Isorhamnetin-7-O-rhamnoside - Compound Card

Isorhamnetin-7-O-rhamnoside

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Isorhamnetin-7-O-rhamnoside

Structure
Zoomed Structure
  • Family: Plantae - Brassicaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonol
Canonical Smiles COc1cc(ccc1O)c1oc2cc(OC3O[C@H](C)[C@H]([C@@H]([C@@H]3O)O)O)cc(c2c(=O)c1O)O
InChI InChI=1S/C22H22O11/c1-8-16(25)18(27)20(29)22(31-8)32-10-6-12(24)15-14(7-10)33-21(19(28)17(15)26)9-3-4-11(23)13(5-9)30-2/h3-8,16,18,20,22-25,27-29H,1-2H3/t8-,16-,18+,20+,22?/m1/s1
InChIKey XLQFMBLUUSGXQY-XOYVNERXSA-N
Formula C22H22O11
HBA 11
HBD 6
MW 462.41
Rotatable Bonds 4
TPSA 179.28
LogP 0.79
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 462.12
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Diplotaxis acris Brassicaceae Plantae 402674

Showing of synonyms

  • Hussein S.R, Marzouk M.M, et al. (2017). Chemosystematic significance of flavonoids isolated from Diplotaxis acris (Brassicaceae) and related taxa. Natural product research, 2017, 31(3), 347-350. [View] [PubMed]

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 462.41 g/mol

Structure

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

Level: 1

Mol. Weight: 462.41 g/mol

Structure

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

Level: 1

Mol. Weight: 462.41 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 462.41 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 462.41 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 462.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.62
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.270
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.030
Plasma Protein Binding
80.69
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
13.700
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.480
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.150
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.730
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
-110.280
Rat (Acute)
2.360
Rat (Chronic Oral)
3.940
Fathead Minnow
4.110
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
583.320
Hydration Free Energy
-3.790
Log(D) at pH=7.4
0.890
Log(P)
0.12
Log S
-4.82
Log(Vapor Pressure)
-10.69
Melting Point
213.4
pKa Acid
5.37
pKa Basic
4.82
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 0.9665
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9528
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9300
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9275
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9176
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9073
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9058
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9044
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9038
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.9019
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9002
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8974
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8920
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8905
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 5 0.8865
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8855
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8853
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8808
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.8792
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8780
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8773
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8761
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 5 0.8749
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8727
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.8671
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 4 0.8661
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.8614
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8600
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8568
Cyclin-dependent kinase 5 Q00535 CDK5_HUMAN Homo sapiens 5 0.8558
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.8531
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8469
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8408
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8373
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8369
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8302
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8271
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8262
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8241
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8239
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8208
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8197
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8151
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8109
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8091
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8086
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8063
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8062
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8059
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8018
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7968
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 4 0.7940
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7935
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7910
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7909
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7891
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7886
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7880
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7872
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7870
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7844
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7837
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7836
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7821
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7816
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 4 0.7807
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7789
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7767
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7757
Cyclin-dependent kinase 6 Q00534 CDK6_HUMAN Homo sapiens 5 0.7751
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7749
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7738
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7724
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7714
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7692
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7667
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7666
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7660
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7650
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7645
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7630
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7621
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 5 0.7613
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7609
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7587
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7573
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7566
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7521
NADPH--cytochrome P450 reductase P00388 NCPR_RAT Rattus norvegicus 4 0.7497
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.7482
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7473
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7470
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7463
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 5 0.7427
NADPH--cytochrome P450 reductase P00388 NCPR_RAT Rattus norvegicus 4 0.7427
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 4 0.7412
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7412
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7393
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7376
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7365
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7359
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7354
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 4 0.7351
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7345
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7339
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7336
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7330
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7323
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7322
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7322
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7306
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7302
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7289
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7269
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7264
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7255
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7251
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7249
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7241
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7239
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7226
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7204
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7198
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7183
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7183
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7179
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7177
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7177
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7167
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7159
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7151
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7134
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7131
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7122
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7118
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7103
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7098
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7096
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7096
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7096
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7080
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7079
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7074
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7049
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7045
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7040
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7038
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7024
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7023
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7022
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7006
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7003

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