Cdk4 inhibitor - Moligand™ , Inhibitor of cyclin dependent kinase 1;Inhibitor of cyclin dependent kinase 2;Inhibitor of cyclin dependent kinase 4, CAS No.546102-60-7, Inhibitor of cyclin dependent kinase 1;Inhibitor of cyclin dependent kinase 2;Inhibitor of cyclin dependent kinase 4

CAS: 546102-60-7 Cat. No.: C336666 Molecular Weight: 404.22 EC Number: 111-110-4

GRADE & PURITY Moligand™

Synonyms

K00024 (cdk4 inhibitor) | SCHEMBL1395043 | DTXSID00416208 | Cdk4 Inhibitor | 2-Bromo-12,13-dihydro-5H-indolo(2,3-a)pyrrolo(3,4-C)carbazole-5,7(6H)-dione | BDBM6860 | Indolocarbazole deriv. 4(d) | UNII-XZ73ATU8W7 | 2-Bromo-12,13-dihydro-5H-indolo[2,3-a]pyr

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

Cdk4 Inhibitor is a cell-permeable, unsymmetrical indolocarbazole compound that displays antiproliferative properties. Acts as a potent, selective, and ATP-competitive inhibitor of Cdk4/cyclin D1 (IC|50|= 76 nM). It inhibits the activity of other Cdk's only at much higher concentrations (IC|50|= 520 nM and 2.1 μM for Cdk2/cyclin E and Cdc2 (Cdk1)/cyclin B, respectively) and shows little activity towards CaMKII, PKA, or GSK-3b (IC|50|≥ 12.4 μM). Shown to inhibit tumor cells growth (IC|50|< 3.0 μM in HCT-116 and NCI-H460 cells) by blocking Rb phosphorylation and inducing G1 cell cycle arrest.

Specifications

Synonyms

K00024 (cdk4 inhibitor) | SCHEMBL1395043 | DTXSID00416208 | Cdk4 Inhibitor | 2-Bromo-12, 13-dihydro-5H-indolo(2, 3-a)pyrrolo(3, 4-C)carbazole-5, 7(6H)-dione | BDBM6860 | Indolocarbazole deriv. 4(d) | UNII-XZ73ATU8W7 | 2-Bromo-12, 13-dihydro-5H-indolo[2, 3-a]pyr

Specifications & Purity

Moligand™

Storage

Store at 2-8°C

Shipped In

Wet ice

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

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Inhibitor of cyclin dependent kinase 1;Inhibitor of cyclin dependent kinase 2;Inhibitor of cyclin dependent kinase 4

Product Properties

• pKa: pKa: 10.27

Names and Identifiers

• Canonical Smiles: C1=CC=C2C(=C1)C3=C4C(=C5C6=C(C=C(C=C6)Br)NC5=C3N2)C(=O)NC4=O
• IUPAC Name: 6-bromo-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17,19,21-nonaene-12,14-dione
• InChIKey: NMFKDDRQSNVETB-UHFFFAOYSA-N
• INCHI: 1S/C20H10BrN3O2/c21-8-5-6-10-12(7-8)23-18-14(10)16-15(19(25)24-20(16)26)13-9-3-1-2-4-11(9)22-17(13)18/h1-7,22-23H,(H,24,25,26)
• Isomeric SMILES: C1=CC=C2C(=C1)C3=C4C(=C5C6=C(C=C(C=C6)Br)NC5=C3N2)C(=O)NC4=O
• Molecular Weight: 404.22
• Reaxy-Rn: 9440845
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=9440845&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Indoles and derivatives
      • Subclass Carbazoles
        • Level5 Pyrrolocarbazoles
          • Level6 Indolocarbazoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Indoles and derivatives
• Subclass: Carbazoles
• Intermediate Tree Nodes: Pyrrolocarbazoles
• Direct Parent: Indolocarbazoles
• Alternative Parents: Pyrrolo[2,3-a]carbazoles Pyrroloindoles Phthalimides Indoles Benzenoids Aryl bromides Pyrroles N-unsubstituted carboxylic acid imides Heteroaromatic compounds Azacyclic compounds Organooxygen compounds Organonitrogen compounds Organobromides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Indolocarbazole - Pyrrolo[2,3-a]carbazole - Pyrroloindole - Phthalimide - Isoindolone - Indole - Isoindoline - Isoindole or derivatives - Aryl bromide - Aryl halide - Benzenoid - Carboxylic acid imide - Heteroaromatic compound - Pyrrole - Carboxylic acid imide, n-unsubstituted - Carboxylic acid derivative - Azacycle - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organohalogen compound - Organobromide - Organonitrogen compound - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as indolocarbazoles. These are polycyclic aromatic compounds containing an indole fused to a carbazole.
• 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)

CDK1 Tchem Cyclin-dependent kinase 1 (1 Activities)

Discover Target: CDK1

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

CDK4 Tclin Cyclin-dependent kinase 4 (1 Activities)

Discover Target: CDK4

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

CDK2 Tchem Cyclin-dependent kinase 2 (1 Activities)

Discover Target: CDK2

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

EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

Discover Target: EGFR

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

INSR Tclin Insulin receptor (5558 Activities)

Discover Target: INSR

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

PDGFRB Tclin Platelet-derived growth factor receptor beta (5195 Activities)

Discover Target: PDGFRB

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

IGF1R Tclin Insulin-like growth factor I receptor (8605 Activities)

Discover Target: IGF1R

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

KIT Tclin Stem cell growth factor receptor (10667 Activities)

Discover Target: KIT

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

DAPK3 Tchem Death-associated protein kinase 3 (2108 Activities)

Discover Target: DAPK3

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

MAPK11 Tchem MAP kinase p38 beta (2785 Activities)

Discover Target: MAPK11

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

LCK Tclin Tyrosine-protein kinase LCK (9212 Activities)

Discover Target: LCK

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

MAPK14 Tchem MAP kinase p38 alpha (12866 Activities)

Discover Target: MAPK14

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

PRKCZ Tchem Protein kinase C zeta (2414 Activities)

Discover Target: PRKCZ

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

MAP2K6 Tchem Dual specificity mitogen-activated protein kinase kinase 6 (1284 Activities)

Discover Target: MAP2K6

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

MYLK Tchem Myosin light chain kinase, smooth muscle (1267 Activities)

Discover Target: MYLK

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

CSNK1G1 Tchem Casein kinase I gamma 1 (2496 Activities)

Discover Target: CSNK1G1

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

FGFR2 Tclin Fibroblast growth factor receptor 2 (3405 Activities)

Discover Target: FGFR2

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

FGFR1 Tclin Fibroblast growth factor receptor 1 (9149 Activities)

Discover Target: FGFR1

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

STK3 Tchem Serine/threonine-protein kinase MST2 (3069 Activities)

Discover Target: STK3

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

CAMK2B Tchem CaM kinase II beta (1626 Activities)

Discover Target: CAMK2B

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

SRC Tclin Tyrosine-protein kinase SRC (10310 Activities)

Discover Target: SRC

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

CHEK2 Tchem Serine/threonine-protein kinase Chk2 (4015 Activities)

Discover Target: CHEK2

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

PDPK1 Tchem 3-phosphoinositide dependent protein kinase-1 (3758 Activities)

Discover Target: PDPK1

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

AKT2 Tchem Serine/threonine-protein kinase AKT2 (4301 Activities)

Discover Target: AKT2

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

AKT3 Tchem Serine/threonine-protein kinase AKT3 (3157 Activities)

Discover Target: AKT3

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

CHUK Tchem Inhibitor of nuclear factor kappa B kinase alpha subunit (3170 Activities)

Discover Target: CHUK

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

IKBKB Tchem Inhibitor of nuclear factor kappa B kinase beta subunit (5554 Activities)

Discover Target: IKBKB

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

DAPK2 Tchem Death-associated protein kinase 2 (740 Activities)

Discover Target: DAPK2

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

AURKB Tchem Serine/threonine-protein kinase Aurora-B (6805 Activities)

Discover Target: AURKB

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

RPS6KA4 Tchem Ribosomal protein S6 kinase alpha 4 (2104 Activities)

Discover Target: RPS6KA4

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

ROCK1 Tclin Rho-associated protein kinase 1 (4723 Activities)

Discover Target: ROCK1

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

PIM1 Tchem Serine/threonine-protein kinase PIM1 (9629 Activities)

Discover Target: PIM1

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

PKN2 Tchem Protein kinase N2 (1991 Activities)

Discover Target: PKN2

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

CSK Tchem Tyrosine-protein kinase CSK (2395 Activities)

Discover Target: CSK

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

JAK3 Tclin Tyrosine-protein kinase JAK3 (8349 Activities)

Discover Target: JAK3

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

RPS6KA5 Tchem Ribosomal protein S6 kinase alpha 5 (3355 Activities)

Discover Target: RPS6KA5

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

PRKCE Tchem Protein kinase C epsilon (1520 Activities)

Discover Target: PRKCE

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

PRKCG Tchem Protein kinase C gamma (2471 Activities)

Discover Target: PRKCG

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

PRKCI Tchem Protein kinase C iota (2821 Activities)

Discover Target: PRKCI

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

PRKD1 Tchem Protein kinase C mu (1904 Activities)

Discover Target: PRKD1

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

RAF1 Tclin Serine/threonine-protein kinase RAF (4169 Activities)

Discover Target: RAF1

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

SYK Tclin Tyrosine-protein kinase SYK (7372 Activities)

Discover Target: SYK

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

PLK1 Tchem Serine/threonine-protein kinase PLK1 (28605 Activities)

Discover Target: PLK1

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

ITK Tclin Tyrosine-protein kinase ITK/TSK (3699 Activities)

Discover Target: ITK

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

RPS6KA1 Tchem Ribosomal protein S6 kinase alpha 1 (2796 Activities)

Discover Target: RPS6KA1

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

JAK2 Tclin Tyrosine-protein kinase JAK2 (12915 Activities)

Discover Target: JAK2

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

RPS6KA6 Tchem Ribosomal protein S6 kinase alpha 6 (2027 Activities)

Discover Target: RPS6KA6

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

CAMK1 Tchem CaM kinase I alpha (1664 Activities)

Discover Target: CAMK1

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

CAMK4 Tbio CaM kinase IV (2116 Activities)

Discover Target: CAMK4

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

FLT1 Tclin Vascular endothelial growth factor receptor 1 (6262 Activities)

Discover Target: FLT1

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

Associated Targets(non-human)

Prkcd Protein kinase C delta (192 Activities)

Discover Target: Prkcd

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

Prkcb Protein kinase C beta (2 Activities)

Discover Target: Prkcb

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

Mapk1 MAP kinase ERK2 (650 Activities)

Discover Target: Mapk1

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

Fgfr4 Fibroblast growth factor receptor 4 (138 Activities)

Discover Target: Fgfr4

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

Camk2g CaM kinase II gamma (1 Activities)

Discover Target: Camk2g

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

Tec Tyrosine-protein kinase TEC (25 Activities)

Discover Target: Tec

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO (1 mg/ml).
• Refractive Index: n20D1.96 (Predicted)
• Melt Point(°C): 325° C (Predicted)
• Molecular Weight: 404.200 g/mol
• XLogP3: 4.300
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 402.996 Da
• Monoisotopic Mass: 402.996 Da
• Topological Polar Surface Area: 77.800 Ų
• Heavy Atom Count: 26
• Formal Charge: 0
• Complexity: 657.000
• 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