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

Details

• Internal ID: 0841dcb9-9bfa-4123-8f55-5417472a401e
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids > Curcuminoids
• IUPAC Name: 1-[(3R,6S)-6-hydroxy-6'-[(E)-2-(4-hydroxyphenyl)ethenyl]-3,4',4',7-tetramethylspiro[3,4,4a,5,6,8a-hexahydrochromene-2,2'-3H-pyran]-5'-yl]-3-(4-hydroxyphenyl)propan-1-one
• SMILES (Canonical): CC1CC2CC(C(=CC2OC13CC(C(=C(O3)C=CC4=CC=C(C=C4)O)C(=O)CCC5=CC=C(C=C5)O)(C)C)C)O
• SMILES (Isomeric): C[C@@H]1CC2C[C@@H](C(=CC2OC13CC(C(=C(O3)/C=C/C4=CC=C(C=C4)O)C(=O)CCC5=CC=C(C=C5)O)(C)C)C)O
• InChI: InChI=1S/C34H40O6/c1-21-17-31-25(19-29(21)38)18-22(2)34(40-31)20-33(3,4)32(28(37)15-9-23-5-11-26(35)12-6-23)30(39-34)16-10-24-7-13-27(36)14-8-24/h5-8,10-14,16-17,22,25,29,31,35-36,38H,9,15,18-20H2,1-4H3/b16-10+/t22-,25?,29+,31?,34?/m1/s1
• InChI Key: HUZJPPZSWVPJKM-MATFNTSRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₀O₆
• Molecular Weight: 544.70 g/mol
• Exact Mass: 544.28248899 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 6.46
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9728	97.28%
Caco-2	-	0.7913	79.13%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7586	75.86%
OATP2B1 inhibitior	-	0.8545	85.45%
OATP1B1 inhibitior	+	0.8108	81.08%
OATP1B3 inhibitior	+	0.9181	91.81%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9904	99.04%
P-glycoprotein inhibitior	+	0.8755	87.55%
P-glycoprotein substrate	+	0.6526	65.26%
CYP3A4 substrate	+	0.6837	68.37%
CYP2C9 substrate	-	0.8103	81.03%
CYP2D6 substrate	-	0.8668	86.68%
CYP3A4 inhibition	-	0.5058	50.58%
CYP2C9 inhibition	-	0.8736	87.36%
CYP2C19 inhibition	-	0.7877	78.77%
CYP2D6 inhibition	-	0.9285	92.85%
CYP1A2 inhibition	-	0.6795	67.95%
CYP2C8 inhibition	+	0.8213	82.13%
CYP inhibitory promiscuity	-	0.8322	83.22%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5830	58.30%
Eye corrosion	-	0.9947	99.47%
Eye irritation	-	0.9253	92.53%
Skin irritation	-	0.5897	58.97%
Skin corrosion	-	0.9425	94.25%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8982	89.82%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.5507	55.07%
skin sensitisation	-	0.7709	77.09%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.8505	85.05%
Acute Oral Toxicity (c)	I	0.5197	51.97%
Estrogen receptor binding	+	0.8553	85.53%
Androgen receptor binding	+	0.8060	80.60%
Thyroid receptor binding	+	0.7085	70.85%
Glucocorticoid receptor binding	+	0.8827	88.27%
Aromatase binding	+	0.7184	71.84%
PPAR gamma	+	0.6906	69.06%
Honey bee toxicity	-	0.7020	70.20%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9969	99.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.27%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	93.00%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.17%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.92%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.01%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.93%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.82%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.35%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.33%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.92%	95.50%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	85.61%	85.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.57%	97.21%
CHEMBL3401	O75469	Pregnane X receptor	83.53%	94.73%
CHEMBL2039	P27338	Monoamine oxidase B	82.99%	92.51%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.87%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.43%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.36%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.95%	90.71%
CHEMBL2179	P04062	Beta-glucocerebrosidase	81.19%	85.31%
CHEMBL5805	Q9NR97	Toll-like receptor 8	80.88%	96.25%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.63%	91.71%
CHEMBL2514	O95665	Neurotensin receptor 2	80.47%	100.00%

Plants that contains it

• Curcuma longa

Cross-Links

• PubChem: 102230685
• NPASS: NPC33101