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Tanacetolide A
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Hydroperoxide
| Canonical Smiles | CCCCCCCCCCCCCCCCC/C=C/[C@@H](C(=O)N[C@@H]([C@H](/C=C/CCCCCCCCCCCCCCCC)O)CO)O |
|---|---|
| InChI | InChI=1S/C42H81NO4/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-41(46)42(47)43-39(38-44)40(45)36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h34-37,39-41,44-46H,3-33,38H2,1-2H3,(H,43,47)/b36-34+,37-35+/t39-,40+,41+/m1/s1 |
| InChIKey | VSOHQMQKYXPZMR-DPOMMMKGSA-N |
| Formula | C42H81NO4 |
| HBA | 4 |
| HBD | 4 |
| MW | 664.11 |
| Rotatable Bonds | 37 |
| TPSA | 89.79 |
| LogP | 11.43 |
| Number Rings | 0 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 47 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.88 |
| Exact Mass | 663.62 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Tanacetum sinaicum | Asteraceae | Plantae | — |
Showing of synonyms
Tanacetolide A
- Hegazy MEF, Hamed AR, et al. (2015). Anti-inflammatory sesquiterpenes from the medicinal herb Tanacetum sinaicum. RSC Advances,2015,5,44895-44901. [View]
No compound-protein relationship available.
No scaffolds available.
Anti-inflammatory
Absorption
- Caco-2 (logPapp)
- -5.29
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.65
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 29.29
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 2.18
- Plasma Protein Binding
- 69.44
- 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
- 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
- Inhibitor
Excretion
- Clearance
- 0.6
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -0.71
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.54
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 4.84
- 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
- -59554.56
- Rat (Acute)
- 2.18
- Rat (Chronic Oral)
- 3.73
- Fathead Minnow
- 91.17
- 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
- 4400.4
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 6.61
- Log(P)
- 15.76
- Log S
- -7.0
- Log(Vapor Pressure)
- -103.63
- Melting Point
- 85.14
- pKa Acid
- 8.78
- pKa Basic
- 4.73
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.9343 |
| Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.9343 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.9302 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.9302 |
| Gag-Pol polyprotein | P0C6F2 | POL_HV1LW | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.9179 |
| Gag-Pol polyprotein | P0C6F2 | POL_HV1LW | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.9179 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.9087 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.9087 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.9037 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.9037 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.9015 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.9015 |
| Glycogenin-1 | P46976 | GLYG_HUMAN | Homo sapiens | 3 | 0.8605 |
| Glycogenin-1 | P46976 | GLYG_HUMAN | Homo sapiens | 3 | 0.8605 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.8556 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.8556 |
| 4-alpha-glucanotransferase | O87172 | MALQ_THETH | Thermus thermophilus | 3 | 0.8514 |
| 4-alpha-glucanotransferase | O87172 | MALQ_THETH | Thermus thermophilus | 3 | 0.8514 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 3 | 0.8420 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 3 | 0.8420 |
| Lactose operon repressor | P03023 | LACI_ECOLI | Escherichia coli | 3 | 0.8419 |
| Lactose operon repressor | P03023 | LACI_ECOLI | Escherichia coli | 3 | 0.8419 |
| Beta-glucosidase | Q8T0W7 | Q8T0W7_9NEOP | Neotermes koshunensis | 3 | 0.8276 |
| Beta-glucosidase | Q8T0W7 | Q8T0W7_9NEOP | Neotermes koshunensis | 3 | 0.8276 |
| Ascorbate-specific PTS system EIIC component | P39301 | ULAA_ECOLI | Escherichia coli | 3 | 0.8239 |
| Ascorbate-specific PTS system EIIC component | P39301 | ULAA_ECOLI | Escherichia coli | 3 | 0.8239 |
| Beta-glucosidase A | Q08638 | BGLA_THEMA | Thermotoga maritima | 3 | 0.8176 |
| Beta-glucosidase A | Q08638 | BGLA_THEMA | Thermotoga maritima | 3 | 0.8176 |
| Beta-glucosidase 1A | Q25BW5 | BGL1A_PHACH | Phanerodontia chrysosporium | 3 | 0.8058 |
| Beta-glucosidase 1A | Q25BW5 | BGL1A_PHACH | Phanerodontia chrysosporium | 3 | 0.8058 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.7870 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.7870 |
| Laminarinase | Q9WXN1 | Q9WXN1_THEMA | Thermotoga maritima | 3 | 0.7673 |
| Laminarinase | Q9WXN1 | Q9WXN1_THEMA | Thermotoga maritima | 3 | 0.7673 |
| Glucosidase II subunit alpha | Q9STC1 | Q9STC1_GRALE | Gracilariopsis lemaneiformis | 3 | 0.7661 |
| Glucosidase II subunit alpha | Q9STC1 | Q9STC1_GRALE | Gracilariopsis lemaneiformis | 3 | 0.7661 |
| Glycogen synthase | P0A6U8 | GLGA_ECOLI | Escherichia coli | 3 | 0.7531 |
| Glycogen synthase | P0A6U8 | GLGA_ECOLI | Escherichia coli | 3 | 0.7531 |
| Procathepsin L | P07711 | CATL1_HUMAN | Homo sapiens | 4 | 0.7364 |
| Procathepsin L | P07711 | CATL1_HUMAN | Homo sapiens | 4 | 0.7364 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 3 | 0.7328 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 3 | 0.7328 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7182 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7182 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 2 | 0.7148 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 2 | 0.7148 |
| Tachylectin-2 | Q27084 | TAL2_TACTR | Tachypleus tridentatus | 3 | 0.7124 |
| Tachylectin-2 | Q27084 | TAL2_TACTR | Tachypleus tridentatus | 3 | 0.7124 |
| Lactose operon repressor | P03023 | LACI_ECOLI | Escherichia coli | 3 | 0.7087 |
| Lactose operon repressor | P03023 | LACI_ECOLI | Escherichia coli | 3 | 0.7087 |
| Iota toxin component Ia | Q46220 | Q46220_CLOPF | Clostridium perfringens | 3 | 0.7065 |
| Iota toxin component Ia | Q46220 | Q46220_CLOPF | Clostridium perfringens | 3 | 0.7065 |