NP-MRD: Showing NP-Card for n-{3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl}-8,10-dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide (NP0198738)

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Record Information

Version

1.0

Created at

2022-09-04 17:14:32 UTC

Updated at

2022-09-04 17:14:32 UTC

NP-MRD ID

NP0198738

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-{3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl}-8,10-dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide

Description

N-{3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl}-8,10-dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-azaspiro[4.6]Undeca-2,7,9-triene-3-carboxamide belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. n-{3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl}-8,10-dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide is found in Pseudoceratina purpurea. Based on a literature review very few articles have been published on N-{3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl}-8,10-dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-azaspiro[4.6]Undeca-2,7,9-triene-3-carboxamide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042219142D          

 34 36  0  0  0  0            999 V2000
   -5.4936    2.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8643    3.2548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0876    2.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4999    3.5555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7666    4.3362    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6808    3.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2471    2.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5254    1.9785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3061    1.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0014    2.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7032    1.7224    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346    3.4697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0277    3.2981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9414    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2269    1.2402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4875    2.4777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2020    2.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9165    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6309    2.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3454    2.4777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0599    2.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3454    0.8277    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6951    2.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8666    1.3351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309042219142D          

 34 36  0  0  0  0            999 V2000
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   -2.6808    3.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0198738

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(Br)CC2(ON=C(C2O)C(=O)NCCCOC2=C(Br)C=C(CCN)C=C2Br)OC=C1Br

> <INCHI_IDENTIFIER>
InChI=1S/C21H23Br4N3O6/c1-31-17-14(24)9-21(33-10-15(17)25)19(29)16(28-34-21)20(30)27-5-2-6-32-18-12(22)7-11(3-4-26)8-13(18)23/h7-8,10,19,29H,2-6,9,26H2,1H3,(H,27,30)

> <INCHI_KEY>
XVHHFAJHWSIGJS-UHFFFAOYSA-N

> <FORMULA>
C21H23Br4N3O6

> <MOLECULAR_WEIGHT>
733.046

> <EXACT_MASS>
728.832037

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
58.28826762827499

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl}-8,10-dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide

> <JCHEM_LOGP>
3.335974661223449

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.634924247243767

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.743164004532435

> <JCHEM_PKA_STRONGEST_BASIC>
9.773983646839099

> <JCHEM_POLAR_SURFACE_AREA>
124.63

> <JCHEM_REFRACTIVITY>
141.6328

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
N-{3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl}-8,10-dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0     -10.255   5.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -9.080   6.076   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -7.630   5.556   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.533   6.637   0.000  0.00  0.00           C+0
HETATM    5 Br   UNK     0      -7.031   8.094   0.000  0.00  0.00          Br+0
HETATM    6  C   UNK     0      -5.004   6.453   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.195   5.143   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.714   3.693   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -6.171   3.196   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.469   4.025   0.000  0.00  0.00           C+0
HETATM   11 Br   UNK     0      -8.779   3.215   0.000  0.00  0.00          Br+0
HETATM   12  O   UNK     0      -3.425   6.477   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0      -1.918   6.157   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -1.757   4.625   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.424   3.855   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.424   2.315   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       0.910   4.625   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.244   3.855   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.577   4.625   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.911   3.855   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.245   4.625   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.578   3.855   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.912   4.625   0.000  0.00  0.00           C+0
HETATM   24 Br   UNK     0       8.912   6.165   0.000  0.00  0.00          Br+0
HETATM   25  C   UNK     0      10.246   3.855   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.246   2.315   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.579   1.545   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.579   0.005   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0      12.913  -0.765   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       8.912   1.545   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.578   2.315   0.000  0.00  0.00           C+0
HETATM   32 Br   UNK     0       6.245   1.545   0.000  0.00  0.00          Br+0
HETATM   33  C   UNK     0      -3.164   3.999   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -3.484   2.492   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   12   33                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    3   11                                                  
CONECT   11   10                                                            
CONECT   12    7   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   33                                                  
CONECT   15   14   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   31                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   26   31                                                       
CONECT   31   30   22   32                                                  
CONECT   32   31                                                            
CONECT   33   14    7   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₃Br₄N₃O₆

Average Mass

733.0460 Da

Monoisotopic Mass

728.83204 Da

IUPAC Name

N-{3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl}-8,10-dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide

Traditional Name

N-{3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl}-8,10-dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide

CAS Registry Number

Not Available

SMILES

COC1=C(Br)CC2(ON=C(C2O)C(=O)NCCCOC2=C(Br)C=C(CCN)C=C2Br)OC=C1Br

InChI Identifier

InChI=1S/C21H23Br4N3O6/c1-31-17-14(24)9-21(33-10-15(17)25)19(29)16(28-34-21)20(30)27-5-2-6-32-18-12(22)7-11(3-4-26)8-13(18)23/h7-8,10,19,29H,2-6,9,26H2,1H3,(H,27,30)

InChI Key

XVHHFAJHWSIGJS-UHFFFAOYSA-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
Pseudoceratina purpurea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Phenethylamines

Alternative Parents

Substituents

Phenethylamine
Phenoxy compound
2-arylethylamine
Phenol ether
Alkyl aryl ether
Bromobenzene
Halobenzene
Aralkylamine
Aryl bromide
Aryl halide
Isoxazoline
Amino acid or derivatives
Carboxamide group
Oxime ether
Secondary alcohol
Secondary carboxylic acid amide
Organoheterocyclic compound
Haloalkene
Bromoalkene
Vinyl halide
Vinyl bromide
Carboxylic acid derivative
Ether
Oxacycle
Azacycle
Primary amine
Primary aliphatic amine
Organohalogen compound
Organobromide
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.34	ChemAxon
pKa (Strongest Acidic)	11.74	ChemAxon
pKa (Strongest Basic)	9.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	124.63 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	141.63 m³·mol⁻¹	ChemAxon
Polarizability	58.29 Å³	ChemAxon
Number of Rings	3	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

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

74033891

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-{3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl}-8,10-dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide (NP0198738)

MOL for NP0198738 (n-{3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl}-8,10-dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide)

3D MOL for NP0198738 (n-{3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl}-8,10-dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide)

3D SDF for NP0198738 (n-{3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl}-8,10-dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide)

3D-SDF for NP0198738 (n-{3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl}-8,10-dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide)

PDB for NP0198738 (n-{3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl}-8,10-dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide)

3D PDB for NP0198738 (n-{3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl}-8,10-dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide)

SMILES for NP0198738 (n-{3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl}-8,10-dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide)

INCHI for NP0198738 (n-{3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl}-8,10-dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide)

Structure for NP0198738 (n-{3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl}-8,10-dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide)

3D Structure for NP0198738 (n-{3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl}-8,10-dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide)