Myricetin 3-O-(4''-O-acetyl)- alpha-L-rhamnopyranoside - Compound Card

Myricetin 3-O-(4''-O-acetyl)- alpha-L-rhamnopyranoside

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Myricetin 3-O-(4''-O-acetyl)- alpha-L-rhamnopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Myrtaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonol Glycoside
Canonical Smiles CC(=O)O[C@@H]1[C@@H](C)O[C@@H]([C@H]([C@H]1O)O)Oc1c(oc2c(c1=O)c(O)cc(c2)O)c1cc(O)c(c(c1)O)O
InChI InChI=1S/C23H22O13/c1-7-20(34-8(2)24)18(31)19(32)23(33-7)36-22-17(30)15-11(26)5-10(25)6-14(15)35-21(22)9-3-12(27)16(29)13(28)4-9/h3-7,18-20,23,25-29,31-32H,1-2H3/t7-,18-,19+,20-,23-/m1/s1
InChIKey SYFGHPIRFKVZAG-OMTPBWFYSA-N
Formula C23H22O13
HBA 13
HBD 7
MW 506.42
Rotatable Bonds 4
TPSA 216.58
LogP 0.77
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.3
Exact Mass 506.11
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Eugenia jambolana Myrtaceae Plantae 260142

Showing of synonyms

  • Mahmoud I.I, Marzouk M.S, et al. (2001). Acylated flavonol glycosides from Eugenia jambolana leaves. Phytochemistry, 2001, 58(8), 1239-44. [View] [PubMed]
Pubchem: 162954904

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 506.42 g/mol

Structure

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

Level: 1

Mol. Weight: 506.42 g/mol

Structure

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

Level: 1

Mol. Weight: 506.42 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 506.42 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 506.42 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 506.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.68
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.42
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
1.22

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.88
Plasma Protein Binding
81.17
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
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
14.78
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.98
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.06
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.88
Micronucleos
Toxic
NR-AhR
Toxic
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
-345.23
Rat (Acute)
2.51
Rat (Chronic Oral)
3.57
Fathead Minnow
4.33
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
632.8
Hydration Free Energy
-3.7
Log(D) at pH=7.4
0.7
Log(P)
1.65
Log S
-3.88
Log(Vapor Pressure)
-10.59
Melting Point
204.19
pKa Acid
6.57
pKa Basic
6.05
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9146
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8936
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8824
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8801
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8779
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8754
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8701
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8525
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8427
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8305
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8086
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8074
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8046
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8046
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8021
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7976
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7968
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7946
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7851
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7806
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 3 0.7805
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7778
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7755
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7721
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7709
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7693
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7665
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 7 0.7664
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7607
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7602
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7579
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7479
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7463
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.7446
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7402
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7398
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7359
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7336
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7317
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7307
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7262
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7256
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7251
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7221
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7218
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7160
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7142
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7107
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7106
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7099
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7097
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7063
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7008
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7007

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