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Isolaricireinol 9-O-beta-d-glucopyranoside

Family: Plantae - Cistaceae
Kingdom: Plantae
Class: Lignan
- Subclass: Lignan Glycoside

Canonical Smiles	OC[C@@H]1[C@@H](COC2OC(CO)C(C(C2O)O)O)Cc2c([C@@H]1c1ccc(c(c1)OC)O)cc(c(c2)OC)O
InChI	InChI=1S/C26H34O11/c1-34-19-6-12(3-4-17(19)29)22-15-8-18(30)20(35-2)7-13(15)5-14(16(22)9-27)11-36-26-25(33)24(32)23(31)21(10-28)37-26/h3-4,6-8,14,16,21-33H,5,9-11H2,1-2H3/t14-,16-,21?,22+,23?,24?,25?,26?/m1/s1
InChIKey	BUQQDANPHQFSEK-RUUKAGPKSA-N
Formula	C₂₆H₃₄O₁₁
HBA	11
HBD	7
MW	522.55
Rotatable Bonds	8
TPSA	178.53
LogP	-0.16
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	37
Formal Charge	0
Fraction CSP3	0.54
Exact Mass	522.21
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Helianthemum sessiliflorum	Cistaceae	Plantae	2650562

Showing of synonyms

Benabdelaziz I, Marcourt L, et al. (2017). Antioxidant and antibacterial activities and polyphenolic constituents of Helianthemum sessiliflorum Pers.. Natural product research, 2017, 31(6), 686-690. [View] [PubMed]

No compound-protein relationship available.

SMILES: O1CCCCC1OCC(Cc(c23)cccc2)CC3c4ccccc4

Level: 2

Mol. Weight: 522.55 g/mol

SMILES: O1CCCCC1OCC(C2)CCc(c23)cccc3

Level: 1

Mol. Weight: 522.55 g/mol

SMILES: c1cccc(c12)CCCC2c3ccccc3

Level: 1

Mol. Weight: 522.55 g/mol

SMILES: C1CCCc(c12)cccc2

Level: 0

Mol. Weight: 522.55 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 522.55 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 522.55 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.58
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.380
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.36

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.850
Plasma Protein Binding: 37.94
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: 13.620
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.660
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.620
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.970
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: -905.110
Rat (Acute): 2.520
Rat (Chronic Oral): 4.110
Fathead Minnow: 4.440
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: 549.280
Hydration Free Energy: -3.120
Log(D) at pH=7.4: 0.650
Log(P): -0.92
Log S: -3.87
Log(Vapor Pressure): -10.63
Melting Point: 193.91
pKa Acid: 5.45
pKa Basic: 5.48

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.9544
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9286
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8907
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.8847
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8820
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8814
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8779
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8778
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8733
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8648
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8594
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8511
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8500
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8431
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8396
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8380
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8358
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	3	0.8266
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8249
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8059
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8038
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8028
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8000
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7960
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7957
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7955
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7945
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7906
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7859
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7858
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7793
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7740
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7740
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7716
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7680
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7672
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7599
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7592
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7567
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7539
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7533
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7516
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.7515
Bromodomain testis-specific protein	Q58F21	BRDT_HUMAN	Homo sapiens	3	0.7489
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7483
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7472
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7469
Putative cytochrome P450	Q70AS3	Q70AS3_STRPE	Streptomyces peucetius	4	0.7443
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7425
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7405
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7404
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7387
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7387
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7345
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7340
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7338
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7317
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7315
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	4	0.7301
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7292
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7289
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7287
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.7280
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7258
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7244
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7239
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7229
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7225
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.7196
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7184
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7160
Orotidine 5'-phosphate decarboxylase	O26232	PYRF_METTH	Methanothermobacter thermautotrophicus	3	0.7159
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7157
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7147
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7140
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7140
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7137
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	3	0.7134
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7131
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	4	0.7128
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7113
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7061
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7026
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7019
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7017
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7004

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