Quercetin-3`-methoxy-3-O-(4``-acetylrhamnoside)-7-O-alpha-rhamnoside - Compound Card

Quercetin-3`-methoxy-3-O-(4``-acetylrhamnoside)-7-O-alpha-rhamnoside

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Quercetin-3`-methoxy-3-O-(4``-acetylrhamnoside)-7-O-alpha-rhamnoside

Structure
Zoomed Structure
  • Family: Plantae - Cleomaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonol Glycoside
Canonical Smiles COc1ccc(cc1)c1oc2cc(OC3CC(O)C(C(C3C)O)O)cc(c2c(=O)c1OC1OC(C)C(C(C1O)O)O)O
InChI InChI=1S/C29H34O13/c1-11-18(10-17(31)23(34)21(11)32)40-15-8-16(30)20-19(9-15)41-27(13-4-6-14(38-3)7-5-13)28(24(20)35)42-29-26(37)25(36)22(33)12(2)39-29/h4-9,11-12,17-18,21-23,25-26,29-34,36-37H,10H2,1-3H3
InChIKey JAPIYYQNTNIBHD-UHFFFAOYSA-N
Formula C29H34O13
HBA 13
HBD 7
MW 590.58
Rotatable Bonds 6
TPSA 208.74
LogP 0.25
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.48
Exact Mass 590.2
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Cleome droserifolia Cleomaceae Plantae 511510

Showing of synonyms

  • Ahmed Youness R, Amr Assal R, et al. (2020). A methoxylated quercetin glycoside harnesses HCC tumor progression in a TP53/miR-15/miR-16 dependent manner. Natural product research, 2020, 34(10), 1475-1480. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCCCC1Oc(cc2)cc(c23)oc(-c4ccccc4)c(c3=O)OC5CCCCO5

Level: 3

Mol. Weight: 590.58 g/mol

Structure

SMILES: C1CCCCC1Oc(cc2)cc(c23)occ(c3=O)OC4CCCCO4

Level: 2

Mol. Weight: 590.58 g/mol

Structure

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

Level: 2

Mol. Weight: 590.58 g/mol

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCC4

Level: 2

Mol. Weight: 590.58 g/mol

Structure

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

Level: 1

Mol. Weight: 590.58 g/mol

Structure

SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCC3

Level: 1

Mol. Weight: 590.58 g/mol

Structure

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

Level: 1

Mol. Weight: 590.58 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 590.58 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 590.58 g/mol

Structure

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 590.58 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 590.58 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.110
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
5.38

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.970
Plasma Protein Binding
1.13
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.310
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.320
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.640
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.440
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-9649.070
Rat (Acute)
3.200
Rat (Chronic Oral)
4.230
Fathead Minnow
23.710
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
453.010
Hydration Free Energy
-3.000
Log(D) at pH=7.4
0.890
Log(P)
1.31
Log S
-3.98
Log(Vapor Pressure)
-12.06
Melting Point
213.07
pKa Acid
4.83
pKa Basic
4.73
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 0.9816
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9541
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9114
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8842
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8419
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8358
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8326
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8262
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8054
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 3 0.7999
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7993
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7965
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7951
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7821
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7764
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7748
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7732
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7731
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7698
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7664
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7644
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7620
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7605
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7584
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7572
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7462
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7434
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7406
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7403
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7381
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7364
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7333
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7265
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7227
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7218
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7179
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7173
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7168
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7148
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7132
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7106
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7104
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7086
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7047

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