Isolinariin A - Compound Card

Isolinariin A

Select a section from the left sidebar

Isolinariin A

Structure
Zoomed Structure
  • Family: Plantae - Plantaginaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone Glycoside
Canonical Smiles COc1c(O[C@@H]2OC(CO[C@@H]3O[C@@H](C)[C@@H](C(C3OC(=O)C)O)O)[C@H]([C@@H](C2O)O)O)cc2c(c1O)c(=O)cc(o2)c1ccc(cc1)OC
InChI InChI=1S/C31H36O16/c1-12-22(34)26(38)29(44-13(2)32)31(43-12)42-11-20-23(35)25(37)27(39)30(47-20)46-19-10-18-21(24(36)28(19)41-4)16(33)9-17(45-18)14-5-7-15(40-3)8-6-14/h5-10,12,20,22-23,25-27,29-31,34-39H,11H2,1-4H3/t12-,20?,22-,23+,25-,26?,27?,29?,30+,31+/m0/s1
InChIKey MGBQEYYOKCRLKS-OBEGZJHLSA-N
Formula C31H36O16
HBA 16
HBD 6
MW 664.61
Rotatable Bonds 9
TPSA 233.27
LogP -0.22
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 47
Formal Charge 0
Fraction CSP3 0.48
Exact Mass 664.2
Number of Lipinski Rule Violations 3
# 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]
Pubchem: 44258452
Chebi: 169275

No compound-protein relationship available.

Structure

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

Level: 3

Mol. Weight: 664.61 g/mol

Structure

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

Level: 2

Mol. Weight: 664.61 g/mol

Structure

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

Level: 2

Mol. Weight: 664.61 g/mol

Structure

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

Level: 1

Mol. Weight: 664.61 g/mol

Structure

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

Level: 1

Mol. Weight: 664.61 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 664.61 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 664.61 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 664.61 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 664.61 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.42
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.890
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
54.34

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.900
Plasma Protein Binding
58.04
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
7.290
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.390
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.760
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.080
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
-99284.540
Rat (Acute)
2.630
Rat (Chronic Oral)
4.160
Fathead Minnow
140.910
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
4489.600
Hydration Free Energy
-2.920
Log(D) at pH=7.4
0.800
Log(P)
1.35
Log S
-4.52
Log(Vapor Pressure)
-209.29
Melting Point
189.69
pKa Acid
5.1
pKa Basic
0.53
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 0.9874
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9615
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9424
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9263
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9211
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9202
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9120
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.9037
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9012
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8943
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8922
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8822
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8748
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8747
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8735
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8671
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8483
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8468
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.8429
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8292
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8274
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.8145
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8119
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8101
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8091
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8088
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8072
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8068
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8065
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.8047
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8032
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8031
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7991
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7954
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7914
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7911
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7893
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7870
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7868
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7855
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7847
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7842
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7831
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7830
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7823
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7787
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7780
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7751
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7716
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7715
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7696
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7681
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7674
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7668
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7660
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7659
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 3 0.7653
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 3 0.7650
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7649
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase Q9WY79 MURE_THEMA Thermotoga maritima 3 0.7621
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7621
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7617
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7616
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7606
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7592
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7591
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7590
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7579
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7544
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7535
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7517
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7507
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7478
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7475
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7474
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7471
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7453
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7427
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7424
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7422
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7421
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7419
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7411
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7408
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7401
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7378
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7364
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7352
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7350
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7345
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7342
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7324
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7319
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7315
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7313
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7300
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7298
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7295
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7285
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7276
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7274
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 4 0.7271
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7257
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7248
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 2 0.7246
Acyl-coenzyme A synthetase ACSM2A, mitochondrial Q08AH3 ACS2A_HUMAN Homo sapiens 2 0.7243
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7239
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7237
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7237
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7233
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7228
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7218
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7202
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7193
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7190
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7188
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7183
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7170
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7170
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7163
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7161
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7159
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7156
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7143
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7131
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7130
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7128
Nucleoside diphosphate kinase Q5HFV4 NDK_STAAC Staphylococcus aureus 2 0.7124
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7120
Phenolphthiocerol/phthiocerol polyketide synthase subunit C P96202 PPSC_MYCTU Mycobacterium tuberculosis 3 0.7120
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7113
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7112
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7100
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7096
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7093
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7093
Neutrophil collagenase P22894 MMP8_HUMAN Homo sapiens 2 0.7091
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7081
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7080
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7075
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7065
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7061
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7059
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7052
Ribosomal protein S6 kinase alpha-3 P51812 KS6A3_HUMAN Homo sapiens 4 0.7051
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7051
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7044
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7044
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7033
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7031
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7021
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7018
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7017
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7016
Genome polyprotein P12823 POLG_DEN2P Dengue virus type 2 3 0.7012
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7003
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7001

Download SDF