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Secoisolariciresinol diglucoside

Family: Plantae - Linaceae
Kingdom: Plantae
Class: Lignan

Canonical Smiles	OC[C@H]1O[C@@H](OC[C@@H]([C@@H](Cc2ccc(c(c2)OC)O)CO[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)Cc2ccc(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C32H46O16/c1-43-21-9-15(3-5-19(21)35)7-17(13-45-31-29(41)27(39)25(37)23(11-33)47-31)18(8-16-4-6-20(36)22(10-16)44-2)14-46-32-30(42)28(40)26(38)24(12-34)48-32/h3-6,9-10,17-18,23-42H,7-8,11-14H2,1-2H3/t17-,18-,23+,24+,25+,26+,27-,28-,29+,30+,31+,32+/m0/s1
InChIKey	SBVBJPHMDABKJV-PGCJWIIOSA-N
Formula	C₃₂H₄₆O₁₆
HBA	16
HBD	10
MW	686.7
Rotatable Bonds	15
TPSA	257.68
LogP	-2.23
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	48
Formal Charge	0
Fraction CSP3	0.62
Exact Mass	686.28
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Linum usitatissimum	Linaceae	Plantae	4006

Showing of synonyms

Gabr A.M.M, Mabrok H.B, et al. (2018). Determination of lignans, phenolic acids and antioxidant capacity in transformed hairy root culture of Linum usitatissimum. Natural product research, 2018, 32(15), 1867-1871. [View] [PubMed]

Pubchem: 9917980

Cas: 158932-33-3

Zinc: ZINC000067940726

Nmrshiftdb2: 60055057

Chembl: CHEMBL2425486

Comptox: DTXSID40432760

CPRiL: 86734

SMILES: O1CCCCC1OCC(Cc2ccccc2)C(Cc3ccccc3)COC4CCCCO4

Level: 3

Mol. Weight: 686.7 g/mol

SMILES: O1CCCCC1OCC(Cc2ccccc2)CCOC3CCCCO3

Level: 2

Mol. Weight: 686.7 g/mol

SMILES: O1CCCCC1OCC(Cc2ccccc2)CCc3ccccc3

Level: 2

Mol. Weight: 686.7 g/mol

SMILES: O1CCCCC1OCCCCOC2CCCCO2

Level: 1

Mol. Weight: 686.7 g/mol

SMILES: c1ccccc1CCCCOC2CCCCO2

Level: 1

Mol. Weight: 686.7 g/mol

SMILES: c1ccccc1CCCOC2CCCCO2

Level: 1

Mol. Weight: 686.7 g/mol

SMILES: c1ccccc1CCCCc2ccccc2

Level: 1

Mol. Weight: 686.7 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 686.7 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 686.7 g/mol

Antioxidant

Absorption

Caco-2 (logPapp): -6.47
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -4.830
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 79.59

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.680
Plasma Protein Binding: 60.51
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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 7.250
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -4.020
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.580
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 6.030
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: -144206.630
Rat (Acute): 2.590
Rat (Chronic Oral): 4.590
Fathead Minnow: 197.300
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: 10540.210
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -0.230
Log(P): -2.49
Log S: -3.88
Log(Vapor Pressure): -339.18
Melting Point: 198.2
pKa Acid: 3.36
pKa Basic: 5.13

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8642
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8562
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8423
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8387
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8236
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7990
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7846
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7672
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7664
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7596
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7443
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7353
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7303
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7274
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7256
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.7188
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7030

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