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Apratoxin A
- Family: Monera - Oscillatoriaceae
- Kingdom: Monera
-
Class: Peptide
- Subclass: Cyclic Depsipeptide
| Canonical Smiles | COc1ccc(cc1)C[C@@H]1NC(=O)/C(=C/[C@H]2CSC(=N2)[C@H](C)[C@@H](O)C[C@H](C)C[C@H](OC(=O)[C@H]2N(C(=O)[C@@H](N(C(=O)[C@@H](N(C1=O)C)C)C)[C@H](CC)C)CCC2)C(C)(C)C)/C |
|---|---|
| InChI | InChI=1S/C45H69N5O8S/c1-13-27(3)38-43(55)50-20-14-15-35(50)44(56)58-37(45(7,8)9)22-26(2)21-36(51)29(5)40-46-32(25-59-40)23-28(4)39(52)47-34(24-31-16-18-33(57-12)19-17-31)42(54)48(10)30(6)41(53)49(38)11/h16-19,23,26-27,29-30,32,34-38,51H,13-15,20-22,24-25H2,1-12H3,(H,47,52)/b28-23+/t26-,27-,29+,30-,32-,34-,35-,36-,37-,38-/m0/s1 |
| InChIKey | KXUJXPZXILTXDA-QLUGYXAUSA-N |
| Formula | C45H69N5O8S |
| HBA | 10 |
| HBD | 2 |
| MW | 840.14 |
| Rotatable Bonds | 5 |
| TPSA | 158.15 |
| LogP | 5.28 |
| Number Rings | 4 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 59 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.69 |
| Exact Mass | 839.49 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Moorea producens | Oscillatoriaceae | Monera | 1155739 |
Showing of synonyms
Apratoxin A
Pubchem:
102508446
CPRiL:
73814
SMILES: C12=NC(CS2)C=CC(=O)NC(Cc3ccccc3)C(=O)NCC(=O)NCC(=O)N4C(CCC4)C(=O)OCCCCCC1
Level: 1
Mol. Weight: 840.14 g/mol
SMILES: C12=NC(CS2)C=CC(=O)NCC(=O)NCC(=O)NCC(=O)N3C(CCC3)C(=O)OCCCCCC1
Level: 0
Mol. Weight: 840.14 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 840.14 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.16
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- 72.180
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 10172.71
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.000
- Plasma Protein Binding
- 97.3
- 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
- 7.990
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- -241.180
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.200
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 4.590
- 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
- -18464769.640
- Rat (Acute)
- 3.520
- Rat (Chronic Oral)
- 0.760
- Fathead Minnow
- 23315.870
- 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
- 2072635.290
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 4.260
- Log(P)
- 4.77
- Log S
- -4.24
- Log(Vapor Pressure)
- -68168.53
- Melting Point
- 234.03
- pKa Acid
- -435.25
- pKa Basic
- 6.99
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.9222 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.9155 |
| 3'-5' exoribonuclease Rv2179c | P9WJ73 | EXRBN_MYCTU | Mycobacterium tuberculosis | 3 | 0.9122 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 3 | 0.9109 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | P0AF12 | MTNN_ECOLI | Escherichia coli | 3 | 0.8905 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.8839 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.8808 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8751 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8741 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8614 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8511 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.8477 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8293 |
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.8260 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8246 |
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 3 | 0.8186 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.8164 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8012 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7788 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7615 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.7600 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.7557 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7519 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 3 | 0.7501 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7492 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7473 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7451 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 2 | 0.7400 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7387 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7385 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7384 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7378 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7365 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7361 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7349 |
| Putative snRNP Sm-like protein | Q8ZYG5 | Q8ZYG5_PYRAE | Pyrobaculum aerophilum | 2 | 0.7348 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 2 | 0.7340 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 2 | 0.7337 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7329 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7317 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7316 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7307 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 2 | 0.7305 |
| Cytidine and deoxycytidylate deaminase zinc-binding region | Q82Y41 | Q82Y41_NITEU | Nitrosomonas europaea | 3 | 0.7304 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 2 | 0.7301 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7298 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7289 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7272 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 2 | 0.7261 |
| Protein mono-ADP-ribosyltransferase PARP14 | Q460N5 | PAR14_HUMAN | Homo sapiens | 3 | 0.7254 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7243 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.7223 |
| Gentisate 1,2-dioxygenase | Q67FT0 | Q67FT0_PSESE | Pseudaminobacter salicylatoxidans | 2 | 0.7203 |
| Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 3 | 0.7186 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7182 |
| Flavin reductase like domain-containing protein | Q4UKE8 | Q4UKE8_RICFE | Rickettsia felis | 4 | 0.7179 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7163 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 2 | 0.7151 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7145 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 2 | 0.7122 |
| tRNA-guanine(15) transglycosylase | O58843 | ATGT_PYRHO | Pyrococcus horikoshii | 2 | 0.7111 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7108 |
| Ribosome-inactivating protein 3 | P25891 | RIP3_MAIZE | Zea mays | 2 | 0.7107 |
| Purine nucleoside phosphorylase | Q8I3X4 | Q8I3X4_PLAF7 | Plasmodium falciparum | 2 | 0.7100 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7089 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7071 |
| Focal adhesion kinase 1 | Q05397 | FAK1_HUMAN | Homo sapiens | 2 | 0.7056 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7055 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7053 |
| Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 2 | 0.7052 |
| Plasma membrane ATPase | Q42932 | Q42932_NICPL | Nicotiana plumbaginifolia | 2 | 0.7035 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 2 | 0.7034 |
| Adenine DNA glycosylase | P83847 | MUTY_GEOSE | Geobacillus stearothermophilus | 3 | 0.7029 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7026 |
| Myosin heavy chain kinase A | P42527 | MHCKA_DICDI | Dictyostelium discoideum | 2 | 0.7024 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 2 | 0.7020 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 2 | 0.7008 |