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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]1OC(CO)[C@H](C([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-/m0/s1
InChIKey	PQQRNPDHSJDAGV-BVDVCCPJSA-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: 162939862

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): -6.57
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: 2.61

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.800
Plasma Protein Binding: 62.89
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: 11.740
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.040
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: Safe
Daphnia Maga: 5.350
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: -5753.990
Rat (Acute): 2.460
Rat (Chronic Oral): 4.210
Fathead Minnow: 14.800
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: 480.180
Hydration Free Energy: -2.940
Log(D) at pH=7.4: 0.210
Log(P): -1.16
Log S: -4.01
Log(Vapor Pressure): -10.22
Melting Point: 177.7
pKa Acid: 5.91
pKa Basic: 4.1

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.9583
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.9583
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8876
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8876
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8639
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8639
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8407
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8407
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8351
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8351
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.8300
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.8300
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.8237
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.8237
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8222
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8222
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8165
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8165
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8121
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8121
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7942
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7942
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7905
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7905
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7828
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7828
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7768
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7768
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7678
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7678
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7653
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7653
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7637
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7637
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7634
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7634
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7468
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7468
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7433
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7433
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7427
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7427
Albumin	P02768	ALBU_HUMAN	Homo sapiens	4	0.7342
Albumin	P02768	ALBU_HUMAN	Homo sapiens	4	0.7342
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7341
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7341
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7335
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7335
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	3	0.7318
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	3	0.7318
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7310
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7310
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7193
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7193
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7099
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7099
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7088
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7088
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7077
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7077
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7065
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7065
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7062
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7062
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7028
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7028
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7025
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7025
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7000
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7000

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