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3-acetylswietenolide
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpene
| Canonical Smiles | COC(=O)[C@@H]([C@H]1C(C)(C)[C@H](OC(=O)C)[C@H]2C(=O)[C@]1(C)C1CC[C@@]3(C(=C1C2)CC(=O)O[C@H]3c1ccoc1)C)O |
|---|---|
| InChI | InChI=1S/C29H36O9/c1-14(30)37-25-17-11-16-18(29(5,23(17)33)22(27(25,2)3)21(32)26(34)35-6)7-9-28(4)19(16)12-20(31)38-24(28)15-8-10-36-13-15/h8,10,13,17-18,21-22,24-25,32H,7,9,11-12H2,1-6H3/t17-,18?,21-,22+,24+,25-,28-,29-/m1/s1 |
| InChIKey | LUDUHKJIKKLONS-UAYPTTMSSA-N |
| Formula | C29H36O9 |
| HBA | 9 |
| HBD | 1 |
| MW | 528.6 |
| Rotatable Bonds | 4 |
| TPSA | 129.34 |
| LogP | 3.7 |
| Number Rings | 5 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 38 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.66 |
| Exact Mass | 528.24 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Quivisia papinae | Meliaceae | Plantae | — |
Showing of synonyms
3-acetylswietenolide
- Coombes PH, Mulholland DA, et al. (2005). Mexicanolide limonoids from the Madagascan MeliaceaeQuivisia papinae. Phytochemistry, 2005, 66(10), 1100–1107. [View]
No compound-protein relationship available.
SMILES: c1occc1C(OC(=O)C2)C3CCC(C4=C23)C5C(=O)C(C4)CCC5
Level: 1
Mol. Weight: 528.6 g/mol
SMILES: C1C(=O)OCC(C1=C23)CCC2C4C(=O)C(C3)CCC4
Level: 0
Mol. Weight: 528.6 g/mol
SMILES: c1ccoc1
Level: 0
Mol. Weight: 528.6 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.2
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.840
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.82
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.870
- Plasma Protein Binding
- 76.86
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- 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
- 10.990
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.470
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.180
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 7.610
- 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
- -1340.630
- Rat (Acute)
- 4.020
- Rat (Chronic Oral)
- 2.510
- Fathead Minnow
- 7.550
- 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
- 455.050
- Hydration Free Energy
- -2.810
- Log(D) at pH=7.4
- 3.190
- Log(P)
- 2.25
- Log S
- -5.21
- Log(Vapor Pressure)
- -9.31
- Melting Point
- 249.39
- pKa Acid
- 6.46
- pKa Basic
- 3.1
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8972 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8916 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8910 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8869 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8856 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8700 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8671 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8621 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8528 |
| Casein kinase II subunit alpha' | P19784 | CSK22_HUMAN | Homo sapiens | 3 | 0.8050 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7886 |
| Acetylcholinesterase | P22303 | ACES_HUMAN | Homo sapiens | 3 | 0.7847 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.7761 |
| cGMP-dependent protein kinase 2 | Q13237 | KGP2_HUMAN | Homo sapiens | 2 | 0.7724 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7707 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.7702 |
| Probable esterase KAI2 | Q9SZU7 | KAI2_ARATH | Arabidopsis thaliana | 3 | 0.7604 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7566 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7547 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7488 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 2 | 0.7461 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 2 | 0.7460 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 2 | 0.7425 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7377 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | P13922 | DRTS_PLAFK | Plasmodium falciparum | 2 | 0.7357 |
| Nucleoside diphosphate kinase | Q5UQL3 | NDK_MIMIV | Acanthamoeba polyphaga mimivirus | 2 | 0.7353 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7329 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 2 | 0.7292 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7291 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7290 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7276 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 2 | 0.7229 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7186 |
| Beta-2 adrenergic receptor | P07550 | ADRB2_HUMAN | Homo sapiens | 2 | 0.7155 |
| 17-beta-hydroxysteroid dehydrogenase 14 | Q9BPX1 | DHB14_HUMAN | Homo sapiens | 2 | 0.7151 |
| Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 2 | 0.7122 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7095 |
| Prenyltransferase | Q4R2T2 | Q4R2T2_STRC1 | Streptomyces sp | 2 | 0.7088 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 2 | 0.7074 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7063 |
| Purine nucleoside phosphorylase DeoD-type | Q5EEL8 | DEOD_BACCE | Bacillus cereus | 2 | 0.7062 |
| Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 | Q9Y3Z3 | SAMH1_HUMAN | Homo sapiens | 2 | 0.7055 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 2 | 0.7050 |