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1alpha,6alpha,8alpha-trihydroxy-5alpha,7betaH-guaia-3,9,11(13)-trien-12-oic acid
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | O[C@H]1C=C(C)[C@]2([C@@H]([C@H]([C@@H]1C(=C)C(=O)O)O)C(=CC2)C)O |
|---|---|
| InChI | InChI=1S/C15H20O5/c1-7-4-5-15(20)8(2)6-10(16)11(9(3)14(18)19)13(17)12(7)15/h4,6,10-13,16-17,20H,3,5H2,1-2H3,(H,18,19)/t10-,11+,12+,13-,15+/m0/s1 |
| InChIKey | PURFAWWKECSNFN-IHWVXMPCSA-N |
| Formula | C15H20O5 |
| HBA | 4 |
| HBD | 4 |
| MW | 280.32 |
| Rotatable Bonds | 2 |
| TPSA | 97.99 |
| LogP | 0.62 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.53 |
| Exact Mass | 280.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Achillea coarctata | Asteraceae | Plantae | 282729 |
Showing of synonyms
1alpha,6alpha,8alpha-trihydroxy-5alpha,7betaH-guaia-3,9,11(13)-trien-12-oic acid
- Hegazy MEF, Abdel-Lateff A, et al. (2008). Anti-inflammatory activity of new guaiane acid derivatives from Achillea coarctata.. Natural Product Communications,2008,3(6),851-856. [View]
No compound-protein relationship available.
SMILES: C1=CCC(C12)C=CCCC2
Level: 0
Mol. Weight: 280.32 g/mol
Anti-inflammatory
Absorption
- Caco-2 (logPapp)
- -5.65
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.79
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.83
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.53
- Plasma Protein Binding
- 47.44
- 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
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 2.08
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.61
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.39
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.12
- Micronucleos
- Safe
- 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
- -1.45
- Rat (Acute)
- 2.04
- Rat (Chronic Oral)
- 2.98
- Fathead Minnow
- 4.05
- 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
- 365.57
- Hydration Free Energy
- -14.35
- Log(D) at pH=7.4
- -1.87
- Log(P)
- 0.79
- Log S
- -1.46
- Log(Vapor Pressure)
- -8.76
- Melting Point
- 162.76
- pKa Acid
- 3.91
- pKa Basic
- 6.34
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 3 | 0.8428 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 3 | 0.8428 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7741 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7741 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7664 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7664 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7052 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7052 |