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Apratoxin C
- 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 |
|---|---|
| InChI | InChI=1S/C44H67N5O8S/c1-12-27(5)38-43(54)49-19-13-14-35(49)44(55)57-37(25(2)3)21-26(4)20-36(50)29(7)40-45-32(24-58-40)22-28(6)39(51)46-34(23-31-15-17-33(56-11)18-16-31)42(53)47(9)30(8)41(52)48(38)10/h15-18,22,25-27,29-30,32,34-38,50H,12-14,19-21,23-24H2,1-11H3,(H,46,51)/b28-22+/t26-,27-,29-,30-,32-,34-,35-,36-,37-,38-/m0/s1 |
| InChIKey | OIRVOJCFIYCVDL-ADWUXKIFSA-N |
| Formula | C44H67N5O8S |
| HBA | 10 |
| HBD | 2 |
| MW | 826.11 |
| Rotatable Bonds | 6 |
| TPSA | 158.15 |
| LogP | 4.89 |
| Number Rings | 4 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 58 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.68 |
| Exact Mass | 825.47 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Moorea producens | Oscillatoriaceae | Monera | 1155739 |
Showing of synonyms
Apratoxin C
CHEBI:35216
(2S,3S,5S,7S,10S,16S,19S,22S,25E,27S)-16-[(2S)-butan-2-yl]-3-hydroxy-22-(4-methoxybenzyl)-2,5,17,19,20,25-hexamethyl-7-(propan-2-yl)-8-oxa-29-thia-14,17,20,23,30-pentaazatricyclo[25.2.1.0(10,14)]triaconta-1(30),25-diene-9,15,18,21,24-pentone
7'''.1,4-anhydro(N-{3-[2-(3,7-dihydroxy-5,8-dimethylnonan-2-yl)-4,5-dihydro-1,3-thiazol-4-yl]-2-methylpropenoyl}-O-methyl-L-tyrosyl-N-methyl-L-alanyl-N-methyl-L-isoleucyl-L-proline)
N-((2E)-3-((4S)-2-((1S,2S,4S,6S)-2,6-dihydroxy-1,4,7-trimethyloctyl)-4,5-dihydro-4-thiazolyl)-2-methyl-1-oxo-2-propenyl)-O-methyl-L-tyrosyl-N-methyl-L-alanyl-N-methyl-L-isoleucyl-L-proline (4-16)-lactone
(2S,3S,5S,7S,10S,16S,19S,22S,25E,27S)-16-((2S)-butan-2-yl)-3-hydroxy-22-((4-methoxyphenyl)methyl)-2,5,17,19,20,25-hexamethyl-7-propan-2-yl-8-oxa-29-thia-14,17,20,23,30-pentazatricyclo(25.2.1.010,14)triaconta-1(30),25-diene-9,15,18,21,24-pentone
(2S,3S,5S,7S,10S,16S,19S,22S,25E,27S)-16-((2S)-butan-2-yl)-3-hydroxy-22-(4-methoxybenzyl)-2,5,17,19,20,25-hexamethyl-7-(propan-2-yl)-8-oxa-29-thia-14,17,20,23,30-pentaazatricyclo(25.2.1.0(10,14))triaconta-1(30),25-diene-9,15,18,21,24-pentone
(2S,3S,5S,7S,10S,16S,19S,22S,25E,27S)-16-[(2S)-butan-2-yl]-3-hydroxy-22-[(4-methoxyphenyl)methyl]-2,5,17,19,20,25-hexamethyl-7-propan-2-yl-8-oxa-29-thia-14,17,20,23,30-pentazatricyclo[25.2.1.010,14]triaconta-1(30),25-diene-9,15,18,21,24-pentone
(3S,5S,7S,8S,9Z,12S,13Z,17S,20S,23S)-23-((S)-sec-butyl)-7-hydroxy-3-isopropyl-17-(4-methoxybenzyl)-5,8,14,19,20,22-hexamethyl-3,4,5,6,7,8,11,12,16,17,19,20,22,23,26,27,28,28a-octadecahydro-1H-9,12-(azeno)pyrrolo(2,1-c)(1)oxa(19)thia(4,7,10,13)tetraazacyclohexacosine-1,15,18,21,24-pentaone
(3S,5S,7S,8S,9Z,12S,13Z,17S,20S,23S)-23-((S)-sec-butyl)-7-hydroxy-3-isopropyl-17-(4-methoxybenzyl)-5,8,14,19,20,22-hexamethyl-3,4,5,6,7,8,11,12,16,17,19,20,22,23,26,27,28,28a-octadecahydro-1H-9,12-(azeno)pyrrolo[2,1-c][1]oxa[19]thia[4,7,10,13]tetraazacyclohexacosine-1,15,18,21,24-pentaone
7'''.1,4-anhydro(N-(3-(2-(3,7-dihydroxy-5,8-dimethylnonan-2-yl)-4,5-dihydro-1,3-thiazol-4-yl)-2-methylpropenoyl)-O-methyl-L-tyrosyl-N-methyl-L-alanyl-N-methyl-L-isoleucyl-L-proline)
DTXCID90118683
444885-30-7
Dtxsid80196192
SCHEMBL2464952
AKOS040750551
Q27116441
No compound-protein relationship available.
SMILES: C12=NC(CS2)C=CC(=O)NC(Cc3ccccc3)C(=O)NCC(=O)NCC(=O)N4C(CCC4)C(=O)OCCCCCC1
Level: 1
Mol. Weight: 826.11 g/mol
SMILES: C12=NC(CS2)C=CC(=O)NCC(=O)NCC(=O)NCC(=O)N3C(CCC3)C(=O)OCCCCCC1
Level: 0
Mol. Weight: 826.11 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 826.11 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.23
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- 54.570
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 7871.59
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.000
- Plasma Protein Binding
- 94.19
- 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
- 8.170
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- -188.300
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.190
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 4.850
- 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
- -14288240.670
- Rat (Acute)
- 3.530
- Rat (Chronic Oral)
- 0.790
- Fathead Minnow
- 18043.760
- 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
- 1602902.690
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 4.180
- Log(P)
- 4.27
- Log S
- -4.03
- Log(Vapor Pressure)
- -52702.68
- Melting Point
- 214.16
- pKa Acid
- -326.81
- pKa Basic
- 6.75
| 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 | 0.9578 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.9503 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.9122 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.8907 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.8724 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8328 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.8243 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8109 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7945 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7849 |
| Proton-gated ion channel | Q7NDN8 | GLIC_GLOVI | Gloeobacter violaceus | 3 | 0.7806 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7705 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7616 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7563 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7558 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 3 | 0.7555 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7549 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7541 |
| 3'-5' exoribonuclease Rv2179c | P9WJ73 | EXRBN_MYCTU | Mycobacterium tuberculosis | 3 | 0.7505 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7484 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 2 | 0.7482 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7443 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7428 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7400 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7394 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7387 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7384 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7379 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7371 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7363 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7360 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 2 | 0.7333 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 2 | 0.7328 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7315 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7311 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7305 |
| Gentisate 1,2-dioxygenase | Q67FT0 | Q67FT0_PSESE | Pseudaminobacter salicylatoxidans | 2 | 0.7300 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7299 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 2 | 0.7293 |
| Ribosome-inactivating protein 3 | P25891 | RIP3_MAIZE | Zea mays | 2 | 0.7289 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 2 | 0.7277 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7243 |
| Plasma membrane ATPase | Q42932 | Q42932_NICPL | Nicotiana plumbaginifolia | 2 | 0.7242 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7233 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7233 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 3 | 0.7221 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7220 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 2 | 0.7213 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7206 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7203 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7184 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7146 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7139 |
| Serine/threonine-protein kinase toxin HipA | P23874 | HIPA_ECOLI | Escherichia coli | 2 | 0.7115 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7105 |
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 3 | 0.7086 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7081 |
| Focal adhesion kinase 1 | Q05397 | FAK1_HUMAN | Homo sapiens | 2 | 0.7077 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7075 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 2 | 0.7059 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 2 | 0.7055 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 2 | 0.7053 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7022 |