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6alpha-angeloyloxy-1alpha-hydroxygermacra-4E,9Z,11-trien-8alpha,12-olide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | C/C=C(\C(=O)O[C@@H]1/C=C(\C)/CC[C@H](/C(=C/2\[C@@H](C1)OC(=O)C2=C)/C)O)/C |
|---|---|
| InChI | InChI=1S/C20H26O5/c1-6-12(3)19(22)24-15-9-11(2)7-8-16(21)13(4)18-14(5)20(23)25-17(18)10-15/h6,9,15-17,21H,5,7-8,10H2,1-4H3/b11-9+,12-6-,18-13-/t15-,16-,17-/m1/s1 |
| InChIKey | HHRYHNHDDGIIOG-GDRORVMCSA-N |
| Formula | C20H26O5 |
| HBA | 5 |
| HBD | 1 |
| MW | 346.42 |
| Rotatable Bonds | 2 |
| TPSA | 72.83 |
| LogP | 3.15 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.5 |
| Exact Mass | 346.18 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Cotula cinerea | Asteraceae | Plantae | — |
Showing of synonyms
6alpha-angeloyloxy-1alpha-hydroxygermacra-4E,9Z,11-trien-8alpha,12-olide
- Metwally MA, El-dahmy S, et al. (1986). Glaucolide-like sesquiterpene lactones from Cotula cinerea. Phytochemistry,1986,25(1),255-257. [View]
No compound-protein relationship available.
SMILES: C=C1C(=O)OC(C1=2)CCC=CCCCC2
Level: 0
Mol. Weight: 346.42 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.67
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.63
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.75
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.44
- Plasma Protein Binding
- 58.69
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- 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
- 6.95
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.46
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.45
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.98
- Micronucleos
- Safe
- 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
- -5.4
- Rat (Acute)
- 2.87
- Rat (Chronic Oral)
- 2.02
- Fathead Minnow
- 4.55
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 363.65
- Hydration Free Energy
- -6.84
- Log(D) at pH=7.4
- 2.34
- Log(P)
- 2.95
- Log S
- -3.54
- Log(Vapor Pressure)
- -6.21
- Melting Point
- 100.25
- pKa Acid
- 9.23
- pKa Basic
- 4.52
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.8270 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.8270 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7892 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7892 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7768 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7768 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7708 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7708 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7557 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7557 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 2 | 0.7511 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 2 | 0.7511 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7467 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7467 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7356 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7356 |
| Gastrotropin | Q6IMW5 | Q6IMW5_DANRE | Danio rerio | 2 | 0.7261 |
| Gastrotropin | Q6IMW5 | Q6IMW5_DANRE | Danio rerio | 2 | 0.7261 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 2 | 0.7117 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 2 | 0.7117 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7046 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7046 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7040 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7040 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7001 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7001 |