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11beta,12alpha-Diacetoxy-14beta,15beta-epoxyneotecleanin
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Limonoid
| Canonical Smiles | CC(=O)O[C@@H]1[C@@H]2[C@@]34CC(=O)C[C@@H]3OC([C@@H]4CC(=O)[C@@]2(C)[C@@]23[C@]([C@H]1OC(=O)C)(C)[C@@H](C[C@H]3O2)c1ccoc1)(C)C |
|---|---|
| InChI | InChI=1S/C30H36O9/c1-14(31)36-23-24-28(6,20(34)11-19-26(3,4)38-21-9-17(33)12-29(19,21)24)30-22(39-30)10-18(16-7-8-35-13-16)27(30,5)25(23)37-15(2)32/h7-8,13,18-19,21-25H,9-12H2,1-6H3/t18-,19-,21-,22+,23+,24-,25-,27+,28+,29+,30+/m0/s1 |
| InChIKey | PVWOAELREUNHIO-OFOYKKCZSA-N |
| Formula | C30H36O9 |
| HBA | 9 |
| HBD | 0 |
| MW | 540.61 |
| Rotatable Bonds | 3 |
| TPSA | 121.64 |
| LogP | 3.53 |
| Number Rings | 7 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 39 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.73 |
| Exact Mass | 540.24 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Turraea wakefieldii | Meliaceae | Plantae | 1899149 |
Showing of synonyms
11beta,12alpha-Diacetoxy-14beta,15beta-epoxyneotecleanin
[(1R,2R,6S,9R,12R,13R,15R,17S,18R,19R,20R)-19-Acetyloxy-17-(furan-3-yl)-8,8,12,18-tetramethyl-4,11-dioxo-7,14-dioxahexacyclo[10.8.0.02,6.02,9.013,15.013,18]icosan-20-yl] acetate
Pubchem:
10951645
Zinc:
ZINC000095910455
No compound-protein relationship available.
SMILES: c1occc1C(CC(C234)O4)C2CCC5C67C(CC(=O)C35)COC6CC(=O)C7
Level: 1
Mol. Weight: 540.61 g/mol
SMILES: C123C(O3)CCC1CCC4C56C(CC(=O)C24)COC5CC(=O)C6
Level: 0
Mol. Weight: 540.61 g/mol
SMILES: c1ccoc1
Level: 0
Mol. Weight: 540.61 g/mol
Larvicidal against larvae of anopheles gambiae s.s.
Absorption
- Caco-2 (logPapp)
- -5.1
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.66
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -0.79
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.37
- Plasma Protein Binding
- 61.98
- 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
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 12.44
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.11
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.08
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 7.82
- 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
- Toxic
- T. Pyriformis
- -2396.61
- Rat (Acute)
- 5.43
- Rat (Chronic Oral)
- 2.56
- Fathead Minnow
- 9.46
- 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
- 454.63
- Hydration Free Energy
- -2.82
- Log(D) at pH=7.4
- 2.29
- Log(P)
- 3.23
- Log S
- -4.32
- Log(Vapor Pressure)
- -9.17
- Melting Point
- 208.69
- pKa Acid
- 3.98
- pKa Basic
- 2.05
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.8723 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.8723 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8328 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8328 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 3 | 0.8108 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 3 | 0.8108 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7760 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7760 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | P13922 | DRTS_PLAFK | Plasmodium falciparum | 2 | 0.7608 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | P13922 | DRTS_PLAFK | Plasmodium falciparum | 2 | 0.7608 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7498 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7498 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7452 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7452 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7449 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7449 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7011 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7011 |