3-O-methylellagic acid-4'-O-alpha-2''-O-acetylrhamnopyranoside - Compound Card

3-O-methylellagic acid-4'-O-alpha-2''-O-acetylrhamnopyranoside

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3-O-methylellagic acid-4'-O-alpha-2''-O-acetylrhamnopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Myrtaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Ellagic Acid Derivative
Canonical Smiles COc1c(O)cc2c3c1oc(=O)c1c3c(oc2=O)c(c(c1)OC1OC(C)C(C(C1OC(=O)C)O)O)O
InChI InChI=1S/C23H20O13/c1-6-14(26)16(28)20(33-7(2)24)23(32-6)34-11-5-9-12-13-8(21(29)35-18(12)15(11)27)4-10(25)17(31-3)19(13)36-22(9)30/h4-6,14,16,20,23,25-28H,1-3H3
InChIKey HGKXWVIFXNLJBP-UHFFFAOYSA-N
Formula C23H20O13
HBA 13
HBD 4
MW 504.4
Rotatable Bonds 4
TPSA 195.33
LogP 0.69
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 504.09
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Syzygium guineense Myrtaceae Plantae 334482

Showing of synonyms

  • Djoukeng J, Abou-Mansour E, et al. (2007). Identification of Ellagic Acid Derivatives from Stem Bark of Syzygium Guineense (Myrtaceae). Natural Product Communications, 2007, 2(3), 261 - 266. [View]
Pubchem: 73068119
Nmrshiftdb2: 70124283

No compound-protein relationship available.

Structure

SMILES: c12c3c4c(=O)oc2cc(OC5CCCCO5)cc1c(=O)oc3ccc4

Level: 1

Mol. Weight: 504.4 g/mol

Structure

SMILES: c12c3c4c(=O)oc2cccc1c(=O)oc3ccc4

Level: 0

Mol. Weight: 504.4 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 504.4 g/mol

Antioxidative

Absorption

Caco-2 (logPapp)
-6.21
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.700
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.25

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.440
Plasma Protein Binding
47.27
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
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
10.070
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.090
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.960
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.650
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
-516.850
Rat (Acute)
2.500
Rat (Chronic Oral)
3.440
Fathead Minnow
5.980
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
562.540
Hydration Free Energy
-2.870
Log(D) at pH=7.4
2.870
Log(P)
0.83
Log S
-4.13
Log(Vapor Pressure)
-9.73
Melting Point
207.3
pKa Acid
7.05
pKa Basic
0.4
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.9315
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9232
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.9067
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8951
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8734
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8634
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8477
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8474
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8375
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8283
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8224
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8186
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8025
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7890
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7874
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7772
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7744
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7713
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7684
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7682
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7663
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7656
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7625
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7583
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7526
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7478
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7442
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7409
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7395
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7392
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7360
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7298
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7283
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7277
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7275
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7268
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7267
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7246
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7243
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7241
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7239
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7239
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7226
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7219
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7203
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7179
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7127
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7074
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7028
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7014
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7001

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