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8alpha-isobutanoyl-10alpha-hydroxy-1alpha,2alpha,3alpha,4alpha-diepoxy-11,13-dehydroguaia-6alpha,12-olide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | O=C(C(C)C)O[C@H]1C[C@@](C)(O)[C@]23[C@@H]([C@@H]4[C@@H]1[C@H](C)C(=O)O4)[C@]1([C@@H]([C@@H]3O2)O1)C |
|---|---|
| InChI | InChI=1S/C19H26O7/c1-7(2)15(20)23-9-6-17(4,22)19-12(11-10(9)8(3)16(21)24-11)18(5)13(25-18)14(19)26-19/h7-14,22H,6H2,1-5H3/t8-,9-,10+,11-,12-,13+,14-,17+,18-,19+/m0/s1 |
| InChIKey | DYYUKEWJHDHASM-RZUWAQNMSA-N |
| Formula | C19H26O7 |
| HBA | 7 |
| HBD | 1 |
| MW | 366.41 |
| Rotatable Bonds | 2 |
| TPSA | 97.89 |
| LogP | 0.81 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.89 |
| Exact Mass | 366.17 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Otanthus maritimus | Asteraceae | Plantae | 1155244 |
Showing of synonyms
8alpha-isobutanoyl-10alpha-hydroxy-1alpha,2alpha,3alpha,4alpha-diepoxy-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]
Pubchem:
162816884
No compound-protein relationship available.
SMILES: C123C(O3)C4C(O4)C1C5C(CC(=O)O5)CCC2
Level: 0
Mol. Weight: 366.41 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.07
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.730
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.29
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.180
- Plasma Protein Binding
- 25.83
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 12.990
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.260
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.120
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 6.370
- 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
- -7.030
- Rat (Acute)
- 4.590
- Rat (Chronic Oral)
- 1.580
- Fathead Minnow
- 3.770
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 397.690
- Hydration Free Energy
- -6.290
- Log(D) at pH=7.4
- 0.630
- Log(P)
- 0.76
- Log S
- -2.42
- Log(Vapor Pressure)
- -7.18
- Melting Point
- 145.5
- pKa Acid
- 5.18
- pKa Basic
- 2.16
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7781 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7781 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7685 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7685 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7257 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7257 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.7052 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.7052 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7052 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7052 |