NP-MRD: Showing NP-Card for aerothionin (NP0141352)

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Record Information

Version

2.0

Created at

2022-08-02 13:54:23 UTC

Updated at

2022-08-02 15:29:02 UTC

NP-MRD ID

NP0141352

Secondary Accession Numbers

None

Natural Product Identification

Common Name

aerothionin

Description

(?)-Aerothionin belongs to the class of organic compounds known as isoxazolines. Isoxazolines are compounds containing a five-member unsaturated aliphatic ring, with an oxygen atom adjacent to a nitrogen atoms, and three carbon atoms. aerothionin is found in Aplysina cavernicola, Aplysina gerardogreeni, Aplysina insularis, Aplysina lacunosa, Himerometra robustipinna, Pseudoceratina durissima, Pseudoceratina purpurea and Tylodina perversa. aerothionin was first documented in 2015 (PMID: 25812033). Based on a literature review a small amount of articles have been published on (?)-Aerothionin (PMID: 28191971) (PMID: 33940466) (PMID: 32369901) (PMID: 25920247).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652308022215542D          

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M  END

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 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 23 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 31 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 26 36  1  0  0  0  0
 36 37  1  1  0  0  0
  8 38  1  0  0  0  0
 38 39  2  0  0  0  0
  3 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0141352

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(Br)[C@@H](O)[C@@]2(CC(=NO2)C(=O)NCCCCNC(=O)C2=NO[C@]3(C2)C=C(Br)C(OC)=C(Br)[C@H]3O)C=C1Br

> <INCHI_IDENTIFIER>
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)/t19-,20-,23+,24+/m1/s1

> <INCHI_KEY>
BJWQSQOWGBUSFC-CHOVIJNXSA-N

> <FORMULA>
C24H26Br4N4O8

> <MOLECULAR_WEIGHT>
818.108

> <EXACT_MASS>
813.848416

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
65.45323614215957

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R,10S)-7,9-dibromo-N-(4-{[(5R,10S)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}butyl)-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide

> <ALOGPS_LOGP>
3.46

> <JCHEM_LOGP>
0.9846364753333334

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.670988125614937

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.079846386222728

> <JCHEM_PKA_STRONGEST_BASIC>
0.21174808983636328

> <JCHEM_POLAR_SURFACE_AREA>
160.29999999999998

> <JCHEM_REFRACTIVITY>
161.6516

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,10S)-7,9-dibromo-N-(4-{[(5R,10S)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}butyl)-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-AUG-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-AUG-22         0                                  
HETATM    1  C   UNK     0     -10.328 -11.049   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -9.423  -9.803   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -7.891  -9.964   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.986  -8.718   0.000  0.00  0.00           C+0
HETATM    5 Br   UNK     0      -7.612  -7.311   0.000  0.00  0.00          Br+0
HETATM    6  C   UNK     0      -5.454  -8.879   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.549  -7.633   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.828 -10.286   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.797  -9.141   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.391  -9.768   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -2.552 -11.299   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      -4.058 -11.619   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.057  -8.998   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.057  -7.458   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       0.277  -9.768   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       1.610  -8.998   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.944  -9.768   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.278  -8.998   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.612  -9.768   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       6.945  -8.998   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       8.279  -9.768   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.279 -11.308   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.613  -8.998   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       9.774  -7.466   0.000  0.00  0.00           N+0
HETATM   25  O   UNK     0      11.280  -7.146   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.050  -8.480   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.019  -9.624   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.955  -7.234   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.487  -7.395   0.000  0.00  0.00           C+0
HETATM   30 Br   UNK     0      15.392  -6.149   0.000  0.00  0.00          Br+0
HETATM   31  C   UNK     0      15.113  -8.802   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      16.645  -8.963   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      17.550  -7.717   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.208 -10.047   0.000  0.00  0.00           C+0
HETATM   35 Br   UNK     0      14.834 -11.454   0.000  0.00  0.00          Br+0
HETATM   36  C   UNK     0      12.676  -9.887   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      11.771 -11.132   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -5.733 -11.532   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -7.265 -11.371   0.000  0.00  0.00           C+0
HETATM   40 Br   UNK     0      -8.170 -12.617   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   39                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   12   38                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    8                                                       
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   27                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28   36                                             
CONECT   27   26   23                                                       
CONECT   28   26   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   31   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   26   37                                                  
CONECT   37   36                                                            
CONECT   38    8   39                                                       
CONECT   39   38    3   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₆Br₄N₄O₈

Average Mass

818.1080 Da

Monoisotopic Mass

813.84842 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=C(Br)[C@@H](O)[C@@]2(CC(=NO2)C(=O)NCCCCNC(=O)C2=NO[C@]3(C2)C=C(Br)C(OC)=C(Br)[C@H]3O)C=C1Br

InChI Identifier

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)/t19-,20-,23+,24+/m1/s1

InChI Key

BJWQSQOWGBUSFC-CHOVIJNXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, simulated)	Charlotte.simmler			2022-08-02	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aplysina cavernicola	LOTUS Database	35616633
Aplysina gerardogreeni	LOTUS Database	35616633
Aplysina insularis	LOTUS Database	35616633
Aplysina lacunosa	LOTUS Database	35616633
Himerometra robustipinna	LOTUS Database	35616633
Pseudoceratina durissima	LOTUS Database	35616633
Pseudoceratina purpurea	LOTUS Database	35616633
Tylodina perversa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoxazolines. Isoxazolines are compounds containing a five-member unsaturated aliphatic ring, with an oxygen atom adjacent to a nitrogen atoms, and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolines

Sub Class

Isoxazolines

Direct Parent

Isoxazolines

Alternative Parents

Substituents

Isoxazoline
Bromohydrin
Carboxamide group
Halohydrin
Oxime ether
Secondary alcohol
Secondary carboxylic acid amide
Haloalkene
Vinyl halide
Vinyl bromide
Carboxylic acid derivative
Oxacycle
Azacycle
Bromoalkene
Organic oxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Organic nitrogen compound
Alcohol
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00038070

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bracket

METLIN ID

Not Available

PubChem Compound

101385812

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nicacio KJ, Ioca LP, Froes AM, Leomil L, Appolinario LR, Thompson CC, Thompson FL, Ferreira AG, Williams DE, Andersen RJ, Eustaquio AS, Berlinck RG: Cultures of the Marine Bacterium Pseudovibrio denitrificans Ab134 Produce Bromotyrosine-Derived Alkaloids Previously Only Isolated from Marine Sponges. J Nat Prod. 2017 Feb 24;80(2):235-240. doi: 10.1021/acs.jnatprod.6b00838. Epub 2017 Feb 13. [PubMed:28191971 ]
Shaala LA, Youssef DT, Badr JM, Sulaiman M, Khedr A: Bioactive secondary metabolites from the Red Sea marine Verongid sponge Suberea species. Mar Drugs. 2015 Mar 24;13(4):1621-31. doi: 10.3390/md13041621. [PubMed:25812033 ]
Khan S, Al-Fadhli AA, Tilvi S: Discovery of cytotoxic natural products from Red Sea sponges: Structure and synthesis. Eur J Med Chem. 2021 Aug 5;220:113491. doi: 10.1016/j.ejmech.2021.113491. Epub 2021 Apr 24. [PubMed:33940466 ]
Drechsel A, Helm J, Ehrlich H, Pantovic S, Bornstein SR, Bechmann N: Anti-Tumor Activity vs. Normal Cell Toxicity: Therapeutic Potential of the Bromotyrosines Aerothionin and Homoaerothionin In Vitro. Mar Drugs. 2020 May 1;18(5). pii: md18050236. doi: 10.3390/md18050236. [PubMed:32369901 ]
Niemann H, Marmann A, Lin W, Proksch P: Sponge derived bromotyrosines: structural diversity through natural combinatorial chemistry. Nat Prod Commun. 2015 Jan;10(1):219-31. [PubMed:25920247 ]

Showing NP-Card for aerothionin (NP0141352)

MOL for NP0141352 (aerothionin)

3D MOL for NP0141352 (aerothionin)

3D SDF for NP0141352 (aerothionin)

3D-SDF for NP0141352 (aerothionin)

PDB for NP0141352 (aerothionin)

3D PDB for NP0141352 (aerothionin)

SMILES for NP0141352 (aerothionin)

INCHI for NP0141352 (aerothionin)

Structure for NP0141352 (aerothionin)

3D Structure for NP0141352 (aerothionin)