LDN-193189 - ≥98% , CAS No.1062368-24-4

CAS: 1062368-24-4 Cat. No.: L127229 Molecular Weight: 479.4

GRADE & PURITY ≥98%

Synonyms

Q27163247 | BCP9000845 | AC-31395 | AS-73735 | DM 3189 hydrochloride | BROMOACETIC-13C2ACID | EX-A424 | BRD-K04853698-003-01-4 | tri-sodium citrate | EX-8677 | NCGC00249389-21 | LDN 193189 | 1062368-24-4 | CHEBI:91387 | LDN193189 free base | 4-{6-[4-(1-pi

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

LDN193189 is a selective BMP signaling inhibitor, inhibits the transcriptional activity of the BMP type I receptors ALK2 and ALK3 with IC50 of 5 nM and 30 nM, respectively, exhibits 200-fold selectivity for BMP versus TGF-β.

Specifications

Synonyms

Q27163247 | BCP9000845 | AC-31395 | AS-73735 | DM 3189 hydrochloride | BROMOACETIC-13C2ACID | EX-A424 | BRD-K04853698-003-01-4 | tri-sodium citrate | EX-8677 | NCGC00249389-21 | LDN 193189 | 1062368-24-4 | CHEBI:91387 | LDN193189 free base | 4-{6-[4-(1-pi

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

LDN193189 is a highly potent small molecule BMP inhibitor; inhibiting BMP type I receptors ALK2 (IC50: 5 nM), ALK3 (IC50: 30 nM) and ALK6 (TGFβ1/BMP signaling) and subsequent SMAD phosphorylation; LDN193189 is useful tool in stem cell biol

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C1CN(CCN1)C2=CC=C(C=C2)C3=CN4C(=C(C=N4)C5=CC=NC6=CC=CC=C56)N=C3
• IUPAC Name: 4-[6-(4-piperazin-1-ylphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]quinoline
• InChIKey: CDOVNWNANFFLFJ-UHFFFAOYSA-N
• INCHI: 1S/C25H22N6/c1-2-4-24-22(3-1)21(9-10-27-24)23-16-29-31-17-19(15-28-25(23)31)18-5-7-20(8-6-18)30-13-11-26-12-14-30/h1-10,15-17,26H,11-14H2
• Isomeric SMILES: C1CN(CCN1)C2=CC=C(C=C2)C3=CN4C(=C(C=N4)C5=CC=NC6=CC=CC=C56)N=C3
• Molecular Weight: 479.4
• Reaxy-Rn: 18849206
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=18849206&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Diazinanes
      • Subclass Piperazines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Diazinanes
• Subclass: Piperazines
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylpiperazines
• Alternative Parents: N-arylpiperazines Quinolines and derivatives Pyrazolo[1,5-a]pyrimidines Dialkylarylamines Aniline and substituted anilines Pyrimidines and pyrimidine derivatives Pyridines and derivatives Pyrazoles Heteroaromatic compounds Dialkylamines Azacyclic compounds Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Phenylpiperazine - N-arylpiperazine - Quinoline - Pyrazolopyrimidine - Pyrazolo[1,5-a]pyrimidine - Tertiary aliphatic/aromatic amine - Dialkylarylamine - Aniline or substituted anilines - Benzenoid - Monocyclic benzene moiety - Pyrimidine - Pyridine - Heteroaromatic compound - Azole - Pyrazole - Tertiary amine - Azacycle - Secondary amine - Secondary aliphatic amine - Organonitrogen compound - Amine - Organic nitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TGFBR1 Tchem TGF-beta receptor type-1 (1 Activities)

Discover Target: TGFBR1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

BMPR1B Tchem Bone morphogenetic protein receptor type-1B (2 Activities)

Discover Target: BMPR1B

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

BMPR1A Tchem Bone morphogenetic protein receptor type-1A (3 Activities)

Discover Target: BMPR1A

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

BMP4 Tchem Bone morphogenetic protein 4 (1 Activities)

Discover Target: BMP4

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ACVR1 Tchem Activin receptor type-1 (4 Activities)

Discover Target: ACVR1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ACVRL1 Tchem Serine/threonine-protein kinase receptor R3 (3 Activities)

Discover Target: ACVRL1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PRKAB1 Tchem AMP-activated protein kinase, beta-1 subunit (56 Activities)

Discover Target: PRKAB1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)

Discover Target: KDR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TGFBR1 Tchem TGF-beta receptor type I (3786 Activities)

Discover Target: TGFBR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

YES1 Tclin Tyrosine-protein kinase YES (2781 Activities)

Discover Target: YES1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HepG2 (196354 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TGFBR2 Tchem TGF-beta receptor type II (795 Activities)

Discover Target: TGFBR2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BMPR1A Tchem Bone morphogenetic protein receptor type-1A (678 Activities)

Discover Target: BMPR1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACVR1B Tchem Activin receptor type-1B (1131 Activities)

Discover Target: ACVR1B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACVRL1 Tchem Serine/threonine-protein kinase receptor R3 (538 Activities)

Discover Target: ACVRL1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BMPR2 Tchem Bone morphogenetic protein receptor type-2 (640 Activities)

Discover Target: BMPR2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BMP4 Tchem Bone morphogenetic protein 4 (33 Activities)

Discover Target: BMP4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BMPR1B Tchem Bone morphogenetic protein receptor type-1B (563 Activities)

Discover Target: BMPR1B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACVR1 Tchem Activin receptor type-1 (1516 Activities)

Discover Target: ACVR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mus musculus (284745 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Tgfbr1 TGF-beta receptor type-1 (52 Activities)

Discover Target: Tgfbr1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO 0.01 mg/mL (<1 mM); Water 0.01 mg/mL (<1 mM); Ethanol <1 mg/mL (<1 mM)
• Molecular Weight: 406.500 g/mol
• XLogP3: 3.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 406.191 Da
• Monoisotopic Mass: 406.191 Da
• Topological Polar Surface Area: 58.400 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 587.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Wangyu Bi, Shanglin Cai, Liping Zhou, Jinglei Zheng, Yanxin Cui, Yingxian Li, Shuting Liu, Hongyu Chen, Shuang Sha, Jiaxin Li, Qiansu Ma, Zhaoshi Bao, Cencan Xing, Hongwu Du, Lei Wang.  (2025)  Integrated Microfluidic Hydrogel-Enhanced Microwell Array for Uniform Self-Assembly, Long-Term Culture, and Neural Differentiation of Mesenchymal Stem Cell Spheroids.  ADVANCED FUNCTIONAL MATERIALS,      [PMID:] [10.1002/adfm.202501265]

2. Qian Tang, Minji Tong, Gang Zheng, Liyan Shen, Ping Shang, Haixiao Liu.  (2018)  Masquelet’s induced membrane promotes the osteogenic differentiation of bone marrow mesenchymal stem cells by activating the Smad and MAPK pathways.  American Journal of Translational Research,      [PMID:29736214] [PMID:29736214]