1,4,6-Heptatrien-3-one, 5-hydroxy-1,7-bis(4-hydroxyphenyl)-

Details

• Internal ID: bc4639bb-92d8-4503-af99-1cb88df1a8dc
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids > Curcuminoids
• IUPAC Name: 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=C1C=CC(=CC(=O)C=CC2=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
• InChI Key: YXAKCQIIROBKOP-UHFFFAOYSA-N
• Popularity: 0 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
• Atomic LogP (AlogP): 3.84
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• 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)-
• 115851-81-5
• 1,4,6-Heptatrien-3-one, 5-hydroxy-1,7-bis(4-hydroxyphenyl)-, (Z,E,E)-
• DTXSID50332828
• AKOS032962606

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9941	99.41%
Caco-2	-	0.7440	74.40%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8312	83.12%
OATP2B1 inhibitior	-	0.7175	71.75%
OATP1B1 inhibitior	+	0.9201	92.01%
OATP1B3 inhibitior	+	0.9237	92.37%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6769	67.69%
P-glycoprotein inhibitior	-	0.8512	85.12%
P-glycoprotein substrate	-	0.9723	97.23%
CYP3A4 substrate	-	0.6897	68.97%
CYP2C9 substrate	-	0.6279	62.79%
CYP2D6 substrate	-	0.8561	85.61%
CYP3A4 inhibition	+	0.6584	65.84%
CYP2C9 inhibition	-	0.5396	53.96%
CYP2C19 inhibition	+	0.6515	65.15%
CYP2D6 inhibition	-	0.9445	94.45%
CYP1A2 inhibition	+	0.8501	85.01%
CYP2C8 inhibition	+	0.4661	46.61%
CYP inhibitory promiscuity	+	0.7628	76.28%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.5808	58.08%
Carcinogenicity (trinary)	Non-required	0.5092	50.92%
Eye corrosion	-	0.9802	98.02%
Eye irritation	+	0.9586	95.86%
Skin irritation	+	0.5354	53.54%
Skin corrosion	-	0.9861	98.61%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7657	76.57%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	-	0.6222	62.22%
skin sensitisation	+	0.6809	68.09%
Respiratory toxicity	-	0.7778	77.78%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.6010	60.10%
Acute Oral Toxicity (c)	III	0.6175	61.75%
Estrogen receptor binding	+	0.9025	90.25%
Androgen receptor binding	+	0.8760	87.60%
Thyroid receptor binding	+	0.6561	65.61%
Glucocorticoid receptor binding	+	0.8086	80.86%
Aromatase binding	+	0.7815	78.15%
PPAR gamma	+	0.8304	83.04%
Honey bee toxicity	-	0.9430	94.30%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9869	98.69%

Targets

Proven Targets:

No proven targets yet!

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 roxburghii
• Curcuma longa
• Curcuma mangga

Cross-Links

• PubChem: 468139
• LOTUS: LTS0052041
• wikiData: Q82097680