Select a section from the left sidebar
19-hydroxy-ent-labda-8(17),13-dien-15,16-olide
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Labdane Diterpenoid
| Canonical Smiles | OC[C@]1(C)CCC[C@@]2([C@@H]1CCC(=C)[C@H]2CCC1=CC(=O)OC1)C |
|---|---|
| InChI | InChI=1S/C20H30O3/c1-14-5-8-17-19(2,13-21)9-4-10-20(17,3)16(14)7-6-15-11-18(22)23-12-15/h11,16-17,21H,1,4-10,12-13H2,2-3H3/t16-,17-,19+,20+/m1/s1 |
| InChIKey | GWLQAIIVWXSSCM-JYBIWHBTSA-N |
| Formula | C20H30O3 |
| HBA | 3 |
| HBD | 1 |
| MW | 318.46 |
| Rotatable Bonds | 4 |
| TPSA | 46.53 |
| LogP | 4.02 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 23 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.75 |
| Exact Mass | 318.22 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Turraeanthus africanus | Meliaceae | Plantae | 1672009 |
Showing of synonyms
19-hydroxy-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: 318.46 g/mol
SMILES: C=C(C1)CCC(C12)CCCC2
Level: 0
Mol. Weight: 318.46 g/mol
SMILES: O=C1C=CCO1
Level: 0
Mol. Weight: 318.46 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.71
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.8
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.18
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.2
- Plasma Protein Binding
- 61.29
- 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
- 8.06
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.2
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.95
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.3
- 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
- -0.43
- Rat (Acute)
- 2.74
- Rat (Chronic Oral)
- 1.75
- Fathead Minnow
- 3.92
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 395.41
- Hydration Free Energy
- -3.47
- Log(D) at pH=7.4
- 3.21
- Log(P)
- 2.75
- Log S
- -4.83
- Log(Vapor Pressure)
- -7.07
- Melting Point
- 127.0
- pKa Acid
- 9.26
- pKa Basic
- 6.71
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.9661 |
| Epoxide hydrolase | Q41415 | Q41415_SOLTU | Solanum tuberosum | 3 | 0.9281 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.9034 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8915 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8897 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P50172 | DHI1_MOUSE | Mus musculus | 3 | 0.8818 |
| Retinol-binding protein 4 | P18902 | RET4_BOVIN | Bos taurus | 3 | 0.8246 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 3 | 0.8173 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8140 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7980 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7950 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7947 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 2 | 0.7852 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7818 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7758 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7758 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7758 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7752 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7730 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7726 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7681 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7676 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7676 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7675 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7671 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7656 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7640 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7638 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7611 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 2 | 0.7606 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7598 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7545 |
| Steroid 21-hydroxylase | P08686 | CP21A_HUMAN | Homo sapiens | 2 | 0.7544 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7543 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7493 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7476 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7472 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7451 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7437 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 2 | 0.7435 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7430 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7417 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7405 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7395 |
| Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 2 | 0.7388 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7380 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7378 |
| Glucocorticoid receptor | P04150 | GCR_HUMAN | Homo sapiens | 3 | 0.7376 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7364 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 2 | 0.7344 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7317 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7296 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7295 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7287 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7269 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7240 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 2 | 0.7238 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7184 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 3 | 0.7170 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7143 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7142 |
| Steroid 17-alpha-hydroxylase/17,20 lyase | P05093 | CP17A_HUMAN | Homo sapiens | 2 | 0.7133 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 2 | 0.7126 |
| Corticosteroid-binding globulin | P31211 | CBG_RAT | Rattus norvegicus | 3 | 0.7119 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 2 | 0.7118 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7112 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7111 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7101 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7095 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7067 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7052 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7052 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7025 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7007 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7001 |