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

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

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3-O-methylellagic acid-4'-O-alpha-3''-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(C1O)OC(=O)C)O)O
InChI InChI=1S/C23H20O13/c1-6-14(26)20(33-7(2)24)16(28)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 PSQAVUUHZLODEY-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: 74342640
Nmrshiftdb2: 70122360

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
-4.780
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.480
Plasma Protein Binding
50.07
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
10.130
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.150
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.900
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
-517.130
Rat (Acute)
2.500
Rat (Chronic Oral)
3.380
Fathead Minnow
5.720
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
559.050
Hydration Free Energy
-2.900
Log(D) at pH=7.4
2.650
Log(P)
0.47
Log S
-4.24
Log(Vapor Pressure)
-9.34
Melting Point
209.1
pKa Acid
7.16
pKa Basic
-0.03
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 0.9418
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9227
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.8999
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8966
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8725
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8609
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8501
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8465
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8429
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8356
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8302
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8249
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8237
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8227
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8142
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8140
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7981
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7951
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7936
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7919
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7918
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7875
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7861
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7826
Cytochrome P450 3A4 P08684 CP3A4_HUMAN Homo sapiens 4 0.7825
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7778
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7735
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7726
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7682
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7557
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7541
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7517
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7516
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7513
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7488
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7468
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7464
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7455
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7430
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7424
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7422
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7384
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7379
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7353
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7345
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7319
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7318
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7318
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7314
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7311
UDP-N-acetylbacillosamine N-acetyltransferase Q0P9D1 PGLD_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 4 0.7291
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7280
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7267
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7264
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7258
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7236
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7221
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7218
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7214
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7210
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7194
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7171
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7151
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7137
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7118
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7103
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7098
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7052
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7019
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7008
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7006

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