Select a section from the left sidebar
8alpha-hydroxyguaia-4(15),10(14),11(13)-trien-6alpha,12-olide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | C=C1CC[C@@H]2[C@H]1[C@H]1OC(=O)C(=C)[C@@H]1[C@H](CC2=C)O |
|---|---|
| InChI | InChI=1S/C15H18O3/c1-7-4-5-10-8(2)6-11(16)13-9(3)15(17)18-14(13)12(7)10/h10-14,16H,1-6H2/t10-,11-,12-,13+,14+/m0/s1 |
| InChIKey | VNKCRRIDZAQRBP-QSLWVIQJSA-N |
| Formula | C15H18O3 |
| HBA | 3 |
| HBD | 1 |
| MW | 246.31 |
| Rotatable Bonds | 0 |
| TPSA | 46.53 |
| LogP | 1.99 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.53 |
| Exact Mass | 246.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Cheirolophus sempervirens | Asteraceae | Plantae | 65000 |
| 2 | Cheirolophus x hortigenus | Asteraceae | Plantae | 41544 |
Showing of synonyms
8alpha-hydroxyguaia-4(15),10(14),11(13)-trien-6alpha,12-olide
- Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones, lignans and aromatic esters ftrom Cheirolophus species. Phytochemistry,1994,37(4),1101-1107. [View]
No compound-protein relationship available.
SMILES: O=C(O1)C(=C)C(C1C23)CCC(=C)C3CCC2=C
Level: 0
Mol. Weight: 246.31 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.64
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.3
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.64
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.65
- Plasma Protein Binding
- 51.23
- 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
- 11.91
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.1
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.14
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 3.86
- 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
- 1.18
- Rat (Acute)
- 3.12
- Rat (Chronic Oral)
- 1.74
- Fathead Minnow
- 3.92
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 333.37
- Hydration Free Energy
- -5.94
- Log(D) at pH=7.4
- 1.37
- Log(P)
- 1.79
- Log S
- -2.73
- Log(Vapor Pressure)
- -5.44
- Melting Point
- 142.91
- pKa Acid
- 7.82
- pKa Basic
- 5.07
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.9113 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.9113 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.8949 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.8949 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8926 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8926 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.8623 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.8623 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.8026 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.8026 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 2 | 0.7131 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 2 | 0.7131 |