Details of the Drug

General Information of Drug (ID: DM12WYV)

Drug Name
6-bromoindirubin-3-oxime
Synonyms 6-bromoindirubin-3'-oxime (BIO)
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 356.17
Logarithm of the Partition Coefficient (xlogp) 3.9
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C16H10BrN3O2
IUPAC Name
6-bromo-3-(3-nitroso-1H-indol-2-yl)-1H-indol-2-ol
Canonical SMILES
C1=CC=C2C(=C1)C(=C(N2)C3=C(NC4=C3C=CC(=C4)Br)O)N=O
InChI
InChI=1S/C16H10BrN3O2/c17-8-5-6-9-12(7-8)19-16(21)13(9)15-14(20-22)10-3-1-2-4-11(10)18-15/h1-7,18-19,21H
InChIKey
SAQUSDSPQYQNBG-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
448949
ChEBI ID
CHEBI:86290
CAS Number
667463-62-9
DrugBank ID
DB03444
TTD ID
D06OAH
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

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]
Glycogen synthase kinase-3 alpha (GSK-3A) TTRZQE3 GSK3A_HUMAN Inhibitor [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
ATP-binding cassette sub-family C member 2 (ABCC2) OTJSIGV5 MRP2_HUMAN Gene/Protein Processing [3]
ATP-binding cassette sub-family C member 4 (ABCC4) OTO27PAL MRP4_HUMAN Gene/Protein Processing [3]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [3]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Gene/Protein Processing [3]
Catenin beta-1 (CTNNB1) OTZ932A3 CTNB1_HUMAN Post-Translational Modifications [4]
Cytochrome P450 1A2 (CYP1A2) OTLLBX48 CP1A2_HUMAN Gene/Protein Processing [5]
G1/S-specific cyclin-D1 (CCND1) OT8HPTKJ CCND1_HUMAN Gene/Protein Processing [3]
Glycogen synthase kinase-3 beta (GSK3B) OTL3L14B GSK3B_HUMAN Gene/Protein Processing [6]
Induced myeloid leukemia cell differentiation protein Mcl-1 (MCL1) OT2YYI1A MCL1_HUMAN Gene/Protein Processing [6]
Leucine-rich repeat-containing G-protein coupled receptor 5 (LGR5) OTMVHF9E LGR5_HUMAN Gene/Protein Processing [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Stable generation of serum- and feeder-free embryonic stem cell-derived mice with full germline-competency by using a GSK3 specific inhibitor. Genesis. 2009 Jun;47(6):414-22.
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 Activation of beta-catenin signalling by GSK-3 inhibition increases p-glycoprotein expression in brain endothelial cells. J Neurochem. 2008 Aug;106(4):1855-65. doi: 10.1111/j.1471-4159.2008.05537.x. Epub 2008 Jul 4.
4 A lentivirus-mediated genetic screen identifies dihydrofolate reductase (DHFR) as a modulator of beta-catenin/GSK3 signaling. PLoS One. 2009 Sep 3;4(9):e6892. doi: 10.1371/journal.pone.0006892.
5 Analysis of glycogen synthase kinase inhibitors that regulate cytochrome P450 expression in primary human hepatocytes by activation of beta-catenin, aryl hydrocarbon receptor and pregnane X receptor signaling. Toxicol Sci. 2015 Nov;148(1):261-75.
6 GSK-3beta inhibition enhances sorafenib-induced apoptosis in melanoma cell lines. J Biol Chem. 2008 Jan 11;283(2):726-32. doi: 10.1074/jbc.M705343200. Epub 2007 Nov 8.