Domatinostat (4SC-202) - ≥97% , CAS No.910462-43-0

CAS: 910462-43-0 Cat. No.: D413781 Molecular Weight: 447.51 EC Number: 859-210-3

GRADE & PURITY ≥97%

Synonyms

DB13101 | DOMATINOSTAT [WHO-DD] | HY-16012A | 4SC202 | 4SC-202 | 4SC-202 (free base) | AS-77606 | A860619 | C3202 | DOMATINOSTAT [INN] | CCG-269205 | SCHEMBL1613943 | 264ARM7UXX | Q27254045 | (E)-N-(2-aminophenyl)-3-(1-((4-(1-methyl-1H-pyrazol-4-yl)phenyl

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

Domatinostat (4SC-202) is a selective class IHDACinhibitor withIC50of 1.20 μM, 1.12 μM, and 0.57 μM for HDAC1, HDAC2, and HDAC3, respectively. Also displays inhibitory activity againstLysine specific demethylase 1 (LSD1). Phase 1.

Targets

HDAC3 (Cell-free assay); HDAC2 (Cell-free assay); HDAC1 (Cell-free assay); HDAC11 (Cell-free assay); HDAC5 (Cell-free assay) 15602,0.57 μM; 1.12 μM; 1.20 μM; 9.7 μM; 11.3 μM

In vitro

In HeLa cells, 4SC-202 induces hyperacetylation of histone H3 with EC50 of 1.1 μM. 4SC-202 induces a G2/M cell cycle arrest by interfering with the normal development of the mitotic spindle and causing collapsed spindle apparatus and multiple nucleation centres. In addition, 4SC-202 shows a broad anti-proliferative activity towards human cancer cell lines with a mean IC50 of 0.7 μM.

In vivo

4SC-202 has a high oral bioavailability, and shows high metabolic stability and a low plasma clearance. 4SC-202 (120 mg/kg p.o.) shows pronounced and robust anti-tumor activity in both A549 NSCLC xenograft and RKO27 colon carcinoma model.

Cell Research(from reference)

Cell lines：CRC lines (HT-29, HCT-116, HT-15, and DLD-1) 

Concentrations：0.1, 1, 5, 10 μM 

Incubation Time：72 hours 

Specifications

Synonyms

DB13101 | DOMATINOSTAT [WHO-DD] | HY-16012A | 4SC202 | 4SC-202 | 4SC-202 (free base) | AS-77606 | A860619 | C3202 | DOMATINOSTAT [INN] | CCG-269205 | SCHEMBL1613943 | 264ARM7UXX | Q27254045 | (E)-N-(2-aminophenyl)-3-(1-((4-(1-methyl-1H-pyrazol-4-yl)phenyl

Specifications & Purity

≥97%

Biochemical and Physiological Mechanisms

Domatinostat (4SC-202) is a selective class I HDAC inhibitor with IC50 of 1.20 μM, 1.12 μM, and 0.57 μM for HDAC1, HDAC2, and HDAC3, respectively. Also displays inhibitory activity against Lysine specific demethylase 1 (LSD1). Phase 1.

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

≥97%

Product Properties

• ALogP: 2.955
• hba_count: 4
• HBD Count: 2
• Rotatable Bond: 6

Names and Identifiers

• Pubchem Sid: 504767996
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504767996
• Canonical Smiles: CN1C=C(C=N1)C2=CC=C(C=C2)S(=O)(=O)N3C=CC(=C3)C=CC(=O)NC4=CC=CC=C4N
• IUPAC Name: (E)-N-(2-aminophenyl)-3-[1-[4-(1-methylpyrazol-4-yl)phenyl]sulfonylpyrrol-3-yl]prop-2-enamide
• InChIKey: PRXXYMVLYKJITB-IZZDOVSWSA-N
• INCHI: 1S/C23H21N5O3S/c1-27-16-19(14-25-27)18-7-9-20(10-8-18)32(30,31)28-13-12-17(15-28)6-11-23(29)26-22-5-3-2-4-21(22)24/h2-16H,24H2,1H3,(H,26,29)/b11-6+
• Isomeric SMILES: CN1C=C(C=N1)C2=CC=C(C=C2)S(=O)(=O)N3C=CC(=C3)/C=C/C(=O)NC4=CC=CC=C4N
• Molecular Weight: 447.51
• Reaxy-Rn: 31334496
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=31334496&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Azoles
      • Subclass Pyrazoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Azoles
• Subclass: Pyrazoles
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylpyrazoles
• Alternative Parents: 2'-Aminoanilides Benzenesulfonamides Benzenesulfonyl compounds N-arylamides Aniline and substituted anilines Substituted pyrroles Sulfonyls Organosulfonic acids and derivatives Heteroaromatic compounds Secondary carboxylic acid amides Amino acids and derivatives Azacyclic compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides Primary amines
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Phenylpyrazole - Benzenesulfonamide - 2'-aminoanilide - Benzenesulfonyl group - Anilide - N-arylamide - Aniline or substituted anilines - Monocyclic benzene moiety - Substituted pyrrole - Benzenoid - Heteroaromatic compound - Sulfonyl - Organosulfonic acid or derivatives - Organic sulfonic acid or derivatives - Pyrrole - Amino acid or derivatives - Secondary carboxylic acid amide - Carboxamide group - Azacycle - Carboxylic acid derivative - Organic oxide - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Primary amine - Carbonyl group - Organic nitrogen compound - Amine - Hydrocarbon derivative - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole 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)

KDM1A Tchem Lysine-specific histone demethylase 1A (1 Activities)

Discover Target: KDM1A

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

HDAC3 Tclin Histone deacetylase 3 (2 Activities)

Discover Target: HDAC3

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

HDAC8 Tclin Histone deacetylase 8 (4516 Activities)

Discover Target: HDAC8

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

HDAC10 Tclin Histone deacetylase 10 (801 Activities)

Discover Target: HDAC10

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

HDAC2 Tclin Histone deacetylase 2 (3971 Activities)

Discover Target: HDAC2

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

HDAC3 Tclin Histone deacetylase 3 (3654 Activities)

Discover Target: HDAC3

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

HDAC4 Tclin Histone deacetylase 4 (2328 Activities)

Discover Target: HDAC4

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

HDAC9 Tclin Histone deacetylase 9 (708 Activities)

Discover Target: HDAC9

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

HDAC11 Tclin Histone deacetylase 11 (967 Activities)

Discover Target: HDAC11

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

HDAC7 Tclin Histone deacetylase 7 (1047 Activities)

Discover Target: HDAC7

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

PC-3 (62116 Activities)

Explore this target

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

KDM1A Tchem Lysine-specific histone demethylase 1 (3916 Activities)

Discover Target: KDM1A

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

Associated Targets(non-human)

Hdac1 Histone deacetylase 1 (93 Activities)

Discover Target: Hdac1

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

Hdac5 Histone deacetylase 5 (5 Activities)

Discover Target: Hdac5

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

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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: Solubility (25°C) In vitro DMSO: 89 mg/mL (198.87 mM); Water: Insoluble; Ethanol: Insoluble
• DMSO(mg / mL) Max Solubility: 89
• DMSO(mM) Max Solubility: 198.8782374
• Water(mg / mL) Max Solubility: ＜1
• Molecular Weight: 447.500 g/mol
• XLogP3: 2.400
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 447.137 Da
• Monoisotopic Mass: 447.137 Da
• Topological Polar Surface Area: 120.000 Ų
• Heavy Atom Count: 32
• Formal Charge: 0
• Complexity: 775.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1