Details of the Drug

General Information of Drug (ID: DMLRQH0)

Drug Name

Indirubin-3'-monoxime

Synonyms

INDIRUBIN-3'-MONOXIME; indirubin-3'-oxime; 160807-49-8; indirubin-3-oxime; Indirubin-3monoxime; Indirubin-3-monoxime; 3-[3-(Hydroxyamino)-1H-indol-2-yl]indol-2-one; CHEBI:43645; Indirubin 3'-monoxime; indirubin-3'-monooxime; Indirubin-3& CHEMBL216543; CHEMBL126077; (Z)-1H,1'H-[2,3']BIINDOLYLIDENE-3,2'-DIONE-3-OXIME; UNM-0000305771; 3-[1,3-dihydro-3-(hydroxyimino)-2H-indol-2-ylidene]-1,3-dihydro-2H-indol-2-one; 667463-82-3; IXM; SR-01000075929; Indirubin-3; Indirubin 3-oxime; Tocris-1813; BiomolKI_000070; Indirubin-3-oxime

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

277.28

Logarithm of the Partition Coefficient (xlogp)

3.2

Rotatable Bond Count (rotbonds)

1

Hydrogen Bond Donor Count (hbonddonor)

3

Hydrogen Bond Acceptor Count (hbondacc)

3

Chemical Identifiers

Formula: C16H11N3O2
IUPAC Name: 3-(3-nitroso-1H-indol-2-yl)-1H-indol-2-ol
Canonical SMILES: C1=CC=C2C(=C1)C(=C(N2)O)C3=C(C4=CC=CC=C4N3)N=O
InChI: InChI=1S/C16H11N3O2/c20-16-13(9-5-1-3-7-11(9)18-16)15-14(19-21)10-6-2-4-8-12(10)17-15/h1-8,17-18,20H
InChIKey: FQCPPVRJPILDIK-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 3707
ChEBI ID: CHEBI:43645
CAS Number: 160807-49-8
DrugBank ID: DB02052
TTD ID: D0Y0ES

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Aurora B messenger RNA (AURKB mRNA)	TT9RTBL	AURKB_HUMAN	Inhibitor	[2]
Aurora kinase A (AURKA)	TTPS3C0	AURKA_HUMAN	Inhibitor	[2]
Aurora kinase C (AURKC)	TTLYXIT	AURKC_HUMAN	Inhibitor	[2]
Cyclin-dependent kinase 1 (CDK1)	TTH6V3D	CDK1_HUMAN	Binder	[3]
Cyclin-dependent kinase 2 (CDK2)	TT7HF4W	CDK2_HUMAN	Inhibitor	[4]
Cyclin-dependent kinase 5 (CDK5)	TTL4Q97	CDK5_HUMAN	Inhibitor	[4]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Actin, cytoplasmic 1 (ACTB)	OT1MCP2F	ACTB_HUMAN	Gene/Protein Processing	[5]
Androgen receptor (AR)	OTUBKAZZ	ANDR_HUMAN	Gene/Protein Processing	[6]
Apoptosis regulator BAX (BAX)	OTAW0V4V	BAX_HUMAN	Gene/Protein Processing	[5]
Bifunctional epoxide hydrolase 2 (EPHX2)	OTPTRCNW	HYES_HUMAN	Gene/Protein Processing	[5]
Cytochrome P450 1A1 (CYP1A1)	OTE4EFH8	CP1A1_HUMAN	Gene/Protein Processing	[5]
Glutathione peroxidase 1 (GPX1)	OTE2O72Q	GPX1_HUMAN	Gene/Protein Processing	[5]
Glutathione reductase, mitochondrial (GSR)	OTM2TUYM	GSHR_HUMAN	Gene/Protein Processing	[5]
Glycogen synthase kinase-3 beta (GSK3B)	OTL3L14B	GSK3B_HUMAN	Gene/Protein Processing	[7]
Prostate-specific antigen (KLK3)	OTFGSBFJ	KLK3_HUMAN	Gene/Protein Processing	[6]
Serine/threonine-protein kinase Sgk1 (SGK1)	OT301T1U	SGK1_HUMAN	Gene/Protein Processing	[7]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Discovery agent

ICD Disease Classification

N.A.

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Aurora kinase A (AURKA)	DTT	AURKA	9.41E-46	-1.78	-2.05

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5989).
2	An integrated computational approach to the phenomenon of potent and selective inhibition of aurora kinases B and C by a series of 7-substituted in... J Med Chem. 2007 Aug 23;50(17):4027-37.
3	The kinase inhibitor indirubin-3'-oxime prevents germinal vesicle breakdown and reduces parthenogenetic development of pig oocytes. Theriogenology. 2006 Mar 1;65(4):744-56.
4	Pharmacological inhibitors of cyclin-dependent kinases. Trends Pharmacol Sci. 2002 Sep;23(9):417-25.
5	The effects of indirubin-3'-monoxime, a novel AHR ligand, on stress and toxicity-related gene/protein expression in human U937 cells undergoing differentiation and activation. J Immunotoxicol. 2006 Jan 1;3(1):1-10.
6	Proliferative and androgenic effects of indirubin derivatives in LNCaP human prostate cancer cells at sub-apoptotic concentrations. Chem Biol Interact. 2011 Feb 1;189(3):177-85. doi: 10.1016/j.cbi.2010.11.008. Epub 2010 Nov 25.
7	The specificities of protein kinase inhibitors: an update. Biochem J. 2003 Apr 1;371(Pt 1):199-204. doi: 10.1042/BJ20021535.