[(2S,3S,4S,5S)-5-[5-[(S)-[(2S,3S,3aS,4S,9bR)-7-hydroxy-2,4-bis(4-hydroxyphenyl)-3,3a,4,9b-tetrahydro-2H-furo[3,2-c]chromen-3-yl]-(2,4-dihydroxyphenyl)methyl]-2,4-dihydroxyphenyl]-2-(4-hydroxyphenyl)-4-[(4-hydroxyphenyl)methyl]oxolan-3-yl]-(2,4-dihydroxyphenyl)methanone

Details

• Internal ID: 45f78836-2163-4ef5-b526-1f2d87f4fe33
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 9,9-epoxylignans
• IUPAC Name: [(2S,3S,4S,5S)-5-[5-[(S)-[(2S,3S,3aS,4S,9bR)-7-hydroxy-2,4-bis(4-hydroxyphenyl)-3,3a,4,9b-tetrahydro-2H-furo[3,2-c]chromen-3-yl]-(2,4-dihydroxyphenyl)methyl]-2,4-dihydroxyphenyl]-2-(4-hydroxyphenyl)-4-[(4-hydroxyphenyl)methyl]oxolan-3-yl]-(2,4-dihydroxyphenyl)methanone
• SMILES (Canonical): C1=CC(=CC=C1CC2C(C(OC2C3=CC(=C(C=C3O)O)C(C4C5C(OC6=C(C5OC4C7=CC=C(C=C7)O)C=CC(=C6)O)C8=CC=C(C=C8)O)C9=C(C=C(C=C9)O)O)C1=CC=C(C=C1)O)C(=O)C1=C(C=C(C=C1)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C[C@H]2[C@@H]([C@H](O[C@@H]2C3=CC(=C(C=C3O)O)[C@@H]([C@H]4[C@@H]5[C@H](OC6=C([C@@H]5O[C@@H]4C7=CC=C(C=C7)O)C=CC(=C6)O)C8=CC=C(C=C8)O)C9=C(C=C(C=C9)O)O)C1=CC=C(C=C1)O)C(=O)C1=C(C=C(C=C1)O)O)O
• InChI: InChI=1S/C60H50O15/c61-33-9-1-29(2-10-33)23-45-52(55(72)41-21-18-38(66)25-47(41)69)56(30-3-11-34(62)12-4-30)74-59(45)44-27-43(48(70)28-49(44)71)51(40-20-17-37(65)24-46(40)68)53-54-58(32-7-15-36(64)16-8-32)73-50-26-39(67)19-22-42(50)60(54)75-57(53)31-5-13-35(63)14-6-31/h1-22,24-28,45,51-54,56-71H,23H2/t45-,51-,52+,53-,54+,56+,57+,58+,59+,60-/m0/s1
• InChI Key: SZANJVUUZYJUNX-PLHMJMAZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆₀H₅₀O₁₅
• Molecular Weight: 1011.00 g/mol
• Exact Mass: 1010.31497088 g/mol
• Topological Polar Surface Area (TPSA): 267.00 Ų
• XlogP: 9.30
• Atomic LogP (AlogP): 10.63
• H-Bond Acceptor: 15
• 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	+	0.9668	96.68%
Caco-2	-	0.8914	89.14%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8034	80.34%
OATP2B1 inhibitior	-	0.7089	70.89%
OATP1B1 inhibitior	+	0.8401	84.01%
OATP1B3 inhibitior	-	0.3773	37.73%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7954	79.54%
P-glycoprotein inhibitior	+	0.7418	74.18%
P-glycoprotein substrate	+	0.6020	60.20%
CYP3A4 substrate	+	0.6686	66.86%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.7567	75.67%
CYP3A4 inhibition	+	0.8493	84.93%
CYP2C9 inhibition	+	0.9336	93.36%
CYP2C19 inhibition	+	0.8425	84.25%
CYP2D6 inhibition	-	0.8298	82.98%
CYP1A2 inhibition	+	0.8415	84.15%
CYP2C8 inhibition	+	0.7277	72.77%
CYP inhibitory promiscuity	+	0.8908	89.08%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5699	56.99%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.8890	88.90%
Skin irritation	-	0.5320	53.20%
Skin corrosion	-	0.9635	96.35%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7293	72.93%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8095	80.95%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8122	81.22%
Acute Oral Toxicity (c)	II	0.5818	58.18%
Estrogen receptor binding	+	0.7771	77.71%
Androgen receptor binding	+	0.7436	74.36%
Thyroid receptor binding	+	0.5733	57.33%
Glucocorticoid receptor binding	+	0.5392	53.92%
Aromatase binding	-	0.5200	52.00%
PPAR gamma	+	0.7218	72.18%
Honey bee toxicity	-	0.7655	76.55%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9258	92.58%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.64%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.61%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.14%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	95.61%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.67%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	92.00%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.22%	95.89%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	89.18%	85.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.00%	99.15%
CHEMBL2535	P11166	Glucose transporter	87.43%	98.75%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.54%	96.95%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.54%	93.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.91%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.08%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.66%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	84.44%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.54%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.30%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.08%	95.50%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	81.94%	93.10%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.89%	95.17%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	81.69%	89.67%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	81.47%	90.93%
CHEMBL340	P08684	Cytochrome P450 3A4	81.37%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.13%	92.62%
CHEMBL3891	P07384	Calpain 1	80.98%	93.04%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.77%	97.36%

Plants that contains it

• Lophira alata

Cross-Links

• PubChem: 101634667
• LOTUS: LTS0254680
• wikiData: Q105263922