(2R,3R,4S,5S,6R)-2-[(3R,5R)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: e8d3fc4f-d4a6-499f-bd0e-fddec85a9be6
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids > Curcuminoids
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[(3R,5R)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(=CC=C1CCC(CC(CCC2=CC=C(C=C2)O)OC3C(C(C(C(O3)CO)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1CC[C@H](C[C@@H](CCC2=CC=C(C=C2)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
• InChI: InChI=1S/C25H34O9/c26-14-21-22(30)23(31)24(32)25(34-21)33-20(12-6-16-3-9-18(28)10-4-16)13-19(29)11-5-15-1-7-17(27)8-2-15/h1-4,7-10,19-32H,5-6,11-14H2/t19-,20-,21-,22-,23+,24-,25-/m1/s1
• InChI Key: WRUJLWFLDOUUHV-UYJXDEQJSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₄O₉
• Molecular Weight: 478.50 g/mol
• Exact Mass: 478.22028266 g/mol
• Topological Polar Surface Area (TPSA): 160.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 0.60
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 11

Synonyms

• BDBM50394343
• [(1R,3R)-1-(4-Hydroxyphenethyl)-3-hydroxy-5-(4-hydroxyphenyl)pentyl]beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7754	77.54%
Caco-2	-	0.8720	87.20%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7945	79.45%
OATP2B1 inhibitior	-	0.8600	86.00%
OATP1B1 inhibitior	+	0.8842	88.42%
OATP1B3 inhibitior	+	0.9170	91.70%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7292	72.92%
BSEP inhibitior	+	0.6692	66.92%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.7004	70.04%
CYP3A4 substrate	+	0.5588	55.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7901	79.01%
CYP3A4 inhibition	-	0.8614	86.14%
CYP2C9 inhibition	-	0.8435	84.35%
CYP2C19 inhibition	-	0.8194	81.94%
CYP2D6 inhibition	-	0.8906	89.06%
CYP1A2 inhibition	-	0.9017	90.17%
CYP2C8 inhibition	-	0.6089	60.89%
CYP inhibitory promiscuity	-	0.8964	89.64%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7094	70.94%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.9283	92.83%
Skin irritation	-	0.8184	81.84%
Skin corrosion	-	0.9638	96.38%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8212	82.12%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.8093	80.93%
skin sensitisation	-	0.8675	86.75%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.7920	79.20%
Acute Oral Toxicity (c)	III	0.6897	68.97%
Estrogen receptor binding	+	0.7624	76.24%
Androgen receptor binding	+	0.7097	70.97%
Thyroid receptor binding	+	0.5919	59.19%
Glucocorticoid receptor binding	-	0.6138	61.38%
Aromatase binding	+	0.5433	54.33%
PPAR gamma	+	0.7331	73.31%
Honey bee toxicity	-	0.6480	64.80%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.7755	77.55%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3979	Q03181	Peroxisome proliferator-activated receptor delta	29300 nM	EC50	PMID: 23031596

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.37%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.22%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.83%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.14%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.79%	86.92%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.70%	95.89%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.82%	94.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.12%	97.09%
CHEMBL242	Q92731	Estrogen receptor beta	87.48%	98.35%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	86.50%	100.00%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	85.54%	85.00%
CHEMBL3401	O75469	Pregnane X receptor	85.18%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.64%	95.89%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	81.80%	96.37%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.53%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.09%	94.45%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.70%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.09%	94.00%

Plants that contains it

• Anthriscus sylvestris
• Tacca chantrieri
• Tacca plantaginea

Cross-Links

• PubChem: 10896097
• NPASS: NPC160854
• ChEMBL: CHEMBL516827
• LOTUS: LTS0183016
• wikiData: Q105311594