(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one

Details

• Internal ID: 21b4f760-da5e-4b21-8714-52fd946dfc9d
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids > Curcuminoids
• IUPAC Name: (1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=CC(=O)C=CC2=CC=C(C=C2)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C(=C/C(=O)/C=C/C2=CC=C(C=C2)O)/O)O
• InChI: InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-13,20-22H/b11-5+,12-6+,18-13-
• InChI Key: YXAKCQIIROBKOP-HSSGTREWSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₆O₄
• Molecular Weight: 308.30 g/mol
• Exact Mass: 308.10485899 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 4.00

Synonyms

• CHEMBL131770
• (1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one
• 1,4,6-Heptatrien-3-one, 5-hydroxy-1,7-bis(4-hydroxyphenyl)-,(1E,4Z,6E)-
• (1E,4Z,6E)-5-Hydroxy-1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one
• p,p-hydroxy-curucumin
• 1,4,6-Heptatrien-3-one
• MLS002473127
• SCHEMBL609967
• MEGxp0_001762
• 1,4,6-Heptatrien-3-one, 5-hydroxy-1,7-bis(4-hydroxyphenyl)-, (Z,E,E)-
• ACon1_002080
• DTXSID001014705
• HMS2224E08
• VUF-9014
• BDBM50145907
• AKOS040762832
• NCGC00179852-01
• SMR001397224
• C17743
• A930227
• 1,7-Bis(4-hydroxyphenyl)-5-hydroxyhepta-1,4,6-trien-3-one
• (1E,4Z,6E)-1,7-Bis(4-hydroxyphenyl)-5-hydroxy-1,4,6-heptatriene-3-one
• (Z,E,E)-5-Hydroxy-1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one
• InChI=1/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-13,20-22H/b11-5+,12-6+,18-13

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4822	P56817	Beta-secretase 1	2540 nM	IC50	PMID: 26696252
CHEMBL262	P49841	Glycogen synthase kinase-3 beta	8390 nM	IC50	PMID: 26696252
CHEMBL5804	Q9NR96	Toll-like receptor 9	9767 nM	IC50	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3194	P02766	Transthyretin	91.61%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.21%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.71%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.95%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.91%	91.11%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.66%	91.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.94%	89.00%
CHEMBL242	Q92731	Estrogen receptor beta	80.46%	98.35%

Plants that contains it

• Alpinia officinarum
• Alpinia roxburghii
• Curcuma aromatica
• Curcuma longa
• Curcuma mangga
• Curcuma wenyujin
• Curcuma zedoaria

Cross-Links

• PubChem: 5324473
• NPASS: NPC130193
• ChEMBL: CHEMBL131770
• LOTUS: LTS0119040
• wikiData: Q76303632