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(3S,5S)-dihydro-5-(3-hydroxy-2-methyl-5-oxocyclopent-1-enyl)-3-methyl-4-((E)-3-oxobut-1-enyl)furan-2(3H)-one
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | CC(=O)/C=C/[C@H]1[C@H](C)C(=O)O[C@@H]1C1=C(C)C(CC1=O)O |
|---|---|
| InChI | InChI=1S/C15H18O5/c1-7(16)4-5-10-8(2)15(19)20-14(10)13-9(3)11(17)6-12(13)18/h4-5,8,10-11,14,17H,6H2,1-3H3/b5-4+/t8-,10-,11?,14-/m0/s1 |
| InChIKey | ANTYQIKMKBUESI-AGJVEWJJSA-N |
| Formula | C15H18O5 |
| HBA | 5 |
| HBD | 1 |
| MW | 278.3 |
| Rotatable Bonds | 3 |
| TPSA | 80.67 |
| LogP | 0.96 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.53 |
| Exact Mass | 278.12 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Otanthus maritimus | Asteraceae | Plantae | 1155244 |
Showing of synonyms
(3S,5S)-dihydro-5-(3-hydroxy-2-methyl-5-oxocyclopent-1-enyl)-3-methyl-4-((E)-3-oxobut-1-enyl)furan-2(3H)-one
- Jakupovic J, Boeker R, et al. (1988). Highly oxygenated guaianolides from Otanthus maritimus. Phytochemistry,1988,27(4),1135-1140. [View]
No compound-protein relationship available.
SMILES: O=C1CCC(O1)C2=CCCC2=O
Level: 1
Mol. Weight: 278.3 g/mol
SMILES: O=C1CCCO1
Level: 0
Mol. Weight: 278.3 g/mol
SMILES: O=C1C=CCC1
Level: 0
Mol. Weight: 278.3 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.68
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.74
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.55
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.63
- Plasma Protein Binding
- 44.92
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- 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
- 4.68
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.31
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.92
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.7
- 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
- 1.89
- Rat (Acute)
- 2.62
- Rat (Chronic Oral)
- 2.05
- Fathead Minnow
- 4.12
- 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
- 361.84
- Hydration Free Energy
- -10.17
- Log(D) at pH=7.4
- 0.27
- Log(P)
- -0.64
- Log S
- -2.04
- Log(Vapor Pressure)
- -6.57
- Melting Point
- 177.56
- pKa Acid
- 7.35
- pKa Basic
- 4.18
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8704 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8704 |
| Gastrotropin | P51161 | FABP6_HUMAN | Homo sapiens | 3 | 0.7582 |
| Gastrotropin | P51161 | FABP6_HUMAN | Homo sapiens | 3 | 0.7582 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7323 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7323 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7170 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7170 |