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15-acetoxy-labda-8(17),12E,14Z-trien-16-al
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Phenolic
- Subclass: Ellagic Acid Derivative
| Canonical Smiles | O=C/C(=C/C[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCCC2(C)C)/C=C\OC(=O)C |
|---|---|
| InChI | InChI=1S/C22H32O3/c1-16-7-10-20-21(3,4)12-6-13-22(20,5)19(16)9-8-18(15-23)11-14-25-17(2)24/h8,11,14-15,19-20H,1,6-7,9-10,12-13H2,2-5H3/b14-11-,18-8+/t19-,20-,22+/m0/s1 |
| InChIKey | JGZWSJYFEUCZRT-FSVASDFMSA-N |
| Formula | C22H32O3 |
| HBA | 3 |
| HBD | 0 |
| MW | 344.5 |
| Rotatable Bonds | 5 |
| TPSA | 43.37 |
| LogP | 5.38 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.64 |
| Exact Mass | 344.24 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Turraeanthus mannii | Meliaceae | Plantae | 1317901 |
Showing of synonyms
15-acetoxy-labda-8(17),12E,14Z-trien-16-al
- Sielinou V, Vardamides J, et al. (2012). Phenolic derivatives and an antifungal and cytototoxic labdane diterpenoid from the root bark of Turraeanthus mannii. Phytochemistry Letters, 2012, 5(3), 409-413. [View]
Pubchem:
162875373
No compound-protein relationship available.
SMILES: C=C(C1)CCC(C12)CCCC2
Level: 0
Mol. Weight: 344.5 g/mol
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.62
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.450
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.43
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.950
- Plasma Protein Binding
- 54.95
- 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
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 2.370
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.660
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.540
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.550
- Micronucleos
- Safe
- 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
- -0.330
- Rat (Acute)
- 4.850
- Rat (Chronic Oral)
- 1.560
- Fathead Minnow
- 4.700
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 382.830
- Hydration Free Energy
- -3.390
- Log(D) at pH=7.4
- 4.290
- Log(P)
- 5.73
- Log S
- -4.7
- Log(Vapor Pressure)
- -5.77
- Melting Point
- 59.11
- pKa Acid
- 8.35
- pKa Basic
- 5.23
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.8826 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8388 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8190 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8167 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.8044 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.8041 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7992 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7870 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7827 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 2 | 0.7763 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7760 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7752 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7712 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7705 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7697 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 2 | 0.7641 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7641 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7607 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7604 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7594 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 3 | 0.7538 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 2 | 0.7532 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7528 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7508 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7497 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7482 |
| Steroid 21-hydroxylase | P08686 | CP21A_HUMAN | Homo sapiens | 2 | 0.7464 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7462 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7459 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7457 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P50172 | DHI1_MOUSE | Mus musculus | 2 | 0.7457 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7439 |
| Gastrotropin | Q6IMW5 | Q6IMW5_DANRE | Danio rerio | 2 | 0.7433 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7403 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 2 | 0.7399 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7372 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 2 | 0.7341 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7321 |
| Steroid 17-alpha-hydroxylase/17,20 lyase | P05093 | CP17A_HUMAN | Homo sapiens | 2 | 0.7320 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7298 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7298 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7290 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7286 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7250 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7228 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7199 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7199 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7176 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7153 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7152 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7148 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 2 | 0.7121 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 2 | 0.7109 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7093 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7091 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7056 |