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Amphicoside
- Family: Plantae - Scrophulariaceae
- Kingdom: Plantae
-
Class: Glycoside
- Subclass: Iridoid Glucoside
| Canonical Smiles | OC[C@H]1O[C@@H](OC2OC=CC3C2[C@@]2(CO)O[C@H]2[C@H]3OC(=O)c2ccc(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C23H28O13/c1-31-12-6-9(2-3-11(12)26)20(30)34-18-10-4-5-32-21(14(10)23(8-25)19(18)36-23)35-22-17(29)16(28)15(27)13(7-24)33-22/h2-6,10,13-19,21-22,24-29H,7-8H2,1H3/t10?,13-,14?,15-,16+,17-,18+,19+,21?,22+,23-/m1/s1 |
| InChIKey | AKNILCMFRRDTEY-PLQWSCRJSA-N |
| Formula | C23H28O13 |
| HBA | 13 |
| HBD | 6 |
| MW | 512.46 |
| Rotatable Bonds | 7 |
| TPSA | 197.13 |
| LogP | -2.01 |
| Number Rings | 5 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 36 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.61 |
| Exact Mass | 512.15 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Veronica anagalIis-aquatica | Scrophulariaceae | Plantae | 1421714 |
Showing of synonyms
Amphicoside
DTXSID90904225
34779-62-9
((2S,4S,5S,10S)-2-(hydroxymethyl)-10-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-3,9-dioxatricyclo(4.4.0.02,4)dec-7-en-5-yl) 4-hydroxy-3-methoxybenzoate
[(2S,4S,5S,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] 4-hydroxy-3-methoxybenzoate
DTXCID301333374
- Lahloub M, Zaghloul M, et al. (1993). Iridoid glycosides from veronica anagallis-aquatica. Phytochemistry, 1993, 33(2), 401-405. [View]
No compound-protein relationship available.
SMILES: c1ccccc1C(=O)OC(C(O2)C23)C4C3C(OC=C4)OC5CCCCO5
Level: 2
Mol. Weight: 512.46 g/mol
SMILES: c1ccccc1C(=O)OC(C(O2)C23)C4C3COC=C4
Level: 1
Mol. Weight: 512.46 g/mol
SMILES: C12C(O2)CC3C1C(OC=C3)OC4CCCCO4
Level: 1
Mol. Weight: 512.46 g/mol
SMILES: C12C(O2)CC3C1COC=C3
Level: 0
Mol. Weight: 512.46 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 512.46 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 512.46 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.68
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.940
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -0.65
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.760
- Plasma Protein Binding
- 34.67
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 9.640
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.950
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.660
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.320
- 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
- -1057.420
- Rat (Acute)
- 2.690
- Rat (Chronic Oral)
- 3.840
- Fathead Minnow
- 2.890
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 526.870
- Hydration Free Energy
- -3.000
- Log(D) at pH=7.4
- -0.710
- Log(P)
- -1.03
- Log S
- -2.21
- Log(Vapor Pressure)
- -11.49
- Melting Point
- 150.1
- pKa Acid
- 5.01
- pKa Basic
- 2.02
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9436 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9255 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.9040 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.9040 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8888 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.8856 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8773 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8769 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8628 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8542 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8521 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8489 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.8446 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.8303 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.8241 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.8120 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.8091 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8044 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.8015 |
| ActVA 6 protein | Q53908 | Q53908_STRCH | Streptomyces coelicolor | 3 | 0.7757 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7730 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7668 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7605 |
| Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial | Q33862 | Q33862_ASCSU | Ascaris suum | 3 | 0.7575 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7540 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7532 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7504 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7471 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7465 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7460 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.7459 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7451 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7444 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7429 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7419 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7406 |
| ATP-dependent protease subunit HslV | P0A7B8 | HSLV_ECOLI | Escherichia coli | 3 | 0.7404 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7391 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7378 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7372 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7369 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7341 |
| Tannase | B3Y018 | B3Y018_LACPN | Lactiplantibacillus plantarum | 3 | 0.7305 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7303 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.7303 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7290 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7274 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7262 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7259 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7257 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.7256 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7245 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7234 |
| 3',5'-cyclic-AMP phosphodiesterase 4B | Q07343 | PDE4B_HUMAN | Homo sapiens | 3 | 0.7231 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7222 |
| Histone-lysine N-methyltransferase EHMT2 | Q96KQ7 | EHMT2_HUMAN | Homo sapiens | 3 | 0.7216 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7205 |
| ADP compounds hydrolase NudE | P45799 | NUDE_ECOLI | Escherichia coli | 2 | 0.7180 |
| Uncharacterized protein YML079W | Q03629 | YMH9_YEAST | Saccharomyces cerevisiae | 2 | 0.7180 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 2 | 0.7178 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 2 | 0.7177 |
| Tannase | B3Y018 | B3Y018_LACPN | Lactiplantibacillus plantarum | 4 | 0.7170 |
| Histone-lysine N-methyltransferase 2A | Q03164 | KMT2A_HUMAN | Homo sapiens | 3 | 0.7149 |
| Cytidine and deoxycytidylate deaminase zinc-binding region | Q82Y41 | Q82Y41_NITEU | Nitrosomonas europaea | 2 | 0.7147 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7136 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7116 |
| Oxygenase | Q194P4 | Q194P4_STRAA | Streptomyces argillaceus | 3 | 0.7115 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7112 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7107 |
| Tannase | B3Y018 | B3Y018_LACPN | Lactiplantibacillus plantarum | 3 | 0.7105 |
| Histone-lysine N-methyltransferase 2C | Q8NEZ4 | KMT2C_HUMAN | Homo sapiens | 3 | 0.7094 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7073 |
| dTDP-4-dehydrorhamnose 3,5-epimerase | A0A6L7H6N0 | A0A1S0QLH9_BACAN | Bacillus anthracis | 3 | 0.7066 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7065 |
| Small heat shock protein StHsp14.0 | Q970D9 | Q970D9_SULTO | Sulfurisphaera tokodaii | 3 | 0.7053 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 2 | 0.7047 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 4 | 0.7044 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | P0AF12 | MTNN_ECOLI | Escherichia coli | 2 | 0.7044 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7039 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7037 |
| Acyl-CoA:acyl-CoA alkyltransferase | Q8PDX2 | OLEA_XANCP | Xanthomonas campestris pv. campestris | 3 | 0.7035 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 2 | 0.7029 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7027 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7015 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7009 |
| Transitional endoplasmic reticulum ATPase | Q01853 | TERA_MOUSE | Mus musculus | 3 | 0.7008 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7007 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7007 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 2 | 0.7007 |
| Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 | Q8GZB6 | SUVH4_ARATH | Arabidopsis thaliana | 3 | 0.7003 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7003 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7001 |