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Silymonin

Family: Plantae - Asteraceae
Kingdom: Plantae
Class: Lignan
- Subclass: Flavonolignan

Canonical Smiles	COc1cc(ccc1O)[C@@H]1[C@H]2COC3([C@H]2C=C([C@H]1C3=O)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O)O
InChI	InChI=1S/C25H22O9/c1-32-19-4-10(2-3-15(19)27)21-13-9-33-25(31)14(13)7-12(22(21)24(25)30)18-8-17(29)23-16(28)5-11(26)6-20(23)34-18/h2-7,13-14,18,21-22,26-28,31H,8-9H2,1H3/t13-,14-,18-,21+,22+,25?/m0/s1
InChIKey	LNLXUVRWFZAUFM-JGRQTAHWSA-N
Formula	C₂₅H₂₂O₉
HBA	9
HBD	4
MW	466.44
Rotatable Bonds	3
TPSA	142.75
LogP	2.02
Number Rings	7
Number Aromatic Rings	2
Heavy Atom Count	34
Formal Charge	0
Fraction CSP3	0.36
Exact Mass	466.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Silybum marianum	Asteraceae	Plantae	92921

Showing of synonyms

AbouZid S.F, Ahmed H.S, et al. (2017). Chemotaxonomic and biosynthetic relationships between flavonolignans produced by Silybum marianum populations. Fitoterapia, 2017, 119, 175-184. [View] [PubMed]

Pubchem: 156051

Cas: 70815-31-5

Zinc: ZINC000031457053

Chebi: 172698

Comptox: DTXSID40858704

No compound-protein relationship available.

SMILES: c1ccccc1C2C(C(=O)C3OCC2C34)C(=C4)C(CC5=O)Oc(c56)cccc6

Level: 2

Mol. Weight: 466.44 g/mol

SMILES: C12C3COC1C(=O)C(C3)C(=C2)C(CC4=O)Oc(c45)cccc5

Level: 1

Mol. Weight: 466.44 g/mol

SMILES: C12C3COC1C(=O)C(C=C2)C3c4ccccc4

Level: 1

Mol. Weight: 466.44 g/mol

SMILES: C12C3COC1C(=O)C(C3)C=C2

Level: 0

Mol. Weight: 466.44 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 466.44 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 466.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.71
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.820
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.56

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.030
Plasma Protein Binding: 77.16
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 14.090
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.360
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.320
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 7.600
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -364.200
Rat (Acute): 2.950
Rat (Chronic Oral): 3.270
Fathead Minnow: 4.480
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 520.240
Hydration Free Energy: -2.990
Log(D) at pH=7.4: 2.340
Log(P): 1.9
Log S: -5.66
Log(Vapor Pressure): -10.54
Melting Point: 265.49
pKa Acid: 6.05
pKa Basic: 3.34

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8929
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8764
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8755
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8710
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8678
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.8671
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8670
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8646
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8318
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8286
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8274
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8271
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8176
Heat shock protein HSP 90-beta	P08238	HS90B_HUMAN	Homo sapiens	3	0.8156
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.8129
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8087
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8057
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.8029
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7956
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7951
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7937
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7912
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7900
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7894
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7870
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7833
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7742
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7729
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.7726
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7706
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7695
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7645
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7614
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7599
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7595
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7578
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7563
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7553
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7544
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7538
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7520
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7509
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7490
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7486
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.7475
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7468
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7455
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7448
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7445
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7445
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7433
Bifunctional protein GAL10	P04397	GAL10_YEAST	Saccharomyces cerevisiae	4	0.7410
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7409
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7402
14-3-3 protein gamma	P61981	1433G_HUMAN	Homo sapiens	3	0.7393
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7361
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7359
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7335
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7313
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7289
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7277
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7259
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7250
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7240
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7238
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7234
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7225
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7217
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7210
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.7193
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	4	0.7182
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7165
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7151
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7144
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7144
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7122
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7119
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7106
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7094
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7086
Nucleoside diphosphate kinase	Q5UQL3	NDK_MIMIV	Acanthamoeba polyphaga mimivirus	2	0.7078
Putative HMP/thiamine-binding protein YkoF	O34911	YKOF_BACSU	Bacillus subtilis	3	0.7065
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7050
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7038
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7036
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7035
Pyridoxal kinase	P82197	PDXK_SHEEP	Ovis aries	3	0.7032
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7026
Ribosome-inactivating protein 3	P25891	RIP3_MAIZE	Zea mays	3	0.7010
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	2	0.7006
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7003

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