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5Halpha,6Hbeta,7Halpha,-15-hydroxy-8alpha-(1',2'-dihydroxyethyl-acryloxy)-elema- 1(2),3(4),11(13)-trien-6,12-olide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | OCC(=C)[C@@H]1[C@H]2OC(=O)C(=C)[C@@H]2[C@H](C[C@@]1(C)C=C)OC(=O)C(=C)C(CO)O |
|---|---|
| InChI | InChI=1S/C20H26O7/c1-6-20(5)7-14(26-18(24)11(3)13(23)9-22)15-12(4)19(25)27-17(15)16(20)10(2)8-21/h6,13-17,21-23H,1-4,7-9H2,5H3/t13?,14-,15+,16+,17-,20+/m0/s1 |
| InChIKey | KUOSLPBZDWVFER-CHGXTBDYSA-N |
| Formula | C20H26O7 |
| HBA | 7 |
| HBD | 3 |
| MW | 378.42 |
| Rotatable Bonds | 7 |
| TPSA | 113.29 |
| LogP | 0.67 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.5 |
| Exact Mass | 378.17 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Centaurea maroccana | Asteraceae | Plantae | 41503 |
Showing of synonyms
5Halpha,6Hbeta,7Halpha,-15-hydroxy-8alpha-(1',2'-dihydroxyethyl-acryloxy)-elema- 1(2),3(4),11(13)-trien-6,12-olide
8-alpha-(3,4-Dihydroxy-2-methylene-butanoyloxy)-dehydromelitensin
[(3aR,4S,6S,7R,7aR)-7-[1-(hydroxymethyl)vinyl]-6-methyl-3-methylene-2-oxo-6-vinyl-4,5,7,7a-tetrahydro-3aH-benzofuran-4-yl] 3,4-dihydroxy-2-methylene-butanoate
- Bicha S, Chalard P, et al. (2013). Maroccanin: a new gamma-lactone and other constituents from Centaurea maroccana ball. (Asteraceae). Records of Natural Products,2013,7(2),114-118. [View]
Pubchem:
483218
No compound-protein relationship available.
SMILES: C=C1C(=O)OC(C12)CCCC2
Level: 0
Mol. Weight: 378.42 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.69
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.710
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.55
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.570
- Plasma Protein Binding
- 62.13
- 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
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 8.490
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.150
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.020
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.270
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Toxic
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -1.790
- Rat (Acute)
- 3.740
- Rat (Chronic Oral)
- 2.670
- Fathead Minnow
- 3.990
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 396.170
- Hydration Free Energy
- -9.160
- Log(D) at pH=7.4
- 1.270
- Log(P)
- 0.71
- Log S
- -2.64
- Log(Vapor Pressure)
- -9.0
- Melting Point
- 126.88
- pKa Acid
- 6.33
- pKa Basic
- 4.07
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.9110 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.9110 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8929 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8929 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.8282 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.8282 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8273 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8273 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8115 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8115 |