Apratoxin H - Compound Card

Apratoxin H

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Apratoxin H

Structure
Zoomed Structure
  • 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)CCCC2)C(C)(C)C)C
InChI InChI=1S/C46H71N5O8S/c1-13-28(3)39-44(56)51-21-15-14-16-36(51)45(57)59-38(46(7,8)9)23-27(2)22-37(52)30(5)41-47-33(26-60-41)24-29(4)40(53)48-35(25-32-17-19-34(58-12)20-18-32)43(55)49(10)31(6)42(54)50(39)11/h17-20,24,27-28,30-31,33,35-39,52H,13-16,21-23,25-26H2,1-12H3,(H,48,53)/t27-,28-,30-,31-,33-,35-,36-,37-,38-,39-/m0/s1
InChIKey VCMQMWKGIHWSPX-BSMJCHRZSA-N
Formula C46H71N5O8S
HBA 10
HBD 2
MW 854.17
Rotatable Bonds 5
TPSA 158.15
LogP 5.67
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 60
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 853.5
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: 139583524

No compound-protein relationship available.

Structure

SMILES: C12=NC(CS2)C=CC(=O)NC(Cc3ccccc3)C(=O)NCC(=O)NCC(=O)N4C(CCCC4)C(=O)OCCCCCC1

Level: 1

Mol. Weight: 854.17 g/mol

Structure

SMILES: C12=NC(CS2)C=CC(=O)NCC(=O)NCC(=O)NCC(=O)N3C(CCCC3)C(=O)OCCCCCC1

Level: 0

Mol. Weight: 854.17 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 854.17 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.19
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
112.020
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
15383.45

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.020
Plasma Protein Binding
97.83
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
7.350
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Toxic
Bioconcentration Factor
-361.110
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.160
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.120
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
-27921829.040
Rat (Acute)
3.530
Rat (Chronic Oral)
0.500
Fathead Minnow
35253.120
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
3136291.500
Hydration Free Energy
-2.920
Log(D) at pH=7.4
4.370
Log(P)
5.18
Log S
-4.41
Log(Vapor Pressure)
-103191.44
Melting Point
236.92
pKa Acid
-687.83
pKa Basic
7.67
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8866
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8864
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8837
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7896
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7891
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7786
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7479
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7391
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7385
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7381
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7363
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 2 0.7331
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7321
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7299
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7289
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7283
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7271
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7246
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7242
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7209
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7183
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 2 0.7181
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7172
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7163
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7161
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7135
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7126
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7088
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7087
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7087
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7086
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7075
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 2 0.7065
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7050
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 2 0.7046
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7026
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 2 0.7022
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 2 0.7016

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