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Apratoxin G
- 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(C)C)C)C)C(C)(C)C)/C |
|---|---|
| InChI | InChI=1S/C43H67N5O8S/c1-24(2)36-41(53)47(12)29(7)42(54)56-35(43(8,9)10)20-25(3)19-34(49)27(5)38-44-31(23-57-38)21-26(4)37(50)45-33(22-30-15-17-32(55-14)18-16-30)40(52)46(11)28(6)39(51)48(36)13/h15-18,21,24-25,27-29,31,33-36,49H,19-20,22-23H2,1-14H3,(H,45,50)/b26-21-/t25-,27-,28-,29-,31?,33-,34-,35-,36-/m0/s1 |
| InChIKey | QYPABEUQMXOENV-NMOSBCMXSA-N |
| Formula | C43H67N5O8S |
| HBA | 10 |
| HBD | 2 |
| MW | 814.1 |
| Rotatable Bonds | 4 |
| TPSA | 158.15 |
| LogP | 4.74 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 57 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.67 |
| Exact Mass | 813.47 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Moorea producens | Oscillatoriaceae | Monera | 1155739 |
Showing of synonyms
Apratoxin G
(2E,6S,9S,12S,15S,18S,20S,22S,23S)-18-tert-butyl-22-hydroxy-6-((4-methoxyphenyl)methyl)-3,8,9,11,14,15,20,23-octamethyl-12-propan-2-yl-17-oxa-25-thia-5,8,11,14,27-pentazabicyclo(22.2.1)heptacosa-2,24(27)-diene-4,7,10,13,16-pentone
(2E,6S,9S,12S,15S,18S,20S,22S,23S)-18-tert-butyl-22-hydroxy-6-[(4-methoxyphenyl)methyl]-3,8,9,11,14,15,20,23-octamethyl-12-propan-2-yl-17-oxa-25-thia-5,8,11,14,27-pentazabicyclo[22.2.1]heptacosa-2,24(27)-diene-4,7,10,13,16-pentone
CHEBI:204586
(2Z,6S,9S,12S,15S,18S,20S,22S,23S)-18-tert-butyl-22-hydroxy-6-[(4-methoxyphenyl)methyl]-3,8,9,11,14,15,20,23-octamethyl-12-propan-2-yl-17-oxa-25-thia-5,8,11,14,27-pentazabicyclo[22.2.1]heptacosa-2,24(27)-diene-4,7,10,13,16-pentone
Pubchem:
139292034
Gnps:
CCMSLIB00000070289
No compound-protein relationship available.
SMILES: C12=NC(CS2)C=CC(=O)NC(Cc3ccccc3)C(=O)NCC(=O)NCC(=O)NCC(=O)OCCCCCC1
Level: 1
Mol. Weight: 814.1 g/mol
SMILES: C12=NC(CS2)C=CC(=O)NCC(=O)NCC(=O)NCC(=O)NCC(=O)OCCCCCC1
Level: 0
Mol. Weight: 814.1 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 814.1 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.08
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- 11.160
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 2184.99
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.910
- Plasma Protein Binding
- 91.9
- 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
- 8.640
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -55.380
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.670
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 4.900
- 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
- -3967594.510
- Rat (Acute)
- 3.460
- Rat (Chronic Oral)
- 0.910
- Fathead Minnow
- 5016.360
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 442230.220
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 3.570
- Log(P)
- 4.49
- Log S
- -3.59
- Log(Vapor Pressure)
- -14487.08
- Melting Point
- 222.01
- pKa Acid
- -60.25
- pKa Basic
- 6.86
| 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 | 0.9334 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.9084 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.8871 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8443 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.8253 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8019 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.8016 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.8009 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 3 | 0.7842 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7615 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7506 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7458 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7451 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7422 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7392 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7390 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7365 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7364 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7358 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 2 | 0.7348 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7323 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7317 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7290 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7278 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7277 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 2 | 0.7257 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 2 | 0.7249 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7243 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7243 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 2 | 0.7229 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 2 | 0.7220 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 2 | 0.7217 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7216 |
| Proton-gated ion channel | Q7NDN8 | GLIC_GLOVI | Gloeobacter violaceus | 2 | 0.7169 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7152 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 2 | 0.7145 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 2 | 0.7140 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 2 | 0.7121 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.7117 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7094 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7088 |
| Myosin heavy chain kinase A | P42527 | MHCKA_DICDI | Dictyostelium discoideum | 2 | 0.7087 |
| 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase | P47229 | BPHD_PARXL | Paraburkholderia xenovorans | 2 | 0.7080 |
| Focal adhesion kinase 1 | Q05397 | FAK1_HUMAN | Homo sapiens | 2 | 0.7065 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7059 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7055 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 2 | 0.7044 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7043 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7040 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 2 | 0.7037 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 2 | 0.7021 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 2 | 0.7020 |