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9-alpha-angeloyloxy-6beta-isobutoyloxy-1beta,4alpha-dihydroxy-eudesm-11(13)-en-5alpha,7alpha,8alpha,12-olide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | C/C=C(\C(=O)O[C@@H]1[C@@H]2OC(=O)C(=C)[C@@H]2[C@H]([C@@H]2[C@]1(C)[C@H](O)CC[C@@]2(C)O)OC(=O)C(C)C)/C |
|---|---|
| InChI | InChI=1S/C24H34O8/c1-8-12(4)21(27)32-19-17-15(13(5)22(28)31-17)16(30-20(26)11(2)3)18-23(6,29)10-9-14(25)24(18,19)7/h8,11,14-19,25,29H,5,9-10H2,1-4,6-7H3/b12-8-/t14-,15-,16-,17-,18+,19-,23-,24+/m1/s1 |
| InChIKey | RDXQYZATVQTRST-XAPHLCJXSA-N |
| Formula | C24H34O8 |
| HBA | 8 |
| HBD | 2 |
| MW | 450.53 |
| Rotatable Bonds | 4 |
| TPSA | 119.36 |
| LogP | 2.07 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 32 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.71 |
| Exact Mass | 450.23 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Wedelia prostrata | Asteraceae | Plantae | 318064 |
Showing of synonyms
9-alpha-angeloyloxy-6beta-isobutoyloxy-1beta,4alpha-dihydroxy-eudesm-11(13)-en-5alpha,7alpha,8alpha,12-olide
- Farag SF, El-Emary NA, et al. (1996). Eudesmanolides from Wedelia prostrata. Chemical and Pharmaceutical Bulletin,1996,44(4),661-664. [View]
No compound-protein relationship available.
SMILES: C=C1C(=O)OC(C12)CC3C(C2)CCCC3
Level: 0
Mol. Weight: 450.53 g/mol
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.6
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.7
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.55
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.43
- Plasma Protein Binding
- 79.67
- 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
- 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
- 7.11
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.63
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.42
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.04
- 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
- -40.39
- Rat (Acute)
- 4.19
- Rat (Chronic Oral)
- 2.21
- Fathead Minnow
- 4.0
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 395.44
- Hydration Free Energy
- -3.13
- Log(D) at pH=7.4
- 2.08
- Log(P)
- 2.73
- Log S
- -3.9
- Log(Vapor Pressure)
- -8.38
- Melting Point
- 153.76
- pKa Acid
- 7.44
- pKa Basic
- 3.29
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8986 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8986 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 4 | 0.8278 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 4 | 0.8278 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7648 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7648 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7598 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7598 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7239 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7239 |