5,7,3',4'-tetrahydroxyflavone-6-C-(2''-O-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside - Compound Card

5,7,3',4'-tetrahydroxyflavone-6-C-(2''-O-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside

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5,7,3',4'-tetrahydroxyflavone-6-C-(2''-O-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Caryophyllaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone Glycoside
Canonical Smiles OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O[C@H]1O[C@H](C)[C@H]([C@@H]([C@@H]1O)O)O)c1c(O)cc2c(c1O)c(=O)cc(o2)c1ccc(c(c1)O)O
InChI InChI=1S/C27H30O15/c1-8-19(33)22(36)24(38)27(39-8)42-26-23(37)20(34)16(7-28)41-25(26)18-13(32)6-15-17(21(18)35)12(31)5-14(40-15)9-2-3-10(29)11(30)4-9/h2-6,8,16,19-20,22-30,32-38H,7H2,1H3/t8-,16-,19-,20-,22+,23+,24+,25+,26-,27-/m1/s1
InChIKey IUYFTHKQEWZTHY-GBGZPRFTSA-N
Formula C27H30O15
HBA 15
HBD 10
MW 594.52
Rotatable Bonds 5
TPSA 260.2
LogP -1.35
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 594.16
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Drymaria cordata Caryophyllaceae Plantae 191453

Showing of synonyms

  • Nono RN, Nguelefack-Mbuyo EP, et al. (2016). Antioxidant C-glycosylflavones of Drymaria cordata (Linn.) Willd.. Archives of pharmacal research,2016, 39(1), 43-50. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4C(CCCO4)OC5CCCCO5

Level: 3

Mol. Weight: 594.52 g/mol

Structure

SMILES: O=c1ccoc(c12)ccc(c2)C3C(CCCO3)OC4CCCCO4

Level: 2

Mol. Weight: 594.52 g/mol

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4CCCCO4

Level: 2

Mol. Weight: 594.52 g/mol

Structure

SMILES: O=c1ccoc(c12)ccc(c2)C3CCCCO3

Level: 1

Mol. Weight: 594.52 g/mol

Structure

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

Level: 1

Mol. Weight: 594.52 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 594.52 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 594.52 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 594.52 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 594.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.42
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.770
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
7.17

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.700
Plasma Protein Binding
68.06
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
11.410
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-3.400
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.770
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.900
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
-8528.320
Rat (Acute)
2.380
Rat (Chronic Oral)
4.340
Fathead Minnow
17.950
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
550.610
Hydration Free Energy
-2.970
Log(D) at pH=7.4
-0.710
Log(P)
0.16
Log S
-4.31
Log(Vapor Pressure)
-12.12
Melting Point
203.3
pKa Acid
3.48
pKa Basic
9.45
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9589
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9430
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9306
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9050
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9048
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8994
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8957
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8823
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8707
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8519
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8427
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8375
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8354
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8338
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8337
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8168
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8137
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7941
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7898
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 4 0.7890
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7745
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7735
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7718
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7709
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7700
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7669
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7607
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 4 0.7590
Tubulin--tyrosine ligase F6Z895 A9ULH4_XENTR Xenopus tropicalis 4 0.7509
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7498
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7420
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7366
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7364
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7287
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7177
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7171
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7149
Replicase polyprotein 1ab P0C6X7 R1AB_CVHSA Human SARS coronavirus 4 0.7133
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7132
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7125
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7067
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7063
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7048
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7018
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7015
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7009
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7003

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