6.21	Inhibition of human recombinant MMP9 catalytic domain incubated for 20 mins by f...	22658537
Macrophage metalloelastase	IC50	=	2750.0	nM	5.56	Inhibition of human recombinant MMP12 catalytic domain incubated for 20 mins by ...	22658537
72 kDa type IV collagenase	IC50	=	3580.0	nM	5.45	Inhibition of human recombinant MMP2 catalytic domain incubated for 20 mins by f...	22658537
MOLM-13	IC50	=	8400.0	nM	5.08	Antiproliferative activity against human MOLM13 cells by Cell-Titer Glo assay	30370766
RAW264.7	IC50	=	11300.0	nM	4.95	Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed a...	31747281
Interstitial collagenase	IC50	=	14740.0	nM	4.83	Inhibition of human recombinant MMP1 catalytic domain incubated for 20 mins by f...	22658537
Interstitial collagenase	IC50	=	14700.0	nM	4.83	Inhibition of human recombinant MMP1 catalytic domain using Dnp-Pro-beta-cyclohe...	23353736
Stromelysin-1	IC50	=	28260.0	nM	4.55	Inhibition of human recombinant MMP3 catalytic domain incubated for 20 mins by f...	22658537
Collagenase 3	IC50	=	29030.0	nM	4.54	Inhibition of human recombinant MMP13 catalytic domain incubated for 20 mins by ...	22658537
SARS-CoV-2	IC50	=	57000.0	nM	4.24	Antiviral activity against SARS-CoV-2 Omicron BA.1 infected in African green mon...	37267066
Unchecked	IC50	=	80000.0	nM	4.1	Inhibition of p56lck SH2 domain by ELISA	17418581
SARS-CoV-2	IC50	=	88920.0	nM	4.05	Antiviral activity against SARS-CoV-2 Delta infected in African green monkey Ver...	37267066

PubMed	DOI	Target Context	# Activities
37267066	10.1021/acs.jnatprod.3c00104	SARS-CoV-2	5
38665828	10.1039/d3md00455d	PC-12	4
38665828	10.1039/d3md00455d	HT-22	4
21530248	10.1016/j.bmcl.2011.02.002	HepG2	3
22658537	10.1016/j.bmc.2012.04.063	Macrophage metalloelastase	2
23353736	10.1016/j.ejmech.2012.09.047	Interstitial collagenase	2
22658537	10.1016/j.bmc.2012.04.063	Collagenase 3	2
22658537	10.1016/j.bmc.2012.04.063	Matrix metalloproteinase-9	2
22658537	10.1016/j.bmc.2012.04.063	Stromelysin-1	2
22658537	10.1016/j.bmc.2012.04.063	72 kDa type IV collagenase	2
22658537	10.1016/j.bmc.2012.04.063	Interstitial collagenase	2
17418581	10.1016/j.bmc.2006.06.059	Jurkat	2
17418581	10.1016/j.bmc.2006.06.059	Unchecked	1
21530248	10.1016/j.bmcl.2011.02.002	Unchecked	1
23333151	10.1016/j.bmcl.2012.12.077	Respiratory syncytial virus	1
30370766	10.1021/acs.jnatprod.8b00638	MOLM-13	1
30370766	10.1021/acs.jnatprod.8b00638	MOLM-14	1
30370766	10.1021/acs.jnatprod.8b00638	MV4-11	1
31747281	10.1021/acs.jnatprod.9b00697	RAW264.7	1
19711986	10.1021/np800781t	72 kDa type IV collagenase	1

Data from ChEMBL 36 via Core Engine