Compound Detail

CHEMBL478629

DORSOMORPHIN

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c1cc(-c2cnn3cc(-c4ccc(OCCN5CCCCC5)cc4)cnc23)ccn1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL478629
Name	DORSOMORPHIN
Phase	Preclinical
Structure Type	MOL
InChI Key	XHBVYDAKJHETMP-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

399.5

MW (Da)

4.32

ALogP

HBA

HBD

55.5

PSA (Å²)

0.48

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C24H25N5O
MW	399.50
Aromatic Rings	4
Heavy Atoms	30
NP-Likeness	-1.45

Activity Summary

IC50 43 meas. best 8.7

Ki 3 meas. best 6.96

EC50 2 meas. best 6.05

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Proto-oncogene tyrosine-protein kinase Src CHEMBL267	IC50	8.7	8.7	2.0	1
Vascular endothelial growth factor receptor 2 CHEMBL279	IC50	8.4	7.58	4.0	4
Ephrin type-A receptor 2 CHEMBL2068	IC50	7.96	7.96	11.0	1
MAP kinase-interacting serine/threonine-protein kinase 1 CHEMBL4718	IC50	7.96	7.96	11.0	1
Vascular endothelial growth factor receptor 1 CHEMBL1868	IC50	7.96	7.96	11.0	1
Tyrosine-protein kinase Lck CHEMBL258	IC50	7.8	7.8	16.0	1
Tyrosine-protein kinase Yes CHEMBL2073	IC50	7.53	7.12	29.8	2
AMP-activated protein kinase, AMPK CHEMBL2096907	IC50	7.39	7.015	41.0	2
Activin receptor type-1 CHEMBL5903	IC50	7.17	7.0567	67.5	3
Bone morphogenetic protein receptor type-2 CHEMBL5467	IC50	7.13	7.13	74.0	2
Bone morphogenetic protein receptor type-1A CHEMBL5275	IC50	7.02	7.02	95.0	2
TGF-beta receptor type-2 CHEMBL4267	IC50	6.99	6.99	102.9	1
Activin receptor type-1-like CHEMBL5311	IC50	6.97	6.97	106.3	1
5'-AMP-activated protein kinase catalytic subunit alpha-2 CHEMBL2116	Ki	6.96	6.96	109.0	1
Unchecked CHEMBL612545	Ki	6.96	5.98	109.0	2
Unchecked CHEMBL612545	IC50	6.96	5.7786	109.0	7
Ribosomal protein S6 kinase alpha-1 CHEMBL2553	IC50	6.68	6.68	210.0	1
5'-AMP-activated protein kinase subunit beta-1 CHEMBL3847	IC50	6.63	6.565	234.6	2
Bone morphogenetic protein receptor type-1B CHEMBL5476	IC50	6.63	6.53	235.0	3
Bone morphogenetic protein 4 CHEMBL5350	IC50	6.37	6.37	430.0	1
A2780 CHEMBL614004	EC50	6.05	6.05	900.0	1
AMP-activated protein kinase, AMPK CHEMBL4524016	IC50	5.89	5.89	1280.0	1
MCF7 CHEMBL387	EC50	5.31	5.31	4900.0	1
TGF-beta receptor type-1 CHEMBL4439	IC50	5.0	4.9275	10000.0	4
Interferon-induced, double-stranded RNA-activated protein kinase CHEMBL5785	IC50	4.8	4.8	16000.0	1
Activin receptor type-1B CHEMBL5310	IC50	4.59	4.59	25740.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	133.0	mL.min-1.g-1	Mus musculus
T1/2	0.1733	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Proto-oncogene tyrosine-protein kinase Src	IC50	=	2.0	nM	8.7	Inhibition of c-SRC by Hot Spot filtration binding assay	20932747
Vascular endothelial growth factor receptor 2	IC50	=	4.0	nM	8.4	Inhibition of KDR by Hot Spot filtration binding assay	20932747
Ephrin type-A receptor 2	IC50	=	11.0	nM	7.96	Inhibition of EphA2 by Hot Spot filtration binding assay	20932747
Vascular endothelial growth factor receptor 1	IC50	=	11.0	nM	7.96	Inhibition of FLT1 by Hot Spot filtration binding assay	20932747
MAP kinase-interacting serine/threonine-protein kinase 1	IC50	=	11.0	nM	7.96	Inhibition of MNK1 by Hot Spot filtration binding assay	20932747
Tyrosine-protein kinase Lck	IC50	=	16.0	nM	7.8	Inhibition of LCK by Hot Spot filtration binding assay	20932747
Vascular endothelial growth factor receptor 2	IC50	=	21.8	nM	7.66	Inhibition of KDR (unknown origin)	23639540
Vascular endothelial growth factor receptor 2	IC50	=	25.14	nM	7.6	Kinase Assay: Kinase assays were performed using the assay kit by Reaction Biolo...	-
Tyrosine-protein kinase Yes	IC50	=	29.8	nM	7.53	Inhibition of Yes1 (unknown origin) by [gamma-33P]-ATP radiolabeled enzyme activ...	23787099
AMP-activated protein kinase, AMPK	IC50	=	41.0	nM	7.39	Inhibition of human AMPK alpha-2/beta-1/gamma-1 by Hot Spot filtration binding a...	20932747
Activin receptor type-1	IC50	=	67.5	nM	7.17	Inhibition of ALK2 (unknown origin)	23639540
Activin receptor type-1	IC50	=	68.0	nM	7.17	Inhibition of ALK2 (unknown origin)	37312836
Bone morphogenetic protein receptor type-2	IC50	=	74.0	nM	7.13	Inhibition of BMPR2 (unknown origin)	37312836
Bone morphogenetic protein receptor type-2	IC50	=	74.0	nM	7.13	Inhibition of BMPR2 (unknown origin)	23639540
Bone morphogenetic protein receptor type-1A	IC50	=	95.0	nM	7.02	Inhibition of ALK3 (unknown origin)	23639540
Bone morphogenetic protein receptor type-1A	IC50	=	95.0	nM	7.02	Inhibition of ALK3 (unknown origin)	37312836
TGF-beta receptor type-2	IC50	=	102.9	nM	6.99	Inhibition of TGFBR2 (unknown origin)	23639540
Activin receptor type-1-like	IC50	=	106.3	nM	6.97	Inhibition of ALK1 (unknown origin)	23639540
5'-AMP-activated protein kinase catalytic subunit alpha-2	Ki	=	109.0	nM	6.96	Binding affinity to AMPK (unknown origin) assessed as inhibition constant	38295689
Unchecked	Ki	=	109.0	nM	6.96	Reversible competitive inhibition of Sprague-Dawley rat liver AMPK using 33P-ATP...	25122135

Literature References

PubMed	DOI	Target Context	# Activities
18026094	10.1038/nchembio.2007.54	Unchecked	129
34837819	10.1016/j.bmc.2021.116522	Mus musculus	8
18026094	10.1038/nchembio.2007.54	Danio rerio	7
34837819	10.1016/j.bmc.2021.116522	Unchecked	6
33635072	10.1021/acs.jnatprod.1c00002	Unchecked	6
18026094	10.1038/nchembio.2007.54	Mus musculus	5
32914624	10.1021/acs.jmedchem.0c01132	Unchecked	5
23398362	10.1042/bj20121418	Tyrosine-protein kinase HCK	4
23398362	10.1042/bj20121418	Tyrosine-protein kinase Lck	4
23398362	10.1042/bj20121418	Serine/threonine-protein kinase mTOR	4
23398362	10.1042/bj20121418	Insulin receptor	4
23398362	10.1042/bj20121418	Cyclin-dependent kinase 5/CDK5 activator 1	4
32914624	10.1021/acs.jmedchem.0c01132	AMP-activated protein kinase, AMPK	4
23398362	10.1042/bj20121418	Insulin-like growth factor 1 receptor	4
23398362	10.1042/bj20121418	Protein kinase C beta type	4
23398362	10.1042/bj20121418	cGMP-dependent protein kinase 1	4
23398362	10.1042/bj20121418	Ephrin type-A receptor 4	2
23398362	10.1042/bj20121418	Inhibitor of nuclear factor kappa-B kinase subunit alpha	2
23398362	10.1042/bj20121418	Tyrosine-protein kinase Fyn	2
23398362	10.1042/bj20121418	Calcium/calmodulin-dependent protein kinase type 1D	2

Data from ChEMBL 36 via Core Engine