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2-hydroxyswietenine
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Limonoid
| Canonical Smiles | C/C=C(/OC(=O)[C@H]1C(C)(C)[C@H]([C@H](C(=O)OC)O)[C@@]2(C(=O)[C@@]1(O)C=C1[C@@H]2CC[C@@]2([C@H]1CC(=O)O[C@H]2c1ccoc1)C)C)\C |
|---|---|
| InChI | InChI=1S/C32H40O10/c1-8-16(2)41-27(36)24-29(3,4)23(22(34)26(35)39-7)31(6)19-9-11-30(5)20(18(19)14-32(24,38)28(31)37)13-21(33)42-25(30)17-10-12-40-15-17/h8,10,12,14-15,19-20,22-25,34,38H,9,11,13H2,1-7H3/b16-8+/t19-,20-,22+,23-,24-,25-,30+,31+,32+/m0/s1 |
| InChIKey | OKSOKDSKQGUUCI-YXRPLECISA-N |
| Formula | C32H40O10 |
| HBA | 10 |
| HBD | 2 |
| MW | 584.66 |
| Rotatable Bonds | 5 |
| TPSA | 149.57 |
| LogP | 3.82 |
| Number Rings | 5 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 42 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.62 |
| Exact Mass | 584.26 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Swietenia mahogani | Meliaceae | Plantae | 459165 |
Showing of synonyms
2-hydroxyswietenine
CHEMBL2271727
No compound-protein relationship available.
SMILES: c1occc1C2OC(=O)CC3C2CCC(C3=4)C5C(=O)C(C4)CCC5
Level: 1
Mol. Weight: 584.66 g/mol
SMILES: C1CCC(C2)C(=O)C1C(C=23)CCC4C3CC(=O)OC4
Level: 0
Mol. Weight: 584.66 g/mol
SMILES: c1ccoc1
Level: 0
Mol. Weight: 584.66 g/mol
Antifeedant
Absorption
- Caco-2 (logPapp)
- -5.3
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.81
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 2.17
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.84
- Plasma Protein Binding
- 89.5
- 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
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 10.42
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.95
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.14
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 8.08
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Toxic
- 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
- -7483.38
- Rat (Acute)
- 4.08
- Rat (Chronic Oral)
- 2.63
- Fathead Minnow
- 22.79
- 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
- 373.54
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 3.48
- Log(P)
- 3.53
- Log S
- -5.26
- Log(Vapor Pressure)
- -12.27
- Melting Point
- 235.73
- pKa Acid
- 6.38
- pKa Basic
- 2.71
| 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 | 0.8913 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8913 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8492 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8492 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8474 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8474 |
| prolyl oligopeptidase | Q9X6R4 | Q9X6R4_AERCA | Aeromonas caviae | 3 | 0.8384 |
| prolyl oligopeptidase | Q9X6R4 | Q9X6R4_AERCA | Aeromonas caviae | 3 | 0.8384 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8340 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8340 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8275 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8275 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.8223 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.8223 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8070 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8070 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7980 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7980 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7875 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7875 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7762 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7762 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7740 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7740 |
| glutaryl-CoA dehydrogenase (ETF) | Q3JP94 | Q3JP94_BURP1 | Burkholderia pseudomallei | 2 | 0.7696 |
| glutaryl-CoA dehydrogenase (ETF) | Q3JP94 | Q3JP94_BURP1 | Burkholderia pseudomallei | 2 | 0.7696 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7695 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7695 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | P13922 | DRTS_PLAFK | Plasmodium falciparum | 2 | 0.7683 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | P13922 | DRTS_PLAFK | Plasmodium falciparum | 2 | 0.7683 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7640 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7640 |
| cGMP-dependent protein kinase 2 | Q13237 | KGP2_HUMAN | Homo sapiens | 2 | 0.7563 |
| cGMP-dependent protein kinase 2 | Q13237 | KGP2_HUMAN | Homo sapiens | 2 | 0.7563 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7542 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7542 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 3 | 0.7500 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 3 | 0.7500 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7481 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7481 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7460 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7460 |
| Casein kinase II subunit alpha' | P19784 | CSK22_HUMAN | Homo sapiens | 3 | 0.7458 |
| Casein kinase II subunit alpha' | P19784 | CSK22_HUMAN | Homo sapiens | 3 | 0.7458 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7421 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7421 |
| Probable esterase KAI2 | Q9SZU7 | KAI2_ARATH | Arabidopsis thaliana | 3 | 0.7408 |
| Probable esterase KAI2 | Q9SZU7 | KAI2_ARATH | Arabidopsis thaliana | 3 | 0.7408 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7380 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7380 |
| prolyl oligopeptidase | Q9X6R4 | Q9X6R4_AERCA | Aeromonas caviae | 3 | 0.7368 |
| prolyl oligopeptidase | Q9X6R4 | Q9X6R4_AERCA | Aeromonas caviae | 3 | 0.7368 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7305 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7305 |
| NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 2 | 0.7304 |
| NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 2 | 0.7304 |
| Thymidine kinase | P0DTH5 | KITH_HHV11 | Human herpesvirus 1 | 3 | 0.7247 |
| Thymidine kinase | P0DTH5 | KITH_HHV11 | Human herpesvirus 1 | 3 | 0.7247 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7194 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7194 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7157 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7157 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7129 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7129 |