2H-Indol-2-one, 3-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-

HCID 10177

Substructure search Find similar structures

Basic information

CAS: 397242-72-7
Standard SMILES: O=C1C(c2c(O)[nH]c3ccccc23)=Nc2ccccc21
InChIKey: CRDNMYFJWFXOCH-UHFFFAOYSA-N
Molecular formula: C16H10N2O2
Average molar mass: 262.26 g/mol

Overview

Indirubin is under investigation in clinical trial NCT01735864 (Dosage Determination Trial for Indigo Naturalis Extract in Oil Ointment).

Names & identifiers

Preferred name: 2H-Indol-2-one, 3-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-
IUPAC: 2-(2-hydroxy-1H-indol-3-yl)indol-3-one
English name: Indirubin
Molecular formula: C16H10N2O2
Molecular weight: 262.26

Names & synonyms

2H-Indol-2-one, 3-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-RefChem:4842852H-Indol-2-one, 3-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-(9CI)610-392-0Indirubin479-41-4Indigopurpurin906748-38-7Couroupitine BIndigo Red(Z)-[2,3'-biindolinylidene]-2',3-dioneIsoindirubin

Show more names

Nsc105327c.i.73200C.I.75790IndirabinIndirubin>

[2,3'-Biindolinylidene]-2',3-dione(E)-[2,3'-biindolinylidene]-2',3-dioneIsoindirubineIsoindogotin397242-72-7(Z)-IndirubinIndirubin [MI]MFCD00956441

Database identifiers

CAS: 397242-72-7、479-41-4、906748-38-7
PubChem CID: 10177
DTXSID: DTXSID201026053
ChEMBL: CHEMBL3185783、CHEMBL35349
UNII: 1LXW6D3W2Z、V86L8P74GI
EC Number: 610-392-0
Nikkaji: J6.158A

Properties

Computed structural properties

XLogP: 2.7
Topological polar surface area: 65.5 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 1
Heavy atoms: 20
Formal charge: 0
Complexity: 448

Experimental & physicochemical properties

Chemical ClassesDye

DrugsPharmaceuticals -> Listed in ZINC15

SpringerMaterials PropertiesCrystal structure

Physicochemical properties

Melting point: 350 °C · 350°C(lit.)
Boiling point: 496.6 · 496.6±45.0 °C(Predicted)
Density: 1.417 · 1.417±0.06 g/cm3(Predicted)
storage temp.: -20 °C · -20°C
solubility: DMSO (Slightly), Methanol (Very Slightly, Heated)
pka: 9.13 · 9.13±0.20(Predicted)
form: Purple powder.
color: Very Dark Red
λmax: 540 nm · 540nm(DMSO)(lit.)
Major Application: food and beverages
Cosmetics Ingredients Functions: SKIN PROTECTINGSKIN CONDITIONING - HUMECTANTSKIN CONDITIONING - EMOLLIENT
InChI: InChI=1S/C16H10N2O2/c19-15-10-6-2-4-8-12(10)17-14(15)13-9-5-1-3-7-11(9)18-16(13)20/h1-8,17H,(H,18,20)
InChIKey: CRDNMYFJWFXOCH-UHFFFAOYSA-N
SMILES: N1C2=C(C=CC=C2)C(=C2C(=O)C3=C(N2)C=CC=C3)C1=O
CAS DataBase Reference: 479 · 479-41-4(CAS DataBase Reference)
FDA UNII: 86 L8P74GI · V86L8P74GI
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 319 · H319-H335-H315
Precautionary statements: 264 · P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
WGK Germany: 1 · WGK 1
RTECS: 2995000 · DU2995000
HS Code: 29339900 · 29339900
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

wgk: WGK 1
rtecs: DU2995000
hs_code: 29339900
Signal word: Warning
Symbol(GHS): GHS07
Storage Class: 11 - Combustible Solids
Hazard statements: H319-H335-H315
Precautionary statements: P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362

Chemistry & industry

Applications · 6 items

DescriptionIndirubin is the active ingredient of Danggui Longhui Wan, a traditional Chinese medicine containing plants such as Indigofera tinctoria L. and Isatis tinctoria L, which are used in traditional Chinese medicine to treat chronic diseases. Indirubin and its analogues are reported as potent inhibitors of cyclin-dependent kinases (CDKs). This could attribute to the positive effect of indirubin on counteracting proliferative diseases, such as chronic myelocytic leukemia (CML), a slowly progressive disease characterized by the overproduction of granulocytes.

DescriptionA further alkaloid isolated from the matured fruit of Couroupita guianensis, this base forms red crystals from EtOH and melts above 340°C. It forms the Nacetyl derivative, m.p. 186°C. The full structure has not yet been established.

HistoryThe report in 1951 showed that indirubin can inhibit eosinophils in the blood of guinea pigs. But this report did not attract attention. Indirubin is the effective component of the traditional Chinese medicine Angelica aloe pill. Since 1966, the scientists in the Institute of Hematonosis, Chinese Academy of Medical Sciences Research, started the research of therapying chronic myelocytic leukemia with the TCM rules using Angelica aloe pills, which had certain effect. Angelica aloe pill consisted of 11 herbs, such as Angelica, Aloe, Rhizoma Coptidis, and natural indigo. It was identified that natural indigo was the effective component of Angelica aloe pill. However, the active ingredient of natural indigo was indirubin.Indirubin is a novel antileukemia drug, which was found by the medical scientists in China in the middle of the 1970s. It has the effects of antibacterial, antiinflammatory, antitumor, and enhancing immune functions. The compound has been applied to the clinical treatment of chronic myeloid leukemia. Indirubin has the characteristics of reliable clinical curative effect, small side effects, and no obvious inhibitory effect on the bone marrow.

UsesIndigopurpurin is a purple 3,2-bisindole derivative and was shown to exhibit inhibitory allergic contact dermatitis via regulating T helper (Th)-mediated immune system in DNCB-induced model. A possible glycogen synthase kinase-3 (GSK-3) inhibitor the active component of a traditional Congolese antiepilepsy treatment.

UsesAn inhibitor of GSK-3β and cyclin-dependent kinases.

General DescriptionThis substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG