Details of the Drug

General Information of Drug (ID: DM0B7NO)

Drug Name
Isoarnebin 4
Synonyms Shikonin; NSC 252844; Shikonin S; Shikonin,(S); Tokyo Violet
Indication
Disease Entry ICD 11 Status REF
Coronavirus Disease 2019 (COVID-19) 1D6Y Investigative [1]
Therapeutic Class
Antiviral Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 288.29
Logarithm of the Partition Coefficient (xlogp) 3
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C16H16O5
IUPAC Name
5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione
Canonical SMILES
CC(=CC[C@H](C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)O)C
InChI
InChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m1/s1
InChIKey
NEZONWMXZKDMKF-SNVBAGLBSA-N
Cross-matching ID
PubChem CID
479503
ChEBI ID
CHEMBL9470
CAS Number
517-89-5
TTD ID
D0QM4U
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
COVID-19 papain-like proteinase (PL-PRO) TTNHMO8 R1AB_SARS2 (819-2763) Inhibitor [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Actin, aortic smooth muscle (ACTA2) OTEDLG8E ACTA_HUMAN Gene/Protein Processing [2]
Cadherin-1 (CDH1) OTFJMXPM CADH1_HUMAN Gene/Protein Processing [3]
Cadherin-2 (CDH2) OTH0Y56P CADH2_HUMAN Gene/Protein Processing [3]
Collagen alpha-1(I) chain (COL1A1) OTI31178 CO1A1_HUMAN Gene/Protein Processing [2]
Collagen alpha-1(III) chain (COL3A1) OTT1EMLM CO3A1_HUMAN Gene/Protein Processing [2]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [4]
Heat shock factor protein 1 (HSF1) OTYNJ4KP HSF1_HUMAN Gene/Protein Processing [5]
Matrilysin (MMP7) OTVT3SEJ MMP7_HUMAN Gene/Protein Processing [3]
Metalloproteinase inhibitor 2 (TIMP2) OT8S1RRP TIMP2_HUMAN Gene/Protein Processing [3]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Structure of Mpro from COVID-19 virus and discovery of its inhibitors. Nature. 2020 Apr 9.
2 Functional and mechanistic investigation of Shikonin in scarring. Chem Biol Interact. 2015 Feb 25;228:18-27. doi: 10.1016/j.cbi.2014.12.037. Epub 2015 Jan 12.
3 Shikonin suppresses small cell lung cancer growth via inducing ATF3-mediated ferroptosis to promote ROS accumulation. Chem Biol Interact. 2023 Sep 1;382:110588. doi: 10.1016/j.cbi.2023.110588. Epub 2023 Jun 1.
4 Shikonin suppresses proliferation and induces cell cycle arrest through the inhibition of hypoxia-inducible factor-1 signaling. Chem Biol Interact. 2017 Aug 25;274:58-67. doi: 10.1016/j.cbi.2017.06.029. Epub 2017 Jul 3.
5 A Gene Expression Biomarker Predicts Heat Shock Factor 1 Activation in a Gene Expression Compendium. Chem Res Toxicol. 2021 Jul 19;34(7):1721-1737. doi: 10.1021/acs.chemrestox.0c00510. Epub 2021 Jun 25.
6 Shikonin attenuates lung cancer cell adhesion to extracellular matrix and metastasis by inhibiting integrin 1 expression and the ERK1/2 signaling pathway. Toxicology. 2013 Jun 7;308:104-12. doi: 10.1016/j.tox.2013.03.015. Epub 2013 Apr 4.