DMH-1

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H20N4O
Molecular Weight	380.4418
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)OC1=CC=C(C=C1)C2=CN3N=CC(=C3N=C2)C4=C5C=CC=CC5=NC=C4

InChI

InChIKey=JMIFGARJSWXZSH-UHFFFAOYSA-N

InChI=1S/C24H20N4O/c1-16(2)29-19-9-7-17(8-10-19)18-13-26-24-22(14-27-28(24)15-18)20-11-12-25-23-6-4-3-5-21(20)23/h3-16H,1-2H3

HIDE SMILES / InChI

Molecular Formula	C24H20N4O
Molecular Weight	380.4418
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20020776
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24603907 | https://www.ncbi.nlm.nih.gov/pubmed/26683138 | https://www.ncbi.nlm.nih.gov/pubmed/26235139

DMH1 is a potent and selective inhibitor of BMP signaling. DMH1 is a direct inhibitor of ALK2 BMP type-I receptor ALK2 (activin receptor like kinase-2). DMH1 potently inhibits neoplastic phenotype in cancer cells.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Activin receptor type-1 3 Target ID: CHEMBL5903 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20020776	Inhibitor 8504		107.9 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Glioma 25 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26683138	Primary	Basic research	Unknown Approved Use Unknown
Non-small cell lung cancer 211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24603907	Primary	Basic research	Unknown Approved Use Unknown
Ovarian cancer 160 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26235139	Primary	Basic research	Unknown Approved Use Unknown
Breast cancer 432 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24998846	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Dorsomorphin homologue 1, a highly selective small-molecule bone morphogenetic protein inhibitor, suppresses medial artery calcification.	2017-08	27374065
BMP Antagonist Gremlin 2 Limits Inflammation After Myocardial Infarction.	2016-07-22	27283840
Bone morphogenetic protein signaling promotes tumorigenesis in a murine model of high-grade glioma.	2016-07	26683138
Small molecule inhibitor of the bone morphogenetic protein pathway DMH1 reduces ovarian cancer cell growth.	2015-11-01	26235139
Directed cardiomyogenesis of human pluripotent stem cells by modulating Wnt/β-catenin and BMP signalling with small molecules.	2015-07-15	26171831
DMH1 (4-[6-(4-isopropoxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]quinoline) inhibits chemotherapeutic drug-induced autophagy.	2015-07	26579463
Inhibition of BMP signaling suppresses metastasis in mammary cancer.	2015-05-07	24998846
(4-[6-(4-isopropoxyphenyl)pyrazolo [1,5-a]pyrimidin-3-yl] quinoline) is a novel inhibitor of autophagy.	2014-11	24943256
DMH1 increases glucose metabolism through activating Akt in L6 rat skeletal muscle cells.	2014	25247550
Bone morphogenetic protein-4 mediates cardiac hypertrophy, apoptosis, and fibrosis in experimentally pathological cardiac hypertrophy.	2013-02	23248151
DMH1, a highly selective small molecule BMP inhibitor promotes neurogenesis of hiPSCs: comparison of PAX6 and SOX1 expression during neural induction.	2012-06-20	22860217
DMH1, a novel BMP small molecule inhibitor, increases cardiomyocyte progenitors and promotes cardiac differentiation in mouse embryonic stem cells.	2012	22848549
Application of small organic molecules reveals cooperative TGFβ and BMP regulation of mesothelial cell behaviors.	2011-09-16	21740033
In vivo structure-activity relationship study of dorsomorphin analogues identifies selective VEGF and BMP inhibitors.	2010-02-19	20020776

Sample Use Guides

In Vivo Use Guide

Female mice expressing MMTV.PyVmT were implanted with a 6 week slow-release osmotic pump containing DMH1

Route of Administration: Unknown

In Vitro Use Guide

10-100 uM DMH1 dose-dependently inhibits astrocytic proliferation and migration in vitro

Substance Class	Chemical Created by `admin` on `Wed Apr 02 18:02:50 GMT 2025` Edited by `admin` on `Wed Apr 02 18:02:50 GMT 2025`
Record UNII	BVR5X3H6XM
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

DMH-1

Code

English

DMH 1

Preferred Name

English

4-[6-[4-(1-Methylethoxy)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]quinoline

Systematic Name

English

Quinoline, 4-[6-[4-(1-methylethoxy)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]-

Systematic Name

English

Code System Code Type Description

PUBCHEM

50997747

Created by admin on Wed Apr 02 18:02:50 GMT 2025 , Edited by admin on Wed Apr 02 18:02:50 GMT 2025

PRIMARY

FDA UNII

BVR5X3H6XM

Created by admin on Wed Apr 02 18:02:50 GMT 2025 , Edited by admin on Wed Apr 02 18:02:50 GMT 2025

PRIMARY

EPA CompTox

DTXSID60679195

Created by admin on Wed Apr 02 18:02:50 GMT 2025 , Edited by admin on Wed Apr 02 18:02:50 GMT 2025

PRIMARY

CAS

1206711-16-1

Created by admin on Wed Apr 02 18:02:50 GMT 2025 , Edited by admin on Wed Apr 02 18:02:50 GMT 2025

PRIMARY

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/20020776Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24603907 | https://www.ncbi.nlm.nih.gov/pubmed/26683138 | https://www.ncbi.nlm.nih.gov/pubmed/26235139

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

Approved Use

PubMed

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20020776
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24603907 | https://www.ncbi.nlm.nih.gov/pubmed/26683138 | https://www.ncbi.nlm.nih.gov/pubmed/26235139