Isosilandrin - Compound Card

Isosilandrin

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Isosilandrin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Lignan
    • Subclass: Flavonolignan
Canonical Smiles OC[C@H]1OC2=CC[C@H](C=C2O[C@@H]1c1ccc(c(c1)OC)O)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O
InChI InChI=1S/C25H24O9/c1-31-20-7-13(2-4-15(20)28)25-23(11-26)32-18-5-3-12(6-21(18)34-25)19-10-17(30)24-16(29)8-14(27)9-22(24)33-19/h2,4-9,12,19,23,25-29H,3,10-11H2,1H3/t12-,19+,23-,25-/m1/s1
InChIKey ZBRFNZMPOWLRBC-FEYNVAAWSA-N
Formula C25H24O9
HBA 9
HBD 4
MW 468.46
Rotatable Bonds 4
TPSA 134.91
LogP 3.08
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 468.14
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]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(CC2=O)C(C3)CC=C(C=34)OCC(O4)c5ccccc5

Level: 2

Mol. Weight: 468.46 g/mol

Structure

SMILES: c1cccc(c12)OC(CC2=O)C(C3)CC=C(C=34)OCCO4

Level: 1

Mol. Weight: 468.46 g/mol

Structure

SMILES: C1CCC=C(C=12)OCC(O2)c3ccccc3

Level: 1

Mol. Weight: 468.46 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 468.46 g/mol

Structure

SMILES: O1CCOC(C1=2)=CCCC2

Level: 0

Mol. Weight: 468.46 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 468.46 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
-4.890
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.85

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.960
Plasma Protein Binding
79.14
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
15.200
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.120
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.090
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.650
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
Safe
T. Pyriformis
-302.580
Rat (Acute)
2.090
Rat (Chronic Oral)
2.900
Fathead Minnow
4.500
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
536.410
Hydration Free Energy
-3.100
Log(D) at pH=7.4
2.670
Log(P)
1.98
Log S
-5.87
Log(Vapor Pressure)
-10.53
Melting Point
246.93
pKa Acid
7.44
pKa Basic
3.03
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9335
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9171
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.9044
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8950
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8891
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8854
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8817
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8770
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8744
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8694
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8684
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8660
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8657
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8618
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.8618
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8569
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8567
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8562
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8495
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8489
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8479
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8479
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8462
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8451
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8421
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8410
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8398
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8380
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8282
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8279
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8195
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8174
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8157
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8131
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.8131
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8126
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8122
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8103
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8097
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8090
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8082
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 4 0.8080
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8070
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8040
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7992
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7988
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7971
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7969
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7958
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7928
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7922
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7904
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7901
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7867
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7851
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7840
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7810
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7790
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7755
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7714
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7704
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 4 0.7684
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7682
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7665
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7633
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7626
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7541
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7536
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7534
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7519
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7512
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7505
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7491
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7484
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7479
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7472
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7442
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7424
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7424
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7424
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7424
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7399
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7394
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7375
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7362
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7362
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7349
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7346
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7338
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7323
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7309
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7309
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7305
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7304
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7295
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7294
ATP-dependent protease subunit HslV P0A7B8 HSLV_ECOLI Escherichia coli 3 0.7278
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7267
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7262
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7260
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7258
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 3 0.7257
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7239
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7224
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7222
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7219
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7216
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7216
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7205
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7203
Rho family GTPase C4M4W4 C4M4W4_ENTHI Entamoeba histolytica 4 0.7202
tRNA-guanine(15) transglycosylase O58843 ATGT_PYRHO Pyrococcus horikoshii 3 0.7186
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7183
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7175
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7171
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7166
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7166
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7163
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7160
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7155
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7152
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7149
Histone-lysine N-methyltransferase EHMT2 Q96KQ7 EHMT2_HUMAN Homo sapiens 3 0.7138
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7137
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7132
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7125
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7121
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7119
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7118
Type II methyltransferase M.HhaI P05102 MTH1_HAEPH Haemophilus parahaemolyticus 3 0.7116
Acetyltransferase YpeA P76539 YPEA_ECOLI Escherichia coli 3 0.7112
DNA-(apurinic or apyrimidinic site) lyase Q97FM4 Q97FM4_CLOAB Clostridium acetobutylicum 4 0.7109
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7108
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7107
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7100
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7083
Uncharacterized protein MJ1225 Q58622 Y1225_METJA Methanocaldococcus jannaschii 4 0.7079
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7077
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7076
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7065
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7060
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7056
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7054
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7048
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7047
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7047
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7044
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7035
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7028
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7025
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7019
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7016

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