Quercetin 3-O-robinobioside - Compound Card

Quercetin 3-O-robinobioside

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Quercetin 3-O-robinobioside

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles Oc1cc(O)c2c(c1)oc(c(c2=O)O[C@@H]1OC(CO[C@@H]2OC(C)[C@@H]([C@@H](C2O)O)O)[C@@H](C(C1O)O)O)c1ccc(c(c1)O)O
InChI InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8?,15?,17-,18-,20-,21?,22?,23?,26+,27-/m0/s1
InChIKey IKGXIBQEEMLURG-PWJZREMGSA-N
Formula C27H30O16
HBA 16
HBD 10
MW 610.52
Rotatable Bonds 6
TPSA 269.43
LogP -1.69
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 43
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 610.15
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Ixora undulata Rubiaceae Plantae 1231253
2 Tephrosia vogelii Leguminosae/Fabaceae Plantae 1157238

Showing of synonyms

  • Stevenson PC, Kite GC, et al. (2012). Distinct chemotypes of Tephrosia vogelii and implications for their use in pest control and soil enrichment.. Phytochemistry,2012(78),135-146. [View] [PubMed]
  • Sugimoto S, Wanas AS, et al. (2014). Structure elucidation of secondary metabolites isolated from the leaves of Ixora undulate and their inhibitory activity toward advanced glycation end-products formation. Phytochemistry,2014,108,189-195. [View] [PubMed]
Pubchem: 44259100
Nmrshiftdb2: 70038282

No compound-protein relationship available.

Structure

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

Level: 3

Mol. Weight: 610.52 g/mol

Structure

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

Level: 2

Mol. Weight: 610.52 g/mol

Structure

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

Level: 2

Mol. Weight: 610.52 g/mol

Structure

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

Level: 1

Mol. Weight: 610.52 g/mol

Structure

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

Level: 1

Mol. Weight: 610.52 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 610.52 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 610.52 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 610.52 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 610.52 g/mol

Inhibitory toward advanced glycation end-products formation

Absorption

Caco-2 (logPapp)
-6.58
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.53
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
8.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.74
Plasma Protein Binding
40.93
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
13.25
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.7
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.97
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.86
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
-13207.69
Rat (Acute)
2.2
Rat (Chronic Oral)
4.49
Fathead Minnow
29.51
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
514.14
Hydration Free Energy
-3.1
Log(D) at pH=7.4
-1.09
Log(P)
-0.01
Log S
-4.44
Log(Vapor Pressure)
-14.3
Melting Point
213.47
pKa Acid
3.5
pKa Basic
8.21
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9759
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9759
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.9022
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.9022
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9011
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9011
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.9004
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.9004
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8986
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8986
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8887
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8887
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8816
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8816
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8677
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8677
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8557
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8557
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8466
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8466
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8422
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8422
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8396
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8396
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8382
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8382
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8368
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8368
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8337
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8337
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8289
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8289
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8280
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8280
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8266
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8266
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8187
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8187
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8118
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8118
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 4 0.8074
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 4 0.8074
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8001
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8001
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7979
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7979
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7971
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7971
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7930
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7930
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7899
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7899
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7861
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7861
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7818
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7818
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7810
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7810
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7805
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7805
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7800
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7800
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7765
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7765
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7761
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7761
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7757
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7757
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7710
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7710
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7692
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7692
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7631
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7631
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7623
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7623
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7614
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7614
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7613
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7613
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7609
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7609
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7520
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7520
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7499
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7499
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7495
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7495
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7493
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7493
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7444
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7444
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7413
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7413
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7389
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7389
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7309
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7309
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 3 0.7232
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 3 0.7232
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7229
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7229
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7217
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7217
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7190
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7190
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7176
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7176
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7133
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7133
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7110
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7110
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7096
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7096
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7068
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7068
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7066
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7066
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7047
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7047
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7037
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7037
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7014
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7014
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 3 0.7003
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7003
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7003
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 3 0.7003

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