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Preussilide D
- Family: Fungi - Sporormiaceae
- Kingdom: Fungi
-
Class: Polyketide
- Subclass: Bicyclic Polyketide
| Canonical Smiles | CC(=O)CC1=C(C)C=C2[C@@H]([C@H]1/C=C(/C=C(\C=C\C(=O)O)/C)\C)[C@H](C)C(=O)[C@@H](C2)C |
|---|---|
| InChI | InChI=1S/C25H32O4/c1-14(7-8-23(27)28)9-15(2)10-22-21(13-18(5)26)16(3)11-20-12-17(4)25(29)19(6)24(20)22/h7-11,17,19,22,24H,12-13H2,1-6H3,(H,27,28)/b8-7+,14-9-,15-10+/t17-,19+,22+,24+/m1/s1 |
| InChIKey | MSPOBTULOAJOIR-FFGGKKJLSA-N |
| Formula | C25H32O4 |
| HBA | 3 |
| HBD | 1 |
| MW | 396.53 |
| Rotatable Bonds | 6 |
| TPSA | 71.44 |
| LogP | 5.23 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 29 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.48 |
| Exact Mass | 396.23 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Preussia similis | Sporormiaceae | Fungi | 269685 |
Showing of synonyms
Preussilide D
(2E,4Z,6E)-7-[(1R,6R,8S,8aS)-3,6,8-trimethyl-7-oxo-2-(2-oxopropyl)-5,6,8,8a-tetrahydro-1H-naphthalen-1-yl]-4,6-dimethylhepta-2,4,6-trienoic acid
(2E,4Z,6E)-7-((1R,6R,8S,8aS)-3,6,8-trimethyl-7-oxo-2-(2-oxopropyl)-5,6,8,8a-tetrahydro-1H-naphthalen-1-yl)-4,6-dimethylhepta-2,4,6-trienoic acid
Preubetailide D
CHEMBL4127726
CHEBI:207492
No compound-protein relationship available.
SMILES: C1CC(=O)CC(C1=2)CC=CC2
Level: 0
Mol. Weight: 396.53 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.83
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.88
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.37
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.49
- Plasma Protein Binding
- 100.37
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- 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
- 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
- -1.18
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.19
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.54
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.2
- 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
- -6.45
- Rat (Acute)
- 2.66
- Rat (Chronic Oral)
- 2.47
- Fathead Minnow
- 4.82
- 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
- 454.67
- Hydration Free Energy
- -3.69
- Log(D) at pH=7.4
- 1.55
- Log(P)
- 3.71
- Log S
- -4.91
- Log(Vapor Pressure)
- -8.1
- Melting Point
- 194.28
- pKa Acid
- 6.98
- pKa Basic
- 4.29
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.9624 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.9559 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.9524 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9419 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.9242 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9223 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.9081 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9011 |
| Retinol-binding protein 2 | P50120 | RET2_HUMAN | Homo sapiens | 3 | 0.8937 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.8924 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.8855 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.8779 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.8743 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.8726 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.8725 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.8722 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.8531 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8524 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8459 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.8432 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.8381 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.8381 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.8201 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.8018 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7970 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7940 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7937 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7893 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7837 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7792 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 3 | 0.7743 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 2 | 0.7742 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7728 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7702 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7671 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7660 |
| Retinol-binding protein 4 | P18902 | RET4_BOVIN | Bos taurus | 3 | 0.7644 |
| Retinol-binding protein 2 | P06768 | RET2_RAT | Rattus norvegicus | 3 | 0.7640 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7625 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7614 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7601 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7596 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7594 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7591 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7587 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7567 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 3 | 0.7564 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7555 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7554 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7554 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 3 | 0.7551 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7544 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 3 | 0.7513 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 3 | 0.7507 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7503 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7501 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7491 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7483 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7455 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7433 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7427 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7427 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7422 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 3 | 0.7420 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7403 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 2 | 0.7400 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7391 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7380 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7376 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7373 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7367 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7342 |
| Chorismate mutase AroH | P19080 | AROH_BACSU | Bacillus subtilis | 2 | 0.7337 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7318 |
| Alanine aminotransferase | Q9P9M8 | Q9P9M8_9EURY | Pyrococcus furiosus | 2 | 0.7315 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7310 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7307 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7285 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7284 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7266 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 2 | 0.7260 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7243 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7219 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.7218 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7216 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7210 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7197 |
| Muconolactone Delta-isomerase | Q8G9L0 | Q8G9L0_RHOOP | Rhodococcus opacus | 2 | 0.7192 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7190 |
| Aromatase | P11511 | CP19A_HUMAN | Homo sapiens | 3 | 0.7190 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7189 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7179 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7176 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7162 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7154 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7153 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7152 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7151 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7150 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7136 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.7131 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7111 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7108 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7101 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 2 | 0.7081 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7041 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7033 |
| 3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase | P19992 | HSD_STREX | Streptomyces exfoliatus | 2 | 0.7033 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7025 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7022 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7014 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7013 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 2 | 0.7011 |