5-[(1R,2R)-2-carboxy-3-[(2S,3S,4S,5S)-3-[(3S,4R)-3-carboxy-4-(3,4-dihydroxyphenyl)-6,7-dihydroxy-3,4-dihydronaphthalene-2-carbonyl]oxy-2-(carboxymethyl)-5-hydroxyoxan-4-yl]oxycarbonyl-6,7-dihydroxy-1,2-dihydronaphthalen-1-yl]-6-oxopyran-2-carboxylic acid

Details

• Internal ID: 96e1d9ff-6edc-482b-b8ca-70cf033d4d03
• Taxonomy: Lignans, neolignans and related compounds > Lignan lactones
• IUPAC Name: 5-[(1R,2R)-2-carboxy-3-[(2S,3S,4S,5S)-3-[(3S,4R)-3-carboxy-4-(3,4-dihydroxyphenyl)-6,7-dihydroxy-3,4-dihydronaphthalene-2-carbonyl]oxy-2-(carboxymethyl)-5-hydroxyoxan-4-yl]oxycarbonyl-6,7-dihydroxy-1,2-dihydronaphthalen-1-yl]-6-oxopyran-2-carboxylic acid
• SMILES (Canonical): C1C(C(C(C(O1)CC(=O)O)OC(=O)C2=CC3=CC(=C(C=C3C(C2C(=O)O)C4=CC(=C(C=C4)O)O)O)O)OC(=O)C5=CC6=CC(=C(C=C6C(C5C(=O)O)C7=CC=C(OC7=O)C(=O)O)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@@H]([C@H]([C@@H](O1)CC(=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)OC(=O)C5=CC6=CC(=C(C=C6[C@@H]([C@H]5C(=O)O)C7=CC=C(OC7=O)C(=O)O)O)O)O
• InChI: InChI=1S/C43H34O22/c44-22-3-1-14(7-23(22)45)32-18-10-26(48)24(46)8-15(18)5-20(34(32)39(55)56)43(61)65-37-30(12-31(51)52)62-13-28(50)36(37)64-42(60)21-6-16-9-25(47)27(49)11-19(16)33(35(21)40(57)58)17-2-4-29(38(53)54)63-41(17)59/h1-11,28,30,32-37,44-50H,12-13H2,(H,51,52)(H,53,54)(H,55,56)(H,57,58)/t28-,30-,32+,33-,34+,35-,36-,37-/m0/s1
• InChI Key: VMWRMZUOUIDYCS-ARUDPIHHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₃₄O₂₂
• Molecular Weight: 902.70 g/mol
• Exact Mass: 902.15417271 g/mol
• Topological Polar Surface Area (TPSA): 379.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.79
• H-Bond Acceptor: 18
• H-Bond Donor: 11
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9236	92.36%
Caco-2	-	0.8838	88.38%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7911	79.11%
OATP2B1 inhibitior	-	0.7116	71.16%
OATP1B1 inhibitior	+	0.8590	85.90%
OATP1B3 inhibitior	+	0.9183	91.83%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7075	70.75%
P-glycoprotein inhibitior	+	0.7236	72.36%
P-glycoprotein substrate	+	0.5531	55.31%
CYP3A4 substrate	+	0.6678	66.78%
CYP2C9 substrate	-	0.5973	59.73%
CYP2D6 substrate	-	0.8588	85.88%
CYP3A4 inhibition	-	0.8068	80.68%
CYP2C9 inhibition	-	0.5696	56.96%
CYP2C19 inhibition	-	0.6301	63.01%
CYP2D6 inhibition	-	0.8419	84.19%
CYP1A2 inhibition	-	0.7747	77.47%
CYP2C8 inhibition	+	0.7407	74.07%
CYP inhibitory promiscuity	-	0.6994	69.94%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6583	65.83%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.8989	89.89%
Skin irritation	-	0.7979	79.79%
Skin corrosion	-	0.9543	95.43%
Ames mutagenesis	+	0.5436	54.36%
Human Ether-a-go-go-Related Gene inhibition	+	0.6463	64.63%
Micronuclear	+	0.7418	74.18%
Hepatotoxicity	-	0.6415	64.15%
skin sensitisation	-	0.7856	78.56%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.9412	94.12%
Acute Oral Toxicity (c)	III	0.4922	49.22%
Estrogen receptor binding	+	0.7669	76.69%
Androgen receptor binding	+	0.7368	73.68%
Thyroid receptor binding	+	0.5170	51.70%
Glucocorticoid receptor binding	-	0.5360	53.60%
Aromatase binding	+	0.5578	55.78%
PPAR gamma	+	0.7290	72.90%
Honey bee toxicity	-	0.7111	71.11%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6250	62.50%
Fish aquatic toxicity	+	0.9871	98.71%

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	99.70%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.17%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.97%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.17%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.89%	99.15%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	93.43%	95.17%
CHEMBL1951	P21397	Monoamine oxidase A	93.40%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.11%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	91.39%	83.82%
CHEMBL3194	P02766	Transthyretin	90.79%	90.71%
CHEMBL3922	P50579	Methionine aminopeptidase 2	89.92%	97.28%
CHEMBL340	P08684	Cytochrome P450 3A4	89.50%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.43%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.09%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.00%	95.56%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	85.09%	89.67%
CHEMBL3492	P49721	Proteasome Macropain subunit	84.01%	90.24%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	83.66%	83.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.37%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.27%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.90%	85.14%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.51%	91.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.08%	94.00%

Plants that contains it

• Bazzania trilobata

Cross-Links

• PubChem: 101231536
• LOTUS: LTS0106649
• wikiData: Q105289352