NP-MRD: Showing NP-Card for Homoaerothionin (NP0076655)

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Record Information

Version

2.0

Created at

2022-04-28 21:50:44 UTC

Updated at

2022-04-28 21:50:44 UTC

NP-MRD ID

NP0076655

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Homoaerothionin

Description

Homoaerothionin 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. Homoaerothionin is found in Aplysina cavernicola, Aplysina fistularis, Aplysina gerardogreeni, Pseudoceratina durissima and Suberea mollis. Based on a literature review very few articles have been published on homoaerothionin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223502D          

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M  END

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  Mrv1652304282223502D          

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  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  4 10  1  1  0  0  0
  3 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 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  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  6  0  0  0
 33 36  1  0  0  0  0
 32 37  1  0  0  0  0
 37 38  1  0  0  0  0
 31 39  1  0  0  0  0
 29 40  1  0  0  0  0
 26 40  1  0  0  0  0
  1 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076655

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H28Br4N4O8/c1-38-18-12(26)8-24(20(34)16(18)28)10-14(32-40-24)22(36)30-6-4-3-5-7-31-23(37)15-11-25(41-33-15)9-13(27)19(39-2)17(29)21(25)35/h8-9,20-21,34-35H,3-7,10-11H2,1-2H3,(H,30,36)(H,31,37)/t20-,21-,24+,25+/m0/s1

> <INCHI_KEY>
UXPNMQCEVMBCIR-KXTAGPOFSA-N

> <FORMULA>
C25H28Br4N4O8

> <MOLECULAR_WEIGHT>
832.135

> <EXACT_MASS>
827.864066

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
68.39366239780885

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.74

> <JCHEM_LOGP>
1.4292051403333348

> <ALOGPS_LOGS>
-4.58

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.672989290836696

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.080578984575029

> <JCHEM_PKA_STRONGEST_BASIC>
0.32164163730413176

> <JCHEM_POLAR_SURFACE_AREA>
160.29999999999998

> <JCHEM_REFRACTIVITY>
166.2526

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.18e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -6.486 -10.004   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.954  -9.843   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.049 -11.089   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.675 -12.496   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.207 -12.657   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.112 -11.411   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -8.643 -11.572   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -9.270 -12.979   0.000  0.00  0.00           C+0
HETATM    9 Br   UNK     0      -6.833 -14.063   0.000  0.00  0.00          Br+0
HETATM   10  O   UNK     0      -3.770 -13.741   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -3.279  -9.755   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      -1.772 -10.075   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -1.611 -11.607   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.018 -12.233   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.278 -12.377   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.278 -13.917   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       1.056 -11.607   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.390 -12.377   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.723 -11.607   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.057 -12.377   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.391 -11.607   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.724 -12.377   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       9.058 -11.607   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      10.392 -12.377   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.392 -13.917   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      11.725 -11.607   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      11.886 -10.075   0.000  0.00  0.00           N+0
HETATM   28  O   UNK     0      13.393  -9.755   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      14.163 -11.089   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.068  -9.843   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.599 -10.004   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.226 -11.411   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      16.321 -12.657   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.789 -12.496   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      13.884 -13.741   0.000  0.00  0.00           O+0
HETATM   36 Br   UNK     0      16.947 -14.063   0.000  0.00  0.00          Br+0
HETATM   37  O   UNK     0      18.757 -11.572   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      19.663 -10.326   0.000  0.00  0.00           C+0
HETATM   39 Br   UNK     0      17.505  -8.758   0.000  0.00  0.00          Br+0
HETATM   40  C   UNK     0      13.132 -12.233   0.000  0.00  0.00           C+0
HETATM   41 Br   UNK     0      -7.391  -8.758   0.000  0.00  0.00          Br+0
CONECT    1    2    6   41                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   11   14                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5                                                            
CONECT   10    4                                                            
CONECT   11    3   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13    3                                                       
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   40                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   34   40                                             
CONECT   30   29   31                                                       
CONECT   31   30   32   39                                                  
CONECT   32   31   33   37                                                  
CONECT   33   32   34   36                                                  
CONECT   34   33   29   35                                                  
CONECT   35   34                                                            
CONECT   36   33                                                            
CONECT   37   32   38                                                       
CONECT   38   37                                                            
CONECT   39   31                                                            
CONECT   40   29   26                                                       
CONECT   41    1                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₈Br₄N₄O₈

Average Mass

832.1350 Da

Monoisotopic Mass

827.86407 Da

IUPAC Name

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

Traditional Name

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C25H28Br4N4O8/c1-38-18-12(26)8-24(20(34)16(18)28)10-14(32-40-24)22(36)30-6-4-3-5-7-31-23(37)15-11-25(41-33-15)9-13(27)19(39-2)17(29)21(25)35/h8-9,20-21,34-35H,3-7,10-11H2,1-2H3,(H,30,36)(H,31,37)/t20-,21-,24+,25+/m0/s1

InChI Key

UXPNMQCEVMBCIR-KXTAGPOFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 fistularis	LOTUS Database	35616633
Aplysina gerardogreeni	LOTUS Database	35616633
Pseudoceratina durissima	LOTUS Database	35616633
Suberea mollis	-	KNApSAcK

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
Bromoalkene
Haloalkene
Vinyl halide
Vinyl bromide
Carboxylic acid derivative
Oxacycle
Azacycle
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Organic nitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
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
logP	3.74	ALOGPS
logP	1.43	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	12.08	ChemAxon
pKa (Strongest Basic)	0.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	160.3 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	166.25 m³·mol⁻¹	ChemAxon
Polarizability	68.39 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00039382

Chemspider ID

90652

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100315

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Homoaerothionin (NP0076655)

MOL for NP0076655 (Homoaerothionin)

3D MOL for NP0076655 (Homoaerothionin)

3D SDF for NP0076655 (Homoaerothionin)

3D-SDF for NP0076655 (Homoaerothionin)

PDB for NP0076655 (Homoaerothionin)

3D PDB for NP0076655 (Homoaerothionin)

SMILES for NP0076655 (Homoaerothionin)

INCHI for NP0076655 (Homoaerothionin)

Structure for NP0076655 (Homoaerothionin)

3D Structure for NP0076655 (Homoaerothionin)