NP-MRD: Showing NP-Card for {3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2e,7r,9e)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulfonic acid (NP0192677)

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Record Information

Version

2.0

Created at

2022-09-04 09:57:02 UTC

Updated at

2022-09-04 09:57:02 UTC

NP-MRD ID

NP0192677

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2e,7r,9e)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulfonic acid

Description

{3-Bromo-4-[2-(dimethylamino)ethyl]-5-[(2E,7R,9E)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulfonic acid belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. {3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2e,7r,9e)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulfonic acid is found in Aplysia kurodai. Based on a literature review very few articles have been published on {3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2E,7R,9E)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulfonic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042211572D          

 36 36  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309042211572D          

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  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 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  1  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 29 35  2  0  0  0  0
  3 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0192677

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OS(O)(=O)=O)C=C(C\C=C(/C)CCC[C@@H](C)C(=O)\C=C\C(C)(C)O)C(CCN(C)C)=C1Br

> <INCHI_IDENTIFIER>
InChI=1S/C26H40BrNO7S/c1-18(9-8-10-19(2)22(29)13-15-26(3,4)30)11-12-20-17-23(35-36(31,32)33)25(34-7)24(27)21(20)14-16-28(5)6/h11,13,15,17,19,30H,8-10,12,14,16H2,1-7H3,(H,31,32,33)/b15-13+,18-11+/t19-/m1/s1

> <INCHI_KEY>
FHQXWTAEQCEPFE-BAVCCXCYSA-N

> <FORMULA>
C26H40BrNO7S

> <MOLECULAR_WEIGHT>
590.57

> <EXACT_MASS>
589.170887

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
59.72902950232041

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2E,7R,9E)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulfonic acid

> <JCHEM_LOGP>
4.1762311983237455

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.98600061218595

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.1751291824462378

> <JCHEM_PKA_STRONGEST_BASIC>
8.908154644432404

> <JCHEM_POLAR_SURFACE_AREA>
113.37

> <JCHEM_REFRACTIVITY>
149.00509999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
{3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2E,7R,9E)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulfonic acid

> <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      -5.335  16.940   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  16.170   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.001  14.630   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  13.860   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334  14.630   0.000  0.00  0.00           O+0
HETATM    6  S   UNK     0       0.000  13.860   0.000  0.00  0.00           S+0
HETATM    7  O   UNK     0      -0.770  12.526   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.770  15.194   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.334  13.090   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.667  12.320   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001  10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.000   7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.335   7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002   7.700   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.772   6.366   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.232   9.034   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -5.335  12.320   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -8.002  12.320   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0      -9.336  11.550   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0      -9.336  10.010   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -10.669  12.320   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.335  13.860   0.000  0.00  0.00           C+0
HETATM   36 Br   UNK     0      -6.668  14.630   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    4   11                                                       
CONECT   11   10   12   29                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25                                                            
CONECT   29   11   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   29    3   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   72    0
END

View in JSmol

Synonyms

Value	Source
{3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2E,7R,9E)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulfonate	Generator
{3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2E,7R,9E)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulphonate	Generator
{3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2E,7R,9E)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulphonic acid	Generator

Chemical Formula

C₂₆H₄₀BrNO₇S

Average Mass

590.5700 Da

Monoisotopic Mass

589.17089 Da

IUPAC Name

{3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2E,7R,9E)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulfonic acid

Traditional Name

{3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2E,7R,9E)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

COC1=C(OS(O)(=O)=O)C=C(C\C=C(/C)CCC[C@@H](C)C(=O)\C=C\C(C)(C)O)C(CCN(C)C)=C1Br

InChI Identifier

InChI=1S/C26H40BrNO7S/c1-18(9-8-10-19(2)22(29)13-15-26(3,4)30)11-12-20-17-23(35-36(31,32)33)25(34-7)24(27)21(20)14-16-28(5)6/h11,13,15,17,19,30H,8-10,12,14,16H2,1-7H3,(H,31,32,33)/b15-13+,18-11+/t19-/m1/s1

InChI Key

FHQXWTAEQCEPFE-BAVCCXCYSA-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
Aplysia kurodai	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Farsesane sesquiterpenoid
Phenylsulfate
Arylsulfate
Phenethylamine
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Bromobenzene
Halobenzene
Aralkylamine
Aryl bromide
Aryl halide
Monocyclic benzene moiety
Benzenoid
Sulfuric acid ester
Sulfuric acid monoester
Sulfate-ester
Tertiary alcohol
Acryloyl-group
Enone
Organic sulfuric acid or derivatives
Alpha,beta-unsaturated ketone
Tertiary aliphatic amine
Tertiary amine
Ketone
Ether
Hydrocarbon derivative
Organic oxide
Organohalogen compound
Carbonyl group
Organopnictogen compound
Organic nitrogen compound
Alcohol
Amine
Organic oxygen compound
Organobromide
Organonitrogen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	4.18	ChemAxon
pKa (Strongest Acidic)	-2.2	ChemAxon
pKa (Strongest Basic)	8.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	113.37 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	149.01 m³·mol⁻¹	ChemAxon
Polarizability	59.73 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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

163185285

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2e,7r,9e)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulfonic acid (NP0192677)

MOL for NP0192677 ({3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2e,7r,9e)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulfonic acid)

3D MOL for NP0192677 ({3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2e,7r,9e)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulfonic acid)

3D SDF for NP0192677 ({3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2e,7r,9e)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulfonic acid)

3D-SDF for NP0192677 ({3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2e,7r,9e)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulfonic acid)

PDB for NP0192677 ({3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2e,7r,9e)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulfonic acid)

3D PDB for NP0192677 ({3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2e,7r,9e)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulfonic acid)

SMILES for NP0192677 ({3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2e,7r,9e)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulfonic acid)

INCHI for NP0192677 ({3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2e,7r,9e)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulfonic acid)

Structure for NP0192677 ({3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2e,7r,9e)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulfonic acid)

3D Structure for NP0192677 ({3-bromo-4-[2-(dimethylamino)ethyl]-5-[(2e,7r,9e)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,9-dien-1-yl]-2-methoxyphenyl}oxidanesulfonic acid)