Silyhermin - Compound Card

Silyhermin

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Silyhermin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Lignan
    • Subclass: Flavonolignan
Canonical Smiles OCC1c2cc(cc(c2OC1c1ccc(c(c1)OC)O)O)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O
InChI InChI=1S/C25H22O9/c1-32-21-6-11(2-3-16(21)28)24-15(10-26)14-4-12(5-19(31)25(14)34-24)20-9-18(30)23-17(29)7-13(27)8-22(23)33-20/h2-8,15,20,24,26-29,31H,9-10H2,1H3/t15?,20-,24?/m0/s1
InChIKey AQRHXQBZDLTXPO-QOTJCZOLSA-N
Formula C25H22O9
HBA 9
HBD 5
MW 466.44
Rotatable Bonds 4
TPSA 145.91
LogP 3.43
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.24
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: 10389806
Chebi: 169173

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(C2)Oc(c23)ccc(c3)C(CC4=O)Oc(c45)cccc5

Level: 2

Mol. Weight: 466.44 g/mol

Structure

SMILES: C1COc(c12)ccc(c2)C(CC3=O)Oc(c34)cccc4

Level: 1

Mol. Weight: 466.44 g/mol

Structure

SMILES: c1cccc(c12)OC(C2)c3ccccc3

Level: 1

Mol. Weight: 466.44 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 466.44 g/mol

Structure

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 466.44 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 466.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.2
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.1
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.26

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.14
Plasma Protein Binding
77.26
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
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.39
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.6
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.81
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.01
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
Toxic
T. Pyriformis
-315.5
Rat (Acute)
2.33
Rat (Chronic Oral)
3.49
Fathead Minnow
5.22
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
560.82
Hydration Free Energy
-3.24
Log(D) at pH=7.4
3.1
Log(P)
2.43
Log S
-6.79
Log(Vapor Pressure)
-9.94
Melting Point
235.08
pKa Acid
7.54
pKa Basic
3.64
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9381
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.9053
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8997
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8962
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8899
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8847
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8826
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8811
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8790
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8786
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8749
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8743
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8687
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8672
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8636
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8606
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8586
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8527
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8504
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 4 0.8497
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8436
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8430
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8379
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8364
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8299
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8279
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8270
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.8261
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.8246
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8239
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8236
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.8235
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8232
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8226
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8197
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8193
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8167
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8164
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8156
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8127
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8078
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8053
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8033
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8021
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7999
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7974
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7971
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7962
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7931
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7881
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7876
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7869
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7866
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7866
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7863
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7823
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7822
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7808
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7765
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7718
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7704
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7703
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7703
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7690
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7684
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7681
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7681
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 5 0.7678
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7673
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7665
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7637
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.7626
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7622
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7613
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7609
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7608
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 4 0.7603
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7602
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7600
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7587
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7587
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7582
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7548
Cytochrome P450 130 P9WPN5 CP130_MYCTU Mycobacterium tuberculosis 3 0.7548
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7540
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7501
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 4 0.7483
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7470
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7462
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7461
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7461
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7459
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7458
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7453
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7453
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7452
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.7449
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7426
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7423
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7417
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7416
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 6 0.7414
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7399
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7363
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7352
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7351
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7343
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7323
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7305
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7304
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 4 0.7304
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7295
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7293
16S rRNA (adenine(1408)-N(1))-methyltransferase A8C927 NPMA_ECOLX Escherichia coli 4 0.7285
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7284
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.7283
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7280
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7279
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7277
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7256
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7246
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7240
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7233
Serine/threonine-protein kinase VRK1 Q99986 VRK1_HUMAN Homo sapiens 3 0.7231
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7229
3-hydroxyisobutyryl-CoA hydrolase, mitochondrial Q6NVY1 HIBCH_HUMAN Homo sapiens 3 0.7213
M17 leucyl aminopeptidase Q8IL11 Q8IL11_PLAF7 Plasmodium falciparum 3 0.7211
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7204
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7200
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 4 0.7186
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7186
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7180
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7178
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7176
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 4 0.7172
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.7168
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7136
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7132
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7130
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7121
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7117
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7109
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7101
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7097
Uncharacterized protein Q55S71 Q55S71_CRYNB Cryptococcus neoformans var. neoformans serotype D 3 0.7096
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7095
RNA-directed RNA polymerase P11124 RDRP_BPPH6 Pseudomonas phage phi6 4 0.7092
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7090
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 5 0.7071
tRNA-guanine(15) transglycosylase O58843 ATGT_PYRHO Pyrococcus horikoshii 3 0.7059
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 4 0.7042
YbaK/aminoacyl-tRNA synthetase-associated domain-containing protein Q5SHN1 Q5SHN1_THET8 Thermus thermophilus 3 0.7036
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7034
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7029
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7028
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7028
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7023
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 3 0.7020
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7019
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7014
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7011
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7010

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