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Aerothionin
- Family: Animalia - Aplysinellidae
- Kingdom: Animalia
-
Class: Alkaloid
- Subclass: Bromotyrosine-Derived Alkaloid
| Canonical Smiles | COC1=C(Br)C(C2(C=C1Br)ON=C(C2)C(=O)NCCCCNC(=O)C1=NOC2(C1)C=C(Br)C(=C(C2O)Br)OC)O |
|---|---|
| InChI | InChI=1S/C24H26Br4N4O8/c1-37-17-11(25)7-23(19(33)15(17)27)9-13(31-39-23)21(35)29-5-3-4-6-30-22(36)14-10-24(40-32-14)8-12(26)18(38-2)16(28)20(24)34/h7-8,19-20,33-34H,3-6,9-10H2,1-2H3,(H,29,35)(H,30,36) |
| InChIKey | BJWQSQOWGBUSFC-UHFFFAOYSA-N |
| Formula | C24H26Br4N4O8 |
| HBA | 10 |
| HBD | 4 |
| MW | 818.11 |
| Rotatable Bonds | 9 |
| TPSA | 160.3 |
| LogP | 2.84 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 40 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.5 |
| Exact Mass | 813.85 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Suberea mollis | Aplysinellidae | Animalia | 1161115 |
Showing of synonyms
Aerothionin
28714-26-3
NSC177380
(+)-aerothionin
7,9-Dibromo-N-[4-[(7,9-dibromo-6-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carbonyl)amino]butyl]-6-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carboxamide
1-Oxa-2-azaspiro(4.5)deca-2,6,8-triene-3-carboxamide, N,N'-1,4-butanediylbis(7,9-dibromo-10-hydroxy-8-methoxy-
SCHEMBL4665946
CHEMBL1999742
DTXSID80951364
NSC-177380
NCI60_001482
N,N'-(Butane-1,4-diyl)bis(7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide)
Pubchem:
301120
Cas:
28714-26-3
Gnps:
CCMSLIB00010012970
Nmrshiftdb2:
70129976
Chembl:
CHEMBL1999742
CPRiL:
229765
SMILES: C1C=CC=CC12CC(=NO2)C(=O)NCCCCNC(=O)C(=NO3)CC34C=CC=CC4
Level: 1
Mol. Weight: 818.11 g/mol
SMILES: O1N=CCC12C=CC=CC2
Level: 0
Mol. Weight: 818.11 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.3
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.120
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 0.12
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.990
- Plasma Protein Binding
- 32.32
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-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
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 2.610
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.710
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.410
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 8.700
- 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
- -3771.050
- Rat (Acute)
- 2.500
- Rat (Chronic Oral)
- 1.650
- Fathead Minnow
- 16.130
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 516.230
- Hydration Free Energy
- -2.900
- Log(D) at pH=7.4
- 3.350
- Log(P)
- 3.3
- Log S
- -3.9
- Log(Vapor Pressure)
- -9.8
- Melting Point
- 232.1
- pKa Acid
- 6.77
- pKa Basic
- 3.35
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Triosephosphate isomerase | P00942 | TPIS_YEAST | Saccharomyces cerevisiae | 3 | 0.9505 |
| Triosephosphate isomerase | P00942 | TPIS_YEAST | Saccharomyces cerevisiae | 3 | 0.9505 |
| Mevalonate kinase | Q4Q6K7 | Q4Q6K7_LEIMA | Leishmania major | 3 | 0.9451 |
| Mevalonate kinase | Q4Q6K7 | Q4Q6K7_LEIMA | Leishmania major | 3 | 0.9451 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.9059 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.9059 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 3 | 0.9049 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 3 | 0.9049 |
| 3-dehydroquinate dehydratase | P9WPX7 | AROQ_MYCTU | Mycobacterium tuberculosis | 3 | 0.8903 |
| 3-dehydroquinate dehydratase | P9WPX7 | AROQ_MYCTU | Mycobacterium tuberculosis | 3 | 0.8903 |
| Shikimate kinase | P9WPY3 | AROK_MYCTU | Mycobacterium tuberculosis | 3 | 0.8759 |
| Shikimate kinase | P9WPY3 | AROK_MYCTU | Mycobacterium tuberculosis | 3 | 0.8759 |
| 2-dehydro-3-deoxyphosphooctonate aldolase | P0A715 | KDSA_ECOLI | Escherichia coli | 3 | 0.8363 |
| 2-dehydro-3-deoxyphosphooctonate aldolase | P0A715 | KDSA_ECOLI | Escherichia coli | 3 | 0.8363 |
| Chorismate mutase AroH | P19080 | AROH_BACSU | Bacillus subtilis | 3 | 0.8205 |
| Chorismate mutase AroH | P19080 | AROH_BACSU | Bacillus subtilis | 3 | 0.8205 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8011 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8011 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7897 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7897 |
| Chorismate mutase AroH | P19080 | AROH_BACSU | Bacillus subtilis | 3 | 0.7868 |
| Chorismate mutase AroH | P19080 | AROH_BACSU | Bacillus subtilis | 3 | 0.7868 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7811 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7811 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7759 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7759 |
| Aspartate carbamoyltransferase catalytic subunit | P05654 | PYRB_BACSU | Bacillus subtilis | 3 | 0.7754 |
| Aspartate carbamoyltransferase catalytic subunit | P05654 | PYRB_BACSU | Bacillus subtilis | 3 | 0.7754 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.7665 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.7665 |
| Mexicain | P84346 | MEX1_JACME | Jacaratia mexicana | 3 | 0.7570 |
| Mexicain | P84346 | MEX1_JACME | Jacaratia mexicana | 3 | 0.7570 |
| Fluoroacetyl-CoA thioesterase | Q1EMV2 | FLK_STRCT | Streptantibioticus cattleyicolor | 3 | 0.7410 |
| Fluoroacetyl-CoA thioesterase | Q1EMV2 | FLK_STRCT | Streptantibioticus cattleyicolor | 3 | 0.7410 |
| 3-hydroxy-3-methylglutaryl-coenzyme A reductase | P13702 | MVAA_PSEMV | Pseudomonas mevalonii | 3 | 0.7117 |
| 3-hydroxy-3-methylglutaryl-coenzyme A reductase | P13702 | MVAA_PSEMV | Pseudomonas mevalonii | 3 | 0.7117 |
| Cytidine deaminase | P19079 | CDD_BACSU | Bacillus subtilis | 3 | 0.7080 |
| Cytidine deaminase | P19079 | CDD_BACSU | Bacillus subtilis | 3 | 0.7080 |
| Uridine phosphorylase | P0A1F6 | UDP_SALTY | Salmonella typhimurium | 3 | 0.7031 |
| Uridine phosphorylase | P0A1F6 | UDP_SALTY | Salmonella typhimurium | 3 | 0.7031 |
| Cytidine deaminase | P19079 | CDD_BACSU | Bacillus subtilis | 4 | 0.7015 |
| Cytidine deaminase | P19079 | CDD_BACSU | Bacillus subtilis | 4 | 0.7015 |