Apratoxin B - Compound Card

Apratoxin B

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Apratoxin B

Structure
Zoomed Structure
  • Family: Monera - Oscillatoriaceae
  • Kingdom: Monera
  • Class: Peptide
    • Subclass: Cyclic Depsipeptide
Canonical Smiles CC[C@@H]([C@@H]1NC(=O)[C@H](C)N(C)C(=O)[C@H](Cc2ccc(cc2)OC)NC(=O)/C(=C/[C@H]2CSC(=N2)[C@H]([C@H](C[C@@H](C[C@H](OC(=O)[C@H]2N(C1=O)CCC2)C(C)(C)C)C)O)C)/C)C
InChI InChI=1S/C44H67N5O8S/c1-12-26(3)37-42(54)49-19-13-14-34(49)43(55)57-36(44(7,8)9)21-25(2)20-35(50)28(5)40-45-31(24-58-40)22-27(4)38(51)46-33(23-30-15-17-32(56-11)18-16-30)41(53)48(10)29(6)39(52)47-37/h15-18,22,25-26,28-29,31,33-37,50H,12-14,19-21,23-24H2,1-11H3,(H,46,51)(H,47,52)/b27-22+/t25-,26-,28-,29-,31-,33-,34-,35-,36-,37-/m0/s1
InChIKey ZSYPDXOLYNZQGO-RNTANXHRSA-N
Formula C44H67N5O8S
HBA 10
HBD 3
MW 826.11
Rotatable Bonds 5
TPSA 166.94
LogP 4.94
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

  • 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: 6419723
Chebi: 35215
Nmrshiftdb2: 60146610
CPRiL: 337759
Structure

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

Structure

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

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 826.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.18
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
45.79
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
6722.16

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.97
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
6.82
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-162.27
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.03
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.14
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
-12201441.85
Rat (Acute)
3.61
Rat (Chronic Oral)
0.71
Fathead Minnow
15409.61
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
1368227.48
Hydration Free Energy
-2.92
Log(D) at pH=7.4
4.43
Log(P)
4.45
Log S
-4.59
Log(Vapor Pressure)
-44972.58
Melting Point
263.31
pKa Acid
-269.71
pKa Basic
6.12
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 0.9431
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.9209
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.9170
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.8884
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8597
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8439
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8426
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8305
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8262
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8215
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8200
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8056
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8044
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7979
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7611
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7590
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7582
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7562
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7354
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7337
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7326
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7316
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 2 0.7315
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7293
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7274
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7248
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7243
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7241
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7228
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 2 0.7220
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7201
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7198
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7170
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7131
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7129
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7119
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7115
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 2 0.7111
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7110
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 2 0.7061
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 2 0.7047
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7046
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7040
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7033
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7026
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7023
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7017
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7013

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