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2-acetoxy-6-p-methoxybenzoyl-jaeschkeanadiol
- Family: Plantae - Apiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene
| Canonical Smiles | COc1ccc(cc1)C(=O)O[C@H]1CC(=CC[C@@]2([C@@H]1[C@@](O)(C[C@@H]2OC(=O)C)C(C)C)C)C |
|---|---|
| InChI | InChI=1S/C25H34O6/c1-15(2)25(28)14-21(30-17(4)26)24(5)12-11-16(3)13-20(22(24)25)31-23(27)18-7-9-19(29-6)10-8-18/h7-11,15,20-22,28H,12-14H2,1-6H3/t20-,21-,22+,24-,25+/m0/s1 |
| InChIKey | VGNXXIHXIBOUBQ-KHYNBEDJSA-N |
| Formula | C25H34O6 |
| HBA | 6 |
| HBD | 1 |
| MW | 430.54 |
| Rotatable Bonds | 5 |
| TPSA | 82.06 |
| LogP | 4.31 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.6 |
| Exact Mass | 430.24 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ferula communis var. brevifolia | Apiaceae | Plantae | 52470 |
Showing of synonyms
2-acetoxy-6-p-methoxybenzoyl-jaeschkeanadiol
98604-75-2
NCGC00385575-01_C25H34O6_(1S,3R,3aS,4S,8aR)-1-Acetoxy-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3,3a,4,5,8,8a-octahydro-4-azulenyl 4-methoxybenzoate
[(1S,3R,3aS,4S,8aR)-1-acetyloxy-3-hydroxy-6,8a-dimethyl-3-propan-2-yl-1,2,3a,4,5,8-hexahydroazulen-4-yl] 4-methoxybenzoate
Compound NP-018443
AKOS040733996
NCGC00385575-01
- Lamnaouer D, Martin MT, et al. (1989). Isolation of daucane esters from Ferula communis var. Brevifolia. Phytochemistry,1989,28(10),2711-2716. [View]
No compound-protein relationship available.
SMILES: c1ccccc1C(=O)OC2CC=CCC(C23)CCC3
Level: 1
Mol. Weight: 430.54 g/mol
SMILES: C1CCC(C12)CCC=CC2
Level: 0
Mol. Weight: 430.54 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 430.54 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.48
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.640
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.68
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.660
- Plasma Protein Binding
- 85.39
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- 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
- 10.190
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.630
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.330
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.750
- 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
- -26.620
- Rat (Acute)
- 3.250
- Rat (Chronic Oral)
- 2.060
- Fathead Minnow
- 4.010
- 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
- 410.210
- Hydration Free Energy
- -3.740
- Log(D) at pH=7.4
- 3.880
- Log(P)
- 5.45
- Log S
- -5.11
- Log(Vapor Pressure)
- -7.42
- Melting Point
- 149.1
- pKa Acid
- 9.22
- pKa Basic
- 4.39
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 4 | 0.7509 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 4 | 0.7509 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7497 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7497 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7351 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7351 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7322 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7322 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7296 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7296 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7274 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7274 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7248 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7248 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 2 | 0.7198 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 2 | 0.7198 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7182 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7182 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7114 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7114 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 2 | 0.7031 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 2 | 0.7031 |