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

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

Canonical Smiles	OC[C@H]1[C@H](CO)Cc2c([C@@H]1c1cc(OC)c(c(c1)OC)O)c(OC)c(c(c2)OC)O[C@@H]1OC(CO)[C@H](C([C@@H]1O)O)O
InChI	InChI=1S/C28H38O13/c1-36-16-6-13(7-17(37-2)22(16)32)20-15(10-30)14(9-29)5-12-8-18(38-3)26(27(39-4)21(12)20)41-28-25(35)24(34)23(33)19(11-31)40-28/h6-8,14-15,19-20,23-25,28-35H,5,9-11H2,1-4H3/t14-,15-,19?,20+,23+,24?,25-,28-/m0/s1
InChIKey	TYCVVKGFKLGEKY-UJEZDFSPSA-N
Formula	C₂₈H₃₈O₁₃
HBA	13
HBD	7
MW	582.6
Rotatable Bonds	10
TPSA	196.99
LogP	-0.49
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	Ruellia tuberosa	Acanthaceae	Plantae	441035
2	Ruellia patula	Acanthaceae	Plantae	441006

Showing of synonyms

Samy MN, Khalil HE, et al. (2013). Chemical constituents from the leaves of Ruellia tuberosa. Chemistry of Natural Compounds,2013,49(1),175-176. [View]
Samy MN, Khalil HE, et al. (2011). Three new flavonoid glycosides, byzantionoside B 6’-O-Sulfate and xyloglucoside of (Z)-hex-3-en-1-ol from Ruellia patula. Chemical and Pharmaceutical Bulletin,2011,59(6),725-729. [View] [PubMed]

Pubchem: 162929172

Nmrshiftdb2: 70057617

No compound-protein relationship available.

SMILES: O1CCCCC1Oc(c2)ccc(c23)CCCC3c4ccccc4

Level: 2

Mol. Weight: 582.6 g/mol

SMILES: C1CCCc(c12)ccc(c2)OC3CCCCO3

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): -6.45
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.170
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 3.14

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.810
Plasma Protein Binding: 60.91
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: 9.390
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.850
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.660
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.050
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: -5931.050
Rat (Acute): 2.560
Rat (Chronic Oral): 4.410
Fathead Minnow: 14.900
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 471.690
Hydration Free Energy: -2.960
Log(D) at pH=7.4: 0.160
Log(P): -1.49
Log S: -3.9
Log(Vapor Pressure): -10.56
Melting Point: 192.69
pKa Acid: 5.9
pKa Basic: 3.17

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.9070
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.9070
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9057
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9057
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8990
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8990
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.8797
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.8797
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8753
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8753
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8679
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8679
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8618
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8618
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8579
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8579
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8329
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8329
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.8280
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.8280
Nuclear receptor subfamily 5 group A member 2	O00482	NR5A2_HUMAN	Homo sapiens	4	0.8192
Nuclear receptor subfamily 5 group A member 2	O00482	NR5A2_HUMAN	Homo sapiens	4	0.8192
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7648
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7648
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7608
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7608
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7512
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7512
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7469
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7469
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	4	0.7384
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	4	0.7384
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7232
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7232
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7189
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7189
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7172
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7172
Orotidine 5'-phosphate decarboxylase	O26232	PYRF_METTH	Methanothermobacter thermautotrophicus	3	0.7168
Orotidine 5'-phosphate decarboxylase	O26232	PYRF_METTH	Methanothermobacter thermautotrophicus	3	0.7168
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7132
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7132
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7130
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7130
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7092
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7092
GMP synthase [glutamine-hydrolyzing]	Q8IJR9	Q8IJR9_PLAF7	Plasmodium falciparum	4	0.7091
GMP synthase [glutamine-hydrolyzing]	Q8IJR9	Q8IJR9_PLAF7	Plasmodium falciparum	4	0.7091

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