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Fusarubin
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi
-
Class: Quinone
- Subclass: Naphthoquinone
| Canonical Smiles | COC1=CC(=O)c2c(C1=O)c(O)c1c(c2O)COC(C1)(C)O |
|---|---|
| InChI | InChI=1S/C15H14O7/c1-15(20)4-6-7(5-22-15)13(18)10-8(16)3-9(21-2)14(19)11(10)12(6)17/h3,17-18,20H,4-5H2,1-2H3 |
| InChIKey | FKJXMYJPOKQPSS-UHFFFAOYSA-N |
| Formula | C15H14O7 |
| HBA | 7 |
| HBD | 3 |
| MW | 306.27 |
| Rotatable Bonds | 1 |
| TPSA | 113.29 |
| LogP | 0.79 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 22 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.33 |
| Exact Mass | 306.07 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Aspergillus versicolor | Trichocomaceae | Fungi | 46472 |
Showing of synonyms
Fusarubin
Oxyjavanicin
1702-77-8
UNII-7O2VQR7EHB
7O2VQR7EHB
FUSARUBIN [MI]
NSC 106193
NSC-106193
1,4-Naphthoquinone, 3-acetonyl-5,8-dihydroxy-2-(hydroxymethyl)-6-methoxy-
1H-Naphtho(2,3-c)pyran-5,10-dione, 3,4-dihydro-3,6,9-trihydroxy-7-methoxy-3-methyl-
5,8-dihydroxy-2-(hydroxymethyl)-6-methoxy-3-(2-oxopropyl)-1,4-naphthalenedione
1,4-NAPHTHALENEDIONE, 5,8-DIHYDROXY-2-(HYDROXYMETHYL)-6-METHOXY-3-(2-OXOPROPYL)-
1H-Naphtho[2,3-c]pyran-5,10-dione, 3,4-dihydro-3,6,9-trihydroxy-7-methoxy-3-methyl-
3,4-DIHYDRO-3,6,9-TRIHYDROXY-7-METHOXY-3-METHYL-1H-NAPHTHO(2,3-C)PYRAN-5,10-DIONE
3,4-Dihydro-3,6,9-trihydroxy-7-methoxy-3-methyl-1H-naphtho[2,3-c]pyran-5,10-dione
3-ACETONYL-5,8-DIHYDROXY-2-(HYDROXYMETHYL)-6-METHOXY-1,4-NAPHTHOQUINONE
1,4-Naphthoquinone, 3-acetonyl-5,8-dihydroxy-2-(hydroxymethyl)-6-methoxy-(8CI)
1H-Naphtho(2,3-c)pyran-5,10-dione, 3,4-dihydro-3,6,9-trihydroxy-7-methoxy-3-methyl-(9CI)
Fkjxmyjpokqpss-uhfffaoysa-n
NSC106193
3,5,10-trihydroxy-7-methoxy-3-methyl-1,4-dihydrobenzo[g]isochromene-6,9-dione
SCHEMBL2136657
CHEMBL1224816
GLXC-22312
NCI60_000144
1, 3-acetonyl-5,8-dihydroxy-2-(hydroxymethyl)-6-methoxy-
1H-Naphtho[2,10-dione, 3,4-dihydro-3,6,9-trihydroxy-7-methoxy-3-methyl-
3,5,10-Trihydroxy-7-methoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromene-6,9-dione #
3,6,9-trihydroxy-7-methoxy-3-methyl-1,4-dihydrobenzo[g]isochromene-5,10-dione
- Abdelwahab M, Kurtán T, et al. (2018). Induced secondary metabolites from the endophytic fungus Aspergillus versicolor through bacterial co-culture and OSMAC approaches. Tetrahedron Letters,2018,59(27),2647-2652. [View]
CPRiL:
112177
SMILES: O=C1C=CC(=O)c(c12)cc3c(c2)CCOC3
Level: 0
Mol. Weight: 306.27 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.07
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.790
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.0
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.490
- Plasma Protein Binding
- 28.42
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- 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
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 9.290
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.240
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.490
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.810
- 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
- 4.220
- Rat (Acute)
- 2.490
- Rat (Chronic Oral)
- 2.980
- Fathead Minnow
- 4.030
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 417.520
- Hydration Free Energy
- -10.870
- Log(D) at pH=7.4
- 0.890
- Log(P)
- 1.22
- Log S
- -3.42
- Log(Vapor Pressure)
- -6.49
- Melting Point
- 207.18
- pKa Acid
- 5.55
- pKa Basic
- 4.67
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.8954 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8917 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8736 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8551 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 3 | 0.8503 |
| DNA polymerase III subunit epsilon | P03007 | DPO3E_ECOLI | Escherichia coli | 3 | 0.8483 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.8373 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7994 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7959 |
| Sepiapterin reductase | Q64105 | SPRE_MOUSE | Mus musculus | 4 | 0.7904 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 4 | 0.7764 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7748 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7688 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.7554 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 4 | 0.7493 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7473 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 4 | 0.7453 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7433 |
| Nucleoside diphosphate kinase A 2 | P52175 | NDKA2_BOVIN | Bos taurus | 3 | 0.7370 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 3 | 0.7344 |
| Thymidylate synthase | P07607 | TYSY_MOUSE | Mus musculus | 4 | 0.7308 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7263 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7208 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 2 | 0.7206 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7174 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 2 | 0.7148 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7105 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.7102 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7089 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7088 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7052 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7035 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 2 | 0.7025 |