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19-acetoxy-ent-labda-8(17),13-dien-15,16-olide
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Labdane Diterpenoid
| Canonical Smiles | CC(=O)OC[C@]1(C)CCC[C@@]2([C@@H]1CCC(=C)[C@H]2CCC1=CC(=O)OC1)C |
|---|---|
| InChI | InChI=1S/C22H32O4/c1-15-6-9-19-21(3,14-26-16(2)23)10-5-11-22(19,4)18(15)8-7-17-12-20(24)25-13-17/h12,18-19H,1,5-11,13-14H2,2-4H3/t18-,19-,21+,22+/m1/s1 |
| InChIKey | PAXVPBKYCURYQJ-WKDRNLAYSA-N |
| Formula | C22H32O4 |
| HBA | 4 |
| HBD | 0 |
| MW | 360.49 |
| Rotatable Bonds | 5 |
| TPSA | 52.6 |
| LogP | 4.59 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.73 |
| Exact Mass | 360.23 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Turraeanthus africanus | Meliaceae | Plantae | 1672009 |
Showing of synonyms
19-acetoxy-ent-labda-8(17),13-dien-15,16-olide
No compound-protein relationship available.
SMILES: C1CCCC(C12)CCC(=C)C2CCC3=CC(=O)OC3
Level: 1
Mol. Weight: 360.49 g/mol
SMILES: C=C(C1)CCC(C12)CCCC2
Level: 0
Mol. Weight: 360.49 g/mol
SMILES: O=C1C=CCO1
Level: 0
Mol. Weight: 360.49 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.69
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.96
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.05
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.43
- Plasma Protein Binding
- 70.45
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- 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
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.43
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.54
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.73
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.74
- Micronucleos
- Safe
- 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
- -2.83
- Rat (Acute)
- 2.57
- Rat (Chronic Oral)
- 1.74
- Fathead Minnow
- 3.93
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 413.67
- Hydration Free Energy
- -3.49
- Log(D) at pH=7.4
- 3.53
- Log(P)
- 3.23
- Log S
- -5.64
- Log(Vapor Pressure)
- -6.85
- Melting Point
- 102.48
- pKa Acid
- 9.88
- pKa Basic
- 6.06
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.9126 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.8673 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8489 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8480 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.8379 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8244 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.8054 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 3 | 0.8026 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.8001 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7978 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7978 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 2 | 0.7949 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7841 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7818 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7738 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7630 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7628 |
| Gastrotropin | Q6IMW5 | Q6IMW5_DANRE | Danio rerio | 2 | 0.7617 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7549 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7547 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7546 |
| Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 2 | 0.7506 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 2 | 0.7505 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7495 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7478 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7472 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7445 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7421 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7420 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7388 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 2 | 0.7354 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7338 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7331 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7328 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7309 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7293 |
| Alcohol dehydrogenase 1C | P00326 | ADH1G_HUMAN | Homo sapiens | 2 | 0.7281 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7245 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7244 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7207 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7205 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7201 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7189 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 2 | 0.7181 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7172 |
| Ferric enterobactin-binding periplasmic protein FepB | P0AEL6 | FEPB_ECOLI | Escherichia coli | 3 | 0.7151 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7150 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7140 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7091 |
| Retinol-binding protein 4 | P18902 | RET4_BOVIN | Bos taurus | 3 | 0.7046 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7010 |