LX7101 - Moligand™, ≥99% , CAS No.1192189-69-7

CAS: 1192189-69-7 Cat. No.: L651755 Molecular Weight: 451.52

GRADE & PURITY Moligand™, ≥99%

Synonyms

LX7101 (HCl) | UNII-74B3C4ZT96 | CARBAMIC ACID, N,N-DIMETHYL-, 3-(((4-(AMINOMETHYL)-1-(5-METHYL-7H-PYRROLO(2,3-D)PYRIMIDIN-4-YL)-4-PIPERIDINYL)CARBONYL)AMINO)PHENYL ESTER

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

LX7101 is a potent LIM-kinase, ROCK and PKA inhibitor with IC50s of 24 nM, 1.6 nM, 10 nM and <1 nM for LIMK1, LIMK2, ROCK2 and PKA, respectively. LX7101 proves significantly selective for LIMK2 with IC50 values of 4.3 nM and 32 nM for LIMK2 and LIMK1 at 2 μM ATP, respectively. LX7101 has the potential for ocular hypertension and associated glaucoma research.

Specifications

Synonyms

LX7101 (HCl) | UNII-74B3C4ZT96 | CARBAMIC ACID, N, N-DIMETHYL-, 3-(((4-(AMINOMETHYL)-1-(5-METHYL-7H-PYRROLO(2, 3-D)PYRIMIDIN-4-YL)-4-PIPERIDINYL)CARBONYL)AMINO)PHENYL ESTER

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

LX7101 is a potent inhibitor of LIMK and ROCK2 with IC 50 values of 24, 1.6 and 10 nM for LIMK1 , LIMK2 and ROCK2 , respectively; also inhibits PKA with an IC 50 less than 1 nM.

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

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CC1=CNC2=C1C(=NC=N2)N3CCC(CC3)(CN)C(=O)NC4=CC(=CC=C4)OC(=O)N(C)C
• IUPAC Name: [3-[[4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carbonyl]amino]phenyl] N,N-dimethylcarbamate
• InChIKey: PWPNYABQEOGNNC-UHFFFAOYSA-N
• INCHI: 1S/C23H29N7O3/c1-15-12-25-19-18(15)20(27-14-26-19)30-9-7-23(13-24,8-10-30)21(31)28-16-5-4-6-17(11-16)33-22(32)29(2)3/h4-6,11-12,14H,7-10,13,24H2,1-3H3,(H,28,31)(H,25,26,27)
• Isomeric SMILES: CC1=CNC2=C1C(=NC=N2)N3CCC(CC3)(CN)C(=O)NC4=CC(=CC=C4)OC(=O)N(C)C
• Alternate CAS: 1192189-69-7;2319882-48-7;1374644-80-0
• MeSH Entry Terms: LX-7101
• Molecular Weight: 451.52

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Beta amino acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives
• Direct Parent: Beta amino acids and derivatives
• Alternative Parents: Anilides Pyrrolo[2,3-d]pyrimidines Piperidinecarboxamides Phenoxy compounds Dialkylarylamines N-arylamides Aminopyrimidines and derivatives Substituted pyrroles Imidolactams Heteroaromatic compounds Carbamate esters Secondary carboxylic acid amides Azacyclic compounds Hydrocarbon derivatives Organic oxides Carbonyl compounds Monoalkylamines
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Beta amino acid or derivatives - Pyrrolo[2,3-d]pyrimidine - Piperidinecarboxamide - Pyrrolopyrimidine - Anilide - Phenoxy compound - N-arylamide - Dialkylarylamine - Aminopyrimidine - Monocyclic benzene moiety - Piperidine - Pyrimidine - Substituted pyrrole - Benzenoid - Imidolactam - Pyrrole - Heteroaromatic compound - Carbamic acid ester - Tertiary amine - Secondary carboxylic acid amide - Carboxamide group - Azacycle - Organoheterocyclic compound - Amine - Organic oxide - Organooxygen compound - Organonitrogen compound - Primary aliphatic amine - Organic nitrogen compound - Primary amine - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.
• 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)

ROCK2 Tclin Rho-associated protein kinase 2 (2 Activities)

Discover Target: ROCK2

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

LIMK1 Tchem LIM domain kinase 1 (2 Activities)

Discover Target: LIMK1

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

LIMK2 Tchem LIM domain kinase 2 (4 Activities)

Discover Target: LIMK2

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

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

ROCK2 Tclin Rho-associated protein kinase 2 (6206 Activities)

Discover Target: ROCK2

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

PRKACA Tchem cAMP-dependent protein kinase alpha-catalytic subunit (3475 Activities)

Discover Target: PRKACA

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

AKT1 Tchem Serine/threonine-protein kinase AKT (9192 Activities)

Discover Target: AKT1

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

RPS6KB1 Tchem Ribosomal protein S6 kinase 1 (4456 Activities)

Discover Target: RPS6KB1

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

LIMK1 Tchem LIM domain kinase 1 (2329 Activities)

Discover Target: LIMK1

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

PRKX Tchem Serine/threonine-protein kinase PRKX (2278 Activities)

Discover Target: PRKX

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

LIMK2 Tchem LIM domain kinase 2 (949 Activities)

Discover Target: LIMK2

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

PRKACB Tchem cAMP-dependent protein kinase (PKA) (929 Activities)

Discover Target: PRKACB

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

LIMK2 Tchem LIM domain kinase 1/2 (20 Activities)

Discover Target: LIMK2

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

Oryctolagus cuniculus (11301 Activities)

Explore this target

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

Rattus norvegicus (775804 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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 150 mg/mL (332.21 mM; Need ultrasonic)
• Molecular Weight: 451.500 g/mol
• XLogP3: 2.000
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 451.233 Da
• Monoisotopic Mass: 451.233 Da
• Topological Polar Surface Area: 129.000 Ų
• Heavy Atom Count: 33
• Formal Charge: 0
• Complexity: 698.000
• 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