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3beta-acetoxy-5alpha-(2alpha-hydroxyethyl)acryloyloxy-7-hydroxycarvotacetone
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Carvotacetone
| Canonical Smiles | OCCC(=C)C(=O)O[C@@H]1C=C(CO)[C@@]([C@H](C1C(=C)C)OC(=O)C)(O)CC(=O)C |
|---|---|
| InChI | InChI=1S/C20H28O8/c1-11(2)17-16(28-19(25)12(3)6-7-21)8-15(10-22)20(26,9-13(4)23)18(17)27-14(5)24/h8,16-18,21-22,26H,1,3,6-7,9-10H2,2,4-5H3/t16-,17?,18+,20+/m1/s1 |
| InChIKey | ZKBJAVURHNBGSX-WATHEOSMSA-N |
| Formula | C20H28O8 |
| HBA | 8 |
| HBD | 3 |
| MW | 396.44 |
| Rotatable Bonds | 9 |
| TPSA | 130.36 |
| LogP | 0.6 |
| Number Rings | 1 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.55 |
| Exact Mass | 396.18 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Sphaeranthus suaveolens | Asteraceae | Plantae | 1548666 |
Showing of synonyms
3beta-acetoxy-5alpha-(2alpha-hydroxyethyl)acryloyloxy-7-hydroxycarvotacetone
- Ahmed AA, Mahmoud AA (1997). Carvotacetone derivatives from the Egyptian plant Sphaeranthus suaveolens. Phytochemistry,1997,45(3),533-535. [View]
No compound-protein relationship available.
SMILES: C1=CCCCC1
Level: 0
Mol. Weight: 396.44 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.8
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.720
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.8
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.330
- Plasma Protein Binding
- 44.77
- 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
- 8.740
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.000
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.970
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.740
- 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
- -2.490
- Rat (Acute)
- 2.880
- Rat (Chronic Oral)
- 2.650
- Fathead Minnow
- 4.030
- 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
- 394.610
- Hydration Free Energy
- -10.200
- Log(D) at pH=7.4
- 0.260
- Log(P)
- -
- Log S
- -1.93
- Log(Vapor Pressure)
- -8.34
- Melting Point
- 110.78
- pKa Acid
- 6.41
- pKa Basic
- 3.79
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.9211 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.9141 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8863 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.8772 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8657 |
| Gag-Pol polyprotein | P0C6F2 | POL_HV1LW | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8525 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.8414 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7902 |
| Ascorbate-specific PTS system EIIC component | P39301 | ULAA_ECOLI | Escherichia coli | 3 | 0.7848 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.7830 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.7712 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.7497 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7273 |
| Small heat shock protein StHsp14.0 | Q970D9 | Q970D9_SULTO | Sulfurisphaera tokodaii | 3 | 0.7101 |
| Beta-amylase | P16098 | AMYB_HORVU | Hordeum vulgare | 4 | 0.7073 |
| Nuclear receptor subfamily 5 group A member 2 | O00482 | NR5A2_HUMAN | Homo sapiens | 3 | 0.7009 |