NP-MRD: Showing NP-Card for methyl (5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate (NP0261884)

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Record Information

Version

2.0

Created at

2022-09-08 04:27:34 UTC

Updated at

2022-09-08 04:27:34 UTC

NP-MRD ID

NP0261884

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate

Description

CHEMBL4644758 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. methyl (5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate is found in Verongula gigantea. Based on a literature review very few articles have been published on CHEMBL4644758.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
    5.5111   -0.1822    0.8693 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1593   -0.3794    0.4950 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5579    0.3999   -0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2601    1.2856   -1.0201 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1819    0.2400   -0.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6055    0.9514   -1.8046 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3195    0.5889   -1.9974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1131    0.0147   -0.7454 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3599    1.1105    0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5167    1.3474    0.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7359    2.8428    1.9000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.7091    0.5153    0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8928    0.8403    1.0718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1081    0.2075    1.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5020   -0.4899   -0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0368   -1.6074   -0.7274 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2442   -0.8497   -1.0386 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9094   -2.1654   -0.5800 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1669   -0.7489   -0.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7472   -0.5651    1.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2042   -0.6049    0.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7045    0.9294    0.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4410    1.8118    0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7913    0.8477    1.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6081    0.2920    0.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1434   -0.8180    1.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4704   -0.9561   -2.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1938   -2.2739    0.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2139   -1.6386   -1.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2621   -0.9457    0.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  8  7  1  6
  8 19  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 19  5  1  0
 17  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 19 29  1  0
 19 30  1  0
  9 23  1  0
 14 24  1  0
 14 25  1  0
 14 26  1  0
 17 27  1  6
 18 28  1  0
M  END


  Mrv1652309082206272D          

 19 20  0  0  1  0            999 V2000
   -2.0886   -0.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -0.1494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674   -0.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5812   -1.3054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6820    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9195    1.8414    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.9195    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7445    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1570    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9195   -1.0164    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.6820   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2695   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  6  0  0  0
  8 19  1  0  0  0  0
  5 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0261884

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=NO[C@@]2(C1)C=C(Br)C(OC)=C(Br)[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C11H11Br2NO5/c1-17-8-5(12)3-11(9(15)7(8)13)4-6(14-19-11)10(16)18-2/h3,9,15H,4H2,1-2H3/t9-,11+/m0/s1

> <INCHI_KEY>
BWARHGMOCWYQHN-GXSJLCMTSA-N

> <FORMULA>
C11H11Br2NO5

> <MOLECULAR_WEIGHT>
397.019

> <EXACT_MASS>
394.900398

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
29.880017606249076

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate

> <JCHEM_LOGP>
1.2519134416666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.059188314311292

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.387088909815123

> <JCHEM_PKA_STRONGEST_BASIC>
-1.7455671401004875

> <JCHEM_POLAR_SURFACE_AREA>
77.35000000000001

> <JCHEM_REFRACTIVITY>
75.1055

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.899  -1.184   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.653  -0.279   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.246  -0.905   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.085  -2.437   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -0.000   1.540   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       1.465   2.016   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.140   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.680   2.104   0.000  0.00  0.00           C+0
HETATM   11 Br   UNK     0       5.450   3.437   0.000  0.00  0.00          Br+0
HETATM   12  C   UNK     0       5.450   0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.990   0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.760   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.680  -0.564   0.000  0.00  0.00           C+0
HETATM   16 Br   UNK     0       5.450  -1.897   0.000  0.00  0.00          Br+0
HETATM   17  C   UNK     0       3.140  -0.564   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.370  -1.897   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   17   19                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    8   18                                                  
CONECT   18   17                                                            
CONECT   19    8    5                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₁Br₂NO₅

Average Mass

397.0190 Da

Monoisotopic Mass

394.90040 Da

IUPAC Name

methyl (5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate

Traditional Name

methyl (5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=NO[C@@]2(C1)C=C(Br)C(OC)=C(Br)[C@@H]2O

InChI Identifier

InChI=1S/C11H11Br2NO5/c1-17-8-5(12)3-11(9(15)7(8)13)4-6(14-19-11)10(16)18-2/h3,9,15H,4H2,1-2H3/t9-,11+/m0/s1

InChI Key

BWARHGMOCWYQHN-GXSJLCMTSA-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, 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
Verongula gigantea	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
Methyl ester
Bromohydrin
Carboxylic acid ester
Halohydrin
Oxime ether
Secondary alcohol
Haloalkene
Oxacycle
Vinyl halide
Vinyl bromide
Carboxylic acid derivative
Azacycle
Bromoalkene
Monocarboxylic acid or derivatives
Organic oxide
Organobromide
Organohalogen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Organooxygen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
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	1.25	ChemAxon
pKa (Strongest Acidic)	12.39	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.35 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	75.11 m³·mol⁻¹	ChemAxon
Polarizability	29.88 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

8748261

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10572874

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate (NP0261884)

MOL for NP0261884 (methyl (5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate)

3D MOL for NP0261884 (methyl (5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate)

3D SDF for NP0261884 (methyl (5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate)

3D-SDF for NP0261884 (methyl (5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate)

PDB for NP0261884 (methyl (5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate)

3D PDB for NP0261884 (methyl (5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate)

SMILES for NP0261884 (methyl (5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate)

INCHI for NP0261884 (methyl (5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate)

Structure for NP0261884 (methyl (5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate)

3D Structure for NP0261884 (methyl (5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate)