ABT-199 (GDC-0199) - Moligand™, ≥99% , Apoptosis regulator Bcl-2 inhibitor, CAS No.1257044-40-8, Apoptosis regulator Bcl-2 inhibitor

CAS: 1257044-40-8 Cat. No.: A124869 Molecular Weight: 868.44 EC Number: 820-130-9

GRADE & PURITY Moligand™, ≥99%

Synonyms

GDC-0199 | A850921 | SCHEMBL19236295 | 10.14272/FFRYUAVNPBUEIC-UHFFFAOYSA-N.3 | 4-[4-[[2-(4-Chlorophenyl)-4,4-dimethyl-1-cyclohexen-1-yl]methyl]-1-piperazinyl]-N-[[3-nitro-4-[[(tetrahydro-2H-pyran-4-yl)methyl]amino]phenyl]sulfonyl]-2-(1H-pyrrolo[2,3-b]pyr

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.
A Bcl-2-selective inhibitor with Ki of <0.01 nM

Specifications

Synonyms

GDC-0199 | A850921 | SCHEMBL19236295 | 10.14272/FFRYUAVNPBUEIC-UHFFFAOYSA-N.3 | 4-[4-[[2-(4-Chlorophenyl)-4, 4-dimethyl-1-cyclohexen-1-yl]methyl]-1-piperazinyl]-N-[[3-nitro-4-[[(tetrahydro-2H-pyran-4-yl)methyl]amino]phenyl]sulfonyl]-2-(1H-pyrrolo[2, 3-b]pyr

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

ABT-199 is a potent and selective inhibitor of B-cell lymphoma-2 (BCL-2) family proteins, currently in clinical trials. ABT-199 inhibits the growth of BCL-2-dependent tumors in vivo and spares human platelets. A single dose of ABT-199 in three patients wi

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

ANTAGONIST, INHIBITOR

Mechanism of action

Apoptosis regulator Bcl-2 inhibitor

Purity

≥99%

Product Properties

• ALogP: 8.2

Names and Identifiers

• Pubchem Sid: 488201440
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/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

Associated Targets(Human)

MCL1 Tchem Induced myeloid leukemia cell differentiation protein Mcl-1 (1 Activities)

Discover Target: MCL1

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

BCL2 Tclin Apoptosis regulator Bcl-2 (10 Activities)

Discover Target: BCL2

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

BCL2L1 Tchem Bcl-2-like protein 1 (10 Activities)

Discover Target: BCL2L1

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

BCL2L2 Tchem Bcl-2-like protein 2 (2 Activities)

Discover Target: BCL2L2

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

PGR Tclin Progesterone receptor (8562 Activities)

Discover Target: PGR

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

ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

Discover Target: ADRB2

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

AR Tclin Androgen Receptor (11781 Activities)

Discover Target: AR

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

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

Discover Target: CHRM1

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

MAOA Tclin Monoamine oxidase A (11911 Activities)

Discover Target: MAOA

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

DRD1 Tclin Dopamine D1 receptor (9720 Activities)

Discover Target: DRD1

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

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

Discover Target: PTGS1

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

SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

Discover Target: SLC6A2

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

SLC6A4 Tclin Serotonin transporter (12625 Activities)

Discover Target: SLC6A4

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

PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

Discover Target: PTGS2

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

HRH1 Tclin Histamine H1 receptor (7573 Activities)

Discover Target: HRH1

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

DRD3 Tclin Dopamine D3 receptor (14368 Activities)

Discover Target: DRD3

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

OPRD1 Tclin Delta opioid receptor (15096 Activities)

Discover Target: OPRD1

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

SLC6A3 Tclin Dopamine transporter (10535 Activities)

Discover Target: SLC6A3

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

KCNH2 Tclin HERG (29587 Activities)

Discover Target: KCNH2

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

PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

Discover Target: PDE3A

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

ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)

Discover Target: ADRA2C

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

ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

Discover Target: ADORA3

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

BAD Tchem Bcl2-antagonist of cell death (BAD) (147 Activities)

Discover Target: BAD

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

CASP3 Tchem Caspase-3 (3632 Activities)

Discover Target: CASP3

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

MC3R Tchem Melanocortin receptor 3 (5659 Activities)

Discover Target: MC3R

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

NR1I2 Tchem Pregnane X receptor (6667 Activities)

Discover Target: NR1I2

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

HL-60 (67320 Activities)

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

K562 (73714 Activities)

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

MCF7 (126967 Activities)

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

MOLT-4 (49676 Activities)

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

RPMI-8226 (44974 Activities)

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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

U-937 (7138 Activities)

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

KG-1 (867 Activities)

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

HeLa (62764 Activities)

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

BCL2L1 Tchem Apoptosis regulator Bcl-X (2604 Activities)

Discover Target: BCL2L1

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

BCL2 Tclin Apoptosis regulator Bcl-2 (3787 Activities)

Discover Target: BCL2

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

MCL1 Tchem Induced myeloid leukemia cell differentiation protein Mcl-1 (3820 Activities)

Discover Target: MCL1

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

BCL2L2 Tchem Apoptosis regulator Bcl-W (121 Activities)

Discover Target: BCL2L2

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

RS4-11 (1012 Activities)

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

U-266 (527 Activities)

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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

HEK-293T (167025 Activities)

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

MOLM-13 (2241 Activities)

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

NCI-H929 (451 Activities)

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

OCI-AML-3 (139 Activities)

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

Toledo (130 Activities)

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

Associated Targets(non-human)

Pde4d Phosphodiesterase 4D (4 Activities)

Discover Target: Pde4d

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

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

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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

SARS-CoV-2 (38078 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: 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. 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]

2. 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]

3. 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]