Aflaquinolone H - Compound Card

Aflaquinolone H

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Aflaquinolone H

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Alkaloid
    • Subclass: Dihydroquinolone Alkaloid
Canonical Smiles CO[C@@H]1C(=O)Nc2c([C@@]1(O)c1ccccc1)c(O)c(cc2)/C=C/[C@]1(C)CCC(=O)[C@@](C1)(C)O
InChI InChI=1S/C26H29NO6/c1-24(14-12-19(28)25(2,31)15-24)13-11-16-9-10-18-20(21(16)29)26(32,17-7-5-4-6-8-17)22(33-3)23(30)27-18/h4-11,13,22,29,31-32H,12,14-15H2,1-3H3,(H,27,30)/b13-11+/t22-,24-,25+,26+/m1/s1
InChIKey OYOKDZBQGKJNKC-YKHZTBTGSA-N
Formula C26H29NO6
HBA 6
HBD 4
MW 451.52
Rotatable Bonds 4
TPSA 116.09
LogP 3.12
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 451.2
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus versicolor Trichocomaceae Fungi 46472

Showing of synonyms

  • Ebada S, El-Neketi M, et al. (2018). Cytotoxic secondary metabolites from the endophytic fungus Aspergillus versicolor KU258497. Phytochemistry Letters,2018,24,88–93. [View]
Pubchem: 146683956
Nmrshiftdb2: 70097024

No compound-protein relationship available.

Structure

SMILES: O=C1CCC(CC1)C=Cc(c2)ccc(c23)NC(=O)CC3c4ccccc4

Level: 2

Mol. Weight: 451.52 g/mol

Structure

SMILES: O=C1CCC(CC1)C=Cc(c2)ccc(c23)NC(=O)CC3

Level: 1

Mol. Weight: 451.52 g/mol

Structure

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

Level: 1

Mol. Weight: 451.52 g/mol

Structure

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

Level: 0

Mol. Weight: 451.52 g/mol

Structure

SMILES: O=C1CCCCC1

Level: 0

Mol. Weight: 451.52 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 451.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.840
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.59

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.030
Plasma Protein Binding
98.25
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.610
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.950
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.590
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.220
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
-99.740
Rat (Acute)
2.850
Rat (Chronic Oral)
2.830
Fathead Minnow
4.370
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
467.850
Hydration Free Energy
-2.680
Log(D) at pH=7.4
2.650
Log(P)
2.65
Log S
-4.62
Log(Vapor Pressure)
-9.33
Melting Point
194.93
pKa Acid
7.21
pKa Basic
5.11
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9326
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.9050
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 4 0.9007
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8980
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.8774
Aurora kinase B-A Q6DE08 AUKBA_XENLA Xenopus laevis 4 0.8728
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8704
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.8693
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8654
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8654
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8578
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8425
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8337
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8324
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7970
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7956
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7941
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 4 0.7854
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 4 0.7852
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7849
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7848
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7814
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7766
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7722
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7709
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7703
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7671
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.7586
High affinity nerve growth factor receptor P04629 NTRK1_HUMAN Homo sapiens 3 0.7557
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7557
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7540
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7536
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7531
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7519
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7511
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7469
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7467
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7424
Pyruvate dehydrogenase E1 component P0AFG8 ODP1_ECOLI Escherichia coli 3 0.7423
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 2 0.7420
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7417
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7405
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7404
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7394
E3 ubiquitin-protein ligase XIAP P98170 XIAP_HUMAN Homo sapiens 3 0.7391
Plasmid segregation protein ParM P11904 PARM_ECOLX Escherichia coli 3 0.7371
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7343
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7342
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7318
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7311
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7305
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7294
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7282
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7281
Abscisic acid receptor PYL1 Q8VZS8 PYL1_ARATH Arabidopsis thaliana 2 0.7263
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7241
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7224
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7222
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 2 0.7203
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7191
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7175
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7174
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7169
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7161
GMP reductase Q81JJ9 GUAC_BACAN Bacillus anthracis 2 0.7159
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.7153
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7149
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 4 0.7134
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7131
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 2 0.7130
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7113
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.7110
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7108
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7096
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7080
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7056
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7044
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7007

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