(22S)-aniduquinolone A - Compound Card

(22S)-aniduquinolone A

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(22S)-aniduquinolone A

Structure
Zoomed Structure
  • 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-/m0/s1
InChIKey MXZQODLZZPOLIG-LXCJKHGGSA-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

  • 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]
Pubchem: 134222700

No compound-protein relationship available.

Structure

SMILES: O1CCCC1C=Cc(c2)ccc(c23)NC(=O)CC3c4ccccc4

Level: 2

Mol. Weight: 435.52 g/mol

Structure

SMILES: O1CCCC1C=Cc(c2)ccc(c23)NC(=O)CC3

Level: 1

Mol. Weight: 435.52 g/mol

Structure

SMILES: c1cccc(c12)NC(=O)CC2c3ccccc3

Level: 1

Mol. Weight: 435.52 g/mol

Structure

SMILES: C1CC(=O)Nc(c12)cccc2

Level: 0

Mol. Weight: 435.52 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 435.52 g/mol

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 435.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.92
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
-1.6

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.200
Plasma Protein Binding
99.03
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
7.020
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
0.300
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
-90.760
Rat (Acute)
2.910
Rat (Chronic Oral)
2.790
Fathead Minnow
4.790
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
456.830
Hydration Free Energy
-3.120
Log(D) at pH=7.4
3.210
Log(P)
4.24
Log S
-4.49
Log(Vapor Pressure)
-9.78
Melting Point
186.29
pKa Acid
7.03
pKa Basic
5.79
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.9047
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 4 0.9012
Aurora kinase B-A Q6DE08 AUKBA_XENLA Xenopus laevis 4 0.8691
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8631
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8568
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8196
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.8136
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8048
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 4 0.7867
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 4 0.7865
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7862
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7839
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7825
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7798
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7785
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7742
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7709
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7684
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7659
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7648
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7636
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7622
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7604
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7600
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7565
High affinity nerve growth factor receptor P04629 NTRK1_HUMAN Homo sapiens 3 0.7538
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7534
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7530
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7530
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7487
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7423
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7422
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7380
Plasmid segregation protein ParM P11904 PARM_ECOLX Escherichia coli 3 0.7369
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7363
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7338
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7306
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7301
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7284
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7253
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 3 0.7240
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7212
E3 ubiquitin-protein ligase XIAP P98170 XIAP_HUMAN Homo sapiens 3 0.7207
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7189
GMP reductase Q81JJ9 GUAC_BACAN Bacillus anthracis 2 0.7188
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7179
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7168
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7166
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7163
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7146
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7132
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7114
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7079
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 2 0.7076
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7059
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7058
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7018
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7016
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7015
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7008

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