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8alpha-O-(4-acetoxy-5-hydroxyangeloyl)-11beta,13-dihydrocnicin
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
Canonical Smiles | OC/C(=C/COC(=O)C)/C(=O)O[C@H]1C/C(=C/CC/C(=C/[C@@H]2[C@@H]1[C@H](C)C(=O)O2)/CO)/C |
---|---|
InChI | InChI=1S/C22H30O8/c1-13-5-4-6-16(11-23)10-19-20(14(2)21(26)29-19)18(9-13)30-22(27)17(12-24)7-8-28-15(3)25/h5,7,10,14,18-20,23-24H,4,6,8-9,11-12H2,1-3H3/b13-5+,16-10-,17-7-/t14-,18-,19+,20+/m0/s1 |
InChIKey | QVMJTYNTCBEZMJ-UZEIXXGISA-N |
Formula | C22H30O8 |
HBA | 8 |
HBD | 2 |
MW | 422.47 |
Rotatable Bonds | 6 |
TPSA | 119.36 |
LogP | 1.61 |
Number Rings | 2 |
Number Aromatic Rings | 0 |
Heavy Atom Count | 30 |
Formal Charge | 0 |
Fraction CSP3 | 0.59 |
Exact Mass | 422.19 |
Number of Lipinski Rule Violations | 0 |
# | Species | Family | Kingdom | NCBI Taxonomy ID |
---|---|---|---|---|
1 | Centaurea pullata | Asteraceae | Plantae | 347528 |
Showing of synonyms
8alpha-O-(4-acetoxy-5-hydroxyangeloyl)-11beta,13-dihydrocnicin
[(3S,3aR,4S,6E,10Z,11aR)-10-(hydroxymethyl)-3,6-dimethyl-2-oxo-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-4-yl] (Z)-4-acetyloxy-2-(hydroxymethyl)but-2-enoate
No compound-protein relationship available.
SMILES: C1C(=O)OC(C12)C=CCCC=CCC2
Level: 0
Mol. Weight: 422.47 g/mol
Antimicrobial
Absorption
- Caco-2 (logPapp)
- -4.78
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.740
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.82
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.460
- Plasma Protein Binding
- 50.69
- 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
- 9.090
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.000
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.490
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.360
- 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
- -20.510
- Rat (Acute)
- 2.700
- Rat (Chronic Oral)
- 2.450
- Fathead Minnow
- 4.130
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 434.050
- Hydration Free Energy
- -5.300
- Log(D) at pH=7.4
- 1.140
- Log(P)
- 1.43
- Log S
- -3.37
- Log(Vapor Pressure)
- -8.37
- Melting Point
- 115.22
- pKa Acid
- 8.79
- pKa Basic
- 4.52
Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
---|---|---|---|---|---|
Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.9506 |
Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.9506 |
Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8811 |
Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8811 |
Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.8473 |
Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.8473 |
Glycogen synthase | P0A6U8 | GLGA_ECOLI | Escherichia coli | 3 | 0.7872 |
Glycogen synthase | P0A6U8 | GLGA_ECOLI | Escherichia coli | 3 | 0.7872 |
Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7399 |
Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7399 |
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7240 |
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7240 |
Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7058 |
Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7058 |
Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7046 |
Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7046 |