(5S)-1-(3,4-dihydroxyphenyl)-7-(3-hydroxyphenyl)-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyheptan-3-one

Details

• Internal ID: cb93f497-9366-4f38-926c-f733b3679adc
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: (5S)-1-(3,4-dihydroxyphenyl)-7-(3-hydroxyphenyl)-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyheptan-3-one
• SMILES (Canonical): C1C(C(C(C(O1)OC(CCC2=CC(=CC=C2)O)CC(=O)CCC3=CC(=C(C=C3)O)O)O)O)O
• SMILES (Isomeric): C1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H](CCC2=CC(=CC=C2)O)CC(=O)CCC3=CC(=C(C=C3)O)O)O)O)O
• InChI: InChI=1S/C24H30O9/c25-16-3-1-2-14(10-16)5-8-18(33-24-23(31)22(30)21(29)13-32-24)12-17(26)7-4-15-6-9-19(27)20(28)11-15/h1-3,6,9-11,18,21-25,27-31H,4-5,7-8,12-13H2/t18-,21+,22-,23+,24-/m0/s1
• InChI Key: OBLUAMRQDSKSPP-RABNCREUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₀O₉
• Molecular Weight: 462.50 g/mol
• Exact Mass: 462.18898253 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.15
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6193	61.93%
Caco-2	-	0.8488	84.88%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8367	83.67%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.9257	92.57%
OATP1B3 inhibitior	+	0.8452	84.52%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8042	80.42%
BSEP inhibitior	+	0.9144	91.44%
P-glycoprotein inhibitior	+	0.5800	58.00%
P-glycoprotein substrate	+	0.5564	55.64%
CYP3A4 substrate	+	0.6465	64.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8192	81.92%
CYP3A4 inhibition	-	0.8052	80.52%
CYP2C9 inhibition	-	0.7771	77.71%
CYP2C19 inhibition	-	0.7142	71.42%
CYP2D6 inhibition	-	0.8733	87.33%
CYP1A2 inhibition	-	0.8136	81.36%
CYP2C8 inhibition	+	0.6058	60.58%
CYP inhibitory promiscuity	-	0.9066	90.66%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7493	74.93%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.8831	88.31%
Skin irritation	-	0.8213	82.13%
Skin corrosion	-	0.9641	96.41%
Ames mutagenesis	+	0.6622	66.22%
Human Ether-a-go-go-Related Gene inhibition	+	0.7469	74.69%
Micronuclear	-	0.6841	68.41%
Hepatotoxicity	-	0.7496	74.96%
skin sensitisation	-	0.8253	82.53%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.9262	92.62%
Acute Oral Toxicity (c)	III	0.7243	72.43%
Estrogen receptor binding	+	0.7913	79.13%
Androgen receptor binding	+	0.6498	64.98%
Thyroid receptor binding	-	0.5116	51.16%
Glucocorticoid receptor binding	-	0.6386	63.86%
Aromatase binding	-	0.5801	58.01%
PPAR gamma	+	0.7111	71.11%
Honey bee toxicity	-	0.6856	68.56%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9244	92.44%

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	99.52%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.31%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.75%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.44%	99.17%
CHEMBL2535	P11166	Glucose transporter	92.85%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.61%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.68%	94.45%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	90.68%	95.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.54%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.28%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	89.42%	94.73%
CHEMBL3437	Q16853	Amine oxidase, copper containing	86.98%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.97%	95.56%
CHEMBL2179	P04062	Beta-glucocerebrosidase	86.51%	85.31%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.02%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.66%	95.50%
CHEMBL3761	Q9HCG7	Beta-glucosidase	83.99%	99.00%
CHEMBL236	P41143	Delta opioid receptor	83.96%	99.35%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.88%	86.33%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	83.22%	100.00%
CHEMBL3891	P07384	Calpain 1	82.07%	93.04%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.05%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.87%	89.00%

Plants that contains it

• Alnus japonica
• Senna spectabilis

Cross-Links

• PubChem: 46230809
• NPASS: NPC180171
• LOTUS: LTS0005337
• wikiData: Q105260605