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15-hydroxygermacra-1(10),4,11(13)-trien-(12,6);(14,8)-diolide 15-O-beta-D-glucopyranoside
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone Glycoside
| Canonical Smiles | OCC1OC(OC/C/2=C\[C@H]3OC(=O)C(=C)[C@@H]3[C@@H]3C/C(=C\CC2)/C(=O)O3)C(C(C1O)O)O |
|---|---|
| InChI | InChI=1S/C21H26O10/c1-9-15-12(29-19(9)26)5-10(3-2-4-11-6-13(15)30-20(11)27)8-28-21-18(25)17(24)16(23)14(7-22)31-21/h4-5,12-18,21-25H,1-3,6-8H2/b10-5-,11-4+/t12-,13+,14?,15+,16?,17?,18?,21?/m1/s1 |
| InChIKey | XLSLLCJGYAYACK-YTHJTXIWSA-N |
| Formula | C21H26O10 |
| HBA | 10 |
| HBD | 4 |
| MW | 438.43 |
| Rotatable Bonds | 4 |
| TPSA | 151.98 |
| LogP | -1.14 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.62 |
| Exact Mass | 438.15 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Urospermum picroides | Asteraceae | Plantae | 268113 |
Showing of synonyms
15-hydroxygermacra-1(10),4,11(13)-trien-(12,6);(14,8)-diolide 15-O-beta-D-glucopyranoside
- Balboul BAAA, Ahmed AA, et al. (1997). Sesquiterpene lactones and glycosides from Urospermum picroides. Phytochemistry,1997,45(2),369-373. [View]
Pubchem:
162978399
No compound-protein relationship available.
SMILES: O=C1OC(C2)C(C(=C)C(=O)O3)C3C=C(CCC=C12)COC4CCCCO4
Level: 1
Mol. Weight: 438.43 g/mol
SMILES: O=C1OC(C2)C(C(=C)C(=O)O3)C3C=CCCC=C12
Level: 0
Mol. Weight: 438.43 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 438.43 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.38
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.83
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.52
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.82
- Plasma Protein Binding
- 46.31
- 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
- 4.84
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.48
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.38
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.98
- Micronucleos
- Toxic
- 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
- -58.22
- Rat (Acute)
- 3.05
- Rat (Chronic Oral)
- 3.14
- Fathead Minnow
- 4.07
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 496.0
- Hydration Free Energy
- -3.8
- Log(D) at pH=7.4
- 0.63
- Log(P)
- -1.78
- Log S
- -1.72
- Log(Vapor Pressure)
- -12.93
- Melting Point
- 179.28
- pKa Acid
- 6.19
- pKa Basic
- 4.82
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8394 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8394 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8364 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8364 |
| Cysteine synthase | P45040 | CYSK_HAEIN | Haemophilus influenzae | 3 | 0.7052 |
| Cysteine synthase | P45040 | CYSK_HAEIN | Haemophilus influenzae | 3 | 0.7052 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7031 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7031 |