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Swietenialide B
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Limonoid
| Canonical Smiles | COC(=O)CC1[C@@]2(C)CC3(C1(C)C14OC5(OC4(C4C3([C@H]2OC(=O)/C(=C\C)/C)O[C@](O4)(CC)OC)C(O5)([C@](CC1O)(C)[C@H](c1ccoc1)OC(=O)C)CC(=O)OC)C)O |
|---|---|
| InChI | InChI=1S/C41H54O17/c1-12-21(3)29(46)53-30-32(5)20-36(47)34(7,24(32)16-26(44)48-9)40-25(43)17-33(6,28(52-22(4)42)23-14-15-51-19-23)37(18-27(45)49-10)41(40,57-35(8,55-37)56-40)31-39(30,36)58-38(13-2,50-11)54-31/h12,14-15,19,24-25,28,30-31,43,47H,13,16-18,20H2,1-11H3/b21-12-/t24?,25?,28-,30-,31?,32+,33-,34?,35?,36?,37?,38+,39?,40?,41?/m0/s1 |
| InChIKey | UHYLXNDBODUIRM-BBJPVVENSA-N |
| Formula | C41H54O17 |
| HBA | 17 |
| HBD | 2 |
| MW | 818.87 |
| Rotatable Bonds | 11 |
| TPSA | 214.18 |
| LogP | 3.28 |
| Number Rings | 8 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 58 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.76 |
| Exact Mass | 818.34 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Swietenia mahogani | Meliaceae | Plantae | 459165 |
Showing of synonyms
Swietenialide B
- Saad MMG, Iwagawa T, et al. (2003). Swietenialides, novel ring D opened phragmalin limonoid orthoesters from Swietenia mahogani JACQ.. Tetrahedron,2003,59(40),8027-8033. [View]
Pubchem:
101758880
No compound-protein relationship available.
SMILES: c1occc1CC(C2OC(O3)O4)CCC4(C235)C6C7C8(C5OCO8)CC(C6)C7
Level: 1
Mol. Weight: 818.87 g/mol
SMILES: O1COC2C1(CC(C3)C4)C4C3C5(C267)CCCC6OC(O7)O5
Level: 0
Mol. Weight: 818.87 g/mol
SMILES: c1ccoc1
Level: 0
Mol. Weight: 818.87 g/mol
Antifeedant
Absorption
- Caco-2 (logPapp)
- -5.47
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- 84.130
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 11692.0
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.320
- Plasma Protein Binding
- 67.35
- 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
- Inhibitor
Excretion
- Clearance
- 5.960
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -274.710
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.280
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.270
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -21221875.860
- Rat (Acute)
- 4.950
- Rat (Chronic Oral)
- 3.320
- Fathead Minnow
- 26794.670
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 2382845.900
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 3.080
- Log(P)
- 3.81
- Log S
- -5.09
- Log(Vapor Pressure)
- -78420.06
- Melting Point
- 188.89
- pKa Acid
- -516.14
- pKa Basic
- 0.35