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
UNII
5H31GI9502
DrugBank ID
DB13950
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.