Details of the Drug

General Information of Drug (ID: DMGOURX)

• Drug Name: USNIC ACID
• Synonyms: usnic acid; 125-46-2; Usniacin; Usno; Usninsaeure [German]; (+-)-Uanic acid; usnic-acid; Usinic acid; L-Usnic acid; NSC 8517; CCRIS 5518; HSDB 7170; NSC5890; 1,3(2H,9bH)-Dibenzofurandione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-; C18H16O7; EINECS 204-740-7; BRN 1299865; 2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H,9bH)-dibenzofurandione; AI3-50457; CHEBI:2264; NSC8517; NSC5889; 2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzo[b,d]furan-1,3(2H,9bh)-dione

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); 344.3
  Logarithm of the Partition Coefficient (xlogp); 1.4
  Rotatable Bond Count (rotbonds); 2
  Hydrogen Bond Donor Count (hbonddonor); 2
  Hydrogen Bond Acceptor Count (hbondacc); 7
• Chemical Identifiers:
  Formula: C18H16O7
  IUPAC Name: 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzofuran-1,3-dione
  Canonical SMILES: CC1=C(C(=C2C(=C1O)C3(C(=CC(=O)C(C3=O)C(=O)C)O2)C)C(=O)C)O
  InChI: InChI=1S/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,11,22-23H,1-4H3
  InChIKey: CUCUKLJLRRAKFN-UHFFFAOYSA-N
• Cross-matching ID:
  PubChem CID: 5646
  ChEBI ID: CHEMBL2264
  CAS Number: 125-46-2
  TTD ID: D09JSD
• Drug Pharmacogenomic Perturbation (DPP)NEW: Click to Jump to the Detailed DPP Information of This Drug
• Drug ADMET Endpoint Profile (DAE)NEW: Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
PTPN1 messenger RNA (PTPN1 mRNA)	TTELIN2	PTN1_HUMAN	Inhibitor	[1]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
C-C motif chemokine 21 (CCL21)	OT7DOXEM	CCL21_HUMAN	Gene/Protein Processing	[2]
Calcium release-activated calcium channel protein 1 (ORAI1)	OT2VE9UU	CRCM1_HUMAN	Gene/Protein Processing	[3]
Cyclic AMP-dependent transcription factor ATF-4 (ATF4)	OTRFV19J	ATF4_HUMAN	Gene/Protein Processing	[3]
Cyclin-C (CCNC)	OTMVK4K4	CCNC_HUMAN	Gene/Protein Processing	[2]
DNA damage-inducible transcript 3 protein (DDIT3)	OTI8YKKE	DDIT3_HUMAN	Gene/Protein Processing	[3]
G1/S-specific cyclin-D3 (CCND3)	OTNKPQ22	CCND3_HUMAN	Gene/Protein Processing	[4]
Histone H2AX (H2AX)	OT18UX57	H2AX_HUMAN	Gene/Protein Processing	[5]
kinase isozyme 1, mitochondrial (PDK1)	OTMABK9Z	PDK1_HUMAN	Post-Translational Modifications	[6]
Mitogen-activated protein kinase 1 (MAPK1)	OTH85PI5	MK01_HUMAN	Post-Translational Modifications	[6]
Mitogen-activated protein kinase 3 (MAPK3)	OTCYKGKO	MK03_HUMAN	Post-Translational Modifications	[6]

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
PTPN1 messenger RNA (PTPN1 mRNA)	DTT	PTPN1	9.44E-01	7.21E-03	0.08

References

• [1] Usimines A-C, bioactive usnic acid derivatives from the Antarctic lichen Stereocaulon alpinum. J Nat Prod. 2008 Apr;71(4):710-2.
• [2] Effects of usnic acid exposure on human hepatoblastoma HepG2 cells in culture. J Appl Toxicol. 2012 Sep;32(9):722-30.
• [3] Endoplasmic Reticulum Stress and Store-Operated Calcium Entry Contribute to Usnic Acid-Induced Toxicity in Hepatic Cells. Toxicol Sci. 2015 Jul;146(1):116-26. doi: 10.1093/toxsci/kfv075. Epub 2015 Apr 13.
• [4] Activation of the Nrf2 signaling pathway in usnic acid-induced toxicity in HepG2 cells. Arch Toxicol. 2017 Mar;91(3):1293-1307.
• [5] Usnic acid induces apoptosis in human gastric cancer cells through ROS generation and DNA damage and causes up-regulation of DNA-PKcs and -H2A.X phosphorylation. Chem Biol Interact. 2020 Jan 5;315:108898. doi: 10.1016/j.cbi.2019.108898. Epub 2019 Nov 9.
• [6] The role of autophagy in usnic acid-induced toxicity in hepatic cells. Toxicol Sci. 2014 Nov;142(1):33-44. doi: 10.1093/toxsci/kfu154. Epub 2014 Jul 30.