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Quinolactacin A1
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi
-
Class: Alkaloid
- Subclass: Quinolone Alkaloid
| Canonical Smiles | CC[C@@H]([C@H]1NC(=O)c2c1n(C)c1c(c2=O)cccc1)C |
|---|---|
| InChI | InChI=1S/C16H18N2O2/c1-4-9(2)13-14-12(16(20)17-13)15(19)10-7-5-6-8-11(10)18(14)3/h5-9,13H,4H2,1-3H3,(H,17,20)/t9-,13+/m0/s1 |
| InChIKey | FLHQAMWKNPOTDV-TVQRCGJNSA-N |
| Formula | C16H18N2O2 |
| HBA | 3 |
| HBD | 1 |
| MW | 270.33 |
| Rotatable Bonds | 2 |
| TPSA | 51.1 |
| LogP | 2.37 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.38 |
| Exact Mass | 270.14 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Penicillium simplicissimum | Trichocomaceae | Fungi | 69488 |
Showing of synonyms
Quinolactacin A1
(3R)-3-[(2S)-butan-2-yl]-4-methyl-2,3-dihydropyrrolo[3,4-b]quinoline-1,9-dione
(3R)-3-((2S)-butan-2-yl)-4-methyl-2,3-dihydropyrrolo(3,4-b)quinoline-1,9-dione
386211-68-3
(+)-Quinolactacin A1
815576-68-2
(3R)-2,3-dihydro-4-methyl-3-[(1S)-1-methylpropyl]-1H-pyrrolo[3,4-b]quinoline-1,9(4H)-dione
HY-N7480A
DA-77300
CS-0136107
- Ebada S, Ebrahim W. (2020). Quinoisobutyride A, an acyclic antibacterial tetrapeptide incorporating an unprecedented heterocyclic amino acid residue from the hypersaline lakederived fungus Penicillium simplicissimum strain WSH17. Phytochemistry Letters, 2020,36,95–94. [View]
No compound-protein relationship available.
SMILES: O=C1NCc(c12)[nH]c3c(c2=O)cccc3
Level: 0
Mol. Weight: 270.33 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.62
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.36
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.24
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.79
- Plasma Protein Binding
- 62.78
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.36
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.56
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.22
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 4.05
- Micronucleos
- Toxic
- NR-AhR
- Safe
- 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
- 1.83
- Rat (Acute)
- 2.96
- Rat (Chronic Oral)
- 1.73
- Fathead Minnow
- 4.04
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 401.58
- Hydration Free Energy
- -11.9
- Log(D) at pH=7.4
- 1.54
- Log(P)
- 2.37
- Log S
- -3.61
- Log(Vapor Pressure)
- -6.96
- Melting Point
- 200.7
- pKa Acid
- 6.3
- pKa Basic
- 7.07
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8905 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8688 |
| D(3) dopamine receptor | P35462 | DRD3_HUMAN | Homo sapiens | 3 | 0.8116 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.8057 |
| Scytalone dehydratase | P56221 | SCYD_MAGO7 | Pyricularia oryzae | 4 | 0.7954 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7861 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7793 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7765 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7744 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7742 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7680 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7674 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7670 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7597 |
| 17-beta-hydroxysteroid dehydrogenase 14 | Q9BPX1 | DHB14_HUMAN | Homo sapiens | 2 | 0.7564 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.7504 |
| Scytalone dehydratase | P56221 | SCYD_MAGO7 | Pyricularia oryzae | 4 | 0.7491 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 2 | 0.7474 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7416 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7380 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 4 | 0.7358 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7353 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7252 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7240 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7182 |
| 3'-5' exoribonuclease Rv2179c | P9WJ73 | EXRBN_MYCTU | Mycobacterium tuberculosis | 3 | 0.7132 |
| Cytochrome P450 | S6BVH1 | S6BVH1_RHOER | Rhodococcus erythropolis | 3 | 0.7082 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7064 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 2 | 0.7048 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7046 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7039 |
| Prostaglandin F2a synthase | Q8I6L9 | Q8I6L9_TRYCR | Trypanosoma cruzi | 2 | 0.7033 |
| Histone deacetylase 8 | Q9BY41 | HDAC8_HUMAN | Homo sapiens | 2 | 0.7031 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 2 | 0.7023 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 2 | 0.7013 |