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Myricoside
- Family: Plantae - Bignoniaceae
- Kingdom: Plantae
-
Class: Phenolic
- Subclass: Phenylethanoid Triglycoside
| Canonical Smiles | OC[C@H]1O[C@@H](OCCc2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O[C@@H]1OC[C@]([C@H]1O)(O)CO)O)O |
|---|---|
| InChI | InChI=1S/C34H44O19/c1-15-24(42)28(52-33-30(45)34(46,13-36)14-48-33)25(43)32(49-15)53-29-26(44)31(47-9-8-17-3-6-19(38)21(40)11-17)50-22(12-35)27(29)51-23(41)7-4-16-2-5-18(37)20(39)10-16/h2-7,10-11,15,22,24-33,35-40,42-46H,8-9,12-14H2,1H3/b7-4+/t15-,22+,24-,25+,26+,27+,28+,29+,30-,31+,32-,33-,34+/m0/s1 |
| InChIKey | KAKUSAKVVYFENV-SBLIKUSGSA-N |
| Formula | C34H44O19 |
| HBA | 19 |
| HBD | 11 |
| MW | 756.71 |
| Rotatable Bonds | 13 |
| TPSA | 304.21 |
| LogP | -2.55 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 53 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.56 |
| Exact Mass | 756.25 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Tecoma mollis | Bignoniaceae | Plantae | 2822953 |
Showing of synonyms
Myricoside
76076-04-5
[(2R,3R,4R,5R,6R)-4-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]oxy-3,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)tetrahydropyran-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
((2R,3R,4R,5R,6R)-4-((2S,3R,4R,5S,6S)-4-((2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl)oxy-3,5-dihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-6-(2-(3,4-dihydroxyphenyl)ethoxy)-5-hydroxy-2-(hydroxymethyl)tetrahydropyran-3-yl) (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
(2R,3R,4R,5R,6R)-4-(((2S,3S,4S,5S,6S)-4-(((2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl)oxy)-3,5-dihydroxy-6-methyloxan-2-yl)oxy)-6-(2-(3,4-dihydroxyphenyl)ethoxy)-5-hydroxy-2-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
(2R,3R,4R,5R,6R)-4-{[(2S,3S,4S,5S,6S)-4-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
[(2R,3R,4R,5R,6R)-4-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
CHEMBL4455571
C10479
AC1NQZ2T
CHEBI:7055
BDBM50528372
HY-N10523
XM172931
CS-0610226
Q27107434
- Abdel-Mageed W, Al-Wahaibi L, et al. (2017). New phenolic glycosides with cyclooxygenase inhibition from the roots of Tecoma mollis. Phytochemistry Letters, 2017, 21, 98-103. [View]
Pubchem:
5281784
Cas:
76076-04-5
Zinc:
ZINC000095630238
Kegg Ligand:
C10479
Chebi:
7055
Chembl:
CHEMBL4455571
Bindingdb:
50528372
No compound-protein relationship available.
SMILES: O1CCCC1OC2CC(OCC2)OC3C(OC(=O)C=Cc4ccccc4)COC(C3)OCCc5ccccc5
Level: 4
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1C=CC(=O)OC(C2OC3CCCCO3)COC(C2)OCCc4ccccc4
Level: 3
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1C=CC(=O)OC(COCC2)C2OC(OCC3)CC3OC4CCCO4
Level: 3
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1CCOC(OCC2)CC2OC(OCC3)CC3OC4CCCO4
Level: 3
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)OCCc3ccccc3
Level: 2
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1C=CC(=O)OC(COCC2)C2OC3CCCCO3
Level: 2
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1CCOC(OCC2)CC2OC3CCCCO3
Level: 2
Mol. Weight: 756.71 g/mol
SMILES: O1CCCC1OC2CC(OCC2)OC3CCOCC3
Level: 2
Mol. Weight: 756.71 g/mol
SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2
Level: 1
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1CCOC2CCCCO2
Level: 1
Mol. Weight: 756.71 g/mol
SMILES: C1COCCC1OC2CCCCO2
Level: 1
Mol. Weight: 756.71 g/mol
SMILES: O1CCCC1OC2CCOCC2
Level: 1
Mol. Weight: 756.71 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 756.71 g/mol
SMILES: C1CCOC1
Level: 0
Mol. Weight: 756.71 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
- 1.230
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 952.36
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.670
- Plasma Protein Binding
- 54.71
- 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
- 9.770
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -21.220
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.460
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 7.110
- 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
- -1727847.380
- Rat (Acute)
- 2.310
- Rat (Chronic Oral)
- 4.740
- Fathead Minnow
- 2188.450
- 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
- 188259.100
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- -0.380
- Log(P)
- -0.88
- Log S
- -4.08
- Log(Vapor Pressure)
- -6159.68
- Melting Point
- 205.79
- pKa Acid
- -11.93
- pKa Basic
- 3.88
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9296 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9258 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.9193 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.9039 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.8973 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8949 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.8914 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.8859 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.8698 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8590 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8525 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8391 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.8345 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8330 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.8316 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.8301 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8258 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 3 | 0.8243 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8218 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.8211 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8111 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8103 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8037 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 3 | 0.7999 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7958 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7900 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7854 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7832 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.7726 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7690 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7615 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7606 |
| Tubulin--tyrosine ligase | F6Z895 | A9ULH4_XENTR | Xenopus tropicalis | 4 | 0.7605 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 3 | 0.7570 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7558 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7475 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7412 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.7408 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7349 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7326 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7320 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 4 | 0.7318 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7300 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7276 |
| Purine nucleoside phosphorylase | P55859 | PNPH_BOVIN | Bos taurus | 3 | 0.7265 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7232 |
| Purine nucleoside phosphorylase | P55859 | PNPH_BOVIN | Bos taurus | 3 | 0.7224 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7223 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 4 | 0.7217 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7216 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7213 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7162 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7162 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 2 | 0.7150 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7143 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7139 |
| Cyclic GMP-AMP phosphodiesterase SMPDL3A | Q92484 | ASM3A_HUMAN | Homo sapiens | 2 | 0.7133 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7133 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7129 |
| Purine nucleoside phosphorylase 2 | P45563 | XAPA_ECOLI | Escherichia coli | 3 | 0.7124 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7115 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7107 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7092 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7091 |
| Small heat shock protein StHsp14.0 | Q970D9 | Q970D9_SULTO | Sulfurisphaera tokodaii | 3 | 0.7079 |
| Purine nucleoside phosphorylase | P55859 | PNPH_BOVIN | Bos taurus | 3 | 0.7075 |
| Tryptophan--tRNA ligase | Q9PIB4 | SYW_CAMJE | Campylobacter jejuni subsp. jejuni serotype O:2 | 4 | 0.7070 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7070 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 4 | 0.7060 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7056 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7045 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7045 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7044 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7036 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7025 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7024 |
| Purine nucleoside phosphorylase | Q9BMI9 | Q9BMI9_SCHMA | Schistosoma mansoni | 3 | 0.7023 |
| Gentisate 1,2-dioxygenase | Q67FT0 | Q67FT0_PSESE | Pseudaminobacter salicylatoxidans | 2 | 0.7020 |
| Ribosomal RNA small subunit methyltransferase NEP1 | Q06287 | NEP1_YEAST | Saccharomyces cerevisiae | 4 | 0.7017 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7016 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7015 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7014 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 2 | 0.7014 |
| DNA ligase | P43813 | DNLJ_HAEIN | Haemophilus influenzae | 3 | 0.7008 |