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]

• Drug Type: Small molecular drug
• #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: CHEMBL43645
  CAS Number: 160807-49-8
  UNII: X6CSG51MBQ
  DrugBank ID: DB02052
  TTD ID: D0Y0ES
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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]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Actin, cytoplasmic 1 (ACTB)	OT1MCP2F	ACTB_HUMAN	Gene/Protein Processing	[5]
Stress-70 protein, mitochondrial (HSPA9)	OT4TMVS9	GRP75_HUMAN	Gene/Protein Processing	[5]
Tyrosine-protein kinase Lck (LCK)	OT883FG9	LCK_HUMAN	Gene/Protein Processing	[6]
Uracil-DNA glycosylase	OTZTWD86	UNG_HUMAN	Gene/Protein Processing	[5]
UV excision repair protein RAD23 homolog A (RAD23A)	OTBPAWHX	RD23A_HUMAN	Gene/Protein Processing	[5]

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

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] The specificities of protein kinase inhibitors: an update. Biochem J. 2003 Apr 1;371(Pt 1):199-204. doi: 10.1042/BJ20021535.