Indirubin-3'-monoxime

HCID 3707
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Grundinformationen

CAS
160807-49-8
Standard-SMILES
O=Nc1c(-c2c(O)[nH]c3ccccc23)[nH]c2ccccc12
InChIKey
FQCPPVRJPILDIK-UHFFFAOYSA-N
Summenformel
C16H11N3O2
Durchschnittliche Molmasse
277,28 g/mol
Monoisotopische Masse
277,0851266

Überblick

Indirubin-3'-monoxime is a member of the class of biindoles that is indirubin in which the keto group at position 3' has undergone condensation with hydroxylamine to form the corresponding oxime. It has a role as an EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor, an osteogenesis regulator, a neuroprotective agent, an anti-obesity agent and an EC 2.7.11.22 (cyclin-dependent kinase) inhibitor. It is an alkaloid, a ketoxime, a ring assembly, a member of oxindoles and a bisindole.

Namen und Bezeichner

Bevorzugter Name
Indirubin-3'-monoxime
IUPAC
3-(3-nitroso-1H-indol-2-yl)-1H-indol-2-ol
Englischer Name
Indirubin-3'-oxime
Summenformel
C16H11N3O2
Molmasse
277.28

Namen und Synonyme

INDIRUBIN-3'-MONOXIMEindirubin-3'-oxime160807-49-8667463-82-3Indirubin-3-monoximeindirubin-3-oximeIndirubin-3monoximeIndirubin 3'-monoxime(2Z,3E)-3-(Hydroxyimino)-[2,3'-biindolinylidene]-2'-oneIndirubin-3 inverted exclamation marka-oxime3-[3-(Hydroxyamino)-1H-indol-2-yl]indol-2-oneIndirubin-3a?oxime
Weitere Namen anzeigen
-oxime-monoximeIndirubin-3Indirubin-3′INDIRUBIN-3'-OXIMEIndirubine-3'-oximeINDIRUBIN-3’-MONOOXIMEIndirubin-3''-monoxime, 10 mM in DMSO
Indirubin-3??-oximeUNII-X6CSG51MBQ3-(Hydroxyimino)-[2,3'-biindolinylidene]-2'-oneBSPBio_0011083-[1,3-dihydro-3-(hydroxyimino)-2H-indol-2-ylidene]-1,3-dihydro-2H-indol-2-one2H-Indol-2-one, 3-[1,3-dihydro-3-(hydroxyimino)-2H-indol-2-ylidene]-1,3-dihydro-CHEMBL126077CHEMBL216543

Datenbank-Bezeichner

CAS
160807-49-8
PubChem CID
3707
DTXSID
DTXSID90416111
ChEMBL
CHEMBL126077、CHEMBL1496098、CHEMBL216543
ChEBI
CHEBI:43645
Nikkaji
J2.522.312H、J3.732.841C、J741.372F

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,2
Polarare Oberfläche (TPSA)
81,2 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
1
Schwere Atome
21

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15

Physikochemische Eigenschaften

Schmelzpunkt
247 · 247-249°C
Siedepunkt
532.2 · 532.2±50.0 °C(Predicted)
Dichte
1.5 · 1.50
storage temp.
room temp
Löslichkeit
10 mg/mL · DMSO: >10 mg/mL
Aggregatzustand
solid

Sicherheit und Regulatorisches

Sicherheitsdaten

wgk
3
Speicherklasse
11 - Combustible Solids

Chemie und Industrie

Anwendungen · 2 Einträge

BeschreibungIndirubin-3’-oxime is a potent inhibitor of glycogen synthase kinase 3β (GSK3β; IC50 = 22 nM). As GSK3β phosphorylates tau protein, indirubin-3’-oxime prevents tau phosphorylation both in vitro and in vivo at Alzheimer’s disease-relevant sites. It also inhibits cyclin-dependent kinases (CDKs) at higher concentrations, including Cdk1/cyclin B (IC50 = 180 nM), Cdk2/cyclin A (IC50 ~500 nM), Cdk2/cyclin E (IC50 = 250nM), Cdk4/cyclin D1 (IC50 = 3.3 μM) and Cdk5/p35 (IC50 = 100 nM). Indirubin-3’-oxime reversibly inhibits the proliferation of many cells types, arresting cycling in the G2/M phase.

VerwendenA potent inhibitor of GSK-3 (IC50=22nM). Also inhibits CDK1 (IC50=180nM) and CDK (IC50=100nM). It reversibly arrests asynchronous HBL-100 cells at G2. It induces apoptosis in the mammary carcinoma cell line MCF-7 (10üM).

Anbieter69 Anbieter

阿诺西（上海）生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]

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