ABT-199 (GDC-0199) - Moligand™,≥95% , Apoptosis regulator Bcl-2 inhibitor, CAS No.1257044-40-8, Apoptosis regulator Bcl-2 inhibitor

CAS: 1257044-40-8 Cat. No.: A1509661 Molecular Weight: 868.44 EC Number: 820-130-9

GRADE & PURITY Moligand™, ≥95%

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

ABT-199 (GDC-0199) is a BH3 mimetic that Bcl-2-selective inhibitor with Ki of <0.01 nM. B-cell lymphoma/leukemia 2 (Bcl-2) is an anti-apoptotic protein that controls cell survival by binding the BH3 domains of pro-death BAD and BAK proteins and preventing permeabilization of the mitochondrial outer membrane. This protein is tightly regulated for the homeostasis between cell growth and cell death.

Specifications

Specifications & Purity

Moligand™, ≥95%

Biochemical and Physiological Mechanisms

ABT-199 is a potent selective inhibitor of B-cell lymphoma-2 (BCL-2) family proteins and is currently undergoing clinical trials. ABT-199 can inhibit the growth of bcl-2-dependent tumors in vivo and protect human platelets. These data indicate that select

Storage

Protected from light, 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

Apoptosis regulator Bcl-2 inhibitor

Purity

≥95%

Product Properties

• ALogP: 8.2

Names and Identifiers

• Pubchem Sid: 488201440
• Canonical Smiles: CC1(CCC(=C(C1)C2=CC=C(C=C2)Cl)CN3CCN(CC3)C4=CC(=C(C=C4)C(=O)NS(=O)(=O)C5=CC(=C(C=C5)NCC6CCOCC6)[N+](=O)[O-])OC7=CN=C8C(=C7)C=CN8)C
• IUPAC Name: 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-N-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonyl-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzamide
• InChIKey: LQBVNQSMGBZMKD-UHFFFAOYSA-N
• INCHI: 1S/C45H50ClN7O7S/c1-45(2)15-11-33(39(26-45)31-3-5-34(46)6-4-31)29-51-17-19-52(20-18-51)35-7-9-38(42(24-35)60-36-23-32-12-16-47-43(32)49-28-36)44(54)50-61(57,58)37-8-10-40(41(25-37)53(55)56)48-27-30-13-21-59-22-14-30/h3-10,12,16,23-25,28,30,48H,11,13-15,17-22,26-27,29H2,1-2H3,(H,47,49)(H,50,54)
• Isomeric SMILES: CC1(CCC(=C(C1)C2=CC=C(C=C2)Cl)CN3CCN(CC3)C4=CC(=C(C=C4)C(=O)NS(=O)(=O)C5=CC(=C(C=C5)NCC6CCOCC6)[N+](=O)[O-])OC7=CN=C8C(=C7)C=CN8)C
• Molecular Weight: 868.44
• Reaxy-Rn: 20908256
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=20908256&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 Aminobenzenesulfonamides Diarylethers Aminobenzoic acids and derivatives Pyrrolopyridines Benzenesulfonyl compounds Nitrobenzenes Aniline and substituted anilines Benzoyl derivatives Dialkylarylamines Nitroaromatic compounds Phenylalkylamines Phenol ethers Phenoxy compounds N-alkylpiperazines Secondary alkylarylamines Chlorobenzenes Aryl chlorides Oxanes Pyridines and derivatives Organosulfonic acids and derivatives Aminosulfonyl compounds Pyrroles Heteroaromatic compounds Amino acids and derivatives Trialkylamines Azacyclic compounds Organic oxoazanium compounds Oxacyclic compounds Propargyl-type 1,3-dipolar organic compounds Dialkyl ethers Organopnictogen compounds Organochlorides Organic zwitterions Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Phenylpiperazine - N-arylpiperazine - Diaryl ether - Aminobenzenesulfonamide - Benzenesulfonamide - Aminobenzoic acid or derivatives - Benzenesulfonyl group - Pyrrolopyridine - Nitrobenzene - Benzoic acid or derivatives - Phenol ether - Tertiary aliphatic/aromatic amine - Phenoxy compound - Phenylalkylamine - Aniline or substituted anilines - Dialkylarylamine - Benzoyl - Nitroaromatic compound - Secondary aliphatic/aromatic amine - Halobenzene - N-alkylpiperazine - Chlorobenzene - Benzenoid - Aryl halide - Monocyclic benzene moiety - Aryl chloride - Oxane - Pyridine - Aminosulfonyl compound - Sulfonyl - Organosulfonic acid or derivatives - Organic sulfonic acid or derivatives - Heteroaromatic compound - Pyrrole - Amino acid or derivatives - C-nitro compound - Organic nitro compound - Tertiary amine - Tertiary aliphatic amine - Oxacycle - Azacycle - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Carboxylic acid derivative - Allyl-type 1,3-dipolar organic compound - Dialkyl ether - Ether - Secondary amine - Organic oxoazanium - Organic oxide - Organopnictogen compound - Hydrocarbon derivative - Organic zwitterion - Amine - Organic nitrogen compound - Organosulfur compound - Organooxygen compound - Organohalogen compound - Organic oxygen compound - Organochloride - Organonitrogen 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

Chemical and Physical Properties

• Solubility: Soluble in DMSO (100 mg/ml (~115mM) at 25 °C), water (<1 mg/ml (< 1mM) at 25 °C), and ethanol (<1 mg/ml (< 1mM) at 25 °C).
• Sensitivity: light sensitive
• Refractive Index: 1.64
• Molecular Weight: 868.400 g/mol
• XLogP3: 8.200
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 12
• Exact Mass: 867.318 Da
• Monoisotopic Mass: 867.318 Da
• Topological Polar Surface Area: 183.000 Ų
• Heavy Atom Count: 61
• Formal Charge: 0
• Complexity: 1640.000
• 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. Fengying Shao, Jianyu Han, Zhaoyan Tian, Zhi Wang, Songqin Liu, Yafeng Wu.  (2023)  Synergistic ROS generation and directional overloading of endogenous calcium induce mitochondrial dysfunction in living cells.  BIOMATERIALS,      [PMID:37619266] [10.1016/j.biomaterials.2023.122284]

2. Chen Zhigang, Zhang Yi, Li Wenlu, Gao Chenyi, Huang Fengbo, Cheng Lu, Jin Menglei, Xu Xiaoming, Huang Jian.  (2023)  Single cell profiling of female breast fibroadenoma reveals distinct epithelial cell compositions and therapeutic targets.  Nature Communications,  14  (1): (1-12).  [PMID:37328469] [10.1038/s41467-023-39059-3]

3. Yun Zhou, Ke Li, Fan Li, Shuang Han, Yang Wang, Xueping Li, Yonghua Zhan.  (2019)  Doxorubicin and ABT-199 Coencapsulated Nanocarriers for Targeted Delivery and Synergistic Treatment against Hepatocellular Carcinoma.  Journal of Nanomaterials,      [PMID:] [10.1155/2019/5274598]