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Rubescin D
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Limonoid
| Canonical Smiles | O[C@@H]1[C@@H]2OC[C@]3([C@H]2[C@]([C@]24[C@]1(C)C1=CC[C@H]([C@]1(C)C[C@@H]4O2)c1cocc1)(C)C(=O)C=C3)C |
|---|---|
| InChI | InChI=1S/C26H30O5/c1-22-9-7-17(27)25(4)20(22)19(30-13-22)21(28)24(3)16-6-5-15(14-8-10-29-12-14)23(16,2)11-18-26(24,25)31-18/h6-10,12,15,18-21,28H,5,11,13H2,1-4H3/t15-,18-,19+,20-,21+,22-,23-,24+,25-,26-/m0/s1 |
| InChIKey | DVAFPZBSLYOHNG-INXKWOFGSA-N |
| Formula | C26H30O5 |
| HBA | 5 |
| HBD | 1 |
| MW | 422.52 |
| Rotatable Bonds | 1 |
| TPSA | 72.2 |
| LogP | 3.79 |
| Number Rings | 7 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.65 |
| Exact Mass | 422.21 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Trichilia rubescens | Meliaceae | Plantae | 1672008 |
| 2 | Trichilia rubescens | Meliaceae | Plantae | 1672008 |
Showing of synonyms
Rubescin D
- Tsamo AT, Melong R, et al. (2019). Rubescins I and J, further limonoid derivatives from the stem bark of Trichilia rubescens (Meliaceae).. Natural product research,2019, 33(2), 196-203. [View] [PubMed]
- Sass G, Tsamo AT, et al. (2019). Vismione B Interferes with Trypanosoma cruzi Infection of Vero Cells and Human Stem Cell-Derived Cardiomyocytes.. The American journal of tropical medicine and hygiene,2019, 101(6), 1359-1368. [View] [PubMed]
CPRiL:
97701
SMILES: c1occc1C2CC=C(C2CC(C345)O5)C3CC6C7C(CO6)C=CC(=O)C47
Level: 1
Mol. Weight: 422.52 g/mol
SMILES: C123C(O3)CC4C(=CCC4)C1CC5C6C(CO5)C=CC(=O)C26
Level: 0
Mol. Weight: 422.52 g/mol
SMILES: c1ccoc1
Level: 0
Mol. Weight: 422.52 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.16
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.64
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.36
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.66
- Plasma Protein Binding
- 55.67
- 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
- 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
- 18.08
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.91
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.01
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 7.3
- 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
- -86.48
- Rat (Acute)
- 4.71
- Rat (Chronic Oral)
- 1.93
- Fathead Minnow
- 3.98
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 459.28
- Hydration Free Energy
- -2.96
- Log(D) at pH=7.4
- 3.31
- Log(P)
- 3.02
- Log S
- -4.61
- Log(Vapor Pressure)
- -8.76
- Melting Point
- 219.26
- pKa Acid
- 4.96
- pKa Basic
- 4.46
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8075 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7912 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7811 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7674 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 2 | 0.7478 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7406 |
| NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 2 | 0.7255 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 2 | 0.7114 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7045 |