Isorhamnetin 3-galactoside - Compound Card

Isorhamnetin 3-galactoside

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Isorhamnetin 3-galactoside

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles OC[C@H]1OC(Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(c(c2)OC)O)[C@@H]([C@H]([C@H]1O)O)O
InChI InChI=1S/C22H22O12/c1-31-12-4-8(2-3-10(12)25)20-21(17(28)15-11(26)5-9(24)6-13(15)32-20)34-22-19(30)18(29)16(27)14(7-23)33-22/h2-6,14,16,18-19,22-27,29-30H,7H2,1H3/t14-,16+,18+,19-,22?/m1/s1
InChIKey CQLRUIIRRZYHHS-MGGBBTSESA-N
Formula C22H22O12
HBA 12
HBD 7
MW 478.41
Rotatable Bonds 5
TPSA 199.51
LogP -0.24
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 478.11
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Aerva javanica Amaranthaceae Plantae 240009
2 Bupleurum spinosum Apiaceae Plantae 199135

Showing of synonyms

  • Saleh NAM, Mansjur RMA and Markham KR. (1990). An acylated isorhamnetin glycoside from Aerva javanica. Phytochemistry,1990,29(4),1344-1345. [View] [PubMed]
  • Bencheraiet R, Kabouche A, et al. (2012). Flavonol 3-O-glycosides from three Algerian Bupleurum species. Records of Natural Products,2012,6(2),171-174. [View]
Pubchem: 91885208
Nmrshiftdb2: 70093121

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 478.41 g/mol

Structure

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 478.41 g/mol

Structure

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

Level: 1

Mol. Weight: 478.41 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 478.41 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 478.41 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 478.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.68
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.46
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
1.28

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.86
Plasma Protein Binding
68.91
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
14.79
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.43
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.09
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.38
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
-184.78
Rat (Acute)
2.29
Rat (Chronic Oral)
4.24
Fathead Minnow
3.91
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
631.03
Hydration Free Energy
-3.77
Log(D) at pH=7.4
0.45
Log(P)
0.12
Log S
-4.66
Log(Vapor Pressure)
-11.31
Melting Point
193.1
pKa Acid
4.93
pKa Basic
6.41
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 0.9461
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9461
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9111
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9111
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9018
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9018
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8976
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8976
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8950
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8950
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8908
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8908
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8776
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8776
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 4 0.8673
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 4 0.8673
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8497
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8497
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8420
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8420
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8393
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8393
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8370
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8370
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8351
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8351
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8339
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8339
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8270
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8270
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8157
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8157
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8040
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8040
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8024
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8024
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.8014
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.8014
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8004
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8004
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7990
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7990
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7959
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7959
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7947
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7947
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7933
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7933
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7921
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7921
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7908
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7908
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7776
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7776
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7721
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7721
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7720
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7720
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7709
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7709
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7650
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7650
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7646
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7646
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7638
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7638
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7616
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7616
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7566
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7566
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7530
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7530
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7516
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7516
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7512
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7512
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7509
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7509
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7486
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7486
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7444
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7444
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7439
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7439
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7393
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7393
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7353
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7353
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7350
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7350
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7326
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7326
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7325
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7325
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7323
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7323
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.7297
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.7297
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7290
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7290
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7283
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7283
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7260
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7260
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7225
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7225
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7190
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7190
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7169
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7169
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7155
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7155
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7141
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7141
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7130
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7130
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7119
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7119
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7117
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7117
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7111
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7111
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7095
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7095
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7089
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7089
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7074
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7074
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7051
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7051
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7039
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7039
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7018
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7018
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7012
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7012
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7011
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7011
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7008
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7008
Kinesin heavy chain Q41460 Q41460_SOLTU Solanum tuberosum 3 0.7002
Kinesin heavy chain Q41460 Q41460_SOLTU Solanum tuberosum 3 0.7002

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