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1alpha,4alpha,10alpha-trihydroxy-2beta,3beta-epoxy-8alpha-valeryloxy-11,13-dehydroguaia-6alpha,12-olide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | CC(CC(=O)O[C@H]1C[C@@](C)(O)[C@]2([C@@H]([C@@H]3[C@@H]1[C@H](C)C(=O)O3)[C@]([C@@H]1[C@H]2O1)(C)O)O)C |
|---|---|
| InChI | InChI=1S/C20H30O8/c1-8(2)6-11(21)26-10-7-18(4,23)20(25)14(19(5,24)15-16(20)28-15)13-12(10)9(3)17(22)27-13/h8-10,12-16,23-25H,6-7H2,1-5H3/t9-,10-,12+,13-,14-,15-,16+,18+,19-,20+/m0/s1 |
| InChIKey | MGXGYVFGGBQQIP-PAMUPXPHSA-N |
| Formula | C20H30O8 |
| HBA | 8 |
| HBD | 3 |
| MW | 398.45 |
| Rotatable Bonds | 3 |
| TPSA | 125.82 |
| LogP | 0.16 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.9 |
| Exact Mass | 398.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Otanthus maritimus | Asteraceae | Plantae | 1155244 |
Showing of synonyms
1alpha,4alpha,10alpha-trihydroxy-2beta,3beta-epoxy-8alpha-valeryloxy-11,13-dehydroguaia-6alpha,12-olide
- 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: C12C(O2)CC3C1CCCC4C3OC(=O)C4
Level: 0
Mol. Weight: 398.45 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.13
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.77
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.87
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.35
- Plasma Protein Binding
- 37.48
- 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
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 10.74
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.09
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.25
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.89
- Micronucleos
- Toxic
- 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
- -9.38
- Rat (Acute)
- 4.97
- Rat (Chronic Oral)
- 2.31
- Fathead Minnow
- 3.82
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 403.05
- Hydration Free Energy
- -8.73
- Log(D) at pH=7.4
- 0.23
- Log(P)
- 0.81
- Log S
- -2.46
- Log(Vapor Pressure)
- -8.43
- Melting Point
- 155.6
- pKa Acid
- 5.3
- pKa Basic
- 3.61
| 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 | 0.8601 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8601 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7889 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7889 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7330 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7330 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.7181 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.7181 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7090 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7090 |