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Quinoisobutyride A
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi
-
Class: Peptide
- Subclass: Acyclic Tetrapeptide
| Canonical Smiles | Oc1ccc(cc1)C[C@H](C(=O)N1CCC[C@@H]1C(=O)N[C@H](C(=O)O)Cc1ccccc1)NC(=O)C(n1c2[C@H](NC(=O)c2c(=O)c2c1cccc2)C(C)C)(C)C |
|---|---|
| InChI | InChI=1S/C41H45N5O8/c1-23(2)33-34-32(37(50)44-33)35(48)27-13-8-9-14-30(27)46(34)41(3,4)40(54)43-28(21-25-16-18-26(47)19-17-25)38(51)45-20-10-15-31(45)36(49)42-29(39(52)53)22-24-11-6-5-7-12-24/h5-9,11-14,16-19,23,28-29,31,33,47H,10,15,20-22H2,1-4H3,(H,42,49)(H,43,54)(H,44,50)(H,52,53)/t28-,29+,31-,33-/m1/s1 |
| InChIKey | FQAVXIODTPIIRT-RCANGYALSA-N |
| Formula | C41H45N5O8 |
| HBA | 8 |
| HBD | 5 |
| MW | 735.84 |
| Rotatable Bonds | 12 |
| TPSA | 187.14 |
| LogP | 3.41 |
| Number Rings | 6 |
| Number Aromatic Rings | 4 |
| Heavy Atom Count | 54 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.37 |
| Exact Mass | 735.33 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Penicillium simplicissimum | Trichocomaceae | Fungi | 69488 |
Showing of synonyms
Quinoisobutyride A
(2S)-2-[[(2R)-1-[(2R)-2-[[2-[(3R)-1,9-dioxo-3-propan-2-yl-2,3-dihydropyrrolo[3,4-b]quinolin-4-yl]-2-methylpropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoic acid
(2S)-2-(((2R)-1-((2R)-2-((2-((3R)-1,9-dioxo-3-propan-2-yl-2,3-dihydropyrrolo(3,4-b)quinolin-4-yl)-2-methylpropanoyl)amino)-3-(4-hydroxyphenyl)propanoyl)pyrrolidine-2-carbonyl)amino)-3-phenylpropanoic acid
CHEBI:214815
- 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: c1cccc(c2=O)c1n(c(c23)CNC3=O)CC(=O)NC(Cc4ccccc4)C(=O)N5CCCC5C(=O)NCCc6ccccc6
Level: 3
Mol. Weight: 735.84 g/mol
SMILES: c1ccccc1CC(C(=O)N2CCCC2)NC(=O)Cn(c(c34)CNC3=O)c5c(c4=O)cccc5
Level: 2
Mol. Weight: 735.84 g/mol
SMILES: c1cccc(c2=O)c1n(c(c23)CNC3=O)CC(=O)NCC(=O)N4CCCC4C(=O)NCCc5ccccc5
Level: 2
Mol. Weight: 735.84 g/mol
SMILES: c1ccccc1CCC(=O)N2CCCC2C(=O)NCCc3ccccc3
Level: 2
Mol. Weight: 735.84 g/mol
SMILES: c1cccc(c2=O)c1n(c(c23)CNC3=O)CC(=O)NCC(=O)N4CCCC4
Level: 1
Mol. Weight: 735.84 g/mol
SMILES: c1cccc(c2=O)c1n(c(c23)CNC3=O)CC(=O)NCCc4ccccc4
Level: 1
Mol. Weight: 735.84 g/mol
SMILES: N1CCCC1C(=O)NCCc2ccccc2
Level: 1
Mol. Weight: 735.84 g/mol
SMILES: C1CCCN1C(=O)CCc2ccccc2
Level: 1
Mol. Weight: 735.84 g/mol
SMILES: O=C1NCc(c12)[nH]c3c(c2=O)cccc3
Level: 0
Mol. Weight: 735.84 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 735.84 g/mol
SMILES: C1CCNC1
Level: 0
Mol. Weight: 735.84 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.93
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- 13.230
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 2519.05
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.260
- Plasma Protein Binding
- 105.0
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- 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
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 3.920
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -62.810
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.040
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.210
- 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
- -4572925.150
- Rat (Acute)
- 3.050
- Rat (Chronic Oral)
- 2.440
- Fathead Minnow
- 5778.380
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 508643.150
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 0.950
- Log(P)
- 2.33
- Log S
- -4.39
- Log(Vapor Pressure)
- -16727.52
- Melting Point
- 232.55
- pKa Acid
- -86.64
- pKa Basic
- 6.82
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Polymerase acidic protein | P03433 | PA_I34A1 | Influenza A virus | 3 | 0.9271 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.9113 |
| 3'-5' exoribonuclease Rv2179c | P9WJ73 | EXRBN_MYCTU | Mycobacterium tuberculosis | 3 | 0.9052 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.9040 |
| Phenylpyruvate C(3)-methyltransferase | Q643C8 | MPPJ_STRHY | Streptomyces hygroscopicus | 3 | 0.9007 |
| Carnitine O-palmitoyltransferase 2, mitochondrial | P18886 | CPT2_RAT | Rattus norvegicus | 3 | 0.8953 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 3 | 0.8864 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.8827 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.8786 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.8739 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8725 |
| VioE domain-containing protein | Q7NSZ5 | Q7NSZ5_CHRVO | Chromobacterium violaceum | 3 | 0.8707 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.8594 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.8558 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8531 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8471 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.8444 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8414 |
| Protease | O38896 | O38896_9HIV1 | Human immunodeficiency virus 1 | 3 | 0.8364 |
| Snake venom metalloproteinase atrolysin-D | P15167 | VM1AD_CROAT | Crotalus atrox | 3 | 0.8316 |
| 1-deoxy-D-xylulose 5-phosphate reductoisomerase | P45568 | DXR_ECOLI | Escherichia coli | 3 | 0.8311 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 3 | 0.8296 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8218 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8147 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7992 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.7991 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7990 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7977 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7962 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7912 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.7861 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7746 |
| Pyridoxal kinase | O00764 | PDXK_HUMAN | Homo sapiens | 3 | 0.7689 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7681 |
| Stimulator of interferon genes protein | Q86WV6 | STING_HUMAN | Homo sapiens | 3 | 0.7667 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7654 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.7647 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7633 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 3 | 0.7625 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7608 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7595 |
| Chloramphenicol 3-O phosphotransferase | Q56148 | CPT_STRVP | Streptomyces venezuelae | 3 | 0.7566 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7543 |
| Cytidine and deoxycytidylate deaminase zinc-binding region | Q82Y41 | Q82Y41_NITEU | Nitrosomonas europaea | 3 | 0.7534 |
| Deacetoxycephalosporin C synthase | P18548 | CEFE_STRCL | Streptomyces clavuligerus | 3 | 0.7524 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.7518 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7488 |
| Nickel-binding periplasmic protein | P33590 | NIKA_ECOLI | Escherichia coli | 3 | 0.7475 |
| Agglutinin alpha chain | P18674 | LECA_MACPO | Maclura pomifera | 3 | 0.7459 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7458 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7451 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 2 | 0.7396 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.7393 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7372 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7366 |
| Glutamate receptor ionotropic, kainate 1 | P22756 | GRIK1_RAT | Rattus norvegicus | 2 | 0.7362 |
| Cytosol aminopeptidase | P00727 | AMPL_BOVIN | Bos taurus | 2 | 0.7329 |
| UTP-monosaccharide-1-phosphate uridylyltransferase | D3G6S4 | D3G6S4_LEIMA | Leishmania major | 3 | 0.7327 |
| Methylmalonyl-CoA decarboxylase | P52045 | SCPB_ECOLI | Escherichia coli | 3 | 0.7301 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 3 | 0.7294 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7253 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7252 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.7235 |
| Angiotensin-converting enzyme 2 | Q9BYF1 | ACE2_HUMAN | Homo sapiens | 2 | 0.7222 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7202 |
| Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7201 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7194 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7186 |
| Gene 2 protein | Q716H3 | Q716H3_BPSFV | Shigella phage Sf6 | 3 | 0.7157 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7155 |
| 5-formyltetrahydrofolate cyclo-ligase | P75430 | MTHFS_MYCPN | Mycoplasma pneumoniae | 2 | 0.7150 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 3 | 0.7148 |
| Chymotrypsinogen A | P00766 | CTRA_BOVIN | Bos taurus | 3 | 0.7124 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7096 |
| 1-deoxy-D-xylulose 5-phosphate reductoisomerase | P45568 | DXR_ECOLI | Escherichia coli | 2 | 0.7087 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7070 |
| Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7051 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7030 |
| Ephrin type-B receptor 4 | P54760 | EPHB4_HUMAN | Homo sapiens | 3 | 0.7010 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7004 |