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Aniduquinolone A
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi
-
Class: Alkaloid
- Subclass: Quinoline Alkaloid
| Canonical Smiles | CO[C@@H]1C(=O)Nc2c([C@@]1(O)c1ccccc1)c(O)c(cc2)/C=C/[C@@]1(C)CC[C@@H](O1)C(=C)C |
|---|---|
| InChI | InChI=1S/C26H29NO5/c1-16(2)20-13-15-25(3,32-20)14-12-17-10-11-19-21(22(17)28)26(30,18-8-6-5-7-9-18)23(31-4)24(29)27-19/h5-12,14,20,23,28,30H,1,13,15H2,2-4H3,(H,27,29)/b14-12+/t20-,23-,25+,26+/m1/s1 |
| InChIKey | MXZQODLZZPOLIG-PECOPZJOSA-N |
| Formula | C26H29NO5 |
| HBA | 5 |
| HBD | 3 |
| MW | 435.52 |
| Rotatable Bonds | 5 |
| TPSA | 88.02 |
| LogP | 4.12 |
| Number Rings | 4 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 32 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.35 |
| Exact Mass | 435.2 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Aspergillus versicolor | Trichocomaceae | Fungi | 46472 |
Showing of synonyms
Aniduquinolone A
(3S,4S)-4,5-dihydroxy-3-methoxy-6-[(E)-2-[(2R,5R)-2-methyl-5-prop-1-en-2-yloxolan-2-yl]ethenyl]-4-phenyl-1,3-dihydroquinolin-2-one
(3S,4S)-4,5-dihydroxy-3-methoxy-6-((E)-2-((2R,5R)-2-methyl-5-prop-1-en-2-yloxolan-2-yl)ethenyl)-4-phenyl-1,3-dihydroquinolin-2-one
CHEMBL2431780
CHEBI:214865
- Ebada S, Ebrahim W. (2020). A new antibacterial quinolone derivative from the endophytic fungus Aspergillus versicolor strain Eich.5.2.2. South African Journal of Botany,2020,134,151-155. [View]
No compound-protein relationship available.
SMILES: O1CCCC1C=Cc(c2)ccc(c23)NC(=O)CC3c4ccccc4
Level: 2
Mol. Weight: 435.52 g/mol
SMILES: O1CCCC1C=Cc(c2)ccc(c23)NC(=O)CC3
Level: 1
Mol. Weight: 435.52 g/mol
SMILES: c1cccc(c12)NC(=O)CC2c3ccccc3
Level: 1
Mol. Weight: 435.52 g/mol
SMILES: C1CC(=O)Nc(c12)cccc2
Level: 0
Mol. Weight: 435.52 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 435.52 g/mol
SMILES: C1CCOC1
Level: 0
Mol. Weight: 435.52 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.93
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.830
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.61
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.200
- Plasma Protein Binding
- 98.63
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.050
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.540
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.290
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.090
- 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
- Safe
- T. Pyriformis
- -90.890
- Rat (Acute)
- 2.910
- Rat (Chronic Oral)
- 2.790
- Fathead Minnow
- 4.750
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 457.350
- Hydration Free Energy
- -3.130
- Log(D) at pH=7.4
- 3.180
- Log(P)
- 4.33
- Log S
- -4.5
- Log(Vapor Pressure)
- -9.75
- Melting Point
- 182.36
- pKa Acid
- 7.03
- pKa Basic
- 5.8
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.9065 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 4 | 0.9009 |
| Aurora kinase B-A | Q6DE08 | AUKBA_XENLA | Xenopus laevis | 4 | 0.8722 |
| Chloramphenicol 3-O phosphotransferase | Q56148 | CPT_STRVP | Streptomyces venezuelae | 3 | 0.8691 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.8670 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8572 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.8418 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.8307 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.8105 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7910 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 4 | 0.7865 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 4 | 0.7864 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7827 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7802 |
| Streptogramin A acetyltransferase | P50870 | VATD_ENTFC | Enterococcus faecium | 3 | 0.7801 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.7795 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7674 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7649 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7643 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 4 | 0.7630 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7627 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7586 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7575 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7558 |
| Cytochrome P450 2C5 | P00179 | CP2C5_RABIT | Oryctolagus cuniculus | 3 | 0.7548 |
| High affinity nerve growth factor receptor | P04629 | NTRK1_HUMAN | Homo sapiens | 3 | 0.7531 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7530 |
| Chloramphenicol 3-O phosphotransferase | Q56148 | CPT_STRVP | Streptomyces venezuelae | 3 | 0.7509 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7477 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7464 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7448 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.7416 |
| Plasmid segregation protein ParM | P11904 | PARM_ECOLX | Escherichia coli | 3 | 0.7372 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7349 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7339 |
| Nucleoside diphosphate kinase | Q5UQL3 | NDK_MIMIV | Acanthamoeba polyphaga mimivirus | 2 | 0.7302 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7299 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7295 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7291 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7280 |
| Camphor 5-monooxygenase | P00183 | CPXA_PSEPU | Pseudomonas putida | 3 | 0.7267 |
| Acetyl-CoA carboxylase | Q00955 | ACAC_YEAST | Saccharomyces cerevisiae | 3 | 0.7254 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7254 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 2 | 0.7216 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7204 |
| GMP reductase | Q81JJ9 | GUAC_BACAN | Bacillus anthracis | 2 | 0.7181 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 4 | 0.7152 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7137 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7137 |
| E3 ubiquitin-protein ligase XIAP | P98170 | XIAP_HUMAN | Homo sapiens | 3 | 0.7136 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7121 |
| Pteridine reductase 1 | Q01782 | PTR1_LEIMA | Leishmania major | 3 | 0.7109 |
| Chloramphenicol 3-O phosphotransferase | Q56148 | CPT_STRVP | Streptomyces venezuelae | 3 | 0.7095 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7071 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7055 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7052 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7035 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7029 |