GRADE & PURITY Analytical standard, ≥98%

Synonyms

(3Z)-3-(3-oxoindolin-2-ylidene)indolin-2-one | 2H-Indol-2-one, 3-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-, (3E)- | AKOS032455876 | KBioGR_000450 | DB12379 | (3E)-3-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-2H-indol-2-one | HMS2234G06 |

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

Indirubin, also known as isoindigotin, is an inhibitor of cyclin-dependent kinases (CDK1/cyclin B (IC50 = 10μM), CDK2/cyclin A (IC50 = 2.2μM), CDK2/cyclin E (IC50 = 7.5μM), CDK4/cyclin D1 (IC50 = 12μM), CDK5/p35 (IC50 = 5.5μM)) and of GSK-3β (IC50 = 600nM). Studies investigating functional isoindigos show that they have the ability to disrupt cell growth and proliferation. The compound is a potent aryl hydrocarbon receptor ligand and is found in human urine and fetal bovine serum. Synthesized isoindigo-based oligothiophenes are used to study heterojunction solar cells. Shown to inhibit allergic contact dermatitis by regulating T helper mediated immune system in a DNCB-induced model.
An inhibitor of GSK-3β and cyclin-dependent kinases.

Specifications

Synonyms

(3Z)-3-(3-oxoindolin-2-ylidene)indolin-2-one | 2H-Indol-2-one, 3-(1, 3-dihydro-3-oxo-2H-indol-2-ylidene)-1, 3-dihydro-, (3E)- | AKOS032455876 | KBioGR_000450 | DB12379 | (3E)-3-(1, 3-Dihydro-3-oxo-2H-indol-2-ylidene)-1, 3-dihydro-2H-indol-2-one | HMS2234G06 |

Specifications & Purity

analytical standard, ≥98%

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Analytical standard

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C1=CC=C2C(=C1)C(=C(N2)O)C3=NC4=CC=CC=C4C3=O
• IUPAC Name: 2-(2-hydroxy-1H-indol-3-yl)indol-3-one
• InChIKey: JNLNPCNGMHKCKO-UHFFFAOYSA-N
• 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/h1-8,18,20H
• Isomeric SMILES: C1=CC=C2C(=C1)C(=C(N2)O)C3=NC4=CC=CC=C4C3=O
• Molecular Weight: 262.26
• Reaxy-Rn: 30107462
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=30107462&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Indoles and derivatives
      • Subclass Hydroxyindoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Indoles and derivatives
• Subclass: Hydroxyindoles
• Intermediate Tree Nodes: Not available
• Direct Parent: Hydroxyindoles
• Alternative Parents: Indoles Aryl ketones Substituted pyrroles Benzenoids Heteroaromatic compounds Ketimines Propargyl-type 1,3-dipolar organic compounds Azacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Hydroxyindole - Indole - Aryl ketone - Benzenoid - Substituted pyrrole - Pyrrole - Heteroaromatic compound - Ketimine - Ketone - Azacycle - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Imine - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organic oxide - Organic oxygen compound - Organic nitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl 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

Chemical and Physical Properties

• Solubility: Soluble in DMSO(warmed) (>2 mg/ml).
• Sensitivity: Heat sensitive.
• Melt Point(°C): 350°C(lit.)
• Molecular Weight: 262.260 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 262.074 Da
• Monoisotopic Mass: 262.074 Da
• Topological Polar Surface Area: 65.500 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 448.000
• 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. Mingyi Yao, Jian Liu, Narengaowa, Yonggu Li, Feng Zhao.  (2023)  In situ detection of natural dyes in archaeological textiles by SERS substrates immobilized on the fiber.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2023.108939]

2. Sun Bing-Yao, Sui Hua-Lu, Liu Zi-Wei, Tao Xin-Yi, Gao Bei, Zhao Ming, Ma Yu-Shu, Zhao Jian, Liu Min, Wang Feng-Qing, Wei Dong-Zhi.  (2022)  Structure-guided engineering of a flavin-containing monooxygenase for the efficient production of indirubin.  Bioresources and Bioprocessing,  9  (1): (1-16).  [PMID:38647553] [10.1186/s40643-022-00559-7]

3. Huifang Yin, Hongping Chen, Meng Yan, Zhikun Li, Rongdi Yang, Yanjiao Li, Yanfang Wang, Jianyi Guan, Huili Mao, Yan Wang, Yuyang Zhang.  (2021)  Efficient Bioproduction of Indigo and Indirubin by Optimizing a Novel Terpenoid Cyclase XiaI in Escherichia coli.  ACS Omega,      [PMID:34396002] [10.1021/acsomega.1c02679]

4. Wu Xunxun, Chen Xiaofei, Jia Dan, Cao Yan, Gao Shouhong, Guo Zhiying, Zerbe Philipp, Chai Yifeng, Diao Yong, Zhang Lei.  (2016)  Characterization of anti-leukemia components from Indigo naturalis using comprehensive two-dimensional K562/cell membrane chromatography and in silico target identification.  Scientific Reports,  6  (1): (1-13).  [PMID:27150638] [10.1038/srep25491]

5. Ling Wang, Xianglu Li, Xinyu Liu, Kang Lu, Na Chen, Peipei Li, Xiao Lv, Xin Wang.  (2015)  Enhancing effects of indirubin on the arsenic disulfide-induced apoptosis of human diffuse large B‑cell lymphoma cells.  Oncology Letters,  9  (4): (1940-1946).  [PMID:25789073] [10.3892/ol.2015.2941]

6. Yancen Li, Chengyu Wan, Fan Li, Guang Xin, Tao Wang, Qilong Zhou, Tingyu Wen, Shiyi Li, Xiaoting Chen, Wen Huang.  (2025)  Indirubin attenuates sepsis by targeting the EGFR/SRC/PI3K and NF-κB/MAPK signaling pathways in macrophages.  Frontiers in Pharmacology,      [PMID:40144662] [10.3389/fphar.2025.1542061]

7. Changwei Zhang, Hua Yuan, Hong Shen, Chuan Li, Jianzhong Ye, Huaxing Zhang, Chengzhang Wang.  (2024)  Physicochemical properties and antibacterial activity evaluation of new indigo extract from Baphicacanthus cusia (Nees) Bremek prepared by chemical conversion method.  Arabian Journal of Chemistry,      [PMID:] [10.1016/j.arabjc.2024.105801]

8. Ma Ke-Yu, Hou Bao-Long, Fan An-Qi, Huang An-Li, Li Bo-Rui, Liang Yan-Ni, Wang Zheng.  (2026)  The mechanism of indigo naturalis and its active ingredients against ulcerative colitis.  Scientific Reports,      [PMID:41535567] [10.1038/s41598-026-35413-9]