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
CHEMBL65737
CAS Number
22608-11-3
TTD ID
D03EDF
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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]
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 [4]
Bcl-2-like protein 1 (BCL2L1) OTRC5K9O B2CL1_HUMAN Gene/Protein Processing [4]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [4]
E3 ubiquitin-protein ligase XIAP OT24GP9B XIAP_HUMAN Gene/Protein Processing [3]
Growth arrest and DNA damage-inducible protein GADD45 alpha (GADD45A) OTDRV63V GA45A_HUMAN Gene/Protein Processing [4]
Metalloproteinase inhibitor 2 (TIMP2) OT8S1RRP TIMP2_HUMAN Gene/Protein Processing [5]
Poly polymerase 1 (PARP1) OT310QSG PARP1_HUMAN Protein Interaction/Cellular Processes [3]
RAF proto-oncogene serine/threonine-protein kinase (RAF1) OT51LSFO RAF1_HUMAN Gene/Protein Processing [3]
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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
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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 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.
5 Curcumin, demethoxycurcumin and bisdemethoxycurcumin differentially inhibit cancer cell invasion through the down-regulation of MMPs and uPA. J Nutr Biochem. 2009 Feb;20(2):87-95. doi: 10.1016/j.jnutbio.2007.12.003. Epub 2008 May 20.