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Preussilide E
- Family: Fungi - Sporormiaceae
- Kingdom: Fungi
-
Class: Polyketide
- Subclass: Bicyclic Polyketide
| Canonical Smiles | COC(=O)/C=C/C(=C/C(=C/[C@H]1C(=C(C)C=C2[C@@H]1[C@H](C)C(=O)[C@@H](C2)C)C[C@@H](O)C)/C)/C |
|---|---|
| InChI | InChI=1S/C26H36O4/c1-15(8-9-24(28)30-7)10-16(2)11-23-22(14-19(5)27)17(3)12-21-13-18(4)26(29)20(6)25(21)23/h8-12,18-20,23,25,27H,13-14H2,1-7H3/b9-8+,15-10+,16-11+/t18-,19+,20+,23+,25+/m1/s1 |
| InChIKey | CJDQRZHRJWJAGG-OXEMTIHYSA-N |
| Formula | C26H36O4 |
| HBA | 4 |
| HBD | 1 |
| MW | 412.57 |
| Rotatable Bonds | 6 |
| TPSA | 63.6 |
| LogP | 5.11 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.54 |
| Exact Mass | 412.26 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Preussia similis | Sporormiaceae | Fungi | 269685 |
Showing of synonyms
Preussilide E
Methyl (2E,4E,6E)-7-[(1R,6R,8S,8aS)-2-[(2S)-2-hydroxypropyl]-3,6,8-trimethyl-7-oxo-5,6,8,8a-tetrahydro-1H-naphthalen-1-yl]-4,6-dimethylhepta-2,4,6-trienoate
Methyl (2E,4E,6E)-7-((1R,6R,8S,8aS)-2-((2S)-2-hydroxypropyl)-3,6,8-trimethyl-7-oxo-5,6,8,8a-tetrahydro-1H-naphthalen-1-yl)-4,6-dimethylhepta-2,4,6-trienoate
Preubetailide E
CHEMBL4129629
CHEBI:207499
No compound-protein relationship available.
SMILES: C1CC(=O)CC(C1=2)CC=CC2
Level: 0
Mol. Weight: 412.57 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.79
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.650
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.08
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.320
- Plasma Protein Binding
- 92.75
- 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
- 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
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 3.400
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.600
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.040
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.670
- Micronucleos
- Safe
- 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
- Toxic
- T. Pyriformis
- -12.250
- Rat (Acute)
- 3.040
- Rat (Chronic Oral)
- 2.290
- Fathead Minnow
- 5.330
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 444.970
- Hydration Free Energy
- -4.440
- Log(D) at pH=7.4
- 3.860
- Log(P)
- 4.49
- Log S
- -5.61
- Log(Vapor Pressure)
- -6.84
- Melting Point
- 151.12
- pKa Acid
- 10.76
- pKa Basic
- 4.04
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.9469 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.9465 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9230 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.9156 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8790 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P50172 | DHI1_MOUSE | Mus musculus | 3 | 0.8750 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 3 | 0.8714 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8659 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8624 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.8419 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8329 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.8285 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8094 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.8083 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.8005 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7993 |
| Gastrotropin | Q6IMW5 | Q6IMW5_DANRE | Danio rerio | 3 | 0.7849 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.7838 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7778 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7739 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7731 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7725 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7718 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7716 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7702 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7661 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7656 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7631 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 2 | 0.7609 |
| Alcohol dehydrogenase 1C | P00326 | ADH1G_HUMAN | Homo sapiens | 2 | 0.7591 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7590 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7582 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7537 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7531 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7508 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7502 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7499 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7492 |
| Retinol-binding protein 2 | P50120 | RET2_HUMAN | Homo sapiens | 3 | 0.7490 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7483 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7478 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7477 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7477 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7464 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7462 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 2 | 0.7454 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7435 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7432 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7427 |
| Retinaldehyde-binding protein 1 | P12271 | RLBP1_HUMAN | Homo sapiens | 3 | 0.7425 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7406 |
| Retinol-binding protein 4 | P18902 | RET4_BOVIN | Bos taurus | 3 | 0.7400 |
| Epoxide hydrolase | Q41415 | Q41415_SOLTU | Solanum tuberosum | 2 | 0.7400 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7399 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 2 | 0.7392 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 3 | 0.7374 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7367 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7366 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 2 | 0.7343 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7339 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 2 | 0.7318 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7310 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7292 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 3 | 0.7289 |
| Cartilage oligomeric matrix protein | P35444 | COMP_RAT | Rattus norvegicus | 3 | 0.7278 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7276 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 2 | 0.7263 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7262 |
| TamL | D3Y1I2 | D3Y1I2_9ACTN | Streptomyces sp. 307-9 | 2 | 0.7261 |
| Lanosterol 14-alpha-demethylase | Q385E8 | Q385E8_TRYB2 | Trypanosoma brucei brucei | 3 | 0.7259 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7256 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7244 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 2 | 0.7241 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7234 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7233 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7232 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7227 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7223 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7196 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 2 | 0.7185 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7163 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7138 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7135 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7122 |
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 2 | 0.7112 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.7104 |
| Retinol-binding protein 4 | P18902 | RET4_BOVIN | Bos taurus | 3 | 0.7067 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7027 |
| Jasmonoyl--L-amino acid synthetase JAR1 | Q9SKE2 | JAR1_ARATH | Arabidopsis thaliana | 3 | 0.7013 |