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Leandreanin C
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Phragmalin Limonoid
| Canonical Smiles | COC(=O)C[C@H]1[C@@]2(C)C[C@@]34[C@]1(COC(=O)C)[C@]15CC[C@@]6([C@H]([C@]5([C@H]([C@]3([C@H]2OC(=O)C)OC(=O)C)OC(=O)C)OC(O1)(O4)C)CC(=O)OC6c1cocc1)C |
|---|---|
| InChI | InChI=1S/C37H44O16/c1-18(38)46-17-33-23(13-25(42)44-8)31(6)16-35(33)37(50-21(4)41,28(31)47-19(2)39)29(48-20(3)40)36-24-14-26(43)49-27(22-9-12-45-15-22)30(24,5)10-11-34(33,36)51-32(7,52-35)53-36/h9,12,15,23-24,27-29H,10-11,13-14,16-17H2,1-8H3/t23-,24+,27?,28-,29+,30+,31+,32?,33-,34-,35+,36+,37-/m0/s1 |
| InChIKey | PJCCXGXHENUWMB-ZSZJNVPTSA-N |
| Formula | C37H44O16 |
| HBA | 16 |
| HBD | 0 |
| MW | 744.74 |
| Rotatable Bonds | 8 |
| TPSA | 198.63 |
| LogP | 2.98 |
| Number Rings | 8 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 53 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.73 |
| Exact Mass | 744.26 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Neobeguea leandriana | Meliaceae | Plantae | 3128761 |
Showing of synonyms
Leandreanin C
- Coombes PH, Mulholland DA, et al. (2003). Phragmalin Limonoids from the Madagascan MeliaceaeNeobeguea leandreana. Journal of natural products, 2003, 66(6), 735–738. [View]
Pubchem:
101253605
No compound-protein relationship available.
SMILES: c1occc1C(OC(=O)C2)C(CC3)C2C4(C356)CC7C8(OC(O6)O4)C5CC(C8)C7
Level: 1
Mol. Weight: 744.74 g/mol
SMILES: C1C(=O)OCC(CC2)C1C3(C245)CC6C7(OC(O5)O3)C4CC(C7)C6
Level: 0
Mol. Weight: 744.74 g/mol
SMILES: c1ccoc1
Level: 0
Mol. Weight: 744.74 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.54
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- 3.020
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 1080.95
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.140
- Plasma Protein Binding
- 85.25
- 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
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 5.610
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -26.240
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.530
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 8.430
- 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
- -1965422.820
- Rat (Acute)
- 5.580
- Rat (Chronic Oral)
- 2.950
- Fathead Minnow
- 2484.960
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 216674.250
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 1.650
- Log(P)
- 1.9
- Log S
- -5.4
- Log(Vapor Pressure)
- -7106.64
- Melting Point
- 272.14
- pKa Acid
- -25.85
- pKa Basic
- -1.56
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.9116 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7894 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7729 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7637 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7475 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7380 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.7182 |
| Nucleoside diphosphate kinase | Q5UQL3 | NDK_MIMIV | Acanthamoeba polyphaga mimivirus | 2 | 0.7166 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7030 |