3-(4-hydroxy-3-methoxyphenyl)-1-[(3R)-6'-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3,4',4',7-tetramethylspiro[3,4,4a,5,6,8a-hexahydrochromene-2,2'-3H-pyran]-5'-yl]propan-1-one

Details

• Internal ID: 408b339a-7cf1-4cc0-b7e7-1cf4c520f4f3
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids > Curcuminoids
• IUPAC Name: 3-(4-hydroxy-3-methoxyphenyl)-1-[(3R)-6'-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3,4',4',7-tetramethylspiro[3,4,4a,5,6,8a-hexahydrochromene-2,2'-3H-pyran]-5'-yl]propan-1-one
• SMILES (Canonical): CC1CC2CCC(=CC2OC13CC(C(=C(O3)C=CC4=CC(=C(C=C4)O)OC)C(=O)CCC5=CC(=C(C=C5)O)OC)(C)C)C
• SMILES (Isomeric): C[C@@H]1CC2CCC(=CC2OC13CC(C(=C(O3)/C=C/C4=CC(=C(C=C4)O)OC)C(=O)CCC5=CC(=C(C=C5)O)OC)(C)C)C
• InChI: InChI=1S/C36H44O7/c1-22-7-12-26-18-23(2)36(43-31(26)17-22)21-35(3,4)34(29(39)15-10-24-8-13-27(37)32(19-24)40-5)30(42-36)16-11-25-9-14-28(38)33(20-25)41-6/h8-9,11,13-14,16-17,19-20,23,26,31,37-38H,7,10,12,15,18,21H2,1-6H3/b16-11+/t23-,26?,31?,36?/m1/s1
• InChI Key: DOKBENGMJOKQTO-AUZZRSQKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₄₄O₇
• Molecular Weight: 588.70 g/mol
• Exact Mass: 588.30870374 g/mol
• Topological Polar Surface Area (TPSA): 94.40 Ų
• XlogP: 6.80
• Atomic LogP (AlogP): 7.51
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9703	97.03%
Caco-2	-	0.7667	76.67%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7692	76.92%
OATP2B1 inhibitior	-	0.8592	85.92%
OATP1B1 inhibitior	+	0.8503	85.03%
OATP1B3 inhibitior	-	0.2337	23.37%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9939	99.39%
P-glycoprotein inhibitior	+	0.9131	91.31%
P-glycoprotein substrate	+	0.5856	58.56%
CYP3A4 substrate	+	0.7193	71.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8535	85.35%
CYP3A4 inhibition	-	0.8212	82.12%
CYP2C9 inhibition	-	0.8404	84.04%
CYP2C19 inhibition	-	0.6479	64.79%
CYP2D6 inhibition	-	0.8768	87.68%
CYP1A2 inhibition	-	0.5774	57.74%
CYP2C8 inhibition	+	0.9125	91.25%
CYP inhibitory promiscuity	-	0.7598	75.98%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6492	64.92%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.9172	91.72%
Skin irritation	-	0.7389	73.89%
Skin corrosion	-	0.9562	95.62%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8215	82.15%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.5248	52.48%
skin sensitisation	-	0.8237	82.37%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.9372	93.72%
Acute Oral Toxicity (c)	III	0.3497	34.97%
Estrogen receptor binding	+	0.8157	81.57%
Androgen receptor binding	+	0.8057	80.57%
Thyroid receptor binding	+	0.6779	67.79%
Glucocorticoid receptor binding	+	0.8786	87.86%
Aromatase binding	+	0.7159	71.59%
PPAR gamma	+	0.7259	72.59%
Honey bee toxicity	-	0.7200	72.00%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9959	99.59%

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	99.24%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.72%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.46%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.37%	95.56%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.37%	95.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.01%	99.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.95%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.49%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.99%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.70%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.59%	95.89%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.26%	96.95%
CHEMBL2581	P07339	Cathepsin D	88.91%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.97%	96.00%
CHEMBL3820	P35557	Hexokinase type IV	87.69%	91.96%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.67%	97.09%
CHEMBL4208	P20618	Proteasome component C5	87.29%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.92%	92.62%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	85.46%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.24%	95.89%
CHEMBL3194	P02766	Transthyretin	83.02%	90.71%
CHEMBL340	P08684	Cytochrome P450 3A4	81.38%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.26%	91.07%
CHEMBL5028	O14672	ADAM10	80.80%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.43%	97.14%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.38%	91.71%

Plants that contains it

• Curcuma longa

Cross-Links

• PubChem: 102230686
• NPASS: NPC281295