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3beta,13-diacetyloxy-1alpha-hydroxygermacra-4,7(11),9-trien-6alpha,12-olide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | CC(=O)OCC1=C2C/C=C(/C)\[C@@H](O)C[C@H](/C(=C\[C@H]2OC1=O)/C)OC(=O)C |
|---|---|
| InChI | InChI=1S/C19H24O7/c1-10-5-6-14-15(9-24-12(3)20)19(23)26-18(14)7-11(2)17(8-16(10)22)25-13(4)21/h5,7,16-18,22H,6,8-9H2,1-4H3/b10-5-,11-7-/t16-,17+,18+/m0/s1 |
| InChIKey | WZJIWOREWCFPIJ-JHLZYJBHSA-N |
| Formula | C19H24O7 |
| HBA | 7 |
| HBD | 1 |
| MW | 364.39 |
| Rotatable Bonds | 3 |
| TPSA | 99.13 |
| LogP | 1.75 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.53 |
| Exact Mass | 364.15 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Achillea fragrantissima | Asteraceae | Plantae | 282738 |
Showing of synonyms
3beta,13-diacetyloxy-1alpha-hydroxygermacra-4,7(11),9-trien-6alpha,12-olide
- Abdel-Mogib M, Jakupovic J, et al. (1989). Glaucolides from Achillea fragrantissima.. Phytochemistry,1989,28(12),3528-3530. [View]
No compound-protein relationship available.
SMILES: C1C(=O)OC(C=12)C=CCCCC=CC2
Level: 0
Mol. Weight: 364.39 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.69
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.64
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.96
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.4
- Plasma Protein Binding
- 42.93
- 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
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-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
- 7.83
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.12
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- 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
- 6.24
- Micronucleos
- Toxic
- 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
- -4.81
- Rat (Acute)
- 2.35
- Rat (Chronic Oral)
- 1.98
- Fathead Minnow
- 4.23
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 382.61
- Hydration Free Energy
- -7.89
- Log(D) at pH=7.4
- 1.31
- Log(P)
- 1.81
- Log S
- -2.91
- Log(Vapor Pressure)
- -6.98
- Melting Point
- 114.64
- pKa Acid
- 8.74
- pKa Basic
- 3.86
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8433 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8433 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7854 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7854 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7578 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7578 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7517 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7517 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7220 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7220 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7095 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7095 |
| Ferric enterobactin-binding periplasmic protein FepB | P0AEL6 | FEPB_ECOLI | Escherichia coli | 3 | 0.7068 |
| Ferric enterobactin-binding periplasmic protein FepB | P0AEL6 | FEPB_ECOLI | Escherichia coli | 3 | 0.7068 |
| Gastrotropin | Q6IMW5 | Q6IMW5_DANRE | Danio rerio | 2 | 0.7021 |
| Gastrotropin | Q6IMW5 | Q6IMW5_DANRE | Danio rerio | 2 | 0.7021 |