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Arugosin C
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi
- Class: Dibenzoxepin
| Canonical Smiles | CC(=CCc1ccc2c(c1O)C(=O)c1c(O)cc(c3c1C(O2)C(CO3)C(O)(C)C)C)C |
|---|---|
| InChI | InChI=1S/C25H28O6/c1-12(2)6-7-14-8-9-17-19(21(14)27)22(28)18-16(26)10-13(3)23-20(18)24(31-17)15(11-30-23)25(4,5)29/h6,8-10,15,24,26-27,29H,7,11H2,1-5H3 |
| InChIKey | MYJGUMZTENHAAQ-UHFFFAOYSA-N |
| Formula | C25H28O6 |
| HBA | 6 |
| HBD | 3 |
| MW | 424.49 |
| Rotatable Bonds | 3 |
| TPSA | 96.22 |
| LogP | 4.36 |
| Number Rings | 4 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.4 |
| Exact Mass | 424.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Aspergillus falconensis | Trichocomaceae | Fungi | 1810910 |
| 2 | Aspergillus sp | Trichocomaceae | Fungi | 5065 |
Showing of synonyms
Arugosin C
50875-10-0
CHEBI:68860
6,8-dihydroxy-1-(2-hydroxypropan-2-yl)-4-methyl-9-(3-methylbut-2-en-1-yl)-1,12a-dihydrochromeno[4,5-bc][1]benzoxepin-7(2h)-one
1,12a-Dihydro-6,8-dihydroxy-1-(1-hydroxy-1-methylethyl)-4-methyl-9-(3-methylbut-2-enyl)(1)benzopy rano(4,5-bc)(1)benzoxepin-7(2H)-one
1,12a-Dihydro-6,8-dihydroxy-1-(1-hydroxy-1-methylethyl)-4-methyl-9-(3-methylbut-2-enyl)(1)benzopyrano(4,5-bc)(1)benzoxepin-7(2H)-one
7,11-dihydroxy-17-(2-hydroxypropan-2-yl)-13-methyl-6-(3-methylbut-2-enyl)-2,15-dioxatetracyclo[8.7.1.03,8.014,18]octadeca-3(8),4,6,10,12,14(18)-hexaen-9-one
6,8-dihydroxy-1-(2-hydroxypropan-2-yl)-4-methyl-9-(3-methylbut-2-en-1-yl)-1,12a-dihydrochromeno(4,5-bc)(1)benzoxepin-7(2H)-one
7,11-dihydroxy-17-(2-hydroxypropan-2-yl)-13-methyl-6-(3-methylbut-2-enyl)-2,15-dioxatetracyclo(8.7.1.03,8.014,18)octadeca-3(8),4,6,10,12,14(18)-hexaen-9-one
[1]Benzopyrano[4,5-bc][1]benzoxepin-7(2H)-one,1,12a-dihydro-6,8-dihydroxy-1-(1-hydroxy- 1-methylethyl)-4-methyl-9-(3-methyl-2- butenyl)-
FD39J64RWK
UNII-FD39J64RWK
MLS004257379
CHEMBL3092848
SMR003082511
Q15410264
- Kamel R.A, Abdel-Razek A.S, et al. (2020). Isoshamixanthone: a new pyrano xanthone from endophytic Aspergillus sp. ASCLA and absolute configuration of epiisoshamixanthone. Nat Prod Res,2020,34(8),1080-1090. [View] [PubMed]
- El-Kashef D.H, Youssef F.S, et al. (2021). Polyketides from the marine-derived fungus Aspergillus falconensis: In silico and in vitro cytotoxicity studies. Bioorg Med Chem,2021,29,115883. [View] [PubMed]
Pubchem:
191158
Cas:
50875-10-0
Chebi:
68860
Nmrshiftdb2:
70108706
Metabolights:
MTBLC68860
Chembl:
CHEMBL3092848
No compound-protein relationship available.
SMILES: c12c3cccc1OCCC2Oc4c(C3=O)cccc4
Level: 0
Mol. Weight: 424.49 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.06
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.78
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.77
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.18
- Plasma Protein Binding
- 58.83
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- 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
- 6.84
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.1
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.69
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.73
- Micronucleos
- Toxic
- 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
- -29.45
- Rat (Acute)
- 2.34
- Rat (Chronic Oral)
- 2.76
- Fathead Minnow
- 5.04
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 475.65
- Hydration Free Energy
- -5.04
- Log(D) at pH=7.4
- 3.51
- Log(P)
- 6.08
- Log S
- -5.7
- Log(Vapor Pressure)
- -9.09
- Melting Point
- 201.05
- pKa Acid
- 7.07
- pKa Basic
- 6.01
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8646 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8596 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7908 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 2 | 0.7731 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7725 |
| HTH-type transcriptional regulator QacR | P0A0N3 | QACR_STAAM | Staphylococcus aureus | 3 | 0.7534 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7530 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7394 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 2 | 0.7365 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.7303 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 2 | 0.7132 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 4 | 0.7072 |
| Calmodulin | P62157 | CALM_BOVIN | Bos taurus | 3 | 0.7070 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7003 |