Details of the Drug

General Information of Drug (ID: DMACBIW)

Drug Name
WIN-55212-2
Synonyms
Win-55212-2; WIN 55212-2; UNII-5H31GI9502; 131543-22-1; CHEMBL188; WIN55212-2; WIN 55,212-2; CHEBI:73295; 5H31GI9502; (2,3-Dihydro-5-methyl-3-((4-morpholinyl)methyl)pyrrolo-(1,2,3-de)-1,4-benzoxazin-6-yl)(1-naphthalenyl)methanone monomethanesulfonate; [(3R)-5-methyl-3-(morpholin-4-ylmethyl)-2,3-dihydro[1,4]oxazino[2,3,4-hi]indol-6-yl](1-naphthyl)methanone; (r)-(+)-[2,3-dihydro-5-methyl-3-(4-morpholinylmethyl)pyrrolo[1,2,3-de]-1,4-benzoxazin-6-yl]-1-naphthalenylmethanone
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 426.5
Logarithm of the Partition Coefficient (xlogp) 4.4
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C27H26N2O3
IUPAC Name
[(11R)-2-methyl-11-(morpholin-4-ylmethyl)-9-oxa-1-azatricyclo[6.3.1.04,12]dodeca-2,4(12),5,7-tetraen-3-yl]-naphthalen-1-ylmethanone
Canonical SMILES
CC1=C(C2=C3N1[C@@H](COC3=CC=C2)CN4CCOCC4)C(=O)C5=CC=CC6=CC=CC=C65
InChI
InChI=1S/C27H26N2O3/c1-18-25(27(30)22-9-4-7-19-6-2-3-8-21(19)22)23-10-5-11-24-26(23)29(18)20(17-32-24)16-28-12-14-31-15-13-28/h2-11,20H,12-17H2,1H3/t20-/m1/s1
InChIKey
HQVHOQAKMCMIIM-HXUWFJFHSA-N
Cross-matching ID
PubChem CID
5311501
ChEBI ID
CHEBI:73295
CAS Number
131543-22-1
TTD ID
D0J7RW
INTEDE ID
DR1718

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Cannabinoid receptor 1 (CB1) TT6OEDT CNR1_HUMAN Inhibitor [1]
Cannabinoid receptor 2 (CB2) TTMSFAW CNR2_HUMAN Inhibitor [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
72 kDa type IV collagenase (MMP2) OT5NIWA2 MMP2_HUMAN Gene/Protein Processing [4]
A disintegrin and metalloproteinase with thrombospondin motifs 4 (ADAMTS4) OT4CA13K ATS4_HUMAN Gene/Protein Processing [5]
Actin, aortic smooth muscle (ACTA2) OTEDLG8E ACTA_HUMAN Gene/Protein Processing [6]
Apoptotic protease-activating factor 1 (APAF1) OTJWIVY0 APAF_HUMAN Gene/Protein Processing [4]
Beclin-1 (BECN1) OT4X293M BECN1_HUMAN Gene/Protein Processing [4]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Gene/Protein Processing [7]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Protein Interaction/Cellular Processes [4]
Caspase-7 (CASP7) OTAPJ040 CASP7_HUMAN Protein Interaction/Cellular Processes [4]
Caspase-8 (CASP8) OTA8TVI8 CASP8_HUMAN Protein Interaction/Cellular Processes [4]
Caspase-9 (CASP9) OTD4RFFG CASP9_HUMAN Gene/Protein Processing [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Cannabinoid receptor 1 (CB1) DTT CNR1 5.59E-02 -0.22 -0.45
Cannabinoid receptor 1 (CB1) DTT CNR1 7.68E-01 -0.06 -0.46
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 4.66E-01 4.25E-02 1.20E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 4.75E-01 5.15E-02 3.64E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Synthesis and pharmacological evaluation of coumarin derivatives as cannabinoid receptor antagonists and inverse agonists. Bioorg Med Chem. 2009 Apr 1;17(7):2842-51.
2 Synthesis and cannabinoid activity of 1-substituted-indole-3-oxadiazole derivatives: novel agonists for the CB1 receptor. Eur J Med Chem. 2008 Mar;43(3):513-39.
3 Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17.
4 WIN55,212-2 induces caspase-independent apoptosis on human glioblastoma cells by regulating HSP70, p53 and Cathepsin D. Toxicol In Vitro. 2019 Jun;57:233-243. doi: 10.1016/j.tiv.2019.02.009. Epub 2019 Feb 15.
5 Cannabinoid WIN?55,212?2 mesylate inhibits ADAMTS?4 activity in human osteoarthritic articular chondrocytes by inhibiting expression of syndecan?1. Mol Med Rep. 2016 Jun;13(6):4569-76. doi: 10.3892/mmr.2016.5137. Epub 2016 Apr 15.
6 Treatment with Cannabinoids as a Promising Approach for Impairing Fibroblast Activation and Prostate Cancer Progression. Int J Mol Sci. 2020 Jan 25;21(3):787. doi: 10.3390/ijms21030787.
7 Inhibition and stimulation of the human breast cancer resistance protein as in vitro predictor of drug-drug interactions of drugs of abuse. Arch Toxicol. 2018 Sep;92(9):2875-2884. doi: 10.1007/s00204-018-2276-y. Epub 2018 Aug 6.
8 The synthetic cannabinoid WIN-55,212 induced-apoptosis in cytotrophoblasts cells by a mechanism dependent on CB1 receptor. Toxicology. 2017 Jun 15;385:67-73. doi: 10.1016/j.tox.2017.04.013. Epub 2017 May 8.