(1R,2S)-3-[(2S,3S,4R,5S)-4,5-dihydroxy-2-[(2R)-2-hydroxy-3-methoxy-3-oxopropyl]oxan-3-yl]oxycarbonyl-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carboxylic acid

Details

• Internal ID: e98e5a34-608d-426c-be64-b875a215d5fe
• Taxonomy: Lignans, neolignans and related compounds > Aryltetralin lignans
• IUPAC Name: (1R,2S)-3-[(2S,3S,4R,5S)-4,5-dihydroxy-2-[(2R)-2-hydroxy-3-methoxy-3-oxopropyl]oxan-3-yl]oxycarbonyl-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carboxylic acid
• SMILES (Canonical): COC(=O)C(CC1C(C(C(CO1)O)O)OC(=O)C2=CC3=CC(=C(C=C3C(C2C(=O)O)C4=CC(=C(C=C4)O)O)O)O)O
• SMILES (Isomeric): COC(=O)[C@@H](C[C@H]1[C@H]([C@@H]([C@H](CO1)O)O)OC(=O)C2=CC3=CC(=C(C=C3[C@H]([C@@H]2C(=O)O)C4=CC(=C(C=C4)O)O)O)O)O
• InChI: InChI=1S/C27H28O14/c1-39-27(38)18(32)8-20-24(23(34)19(33)9-40-20)41-26(37)13-4-11-6-16(30)17(31)7-12(11)21(22(13)25(35)36)10-2-3-14(28)15(29)5-10/h2-7,18-24,28-34H,8-9H2,1H3,(H,35,36)/t18-,19+,20+,21-,22-,23-,24-/m1/s1
• InChI Key: WPPCSTMOGIKOOD-CEMGRNOWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₈O₁₄
• Molecular Weight: 576.50 g/mol
• Exact Mass: 576.14790556 g/mol
• Topological Polar Surface Area (TPSA): 241.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.30
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8848	88.48%
Caco-2	-	0.9169	91.69%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7652	76.52%
OATP2B1 inhibitior	-	0.8427	84.27%
OATP1B1 inhibitior	+	0.8717	87.17%
OATP1B3 inhibitior	+	0.9626	96.26%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9408	94.08%
P-glycoprotein inhibitior	-	0.5071	50.71%
P-glycoprotein substrate	+	0.5481	54.81%
CYP3A4 substrate	+	0.6760	67.60%
CYP2C9 substrate	-	0.7955	79.55%
CYP2D6 substrate	-	0.8505	85.05%
CYP3A4 inhibition	-	0.8511	85.11%
CYP2C9 inhibition	-	0.5615	56.15%
CYP2C19 inhibition	-	0.6082	60.82%
CYP2D6 inhibition	-	0.8736	87.36%
CYP1A2 inhibition	-	0.5474	54.74%
CYP2C8 inhibition	+	0.6962	69.62%
CYP inhibitory promiscuity	-	0.7315	73.15%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6380	63.80%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9085	90.85%
Skin irritation	-	0.8098	80.98%
Skin corrosion	-	0.9495	94.95%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7459	74.59%
Micronuclear	+	0.6559	65.59%
Hepatotoxicity	-	0.6837	68.37%
skin sensitisation	-	0.8483	84.83%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.9025	90.25%
Acute Oral Toxicity (c)	III	0.4602	46.02%
Estrogen receptor binding	+	0.7961	79.61%
Androgen receptor binding	+	0.6799	67.99%
Thyroid receptor binding	-	0.5193	51.93%
Glucocorticoid receptor binding	-	0.4917	49.17%
Aromatase binding	-	0.6710	67.10%
PPAR gamma	+	0.5899	58.99%
Honey bee toxicity	-	0.7682	76.82%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9829	98.29%

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	99.86%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.29%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.31%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.40%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	93.89%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.60%	97.09%
CHEMBL2581	P07339	Cathepsin D	93.50%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	92.15%	83.82%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.01%	99.15%
CHEMBL226	P30542	Adenosine A1 receptor	87.81%	95.93%
CHEMBL340	P08684	Cytochrome P450 3A4	87.14%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	86.77%	90.17%
CHEMBL3922	P50579	Methionine aminopeptidase 2	86.58%	97.28%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.04%	96.38%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.63%	99.17%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	84.46%	89.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.78%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.27%	92.62%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.12%	90.71%
CHEMBL5028	O14672	ADAM10	82.99%	97.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.98%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.79%	89.00%
CHEMBL4208	P20618	Proteasome component C5	82.74%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.44%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	81.25%	92.50%

Plants that contains it

• Bazzania trilobata

Cross-Links

• PubChem: 163005904
• LOTUS: LTS0003217
• wikiData: Q105310106