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Oxyskyrin
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi
-
Class: Alkaloid
- Subclass: Cyclic Peptide
| Canonical Smiles | OCc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)cc(c1c1c(O)cc(c2c1C(=O)c1cc(C)cc(c1C2=O)O)O)O |
|---|---|
| InChI | InChI=1S/C30H18O11/c1-9-2-11-19(13(32)3-9)29(40)23-17(36)6-15(34)21(25(23)27(11)38)22-16(35)7-18(37)24-26(22)28(39)12-4-10(8-31)5-14(33)20(12)30(24)41/h2-7,31-37H,8H2,1H3 |
| InChIKey | BTHHWOXILLICEL-UHFFFAOYSA-N |
| Formula | C30H18O11 |
| HBA | 11 |
| HBD | 7 |
| MW | 554.46 |
| Rotatable Bonds | 2 |
| TPSA | 209.89 |
| LogP | 2.94 |
| Number Rings | 6 |
| Number Aromatic Rings | 4 |
| Heavy Atom Count | 41 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.07 |
| Exact Mass | 554.08 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Talaromyces wortmannii | Trichocomaceae | Fungi | 28567 |
Showing of synonyms
Oxyskyrin
23310-12-5
Oxyskyrin, (S)-
DIL81J072H
UNII-DIL81J072H
2,4,5-trihydroxy-7-methyl-1-[2,4,5-trihydroxy-7-(hydroxymethyl)-9,10-dioxoanthracen-1-yl]anthracene-9,10-dione
(1,1'-Bianthracene)-9,9',10,10'-tetrone, 2,2',4,4',5,5'-hexahydroxy-7-(hydroxymethyl)-7'-methyl-, (1S)-
(1S)-2,2',4,4',5,5'-Hexahydroxy-7-(hydroxymethyl)-7'-methyl(1,1'-bianthracene)-9,9',10,10'-tetrone
2,4,5-trihydroxy-7-methyl-1-(2,4,5-trihydroxy-7-(hydroxymethyl)-9,10-dioxoanthracen-1-yl)anthracene-9,10-dione
2,2',4,4',5,5'-Hexahydroxy-7-(hydroxymethyl)-7'-methyl-1,1'-bi(9,10-anthraquinone)
CHEBI:201239
AKOS040735263
Q27896792
- Bara R (2012). Natural Products from Endophytic Fungus Talaromyces wortmannii: Their Structure and mechanism of Actions. PhD Thesis, Institute for Pharmaceutical Biology and Biotechnology, University of Dusseldorf,2012, pp. 1-142.. [View]
No compound-protein relationship available.
SMILES: c1cccc(C2=O)c1C(=O)c(c23)cccc3-c4cccc(c45)C(=O)c6c(C5=O)cccc6
Level: 1
Mol. Weight: 554.46 g/mol
SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3
Level: 0
Mol. Weight: 554.46 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.32
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.21
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 4.27
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.83
- Plasma Protein Binding
- 76.26
- 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
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 9.68
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.4
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.86
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.95
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- 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
- -6161.36
- Rat (Acute)
- 2.45
- Rat (Chronic Oral)
- 4.63
- Fathead Minnow
- 18.16
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 599.17
- Hydration Free Energy
- -3.16
- Log(D) at pH=7.4
- 1.56
- Log(P)
- 5.57
- Log S
- -6.45
- Log(Vapor Pressure)
- -7.69
- Melting Point
- 336.33
- pKa Acid
- 9.78
- pKa Basic
- 0.85
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8649 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8649 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8421 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8421 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.8416 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.8416 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.8215 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.8215 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8135 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8135 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8025 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8025 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 3 | 0.8008 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 3 | 0.8008 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.7937 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.7937 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7896 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7896 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7818 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7818 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.7597 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.7597 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 4 | 0.7562 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 4 | 0.7562 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q4WP27 | Q4WP27_ASPFU | Aspergillus fumigatus | 3 | 0.7494 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q4WP27 | Q4WP27_ASPFU | Aspergillus fumigatus | 3 | 0.7494 |
| Tyrosine-protein kinase SYK | P43405 | KSYK_HUMAN | Homo sapiens | 4 | 0.7423 |
| Tyrosine-protein kinase SYK | P43405 | KSYK_HUMAN | Homo sapiens | 4 | 0.7423 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7238 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7238 |
| 3-hydroxy-3-methylglutaryl-coenzyme A reductase | P04035 | HMDH_HUMAN | Homo sapiens | 3 | 0.7234 |
| 3-hydroxy-3-methylglutaryl-coenzyme A reductase | P04035 | HMDH_HUMAN | Homo sapiens | 3 | 0.7234 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7224 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7224 |
| 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase | Q3JRA0 | ISPF_BURP1 | Burkholderia pseudomallei | 4 | 0.7157 |
| 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase | Q3JRA0 | ISPF_BURP1 | Burkholderia pseudomallei | 4 | 0.7157 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7112 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7112 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7108 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7108 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7106 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7106 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7082 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7082 |
| Beta-lactamase | P00811 | AMPC_ECOLI | Escherichia coli | 4 | 0.7078 |
| Beta-lactamase | P00811 | AMPC_ECOLI | Escherichia coli | 4 | 0.7078 |