NP-MRD: Showing NP-Card for (5r,10s)-7,9-dibromo-n-(2-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}ethyl)-10-hydroxy-8-methoxy-n-methyl-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide (NP0148905)

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Record Information

Version

2.0

Created at

2022-09-02 04:43:09 UTC

Updated at

2022-09-02 04:43:09 UTC

NP-MRD ID

NP0148905

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5r,10s)-7,9-dibromo-n-(2-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}ethyl)-10-hydroxy-8-methoxy-n-methyl-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide

Description

(5R,10S)-7,9-dibromo-N-(2-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}ethyl)-10-hydroxy-8-methoxy-N-methyl-1-oxa-2-azaspiro[4.5]Deca-2,6,8-triene-3-carboxamide belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. (5r,10s)-7,9-dibromo-n-(2-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}ethyl)-10-hydroxy-8-methoxy-n-methyl-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide is found in Pseudoceratina purpurea. Based on a literature review very few articles have been published on (5R,10S)-7,9-dibromo-N-(2-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}ethyl)-10-hydroxy-8-methoxy-N-methyl-1-oxa-2-azaspiro[4.5]Deca-2,6,8-triene-3-carboxamide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022206432D          

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  Mrv1652309022206432D          

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 24 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 20 34  1  0  0  0  0
 13 35  2  0  0  0  0
 35 36  1  0  0  0  0
  8 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0148905

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(Br)[C@@H](O)[C@@]2(CC(=NO2)C(=O)N(C)CCC2=CC(Br)=C(OCCCN(C)C)C(Br)=C2)C=C1Br

> <INCHI_IDENTIFIER>
InChI=1S/C24H29Br4N3O5/c1-30(2)7-5-9-35-20-15(25)10-14(11-16(20)26)6-8-31(3)23(33)18-13-24(36-29-18)12-17(27)21(34-4)19(28)22(24)32/h10-12,22,32H,5-9,13H2,1-4H3/t22-,24+/m1/s1

> <INCHI_KEY>
VCCOVKIVTNNRGV-VWNXMTODSA-N

> <FORMULA>
C24H29Br4N3O5

> <MOLECULAR_WEIGHT>
759.128

> <EXACT_MASS>
754.884073

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
62.64427671248792

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R,10S)-7,9-dibromo-N-(2-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}ethyl)-10-hydroxy-8-methoxy-N-methyl-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide

> <ALOGPS_LOGP>
4.87

> <JCHEM_LOGP>
3.9846681386666667

> <ALOGPS_LOGS>
-5.18

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.869202737305454

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.387473895503238

> <JCHEM_PKA_STRONGEST_BASIC>
9.256384009136843

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
155.91289999999992

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.06e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,10S)-7,9-dibromo-N-(2-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}ethyl)-10-hydroxy-8-methoxy-N-methyl-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0     -26.036  15.032   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -24.505  14.871   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0     -23.879  13.464   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -22.347  13.303   0.000  0.00  0.00           C+0
HETATM    5 Br   UNK     0     -21.442  14.549   0.000  0.00  0.00          Br+0
HETATM    6  C   UNK     0     -21.721  11.896   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -20.189  11.735   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0     -22.626  10.650   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -24.157  10.811   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -24.784  12.218   0.000  0.00  0.00           C+0
HETATM   11 Br   UNK     0     -26.315  12.379   0.000  0.00  0.00          Br+0
HETATM   12  C   UNK     0     -21.119  10.330   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -20.958   8.798   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -19.625   8.028   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0     -19.625   6.488   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0     -18.291   8.798   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0     -18.291  10.338   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -16.957   8.028   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -15.624   8.798   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -14.290   8.028   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -12.956   8.798   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -11.623   8.028   0.000  0.00  0.00           C+0
HETATM   23 Br   UNK     0     -10.289   8.798   0.000  0.00  0.00          Br+0
HETATM   24  C   UNK     0     -11.623   6.488   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -10.289   5.718   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -8.955   6.488   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.622   5.718   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.288   6.488   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0      -4.954   5.718   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      -3.621   6.488   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.954   4.178   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -12.956   5.718   0.000  0.00  0.00           C+0
HETATM   33 Br   UNK     0     -12.956   4.178   0.000  0.00  0.00          Br+0
HETATM   34  C   UNK     0     -14.290   6.488   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0     -22.365   8.172   0.000  0.00  0.00           N+0
HETATM   36  O   UNK     0     -23.396   9.316   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    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   12   36                                             
CONECT    9    8   10                                                       
CONECT   10    9    3   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14   35                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   34                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   24   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   20                                                       
CONECT   35   13   36                                                       
CONECT   36   35    8                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₉Br₄N₃O₅

Average Mass

759.1280 Da

Monoisotopic Mass

754.88407 Da

IUPAC Name

(5R,10S)-7,9-dibromo-N-(2-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}ethyl)-10-hydroxy-8-methoxy-N-methyl-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide

Traditional Name

(5R,10S)-7,9-dibromo-N-(2-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}ethyl)-10-hydroxy-8-methoxy-N-methyl-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide

CAS Registry Number

Not Available

SMILES

COC1=C(Br)[C@@H](O)[C@@]2(CC(=NO2)C(=O)N(C)CCC2=CC(Br)=C(OCCCN(C)C)C(Br)=C2)C=C1Br

InChI Identifier

InChI=1S/C24H29Br4N3O5/c1-30(2)7-5-9-35-20-15(25)10-14(11-16(20)26)6-8-31(3)23(33)18-13-24(36-29-18)12-17(27)21(34-4)19(28)22(24)32/h10-12,22,32H,5-9,13H2,1-4H3/t22-,24+/m1/s1

InChI Key

VCCOVKIVTNNRGV-VWNXMTODSA-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 phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol ethers

Sub Class

Not Available

Direct Parent

Phenol ethers

Alternative Parents

Substituents

Phenoxy compound
Phenol ether
Alkyl aryl ether
Halobenzene
Bromobenzene
Aryl bromide
Aryl halide
Monocyclic benzene moiety
Isoxazoline
Tertiary carboxylic acid amide
Amino acid or derivatives
Halohydrin
Carboxamide group
Bromohydrin
Oxime ether
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Bromoalkene
Ether
Oxacycle
Haloalkene
Azacycle
Vinyl bromide
Vinyl halide
Organoheterocyclic compound
Alcohol
Organohalogen compound
Organobromide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
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	4.87	ALOGPS
logP	3.98	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	12.39	ChemAxon
pKa (Strongest Basic)	9.26	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	155.91 m³·mol⁻¹	ChemAxon
Polarizability	62.64 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

162949629

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5r,10s)-7,9-dibromo-n-(2-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}ethyl)-10-hydroxy-8-methoxy-n-methyl-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide (NP0148905)

MOL for NP0148905 ((5r,10s)-7,9-dibromo-n-(2-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}ethyl)-10-hydroxy-8-methoxy-n-methyl-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide)

3D MOL for NP0148905 ((5r,10s)-7,9-dibromo-n-(2-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}ethyl)-10-hydroxy-8-methoxy-n-methyl-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide)

3D SDF for NP0148905 ((5r,10s)-7,9-dibromo-n-(2-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}ethyl)-10-hydroxy-8-methoxy-n-methyl-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide)

3D-SDF for NP0148905 ((5r,10s)-7,9-dibromo-n-(2-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}ethyl)-10-hydroxy-8-methoxy-n-methyl-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide)

PDB for NP0148905 ((5r,10s)-7,9-dibromo-n-(2-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}ethyl)-10-hydroxy-8-methoxy-n-methyl-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide)

3D PDB for NP0148905 ((5r,10s)-7,9-dibromo-n-(2-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}ethyl)-10-hydroxy-8-methoxy-n-methyl-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide)

SMILES for NP0148905 ((5r,10s)-7,9-dibromo-n-(2-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}ethyl)-10-hydroxy-8-methoxy-n-methyl-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide)

INCHI for NP0148905 ((5r,10s)-7,9-dibromo-n-(2-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}ethyl)-10-hydroxy-8-methoxy-n-methyl-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide)

Structure for NP0148905 ((5r,10s)-7,9-dibromo-n-(2-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}ethyl)-10-hydroxy-8-methoxy-n-methyl-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide)

3D Structure for NP0148905 ((5r,10s)-7,9-dibromo-n-(2-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}ethyl)-10-hydroxy-8-methoxy-n-methyl-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide)