U-73122

Iupac Name：1-[6-[[(8R,9S,13S,14S,17S)-3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,
17-decahydrocyclopenta[a]phenanthren-17-yl]amino]hexyl]pyrrole-2,5-dione

CAS No.: 112648-68-7

Molecular Weight：464.6395

Modify Date.: 2023-03-17 20:03

Introduction: ChEBI: An aza-steroid that is 3-O-methyl-17beta-estradiol in which the 17beta-hydroxy group is replaced by a 6-(maleimid-1-yl)hexylamino group. An inibitor of phospholipase C. View more+

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1. Names and Identifiers

1.1 Name: U-73122
1.2 Synonyms: (17β)-3-Methoxy-17-[6-[(2,5-dihydro-2,5-dioxo-1H-pyrrol)-1-yl]hexylamino]estra-1,3,5(10)-triene 1-(6-{[(17Β)-3-Methoxyestra-1,3,5(10)-trien-17-yl]amino}hexyl)-1H-pyrrole-2,5-dione 1-(6-{[(8ξ,9ξ,14ξ,17β)-3-Methoxyestra-1(10),2,4-trien-17-yl]amino}hexyl)-1H-pyrrole-2,5-dione 1-(6-{[(8ξ,9ξ,14ξ,17β)-3-Methoxyestra-1,3,5(10)-trien-17-yl]amino}hexyl)-1H-pyrrole-2,5-dione 1-(6-{[3-Methoxyestra-1,3,5(10)-trien-17-yl]amino}hexyl)-1H-pyrrole-2,5-dione 1-[6-((17BETA-3-METHOXYESTRA-1,3,5(10)-TRIEN-17-YL)AMINO)HEXYL]-1H-PYRROLE-2,5-DIONE 1-[6-[((17β)-3-methoxyestra-1,3,5[10]-trien-17-yl)amino]hexyl]-1h-pyrrole-2,5-dione 1-[6-[[(17B)-3-METHOXYESTRA-1,3,5(10)-TRIEN-17-YL]AMINO]HEXYL]-1H-PYRROLE-2,5-DIONE 1-[6-[[(17β)-3-Methoxyestra-1,3,5(10)-trien-17-yl]amino]hexyl]-1H-pyrrole-2,5-dione 1-[6-[[(8R,9S,13S,14S,17S)-3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]amino]hexyl]pyrrole-2,5-dione 1-[6-[[3-Methoxyestra-1,3,5(10)-triene-17β-yl]amino]hexyl]-1H-pyrrole-2,5-dione 1H-Pyrrole-2,5-dione, 1-[6-[[(17Β)-3-methoxyestra-1,3,5(10)-trien-17-yl]amino]hexyl]- 1H-pyrrole-2,5-dione, 1-[6-[[(8ξ,9ξ,14ξ,17β)-3-methoxyestra-1(10),2,4-trien-17-yl]amino]hexyl]- 1H-Pyrrole-2,5-dione, 1-[6-[[(8ξ,9ξ,14ξ,17β)-3-methoxyestra-1,3,5(10)-trien-17-yl]amino]hexyl]- 1H-Pyrrole-2,5-dione, 1-[6-[[3-methoxyestra-1,3,5(10)-trien-17-yl]amino]hexyl]- U 73122,1-[6-[[(17Β)-3-Methoxyestra-1,3,5(10)-trien-17-yl]amino]hexyl]-1H-pyrrole-2,5-dione U-73122 hydrate U-73122 hydrate

1.3 CAS No.: 112648-68-7

1.4 CID: 104794

1.5 Molecular Formula: C29H40N2O3 (isomer)

1.6 Inchi: InChI=1S/C29H40N2O3/c1-29-16-15-23-22-10-8-21(34-2)19-20(22)7-9-24(23)25(29)11-12-26(29)30-17-5-3-4-6-18-31-27(32)13-14-28(31)33/h8,10,13-14,19,23-26,30H,3-7,9,11-12,15-18H2,1-2H3/t23-,24-,25+,26+,29+/m1/s1

1.7 InChkey: LUFAORPFSVMJIW-ZRJUGLEFSA-N

1.8 Canonical Smiles: CC12CCC3C(C1CCC2NCCCCCCN4C(=O)C=CC4=O)CCC5=C3C=CC(=C5)OC

1.9 Isomers Smiles: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2NCCCCCCN4C(=O)C=CC4=O)CCC5=C3C=CC(=C5)OC

2. Properties

2.1 Density: 1.16

2.1 Boiling point: 617.1oC at 760 mmHg

2.1 Refractive index: 1.589

2.1 Flash Point: 327 oC

2.1 Precise Quality: 464.30400

2.1 PSA: 58.64000

2.1 logP: 5.32370

2.1 Solubility: Insuluble (9.3E-5 g/L) (25 oC),

2.2 Appearance: solid off-white

2.3 Storage: Ambient temperatures.

2.4 Color/Form: off-white

2.5 pKa: 10.69±0.40(Predicted)

2.6 Water Solubility: ethanol: 0.7?mg/mL | Soluble in DMSO, ethanol, or DMF at approx. 0.5mg/ml. May require heating or overnight mixing. Insoluble in water

2.7 StorageTemp: Keep in dark place,Inert atmosphere,Room temperature

3. Use and Manufacturing

3.1 Definition: ChEBI: An aza-steroid that is 3-O-methyl-17beta-estradiol in which the 17beta-hydroxy group is replaced by a 6-(maleimid-1-yl)hexylamino group. An inibitor of phospholipase C.

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: 26-36

4.1 WGK Germany: 3

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

Predict 1H proton NMR

7. Other Information

7.0 Definition: ChEBI: An aza-steroid that is 3-O-methyl-17beta-estradiol in which the 17beta-hydroxy group is replaced by a 6-(maleimid-1-yl)hexylamino group. An inibitor of phospholipase C.

7.1 Biological Activity: Phospholipase C inhibitor. Inhibits agonist-induced platelet aggregation with IC 50 values of 1-5 μ M. Potently inhibits human polymorphonuclear neutrophil adhesion on biological surfaces (IC 50 < 50 nM) and exhibits antinociceptive activity in vivo .

7.2 Target: Value

7.3 Description: U-73122 is an inhibitor of PLC-dependent processes, however, the mechanism of action remains unclear. The IC₅₀ values for inhibition of platelet aggregation induced by collagen or thrombin are 0.6 and 5 μM, respectively. It also exhibits inhibitory activity against HIV-1 integrase with an IC₅₀ value of 7 μM.

7.4 Biochem/physiol Actions: Inhibits the hydrolysis of PPI to IP3, which leads to a decrease in cytosolic free calcium. Inhibits the coupling of G protein-phospholipase C activation, while remaining unaffected by production of cAMP.

7.5 Usage: It is used as a phospholipase C, phospholipase A2, and 5-LO inhibitor. It is also determined that in SK-N-SH neuroblastoma cells, U-73122 inhibits agonist-induced down-regulation of muscarinic receptors. In addition, it is a useful tool to investigate receptor-mediated PI turnover in signal transduction. U-73122 is a potent inhibitor of human neutrophil adhesion to biological surfaces (IC50 = 50 nM) as well as adhesion-dependent granule exocytosis and oxidative burst. U-73343 (sc-201422) is useful as a negative control for investigations of U-73122 phospholipase C antagonism and its cellular consequences.

8. Computational chemical data

Molecular Weight: 464.6395g/mol
Molecular Formula: C₂₉H₄₀N₂O₃
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 464.30389314
Monoisotopic Mass: 464.30389314
Complexity: 763
Rotatable Bond Count: 9
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 58.6
Heavy Atom Count: 34
Defined Atom Stereocenter Count: 5
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB7MAAAAAAAAAAAAAAAAAAAAYIAAAAwYMAAAAAAAGDBAAAAHgAQAAAADyzBmAYyBoPABACIAiFSEACCCAAgIAAIiIAOCMgMJiKEsRqEMCAk1jGIqYeQwPAPoAABAAAQAADAAAYAACAAACAACQAAAA==

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