Methyl (9S,10R,12R)-2,3,9,10,11,12-hexahydro-10-methoxy-2,9-dimethyl-1-oxo-9,12-epoxy-1H-diindolo(1,2,3-fg:3',2',1'-kl)pyrrolo(3,4-i)(1,6)benzodiazocine-10-carboxylate
Basic information
- CAS
126643-37-6- Standard SMILES
COC(=O)[C@@]1(OC)C[C@H]2O[C@]1(C)n1c3ccccc3c3c4c(c5c6ccccc6n2c5c31)C(=O)N(C)C4- InChIKey
QTYMDECKVKSGSM-YMUMJAELSA-N- Molecular formula
- C29H25N3O5
- Average molar mass
- 495.5 g/mol
- Monoisotopic mass
- 495.17942091
Overview
KT 5823 is an organic heterooctacyclic compound that is 1H,1'H-2,2'-biindole in which the nitrogens have undergone formal oxidative coupling to positions 2 and 5 of methyl (3R)-3-methoxy-2-methyltetrahydrofuran-3-carboxylate (the 2S,3R,5R product), and in which the 3 and 3' positions of the biindole moiety have also undergone formal oxidative coupling to positions 3 and 4 of 1-methyl-1,5-dihydro-2H-pyrrol-2-one. It has a role as an EC 2.7.11.12 (cGMP-dependent protein kinase) inhibitor. It is a methyl ester, an organic heterooctacyclic compound, an indolocarbazole, a hemiaminal and a gamma-lactam.
Names & identifiers
- Preferred name
- Methyl (9S,10R,12R)-2,3,9,10,11,12-hexahydro-10-methoxy-2,9-dimethyl-1-oxo-9,12-epoxy-1H-diindolo(1,2,3-fg:3',2',1'-kl)pyrrolo(3,4-i)(1,6)benzodiazocine-10-carboxylate
- IUPAC
- methyl (15S,16R,18R)-16-methoxy-4,15-dimethyl-3-oxo-28-oxa-4,14,19-triazaoctacyclo[12.11.2.115,18.02,6.07,27.08,13.019,26.020,25]octacosa-1,6,8,10,12,20,22,24,26-nonaene-16-carboxylate
- English name
- KT5823
- Molecular formula
- C29H25N3O5
- Molecular weight
- 495.53
Names & synonyms
kt 5823126643-37-6KT5823KT-5823WY40BAB02WDTXSID40925642CHEBI:851029,12-Epoxy-1H-diindolo(1,2,3-fg:3',2',1'-kl)pyrrolo(3,4-i)(1,6)benzodiazocine-10-carboxylic acid, 2,3,9,10,11,12-hexahydro-10-methoxy-2,9-dimethyl-1-oxo-, methyl ester, (9R-(9alpha,10beta,12alpha))-methyl (15S,16R,18R)-16-methoxy-4,15-dimethyl-3-oxo-28-oxa-4,14,19-triazaoctacyclo[12.11.2.1^{15,18}.0^{2,6}.0^{7,27}.0^{8,13}.0^{19,26}.0^{20,25}]octacosa-1(26),2(6),7(27),8,10,12,20,22,24-nonaene-16-carboxylatemethyl (15S,16R,18R)-16-methoxy-4,15-dimethyl-3-oxo-28-oxa-4,14,19-triazaoctacyclo(12.11.2.1^(15,18).0^(2,6).0^(7,27).0^(8,13).0^(19,26).0^(20,25))octacosa-1(26),2(6),7(27),8,10,12,20,22,24-nonaene-16-carboxylateRefChem:925627DTXCID001354468
Show more names
KT 5283KT5823, inhibitor of PKGPROTEIN KINASE INHIBITOR KT 5823KT5823 - CAS 126643-37-6 - Calbiochem9-Methoxy-9-methoxycarbonyl-8-methyl-2,3,9,10-tetrahydro-8,11-epxoy-1H,8H,11H-2,7B-11A-triazadibenzo(A,G)cycloocta(cde)-trinden-1-one
Properties
Computed structural properties
- XLogP
- 3.5
- Topological polar surface area
- 74.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 3
- Heavy atoms
- 37
- Formal charge
- 0
- Complexity
- 1,020
Physicochemical properties
- Boiling point
- 629.2 · 629.2±55.0 °C(Predicted)
- Density
- 1.52 · 1.52±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 5 mg/mL · ethyl acetate: 5 mg/mL
- form
- lyophilized powder
- pka
- -1.01 · -1.01±0.60(Predicted)
- color
- white
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO or DMF may be stored at -20° for up to 3 months.
- InChIKey
- XCMSIGRHKNQVBF-UDUFFBJHNA-N
- SMILES
- N12C3=C(C4=C1C1=C(C5=C(N1[C@]1([H])O[C@@]2(C)[C@](C)(C(OOC)=O)C1)C=CC=C5)C1C(=O)N(C)CC=14)C=CC=C3 |&1:10,13,15,r|
- FDA UNII
- 40 BAB02W · WY40BAB02W
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 10
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29349990
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P280-P271
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationAgents that inhibit PROTEIN KINASES.
Applications
DescriptionKT5823 (126643-37-6) is a selective protein kinase G inhibitor (K>i =0.23, 4 and >10 μM for PKG, PKC and PKA respectively.1Arrests human skin fibroblast cell cycle after the G0/G1 boundary.2 KT5823 abolishes the cGMP-induced relaxation in smooth muscle cells (IC50=60 nM).3Cell permeable.
UsesKT 5823 is a protein kinase inhibitor shown to increase TSH-induced NIS expression, and thus iodide uptake, in thyroid cells.
UsesKT 5823 has been used as cyclic guanosine monophosphate (cGMP)-dependent protein kinase (PKG) inhibitor in cortical cultures, cortical neurons and in mouse brain capillary endothelial cells.
General DescriptionHighly specific cell-permeable, reversible, and ATP-competitive inhibitor of protein kinase G (Ki = 234 nM). Inhibits protein kinase C (Ki = 4.0 μM) and protein kinase A (Ki >10.0 μM) at higher concentrations.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: KT 5823 is an organic heterooctacyclic compound that is 1H,1'H-2,2'-biindole in which the nitrogens have undergone formal oxidative coupling to positions 2 and 5 of methyl (3R)-3-methoxy-2-methyltetrahydrofuran-3-carboxylate (the 2S,3R,5R product), and in which the 3 and 3' positions of the biindole moiety have also undergone formal oxidative coupling to positions 3 and 4 of 1-methyl-1,5-dihydro-2H-pyrrol-2-one. It has a role as an EC 2.7.11.12 (cGMP-dependent protein kinase) inhibitor. It is a gamma-lactam, an organic heterooctacyclic compound, a methyl ester, a hemiaminal and an indolocarbazole.
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