3-hydroxy-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl]oxolan-2-one

Details

• Internal ID: aacc0daa-3f83-4ae8-8aae-4750698dd148
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: 3-hydroxy-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl]oxolan-2-one
• SMILES (Canonical): COC1=C(C=CC(=C1)CC2COC(=O)C2(CC3=CC(=C(C=C3)O)OC)O)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)CC2COC(=O)C2(CC3=CC(=C(C=C3)O)OC)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C26H32O12/c1-34-18-9-14(3-5-16(18)28)10-26(33)15(12-36-25(26)32)7-13-4-6-17(19(8-13)35-2)37-24-23(31)22(30)21(29)20(11-27)38-24/h3-6,8-9,15,20-24,27-31,33H,7,10-12H2,1-2H3/t15?,20-,21-,22+,23-,24-,26?/m1/s1
• InChI Key: ITTBAZPFKIZCOW-SCAPWDEESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₂O₁₂
• Molecular Weight: 536.50 g/mol
• Exact Mass: 536.18937645 g/mol
• Topological Polar Surface Area (TPSA): 185.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): -0.72
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6011	60.11%
Caco-2	-	0.8636	86.36%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7511	75.11%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.9036	90.36%
OATP1B3 inhibitior	+	0.9537	95.37%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6438	64.38%
P-glycoprotein inhibitior	-	0.4314	43.14%
P-glycoprotein substrate	-	0.6273	62.73%
CYP3A4 substrate	+	0.6455	64.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8389	83.89%
CYP3A4 inhibition	-	0.8342	83.42%
CYP2C9 inhibition	-	0.9057	90.57%
CYP2C19 inhibition	-	0.8540	85.40%
CYP2D6 inhibition	-	0.9068	90.68%
CYP1A2 inhibition	-	0.8863	88.63%
CYP2C8 inhibition	+	0.6183	61.83%
CYP inhibitory promiscuity	-	0.8650	86.50%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6353	63.53%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9300	93.00%
Skin irritation	-	0.8349	83.49%
Skin corrosion	-	0.9550	95.50%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6666	66.66%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8495	84.95%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7509	75.09%
Acute Oral Toxicity (c)	III	0.6472	64.72%
Estrogen receptor binding	+	0.7867	78.67%
Androgen receptor binding	+	0.5814	58.14%
Thyroid receptor binding	+	0.5702	57.02%
Glucocorticoid receptor binding	+	0.5804	58.04%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6885	68.85%
Honey bee toxicity	-	0.7837	78.37%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.8636	86.36%

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	99.06%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.36%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.81%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.55%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.09%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.55%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.25%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.54%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.74%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.62%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.10%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.73%	99.17%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	84.21%	97.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.78%	97.09%
CHEMBL220	P22303	Acetylcholinesterase	83.25%	94.45%
CHEMBL5555	O00767	Acyl-CoA desaturase	82.83%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.98%	97.14%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.76%	95.83%
CHEMBL2535	P11166	Glucose transporter	80.37%	98.75%
CHEMBL1255126	O15151	Protein Mdm4	80.12%	90.20%

Plants that contains it

• Daphne odora
• Trachelospermum jasminoides

Cross-Links

• PubChem: 5320221
• NPASS: NPC266238