3-O-ellagic acid-4'-O-alpha-rhampyranonoside - Compound Card

3-O-ellagic acid-4'-O-alpha-rhampyranonoside

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3-O-ellagic acid-4'-O-alpha-rhampyranonoside

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(C1O)O)O)O
InChI InChI=1S/C21H18O12/c1-5-12(23)14(25)15(26)21(30-5)31-9-4-7-10-11-6(19(27)32-17(10)13(9)24)3-8(22)16(29-2)18(11)33-20(7)28/h3-5,12,14-15,21-26H,1-2H3
InChIKey IAYGIELPGJHKME-UHFFFAOYSA-N
Formula C21H18O12
HBA 12
HBD 5
MW 462.36
Rotatable Bonds 3
TPSA 189.26
LogP 0.12
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 462.08
Number of Lipinski Rule Violations 1
# 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: 56670519
Nmrshiftdb2: 70083700

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 462.36 g/mol

Structure

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

Level: 0

Mol. Weight: 462.36 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 462.36 g/mol

Antioxidative

Absorption

Caco-2 (logPapp)
-6.4
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.080
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.0

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.390
Plasma Protein Binding
54.97
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
9.380
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.580
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.910
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.860
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
-136.910
Rat (Acute)
2.440
Rat (Chronic Oral)
3.550
Fathead Minnow
4.740
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
578.690
Hydration Free Energy
-3.380
Log(D) at pH=7.4
1.960
Log(P)
0.12
Log S
-4.16
Log(Vapor Pressure)
-9.92
Melting Point
204.79
pKa Acid
6.88
pKa Basic
2.22
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 0.9301
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9243
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.8976
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8950
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8720
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8625
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8588
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8470
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8401
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8364
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8284
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8250
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8160
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8045
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7985
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7975
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7960
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7910
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7844
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7792
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7693
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7690
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7681
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7646
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7641
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7619
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7615
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7571
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7516
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7498
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7488
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7482
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7440
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7394
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7392
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7378
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7356
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7325
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7309
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7308
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7284
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7281
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7276
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7275
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7269
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7259
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7244
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7238
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7234
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7233
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7226
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7212
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7208
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7198
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7153
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7128
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7126
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7055
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7033
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7028

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