Isorhamnetin 3-O-gentobioside - Compound Card

Isorhamnetin 3-O-gentobioside

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Isorhamnetin 3-O-gentobioside

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavone Glycoside
Canonical Smiles OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](Oc3c(oc4c(c3=O)c(O)cc(c4)O)c3ccc(c(c3)OC)O)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C28H32O17/c1-40-13-4-9(2-3-11(13)31)25-26(20(35)17-12(32)5-10(30)6-14(17)42-25)45-28-24(39)22(37)19(34)16(44-28)8-41-27-23(38)21(36)18(33)15(7-29)43-27/h2-6,15-16,18-19,21-24,27-34,36-39H,7-8H2,1H3/t15-,16-,18-,19-,21+,22+,23-,24-,27-,28+/m1/s1
InChIKey GPZLFWVUSQREQH-QDYVESOYSA-N
Formula C28H32O17
HBA 17
HBD 10
MW 640.55
Rotatable Bonds 8
TPSA 278.66
LogP -2.41
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 45
Formal Charge 0
Fraction CSP3 0.46
Exact Mass 640.16
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Pituranthos scoparius Apiaceae Plantae 489362

Showing of synonyms

  • Dahia M, Siracusa L, et al. (2009). Constituents of the polar extracts from Algerian Pituranthos scoparius. Natural Product Communications,2009,4(12),1691-1692. [View] [PubMed]
CPRiL: 410594
Structure

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 640.55 g/mol

Structure

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 640.55 g/mol

Structure

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

Level: 2

Mol. Weight: 640.55 g/mol

Structure

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

Level: 1

Mol. Weight: 640.55 g/mol

Structure

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

Level: 1

Mol. Weight: 640.55 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 640.55 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 640.55 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 640.55 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 640.55 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.6
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.300
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
22.99

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.760
Plasma Protein Binding
61.92
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
10.700
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.470
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.890
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.590
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
-38114.930
Rat (Acute)
2.250
Rat (Chronic Oral)
4.520
Fathead Minnow
65.060
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
350.270
Hydration Free Energy
-2.920
Log(D) at pH=7.4
-0.730
Log(P)
-1.35
Log S
-4.74
Log(Vapor Pressure)
-21.03
Melting Point
201.82
pKa Acid
3.37
pKa Basic
6.99
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9217
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9217
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9130
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9130
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9005
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9005
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8987
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8987
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8895
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8895
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8830
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8830
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8777
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8777
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8740
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8740
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8614
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8614
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8598
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8598
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8317
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8317
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8290
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8290
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8239
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8239
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8214
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8214
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8191
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8191
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8189
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8189
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8169
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8169
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8158
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8158
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.8090
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.8090
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8040
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8040
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8025
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8025
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7971
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7971
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7937
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7937
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7905
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7905
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7856
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7856
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7855
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7855
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7799
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7799
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7789
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7789
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7760
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7760
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7760
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7760
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7760
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7760
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7753
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7753
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7724
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7724
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7692
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7692
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7662
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7662
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7637
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7637
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7623
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7623
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7603
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7603
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7601
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7601
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7547
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7547
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7528
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7528
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7517
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7517
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7460
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7460
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7459
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7459
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7432
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7432
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7426
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7426
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7415
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7415
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7388
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7388
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7354
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7354
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7321
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7321
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.7301
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.7301
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7291
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7291
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7289
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7289
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7281
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7281
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7276
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7276
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7276
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7276
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 4 0.7275
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 4 0.7275
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7272
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7272
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7243
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7243
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7196
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7196
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7191
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7191
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7183
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7183
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 3 0.7168
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 3 0.7168
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7167
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7167
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7165
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7165
Kinesin heavy chain Q41460 Q41460_SOLTU Solanum tuberosum 3 0.7160
Kinesin heavy chain Q41460 Q41460_SOLTU Solanum tuberosum 3 0.7160
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7124
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7124
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7123
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7123
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7113
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7113
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7099
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7099
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7089
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7089
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7059
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7059
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7044
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7044
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7021
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7021

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