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6-O-foliamenthoyl-(6'-O-cinnamoyl)-antirrhinoside
- Family: Plantae - Plantaginaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Iridoid Glycoside
| Canonical Smiles | OC/C=C(/CC/C=C(/C(=O)O[C@@H]1[C@@H]2O[C@@]2(C2[C@@]1(O)C=CO[C@H]2O[C@@H]1OC(COC(=O)/C=C/c2ccccc2)[C@H](C([C@@H]1O)O)O)C)\C)\C |
|---|---|
| InChI | InChI=1S/C34H42O13/c1-19(14-16-35)8-7-9-20(2)30(40)45-29-28-33(3,47-28)27-32(42-17-15-34(27,29)41)46-31-26(39)25(38)24(37)22(44-31)18-43-23(36)13-12-21-10-5-4-6-11-21/h4-6,9-15,17,22,24-29,31-32,35,37-39,41H,7-8,16,18H2,1-3H3/b13-12+,19-14+,20-9+/t22?,24-,25?,26+,27?,28+,29-,31+,32+,33-,34+/m1/s1 |
| InChIKey | BMUNDUFBXVVORI-LPVXWZIQSA-N |
| Formula | C34H42O13 |
| HBA | 13 |
| HBD | 5 |
| MW | 658.7 |
| Rotatable Bonds | 12 |
| TPSA | 193.97 |
| LogP | 1.03 |
| Number Rings | 5 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 47 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.53 |
| Exact Mass | 658.26 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Anarrhinum pubescens | Plantaginaceae | Plantae | 2026105 |
Showing of synonyms
6-O-foliamenthoyl-(6'-O-cinnamoyl)-antirrhinoside
No compound-protein relationship available.
SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)OC(OC=C3)C4C3CC(O5)C45
Level: 2
Mol. Weight: 658.7 g/mol
SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2
Level: 1
Mol. Weight: 658.7 g/mol
SMILES: C12C(O2)CC3C1C(OC=C3)OC4CCCCO4
Level: 1
Mol. Weight: 658.7 g/mol
SMILES: C12C(O2)CC3C1COC=C3
Level: 0
Mol. Weight: 658.7 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 658.7 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 658.7 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.52
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.49
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 76.57
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.87
- Plasma Protein Binding
- 51.54
- 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
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.15
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.47
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.59
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.59
- 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
- -143435.32
- Rat (Acute)
- 2.88
- Rat (Chronic Oral)
- 3.73
- Fathead Minnow
- 195.95
- 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
- 11060.02
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 1.28
- Log(P)
- 2.88
- Log S
- -3.11
- Log(Vapor Pressure)
- -385.43
- Melting Point
- 126.78
- pKa Acid
- 5.13
- pKa Basic
- 0.61
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.9028 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8798 |
| Purine nucleoside phosphorylase | Q8I3X4 | Q8I3X4_PLAF7 | Plasmodium falciparum | 3 | 0.8726 |
| Disintegrin and metalloproteinase domain-containing protein 17 | P78536 | ADA17_HUMAN | Homo sapiens | 3 | 0.8049 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7846 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7605 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7581 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7562 |
| Caffeoyl-CoA O-methyltransferase | Q40313 | CAMT_MEDSA | Medicago sativa | 3 | 0.7539 |
| Chorismate mutase AroH | P19080 | AROH_BACSU | Bacillus subtilis | 2 | 0.7353 |
| Plasma membrane ATPase | Q42932 | Q42932_NICPL | Nicotiana plumbaginifolia | 2 | 0.7321 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7312 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7266 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7261 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 2 | 0.7242 |
| Muconolactone Delta-isomerase | Q8G9L0 | Q8G9L0_RHOOP | Rhodococcus opacus | 2 | 0.7239 |
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 2 | 0.7236 |
| Carnitine O-acetyltransferase | P47934 | CACP_MOUSE | Mus musculus | 2 | 0.7200 |
| NAD(P) transhydrogenase subunit alpha part 1 | Q2RSB2 | PNTAA_RHORT | Rhodospirillum rubrum | 3 | 0.7181 |
| Deacetoxycephalosporin C synthase | P18548 | CEFE_STRCL | Streptomyces clavuligerus | 2 | 0.7163 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7136 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7129 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7123 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7116 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7110 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7093 |
| Polymerase basic protein 2 | P31345 | PB2_I75A3 | Influenza A virus | 2 | 0.7065 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7064 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 2 | 0.7052 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7048 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 2 | 0.7043 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 2 | 0.7027 |