Adavivint (SM04690) - Moligand™, ≥97% , Inhibitor of CDC like kinase 2;Inhibitor of dual specificity tyrosine phosphorylation regulated kinase 1A, CAS No.1467093-03-3, Inhibitor of CDC like kinase 2;Inhibitor of dual specificity tyrosine phosphorylation regulated kinase 1A

CAS: 1467093-03-3 Cat. No.: A414162 Molecular Weight: 505.55

GRADE & PURITY Moligand™, ≥97%

Synonyms

1467093-03-3 (free base) | AC-31570 | 42EK42WHI5 | AKOS040758781 | GTPL9620 | SCHEMBL23777531 | (+)-clopidogrel1R(-)camphor-10-sulphonic acid salt | N-(5-{3-[7-(3-fluorophenyl)-1H-imidazo[4,5-c]pyridin-2-yl]-1H-indazol-5-yl}pyridin-3-yl)-3-methylbutanamid

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

Adavivint (SM04690) Adavivint (SM04690) is a potent and specific inhibitor of canonical Wnt signaling with an EC50 of 19.5 nM for inhibiting the TCF/LEF reporter. It is ∼150- to 500-fold more potent than the other known Wnt inhibitors across multiple cellular assays.

Targets

Wnt

In vitro

Bone-marrow-derived hMSCs (CD29+, CD44+ CD166+ CD105+ CD45-), treated with SM04690, show a dose-dependent decrease in the expression of Wnt pathway genes (ASCL1, LEF1, TCF7L2, TCF7, C-262 MYC and AXIN2). M04690 also inhibits the expression of AXIN2, TCF7 and LEF1 in hMSCs and AXIN2 and LGR5 in IEC6 (intestinal stem cells sensitive to Wnt activation) when the Wnt pathway is selectively activated using either Wnt3a or a GSK3β inhibitor, CHIR-99021. SM04690 has minimal effects on the non-canonical Wnt pathway and the BMP pathway. SM04690 protects chondrocytes from catabolic breakdown in vitro.

In vivo

Intra-articular injection of SM04690 promotes cartilage growth and improves joint health in a rat model of knee osteoarthritis. It decreases cartilage breakdown in vivo.

Cell Research(from reference)

Cell lines：SW480 cells and hMSCs 

Concentrations：10, 30 and 100 nM 

Incubation Time：48 h 

Specifications

Synonyms

1467093-03-3 (free base) | AC-31570 | 42EK42WHI5 | AKOS040758781 | GTPL9620 | SCHEMBL23777531 | (+)-clopidogrel1R(-)camphor-10-sulphonic acid salt | N-(5-{3-[7-(3-fluorophenyl)-1H-imidazo[4, 5-c]pyridin-2-yl]-1H-indazol-5-yl}pyridin-3-yl)-3-methylbutanamid

Specifications & Purity

Moligand™, ≥97%

Biochemical and Physiological Mechanisms

Adavivint (SM04690) is a potent and specific inhibitor of canonical Wnt signaling with an EC50 of 19.5 nM for inhibiting the TCF/LEF reporter. It is ∼150- to 500-fold more potent than the other known Wnt inhibitors across multiple cellular assays.

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.

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Inhibitor of CDC like kinase 2;Inhibitor of dual specificity tyrosine phosphorylation regulated kinase 1A

Purity

≥97%

Product Properties

• ALogP: 4.779
• hba_count: 5
• HBD Count: 3
• Rotatable Bond: 6

Names and Identifiers

• Pubchem Sid: 488202971
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488202971
• Canonical Smiles: CC(C)CC(=O)NC1=CN=CC(=C1)C2=CC3=C(C=C2)NN=C3C4=NC5=C(N4)C=NC=C5C6=CC(=CC=C6)F
• IUPAC Name: N-[5-[3-[7-(3-fluorophenyl)-3H-imidazo[4,5-c]pyridin-2-yl]-1H-indazol-5-yl]pyridin-3-yl]-3-methylbutanamide
• InChIKey: AQDWDWAYVBQMAM-UHFFFAOYSA-N
• INCHI: 1S/C29H24FN7O/c1-16(2)8-26(38)33-21-10-19(12-31-13-21)17-6-7-24-22(11-17)28(37-36-24)29-34-25-15-32-14-23(27(25)35-29)18-4-3-5-20(30)9-18/h3-7,9-16H,8H2,1-2H3,(H,33,38)(H,34,35)(H,36,37)
• Isomeric SMILES: CC(C)CC(=O)NC1=CN=CC(=C1)C2=CC3=C(C=C2)NN=C3C4=NC5=C(N4)C=NC=C5C6=CC(=CC=C6)F
• Alternate CAS: 1467093-03-3
• MeSH Entry Terms: adavivint;lorecivivint;N-(5-((3Z)-3-(7-(3-fluorophenyl)imidazo(4,5-c)pyridin-2-ylidene)-1,2-dihydroindazol-5-yl)pyridin-3-yl)-3-methylbutanamide;SM-04690;SM04690
• Molecular Weight: 505.55
• Reaxy-Rn: 23960998
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=23960998&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pyridines and derivatives
      • Subclass Phenylpyridines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pyridines and derivatives
• Subclass: Phenylpyridines
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylpyridines
• Alternative Parents: Indazoles Imidazo-[4,5-c]pyridines N-arylamides Fluorobenzenes Fatty amides Aryl fluorides Pyrazoles Imidazoles Heteroaromatic compounds Secondary carboxylic acid amides Azacyclic compounds Organopnictogen compounds Organofluorides Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 3-phenylpyridine - Imidazo-[4,5-c]pyridine - Indazole - Imidazopyridine - Benzopyrazole - N-arylamide - Halobenzene - Fluorobenzene - Fatty acyl - Benzenoid - Fatty amide - Monocyclic benzene moiety - Aryl halide - Aryl fluoride - Heteroaromatic compound - Pyrazole - Imidazole - Azole - Secondary carboxylic acid amide - Carboxamide group - Azacycle - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organofluoride - Organohalogen compound - Carbonyl group - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond.
• 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)

DYRK1A Tchem Dual specificity tyrosine-phosphorylation-regulated kinase 1A (2 Activities)

Discover Target: DYRK1A

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

CLK2 Tchem Dual specificity protein kinase CLK2 (2 Activities)

Discover Target: CLK2

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

ABL1 Tclin Tyrosine-protein kinase ABL (18331 Activities)

Discover Target: ABL1

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

GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)

Discover Target: GSK3B

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

CSNK1D Tchem Casein kinase I delta (4546 Activities)

Discover Target: CSNK1D

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

CSNK1E Tclin Casein kinase I epsilon (1412 Activities)

Discover Target: CSNK1E

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

CDK2 Tchem Cyclin-dependent kinase 2 (9050 Activities)

Discover Target: CDK2

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

DYRK1A Tchem Dual-specificity tyrosine-phosphorylation regulated kinase 1A (6484 Activities)

Discover Target: DYRK1A

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

AURKA Tchem Serine/threonine-protein kinase Aurora-A (10240 Activities)

Discover Target: AURKA

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

CLK1 Tchem Dual specificty protein kinase CLK1 (2189 Activities)

Discover Target: CLK1

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

CLK2 Tchem Dual specificity protein kinase CLK2 (3942 Activities)

Discover Target: CLK2

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

CLK3 Tchem Dual specificity protein kinase CLK3 (2711 Activities)

Discover Target: CLK3

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

CLK4 Tchem Dual specificity protein kinase CLK4 (4053 Activities)

Discover Target: CLK4

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

U2OS (164939 Activities)

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

DYRK2 Tchem Dual-specificity tyrosine-phosphorylation regulated kinase 2 (2095 Activities)

Discover Target: DYRK2

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

DYRK3 Tchem Dual-specificity tyrosine-phosphorylation regulated kinase 3 (1018 Activities)

Discover Target: DYRK3

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

DYRK1B Tchem Dual specificity tyrosine-phosphorylation-regulated kinase 1B (2654 Activities)

Discover Target: DYRK1B

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

DYRK4 Tchem Dual specificity tyrosine-phosphorylation-regulated kinase 4 (692 Activities)

Discover Target: DYRK4

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

BRD4 Tchem Bromodomain-containing protein 4 (13122 Activities)

Discover Target: BRD4

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

CDK5 Tchem Cyclin-dependent kinase 5/CDK5 activator 1 (3697 Activities)

Discover Target: CDK5

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

TRIM24 Tchem Transcription intermediary factor 1-alpha (2087 Activities)

Discover Target: TRIM24

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

BRPF1 Tchem Peregrin (2217 Activities)

Discover Target: BRPF1

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

Associated Targets(non-human)

Mapk1 MAP kinase ERK2 (650 Activities)

Discover Target: Mapk1

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

Fgfr3 Fibroblast growth factor receptor 3 (21 Activities)

Discover Target: Fgfr3

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

HT-22 (3261 Activities)

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 30 mg/mL (59.34 mM); Water: Insoluble; Ethanol: Insoluble
• DMSO(mg / mL) Max Solubility: 30
• DMSO(mM) Max Solubility: 59.3413114429829
• Water(mg / mL) Max Solubility: ＜1
• Molecular Weight: 505.500 g/mol
• XLogP3: 4.500
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 505.203 Da
• Monoisotopic Mass: 505.203 Da
• Topological Polar Surface Area: 112.000 Ų
• Heavy Atom Count: 38
• Formal Charge: 0
• Complexity: 816.000
• 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