NP-MRD: Showing NP-Card for Caissarine B (NP0078950)

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Record Information

Version

2.0

Created at

2022-04-29 00:01:59 UTC

Updated at

2022-04-29 00:01:59 UTC

NP-MRD ID

NP0078950

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Caissarine B

Description

(5R,10S)-7,9-dibromo-N-[(2R)-7-{[(5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]Deca-2,6,8-trien-3-yl]formamido}-2-hydroxyheptyl]-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]Deca-2,6,8-triene-3-carboxamide 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. Caissarine B is found in Aplysina caissara. Based on a literature review very few articles have been published on (5R,10S)-7,9-dibromo-N-[(2R)-7-{[(5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]Deca-2,6,8-trien-3-yl]formamido}-2-hydroxyheptyl]-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]Deca-2,6,8-triene-3-carboxamide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202022D          

 44 47  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304292202022D          

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    6.6988   -8.8531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4133   -7.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4995   -6.7952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3065   -6.6236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7190   -7.3381    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2039   -6.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0244   -6.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3599   -7.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8750   -8.1780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0545   -8.0918    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5696   -8.7592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2106   -8.9317    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   11.1804   -7.5968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5160   -8.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5093   -6.0895    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    8.1669   -7.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6975   -6.7906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6155   -5.9170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2564   -6.0895    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.9275   -7.5968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2631   -8.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  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
  4  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 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  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 28 27  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  6  0  0  0
 32 35  1  0  0  0  0
 31 36  1  0  0  0  0
 36 37  1  0  0  0  0
 30 38  1  0  0  0  0
 28 39  1  0  0  0  0
 25 39  1  0  0  0  0
 16 40  1  6  0  0  0
  3 41  1  1  0  0  0
  2 42  1  0  0  0  0
  1 43  1  0  0  0  0
 43 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078950

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H32Br4N4O9/c1-41-20-14(28)8-26(22(37)18(20)30)10-16(34-43-26)24(39)32-7-5-3-4-6-13(36)12-33-25(40)17-11-27(44-35-17)9-15(29)21(42-2)19(31)23(27)38/h8-9,13,22-23,36-38H,3-7,10-12H2,1-2H3,(H,32,39)(H,33,40)/t13-,22+,23-,26-,27+/m1/s1

> <INCHI_KEY>
FQVRCGJJPSNVLI-HFETZQJPSA-N

> <FORMULA>
C27H32Br4N4O9

> <MOLECULAR_WEIGHT>
876.188

> <EXACT_MASS>
871.890281

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
72.73472886598218

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
1.243438863333333

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.577510353652709

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.038747513188277

> <JCHEM_PKA_STRONGEST_BASIC>
0.25567842737446245

> <JCHEM_POLAR_SURFACE_AREA>
180.52999999999997

> <JCHEM_REFRACTIVITY>
176.8161

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.22e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -7.666 -14.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.040 -12.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.509 -12.452   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.603 -13.698   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.230 -15.105   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.761 -15.266   0.000  0.00  0.00           C+0
HETATM    7 Br   UNK     0      -7.388 -16.672   0.000  0.00  0.00          Br+0
HETATM    8  O   UNK     0      -3.833 -12.364   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      -2.327 -12.684   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -2.166 -14.216   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.573 -14.842   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.832 -14.986   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.832 -16.526   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       0.501 -14.216   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       1.835 -14.986   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.169 -14.216   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.502 -14.986   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.836 -14.216   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.170 -14.986   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.503 -14.216   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.837 -14.986   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      11.171 -14.216   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      12.504 -14.986   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.504 -16.526   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      13.838 -14.216   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      13.999 -12.684   0.000  0.00  0.00           N+0
HETATM   27  O   UNK     0      15.505 -12.364   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      16.275 -13.698   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.181 -12.452   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      18.712 -12.613   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      19.339 -14.020   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      18.433 -15.266   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      16.902 -15.105   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      15.997 -16.351   0.000  0.00  0.00           O+0
HETATM   35 Br   UNK     0      19.060 -16.672   0.000  0.00  0.00          Br+0
HETATM   36  O   UNK     0      20.870 -14.181   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      21.496 -15.588   0.000  0.00  0.00           C+0
HETATM   38 Br   UNK     0      19.617 -11.367   0.000  0.00  0.00          Br+0
HETATM   39  C   UNK     0      15.245 -14.842   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       3.169 -12.676   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -4.882 -11.045   0.000  0.00  0.00           O+0
HETATM   42 Br   UNK     0      -7.945 -11.367   0.000  0.00  0.00          Br+0
HETATM   43  O   UNK     0      -9.198 -14.181   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -9.824 -15.588   0.000  0.00  0.00           C+0
CONECT    1    2    6   43                                                  
CONECT    2    1    3   42                                                  
CONECT    3    2    4   41                                                  
CONECT    4    3    5    8   11                                             
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    4                                                       
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   40                                                  
CONECT   17   16   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   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   39                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   33   39                                             
CONECT   29   28   30                                                       
CONECT   30   29   31   38                                                  
CONECT   31   30   32   36                                                  
CONECT   32   31   33   35                                                  
CONECT   33   32   28   34                                                  
CONECT   34   33                                                            
CONECT   35   32                                                            
CONECT   36   31   37                                                       
CONECT   37   36                                                            
CONECT   38   30                                                            
CONECT   39   28   25                                                       
CONECT   40   16                                                            
CONECT   41    3                                                            
CONECT   42    2                                                            
CONECT   43    1   44                                                       
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂Br₄N₄O₉

Average Mass

876.1880 Da

Monoisotopic Mass

871.89028 Da

IUPAC Name

(5S,10R)-7,9-dibromo-N-[(6R)-7-{[(5R,10S)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}-6-hydroxyheptyl]-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)NCCCCC[C@@H](O)CNC(=O)C2=NO[C@]3(C2)C=C(Br)C(OC)=C(Br)[C@H]3O)C=C1Br

InChI Identifier

InChI=1S/C27H32Br4N4O9/c1-41-20-14(28)8-26(22(37)18(20)30)10-16(34-43-26)24(39)32-7-5-3-4-6-13(36)12-33-25(40)17-11-27(44-35-17)9-15(29)21(42-2)19(31)23(27)38/h8-9,13,22-23,36-38H,3-7,10-12H2,1-2H3,(H,32,39)(H,33,40)/t13-,22+,23-,26-,27+/m1/s1

InChI Key

FQVRCGJJPSNVLI-HFETZQJPSA-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 caissara	Animalia	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
Secondary carboxylic acid amide
Secondary alcohol
Oxime ether
Halohydrin
Carboxamide group
Bromohydrin
Oxacycle
Azacycle
Bromoalkene
Haloalkene
Vinyl halide
Vinyl bromide
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Carbonyl group
Alcohol
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	3.54	ALOGPS
logP	1.24	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	12.04	ChemAxon
pKa (Strongest Basic)	0.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	180.53 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	176.82 m³·mol⁻¹	ChemAxon
Polarizability	72.73 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163059752

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Caissarine B (NP0078950)

MOL for NP0078950 (Caissarine B)

3D MOL for NP0078950 (Caissarine B)

3D SDF for NP0078950 (Caissarine B)

3D-SDF for NP0078950 (Caissarine B)

PDB for NP0078950 (Caissarine B)

3D PDB for NP0078950 (Caissarine B)

SMILES for NP0078950 (Caissarine B)

INCHI for NP0078950 (Caissarine B)

Structure for NP0078950 (Caissarine B)

3D Structure for NP0078950 (Caissarine B)