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(-)-lyoniresinol 3alpha-O-beta-D-glucopyranoside

Family: Plantae - Bignoniaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Phenolic Glycoside

Canonical Smiles	OC[C@H]1Cc2cc(OC)c(c(c2[C@H]([C@@H]1CO[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)c1cc(OC)c(c(c1)OC)O)OC)O
InChI	InChI=1S/C28H38O13/c1-36-16-7-13(8-17(37-2)22(16)31)20-15(11-40-28-26(35)25(34)23(32)19(10-30)41-28)14(9-29)5-12-6-18(38-3)24(33)27(39-4)21(12)20/h6-8,14-15,19-20,23,25-26,28-35H,5,9-11H2,1-4H3/t14-,15-,19-,20+,23-,25+,26-,28-/m1/s1
InChIKey	PQQRNPDHSJDAGV-UGJKOEBBSA-N
Formula	C₂₈H₃₈O₁₃
HBA	13
HBD	7
MW	582.6
Rotatable Bonds	10
TPSA	196.99
LogP	-0.14
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	41
Formal Charge	0
Fraction CSP3	0.57
Exact Mass	582.23
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Amphilophium paniculatum	Bignoniaceae	Plantae	353927

Showing of synonyms

Samy MN, Khalil HE, et al. (2015). Amphipaniculosides A-D, triterpenoid glycosides, and amphipaniculoside E, an aliphatic alcohol glycoside from the leaves of Amphilophium paniculatum. Phytochemistry,2015,115,261-268. [View] [PubMed]

Pubchem: 10031185

Cas: 143236-02-6

Zinc: ZINC000084153866

Nmrshiftdb2: 60059430

Chembl: CHEMBL2332109

No compound-protein relationship available.

SMILES: O1CCCCC1OCC(C2c3ccccc3)CCc(c24)cccc4

Level: 2

Mol. Weight: 582.6 g/mol

SMILES: O1CCCCC1OCC(C2)CCc(c23)cccc3

Level: 1

Mol. Weight: 582.6 g/mol

SMILES: c1cccc(c12)CCCC2c3ccccc3

Level: 1

Mol. Weight: 582.6 g/mol

SMILES: C1CCCc(c12)cccc2

Level: 0

Mol. Weight: 582.6 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 582.6 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 582.6 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.56
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.320
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 2.63

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.800
Plasma Protein Binding: 70.07
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 11.770
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.100
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.600
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 5.340
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -5754.590
Rat (Acute): 2.460
Rat (Chronic Oral): 4.200
Fathead Minnow: 14.770
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 482.160
Hydration Free Energy: -2.940
Log(D) at pH=7.4: 0.210
Log(P): -1.07
Log S: -4.06
Log(Vapor Pressure): -10.38
Melting Point: 181.75
pKa Acid: 5.9
pKa Basic: 4.1

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9215
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9215
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9083
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9083
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.9044
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.9044
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9005
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9005
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8947
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8947
Bromodomain testis-specific protein	Q58F21	BRDT_HUMAN	Homo sapiens	3	0.8918
Bromodomain testis-specific protein	Q58F21	BRDT_HUMAN	Homo sapiens	3	0.8918
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8802
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8802
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8687
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8687
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8611
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8611
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	5	0.8606
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	5	0.8606
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8525
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8525
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8505
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8505
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8467
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8467
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8263
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8263
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8072
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8072
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7974
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7974
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7973
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7973
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7769
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7769
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7765
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7765
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7702
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7702
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.7613
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.7613
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	3	0.7534
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	3	0.7534
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7503
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7503
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7457
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7457
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7422
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7422
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7377
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7377
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7377
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7377
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7311
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7311
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	5	0.7306
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	5	0.7306
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7280
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7280
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7240
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7240
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7216
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7216
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7214
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7214
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7210
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7210
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7183
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7183
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	4	0.7160
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7160
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7160
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	4	0.7160
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7133
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7133
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7095
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7095
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	4	0.7049
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	4	0.7049
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7047
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7047

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