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Zapoterin
- Family: Plantae - Rutaceae
- Kingdom: Plantae
- Class: Coumarin
| Canonical Smiles | O=C1C=C[C@]2([C@H](C(O1)(C)C)CC(=O)[C@@]1([C@@H]2[C@@H](O)C[C@@]2([C@]31O[C@@H]3C(=O)O[C@H]2c1ccoc1)C)C)C |
|---|---|
| InChI | InChI=1S/C26H30O8/c1-22(2)15-10-16(28)25(5)18(23(15,3)8-6-17(29)33-22)14(27)11-24(4)19(13-7-9-31-12-13)32-21(30)20-26(24,25)34-20/h6-9,12,14-15,18-20,27H,10-11H2,1-5H3/t14-,15-,18+,19-,20+,23-,24-,25+,26+/m0/s1 |
| InChIKey | OZGKITZRRFNYRV-CHALWBKJSA-N |
| Formula | C26H30O8 |
| HBA | 8 |
| HBD | 1 |
| MW | 470.52 |
| Rotatable Bonds | 1 |
| TPSA | 115.57 |
| LogP | 2.9 |
| Number Rings | 6 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.65 |
| Exact Mass | 470.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Casimiroa edulis | Rutaceae | Plantae | 68535 |
Showing of synonyms
Zapoterin
23885-43-0
11alpha-Hydroxyobacunoic acid 3,4-lactone
CHEBI:10105
C08788
(1R,2R,4S,7S,8S,10S,11R,12R,18R)-7-(furan-3-yl)-10-hydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.02,4.02,8.012,18]icos-13-ene-5,15,20-trione
AC1L9BPG
CHEMBL3235617
DTXSID50331634
AKOS040763040
FS-9795
11|A-Hydroxyobacunoic acid 3,4-lactone
Q27108585
- Awaad AS, Maitland DJ, et al. (2007). New alkaloids from Casimiroa edulis fruits and their pharmacological activity. Chemistry of Natural Compounds,2007,43(5),576-580. [View]
Pubchem:
441812
Cas:
23885-43-0
Zinc:
ZINC000004097793
Kegg Ligand:
C08788
Chebi:
10105
Chembl:
CHEMBL3235617
Comptox:
DTXSID50331634
No compound-protein relationship available.
SMILES: c1occc1C(OC(=O)C(C234)O4)C3CCC5C2C(=O)CC6C5C=CC(=O)OC6
Level: 1
Mol. Weight: 470.52 g/mol
SMILES: C123C(O3)C(=O)OCC2CCC4C1C(=O)CC5C4C=CC(=O)OC5
Level: 0
Mol. Weight: 470.52 g/mol
SMILES: c1ccoc1
Level: 0
Mol. Weight: 470.52 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.17
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.910
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.71
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.550
- Plasma Protein Binding
- 46.83
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- 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
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 12.040
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.290
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.130
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.910
- 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
- -242.150
- Rat (Acute)
- 5.420
- Rat (Chronic Oral)
- 1.890
- Fathead Minnow
- 4.060
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 501.460
- Hydration Free Energy
- -2.870
- Log(D) at pH=7.4
- 1.960
- Log(P)
- 1.46
- Log S
- -4.9
- Log(Vapor Pressure)
- -9.57
- Melting Point
- 277.73
- pKa Acid
- 4.16
- pKa Basic
- 4.03
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.7827 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.7827 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7495 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7495 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7348 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7348 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7331 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7331 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7328 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7328 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7304 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7304 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7180 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7180 |
| Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 2 | 0.7083 |
| Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 2 | 0.7083 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 3 | 0.7012 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 3 | 0.7012 |