Details of the Drug

General Information of Drug (ID: DMO5UGV)

Drug Name
DEMETHOXYCURCUMIN
Synonyms
Demethoxycurcumin; monodemethoxycurcumin; 22608-11-3; BHCFM; 24939-17-1; 4-Hydroxycinnamoyl(feroyl)methane; desmethoxycurcumin; Feruloyl-P-hydroxycinnnamoylmethane; curcuminII; UNII-W2F8059T80; 33171-16-3; 4-hydroxycinnamoyl(feruloyl)methane; NSC687841; W2F8059T80; 1,6-Heptadiene-3,5-dione, 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-; 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione; (1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione; demethoxy-curcumin
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) 338.4
Logarithm of the Partition Coefficient (xlogp) 3.3
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C20H18O5
IUPAC Name
(1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
Canonical SMILES
COC1=C(C=CC(=C1)/C=C/C(=O)CC(=O)/C=C/C2=CC=C(C=C2)O)O
InChI
InChI=1S/C20H18O5/c1-25-20-12-15(6-11-19(20)24)5-10-18(23)13-17(22)9-4-14-2-7-16(21)8-3-14/h2-12,21,24H,13H2,1H3/b9-4+,10-5+
InChIKey
HJTVQHVGMGKONQ-LUZURFALSA-N
Cross-matching ID
PubChem CID
5469424
ChEBI ID
CHEBI:65737
CAS Number
22608-11-3
TTD ID
D03EDF

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Prostaglandin G/H synthase 1 (COX-1) TT8NGED PGH1_HUMAN Inhibitor [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Amyloid-beta precursor protein (APP) OTKFD7R4 A4_HUMAN Protein Interaction/Cellular Processes [2]
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [3]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [3]
ATP-binding cassette sub-family C member 2 (ABCC2) OTJSIGV5 MRP2_HUMAN Gene/Protein Processing [4]
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [3]
Bcl-2 homologous antagonist/killer (BAK1) OTDP6ILW BAK_HUMAN Gene/Protein Processing [5]
Bcl-2-like protein 1 (BCL2L1) OTRC5K9O B2CL1_HUMAN Gene/Protein Processing [5]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [5]
Caspase-8 (CASP8) OTA8TVI8 CASP8_HUMAN Gene/Protein Processing [5]
Caspase-9 (CASP9) OTD4RFFG CASP9_HUMAN Gene/Protein Processing [5]
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
Prostaglandin G/H synthase 1 (COX-1) DTT PTGS1 3.97E-03 0.16 0.43
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Design, synthesis, biological evaluation and molecular docking of curcumin analogues as antioxidant, cyclooxygenase inhibitory and anti-inflammator... Bioorg Med Chem Lett. 2005 Apr 1;15(7):1793-7.
2 Optimized turmeric extracts have potent anti-amyloidogenic effects. Curr Alzheimer Res. 2009 Dec;6(6):564-71. doi: 10.2174/156720509790147115.
3 Demethoxycurcumin induces apoptosis in HER2 overexpressing bladder cancer cells through degradation of HER2 and inhibiting the PI3K/Akt pathway. Environ Toxicol. 2021 Nov;36(11):2186-2195. doi: 10.1002/tox.23332. Epub 2021 Jul 22.
4 Inhibition of multidrug resistance proteins MRP1 and MRP2 by a series of alpha,beta-unsaturated carbonyl compounds. Biochem Pharmacol. 2005 Jun 15;69(12):1879-90. doi: 10.1016/j.bcp.2005.04.001.
5 Dimethoxycurcumin reduces proliferation and induces apoptosis in renal tumor cells more efficiently than demethoxycurcumin and curcumin. Chem Biol Interact. 2021 Apr 1;338:109410. doi: 10.1016/j.cbi.2021.109410. Epub 2021 Feb 12.