(1,7-Bis(4-hydroxyphenyl)-1-heptene-3,5-dione)

Details

• Internal ID: faf56505-2e86-4f87-a1da-6c4007b0117d
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids > Curcuminoids
• IUPAC Name: 1,7-bis(4-hydroxyphenyl)hept-1-ene-3,5-dione
• SMILES (Canonical): C1=CC(=CC=C1CCC(=O)CC(=O)C=CC2=CC=C(C=C2)O)O
• SMILES (Isomeric): C1=CC(=CC=C1CCC(=O)CC(=O)C=CC2=CC=C(C=C2)O)O
• InChI: InChI=1S/C19H18O4/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/h1-5,7-11,20-21H,6,12-13H2
• InChI Key: AWUBJLRYWHOLFW-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈O₄
• Molecular Weight: 310.30 g/mol
• Exact Mass: 310.12050905 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.27
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9763	97.63%
Caco-2	-	0.8205	82.05%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8687	86.87%
OATP2B1 inhibitior	-	0.8607	86.07%
OATP1B1 inhibitior	+	0.9215	92.15%
OATP1B3 inhibitior	+	0.9392	93.92%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7077	70.77%
P-glycoprotein inhibitior	-	0.8447	84.47%
P-glycoprotein substrate	-	0.7941	79.41%
CYP3A4 substrate	-	0.5819	58.19%
CYP2C9 substrate	-	0.6056	60.56%
CYP2D6 substrate	-	0.7881	78.81%
CYP3A4 inhibition	+	0.7977	79.77%
CYP2C9 inhibition	+	0.5925	59.25%
CYP2C19 inhibition	+	0.5797	57.97%
CYP2D6 inhibition	-	0.8635	86.35%
CYP1A2 inhibition	+	0.5164	51.64%
CYP2C8 inhibition	+	0.7105	71.05%
CYP inhibitory promiscuity	-	0.5825	58.25%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7216	72.16%
Carcinogenicity (trinary)	Non-required	0.5996	59.96%
Eye corrosion	-	0.9762	97.62%
Eye irritation	+	0.7110	71.10%
Skin irritation	-	0.7371	73.71%
Skin corrosion	-	0.9676	96.76%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4369	43.69%
Micronuclear	-	0.6582	65.82%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8283	82.83%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	-	0.7500	75.00%
Nephrotoxicity	-	0.6952	69.52%
Acute Oral Toxicity (c)	III	0.6672	66.72%
Estrogen receptor binding	+	0.9292	92.92%
Androgen receptor binding	+	0.6731	67.31%
Thyroid receptor binding	+	0.5252	52.52%
Glucocorticoid receptor binding	+	0.7702	77.02%
Aromatase binding	+	0.8128	81.28%
PPAR gamma	+	0.7328	73.28%
Honey bee toxicity	-	0.8476	84.76%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9799	97.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.67%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.85%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.31%	94.45%
CHEMBL2581	P07339	Cathepsin D	88.31%	98.95%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	87.87%	89.33%
CHEMBL3437	Q16853	Amine oxidase, copper containing	87.75%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.90%	96.09%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	84.72%	85.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.00%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.29%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.10%	86.33%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	81.32%	96.67%
CHEMBL2535	P11166	Glucose transporter	81.24%	98.75%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	80.21%	100.00%

Plants that contains it

• Curcuma longa

Cross-Links

• PubChem: 53666293
• LOTUS: LTS0005122
• wikiData: Q104920275