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
Structure
3D MOL 2D MOL
#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
CHEBI:2264
CAS Number
125-46-2
TTD ID
D09JSD

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
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [2]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [2]
C-C motif chemokine 21 (CCL21) OT7DOXEM CCL21_HUMAN Gene/Protein Processing [3]
Calcium release-activated calcium channel protein 1 (ORAI1) OT2VE9UU CRCM1_HUMAN Gene/Protein Processing [4]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [2]
Caspase-4 (CASP4) OTVQTV1L CASP4_HUMAN Protein Interaction/Cellular Processes [4]
Caspase-7 (CASP7) OTAPJ040 CASP7_HUMAN Gene/Protein Processing [5]
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Gene/Protein Processing [2]
Cyclic AMP-dependent transcription factor ATF-4 (ATF4) OTRFV19J ATF4_HUMAN Gene/Protein Processing [4]
Cyclin-C (CCNC) OTMVK4K4 CCNC_HUMAN Gene/Protein Processing [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

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
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

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 Lichen secondary metabolites are responsible for induction of apoptosis in HT-29 and A2780 human cancer cell lines. Toxicol In Vitro. 2012 Apr;26(3):462-8. doi: 10.1016/j.tiv.2012.01.017. Epub 2012 Jan 21.
3 Effects of usnic acid exposure on human hepatoblastoma HepG2 cells in culture. J Appl Toxicol. 2012 Sep;32(9):722-30.
4 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.
5 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.