Isolinariin B - Compound Card

Isolinariin B

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Isolinariin B

Structure
Zoomed Structure
  • Family: Plantae - Plantaginaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone Glycoside
Canonical Smiles COc1c(OC2OC(COC3OC(C)C(C(C3O)OC(=O)C)OC(=O)C)C(C(C2O)O)O)cc2c(c1O)c(=O)cc(o2)c1ccc(cc1)OC
InChI InChI=1S/C33H38O17/c1-13-29(46-14(2)34)31(47-15(3)35)28(41)32(45-13)44-12-22-24(37)26(39)27(40)33(50-22)49-21-11-20-23(25(38)30(21)43-5)18(36)10-19(48-20)16-6-8-17(42-4)9-7-16/h6-11,13,22,24,26-29,31-33,37-41H,12H2,1-5H3
InChIKey XLLZQSCZTNLNFG-UHFFFAOYSA-N
Formula C33H38O17
HBA 17
HBD 5
MW 706.65
Rotatable Bonds 10
TPSA 239.34
LogP 0.35
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 50
Formal Charge 0
Fraction CSP3 0.48
Exact Mass 706.21
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Linaria reflexa Plantaginaceae Plantae 1070263

Showing of synonyms

  • Cheriet T, Hanfer M, et al. (2017). Glycosyl flavonoid profile, in vivo antidiabetic and in vitro antioxidant properties of Linaria reflexa Desf. Natural product research, 2017, 31(17), 2042-2048. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(cc3)cc(c34)oc(cc4=O)-c5ccccc5

Level: 3

Mol. Weight: 706.65 g/mol

Structure

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(cc3)cc(c34)occc4=O

Level: 2

Mol. Weight: 706.65 g/mol

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 706.65 g/mol

Structure

SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 706.65 g/mol

Structure

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 706.65 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 706.65 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 706.65 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 706.65 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 706.65 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.27
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-3.960
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
200.94

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.830
Plasma Protein Binding
-6.3
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
7.260
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.310
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.800
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.470
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
-365978.430
Rat (Acute)
2.620
Rat (Chronic Oral)
4.000
Fathead Minnow
475.690
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
33967.140
Hydration Free Energy
-2.920
Log(D) at pH=7.4
0.920
Log(P)
1.81
Log S
-4.42
Log(Vapor Pressure)
-1188.98
Melting Point
185.03
pKa Acid
4.23
pKa Basic
-0.6
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9861
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9570
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9331
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9285
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9267
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9050
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.9038
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8941
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8924
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.8842
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8835
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8829
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8793
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8768
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8689
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8579
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8525
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8521
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8514
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8481
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8431
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8417
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8297
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8272
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8262
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8253
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8211
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8164
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8131
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8100
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8090
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8075
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7977
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7967
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7964
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.7942
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7925
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7919
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7918
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7913
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7903
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7889
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7863
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7848
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7832
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7831
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7803
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7788
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7769
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7730
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7727
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7717
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7680
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7678
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7674
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.7674
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7664
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7626
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7618
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7615
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7612
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7606
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7568
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7555
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7547
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7546
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7541
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7519
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7486
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7441
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7439
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7428
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7420
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7419
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7410
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7406
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7402
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7394
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 4 0.7386
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7382
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7361
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7357
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7340
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7338
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7330
Ribosomal protein S6 kinase alpha-3 P51812 KS6A3_HUMAN Homo sapiens 4 0.7315
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7303
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7302
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7300
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 3 0.7299
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7298
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7297
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7285
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7271
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7268
Acyl-coenzyme A synthetase ACSM2A, mitochondrial Q08AH3 ACS2A_HUMAN Homo sapiens 2 0.7241
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7239
Phenolphthiocerol/phthiocerol polyketide synthase subunit C P96202 PPSC_MYCTU Mycobacterium tuberculosis 3 0.7239
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7235
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7227
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7204
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7195
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7195
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7192
Farnesyl pyrophosphate synthase P14324 FPPS_HUMAN Homo sapiens 2 0.7177
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7172
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7168
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7166
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7157
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7155
Neutrophil collagenase P22894 MMP8_HUMAN Homo sapiens 2 0.7150
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7146
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7142
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7136
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7135
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 3 0.7128
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7125
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7113
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7112
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7109
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7106
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7103
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7095
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7087
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7085
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7079
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7078
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7078
Nucleoside diphosphate kinase Q5HFV4 NDK_STAAC Staphylococcus aureus 2 0.7066
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7062
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7060
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7057
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 2 0.7042
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7042
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7039
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7038
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7036
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7034
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7030
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 5 0.7021
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7014
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7011
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7010

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