Apratoxin F - Compound Card

Apratoxin F

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Apratoxin F

Structure
Zoomed Structure
  • Family: Monera - Oscillatoriaceae
  • Kingdom: Monera
  • Class: Peptide
    • Subclass: Cyclic Depsipeptide
Canonical Smiles COc1ccc(cc1)C[C@@H]1NC(=O)/C(=C\C2CSC(=N2)[C@@H](C)[C@@H](O)C[C@H](C)C[C@H](OC(=O)[C@@H](N(C(=O)[C@@H](N(C(=O)[C@@H](N(C1=O)C)C)C)[C@H](CC)C)C)C)C(C)(C)C)/C
InChI InChI=1S/C44H69N5O8S/c1-15-26(3)37-42(54)48(12)30(7)43(55)57-36(44(8,9)10)21-25(2)20-35(50)28(5)39-45-32(24-58-39)22-27(4)38(51)46-34(23-31-16-18-33(56-14)19-17-31)41(53)47(11)29(6)40(52)49(37)13/h16-19,22,25-26,28-30,32,34-37,50H,15,20-21,23-24H2,1-14H3,(H,46,51)/b27-22-/t25-,26-,28-,29-,30-,32?,34-,35-,36-,37-/m0/s1
InChIKey BAYCKSGCVUIVNR-MJEAVDSUSA-N
Formula C44H69N5O8S
HBA 10
HBD 2
MW 828.13
Rotatable Bonds 5
TPSA 158.15
LogP 5.13
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 58
Formal Charge 0
Fraction CSP3 0.68
Exact Mass 827.49
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Moorea producens Oscillatoriaceae Monera 1155739

Showing of synonyms

  • Thornburg C.C, Cowley E.S, et al. (2013). Apratoxin H and apratoxin A sulfoxide from the Red Sea cyanobacterium Moorea producens.. Journal of natural products,2013, 76(9), 1781-8. [View] [PubMed]
Pubchem: 139291790

No compound-protein relationship available.

Structure

SMILES: C12=NC(CS2)C=CC(=O)NC(Cc3ccccc3)C(=O)NCC(=O)NCC(=O)NCC(=O)OCCCCCC1

Level: 1

Mol. Weight: 828.13 g/mol

Structure

SMILES: C12=NC(CS2)C=CC(=O)NCC(=O)NCC(=O)NCC(=O)NCC(=O)OCCCCCC1

Level: 0

Mol. Weight: 828.13 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 828.13 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.15
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
23.370
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
3786.23

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.980
Plasma Protein Binding
95.73
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
Non-Inhibitor
CYP 2C19 Substrate
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
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
8.460
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-93.980
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.520
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.530
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
-6873942.270
Rat (Acute)
3.420
Rat (Chronic Oral)
0.810
Fathead Minnow
8685.190
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
768982.150
Hydration Free Energy
-2.920
Log(D) at pH=7.4
3.800
Log(P)
4.82
Log S
-3.8
Log(Vapor Pressure)
-25246.97
Melting Point
219.26
pKa Acid
-136.31
pKa Basic
7.09
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9618
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8813
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8514
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8482
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8336
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8150
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7945
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7921
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7842
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7777
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7655
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7633
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7616
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7598
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7595
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7594
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7518
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7518
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7468
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7412
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7401
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7400
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7388
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7383
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7382
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7379
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7371
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7363
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7357
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 2 0.7355
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7353
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 2 0.7344
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7341
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7314
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7313
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7309
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7306
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7305
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7274
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7274
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7248
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7244
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7244
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7232
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7226
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7223
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 2 0.7221
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 2 0.7218
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7215
Protein kinase C iota type Q62074 KPCI_MOUSE Mus musculus 2 0.7213
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7203
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 2 0.7193
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 2 0.7190
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7185
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7177
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7163
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7153
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7153
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7138
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7130
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7127
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7116
Alanine racemase Q180W0 Q180W0_CLOD6 Clostridioides difficile 2 0.7110
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7108
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7097
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7086
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7085
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase P47229 BPHD_PARXL Paraburkholderia xenovorans 2 0.7083
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 2 0.7079
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 2 0.7078
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7077
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 2 0.7066
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7063
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7054
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7051
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7050
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7048
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7034
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 2 0.7034
Proline iminopeptidase O32449 PIP_SERMA Serratia marcescens 2 0.7033
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7032
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7017
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 2 0.7007
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7003

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