Select a section from the left sidebar
1alpha,3beta-dihydroxy-7alpha,11betaH-germacra-4Z,9Z-dien-12,6alpha-olide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | O=C1O[C@H]2[C@H]([C@@H]1C)C/C=C(/C)\[C@H](C[C@@H](/C(=C/2)/C)O)O |
|---|---|
| InChI | InChI=1S/C15H22O4/c1-8-4-5-11-10(3)15(18)19-14(11)6-9(2)13(17)7-12(8)16/h4,6,10-14,16-17H,5,7H2,1-3H3/b8-4-,9-6+/t10-,11-,12-,13-,14+/m0/s1 |
| InChIKey | PQCNNCMXLJZLIA-KTWWBTSVSA-N |
| Formula | C15H22O4 |
| HBA | 4 |
| HBD | 2 |
| MW | 266.34 |
| Rotatable Bonds | 0 |
| TPSA | 66.76 |
| LogP | 1.57 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.67 |
| Exact Mass | 266.15 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Pyrethrum santolinoides | Asteraceae | Plantae | 2072400 |
| 2 | Tanacetum sinaicum | Asteraceae | Plantae | — |
Showing of synonyms
1alpha,3beta-dihydroxy-7alpha,11betaH-germacra-4Z,9Z-dien-12,6alpha-olide
- Mahmoud AA, Ahmed AA, et al. (1994). 2,3-secogermacranolides and germacranolides from Pyrethrum santolionoides. Phytochemistry,1994,36(2),393-398. [View]
- Hegazy MEF, Hamed AR, et al. (2015). Anti-inflammatory sesquiterpenes from the medicinal herb Tanacetum sinaicum. RSC Advances,2015,5,44895-44901. [View]
Pubchem:
162996908
No compound-protein relationship available.
SMILES: C1C(=O)OC(C12)C=CCCCC=CC2
Level: 0
Mol. Weight: 266.34 g/mol
Anti-inflammatory
Absorption
- Caco-2 (logPapp)
- -4.77
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.12
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.27
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.52
- Plasma Protein Binding
- 39.51
- 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
- 5.64
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.35
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.18
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 3.66
- 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
- -3.23
- Rat (Acute)
- 2.22
- Rat (Chronic Oral)
- 2.04
- Fathead Minnow
- 3.92
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 356.39
- Hydration Free Energy
- -10.66
- Log(D) at pH=7.4
- 0.66
- Log(P)
- 1.27
- Log S
- -1.84
- Log(Vapor Pressure)
- -6.53
- Melting Point
- 154.23
- pKa Acid
- 9.06
- pKa Basic
- 5.56
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Endoplasmin, putative | Q8I0V4 | Q8I0V4_PLAF7 | Plasmodium falciparum | 4 | 0.7829 |
| Endoplasmin, putative | Q8I0V4 | Q8I0V4_PLAF7 | Plasmodium falciparum | 4 | 0.7829 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7817 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7817 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7701 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7701 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7438 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7438 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7387 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7387 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7327 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7327 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7262 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7262 |