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Trichirubine A
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Limonoid
| Canonical Smiles | OC1OC(=O)C(=C1)[C@@H]1C[C@@H]2[C@]3([C@@]1(C)C[C@@H]1O[C@@]41[C@@]3(C)C=C1[C@@H]3[C@]4(C)C(=O)C=C[C@]3(CO1)C)O2 |
|---|---|
| InChI | InChI=1S/C26H28O7/c1-21-6-5-15(27)24(4)19(21)14(30-11-21)9-23(3)25-16(32-25)8-13(12-7-18(28)31-20(12)29)22(25,2)10-17-26(23,24)33-17/h5-7,9,13,16-19,28H,8,10-11H2,1-4H3/t13-,16+,17-,18?,19-,21-,22-,23-,24-,25+,26-/m0/s1 |
| InChIKey | KCEMPVMLWXZZLR-ZCVPZFCJSA-N |
| Formula | C26H28O7 |
| HBA | 7 |
| HBD | 1 |
| MW | 452.5 |
| Rotatable Bonds | 1 |
| TPSA | 97.89 |
| LogP | 2.19 |
| Number Rings | 8 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.69 |
| Exact Mass | 452.18 |
| 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
Trichirubine A
(1S,2S,4S,6S,7R,9R,11R,12S,17R,21S)-7-(2-Hydroxy-5-oxo-2H-furan-4-yl)-1,6,12,17-tetramethyl-3,10,15-trioxaheptacyclo[12.6.1.02,4.02,12.06,11.09,11.017,21]henicosa-13,18-dien-20-one
(1S,2S,4S,6S,7R,9R,11R,12S,17R,21S)-7-(2-hydroxy-5-oxo-2H-furan-4-yl)-1,6,12,17-tetramethyl-3,10,15-trioxaheptacyclo(12.6.1.02,4.02,12.06,11.09,11.017,21)henicosa-13,18-dien-20-one
CHEMBL1172217
- Tsamo AT, Pagna JIM, et al. (2019). Rubescins F-H, new vilasinin-type limonoids from the leaves of Trichilia rubescens (Meliaceae).. Zeitschrift fur Naturforschung. C, Journal of biosciences,2019, 74(7-8), 175-182. [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]
Pubchem:
10389151
Chembl:
CHEMBL1172217
No compound-protein relationship available.
SMILES: O=C1OCC=C1C(CC(C234)O4)C2CC5C6(O5)C3C=C7C8C(CO7)C=CC(=O)C68
Level: 1
Mol. Weight: 452.5 g/mol
SMILES: C123C(O3)CCC1CC4C5(O4)C2C=C6C7C(CO6)C=CC(=O)C57
Level: 0
Mol. Weight: 452.5 g/mol
SMILES: O=C1C=CCO1
Level: 0
Mol. Weight: 452.5 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.17
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.83
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.45
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.45
- Plasma Protein Binding
- 39.34
- 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
- 11.6
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.19
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.05
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 7.39
- 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
- -333.84
- Rat (Acute)
- 4.98
- Rat (Chronic Oral)
- 1.43
- Fathead Minnow
- 3.88
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 500.77
- Hydration Free Energy
- -3.08
- Log(D) at pH=7.4
- 2.16
- Log(P)
- 1.43
- Log S
- -4.5
- Log(Vapor Pressure)
- -8.51
- Melting Point
- 255.5
- pKa Acid
- 3.25
- pKa Basic
- 2.52
| 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 | 0.7910 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7666 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7188 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7095 |