NP-MRD: Showing NP-Card for 3,5-Dibromo-4-[3-(dimethylamino)propoxy]cinnamic acid (NP0141324)

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Record Information

Version

2.0

Created at

2022-06-29 22:44:43 UTC

Updated at

2022-06-29 22:44:43 UTC

NP-MRD ID

NP0141324

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,5-Dibromo-4-[3-(dimethylamino)propoxy]cinnamic acid

Description

3-{3,5-Dibromo-4-[3-(dimethylamino)propoxy]phenyl}prop-2-enoic acid belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. 3-{3,5-Dibromo-4-[3-(dimethylamino)propoxy]phenyl}prop-2-enoic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 37  0  0  0  0  0  0  0  0999 V2000
   -5.5692    0.6586    0.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7320   -0.3939   -0.1840 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9217   -1.6258    0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3735    0.0227   -0.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8167    0.2520    1.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3752    0.7188    0.9197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7092   -0.3171    0.2326 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6058   -0.2990   -0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0470    0.1897   -1.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2509    0.8676   -2.5388 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.3754    0.2105   -1.6985 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3348   -0.2874   -0.8175 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7442   -0.2785   -1.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6676   -0.7245   -0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0698   -0.6799   -0.8343 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3203   -0.2127   -1.9659 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0919   -1.1404   -0.0299 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9140   -0.7825    0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5562   -0.7865    0.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0427   -1.4885    2.4345 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.9994    1.6031    0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3605    0.9501   -0.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1122    0.4185    1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0159   -1.8768    0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3420   -2.4264   -0.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6223   -1.5732    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3697    0.9739   -0.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7337   -0.6779   -0.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8077   -0.7294    1.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3997    0.9338    1.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9181    0.9782    1.8950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4064    1.6555    0.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7063    0.5972   -2.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9800    0.1280   -2.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4654   -1.1170    0.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3315   -0.5822    0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5829   -1.1884    1.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 17  1  0
 15 16  2  0
 12 18  1  0
 18 19  2  0
 19 20  1  0
 19  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 17 36  1  0
 18 37  1  0
M  END


  Mrv1533004191523022D          

 20 20  0  0  0  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 Br  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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 12  1  4  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  2  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0141324

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(C)CCCOC1=C(Br)C=C(C=CC(O)=O)C=C1Br

> <INCHI_IDENTIFIER>
InChI=1S/C14H17Br2NO3/c1-17(2)6-3-7-20-14-11(15)8-10(9-12(14)16)4-5-13(18)19/h4-5,8-9H,3,6-7H2,1-2H3,(H,18,19)

> <INCHI_KEY>
CEJAIYZSSZZLIZ-UHFFFAOYSA-N

> <FORMULA>
C14H17Br2NO3

> <MOLECULAR_WEIGHT>
407.102

> <EXACT_MASS>
404.957519

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
34.90876509847186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}prop-2-enoic acid

> <ALOGPS_LOGP>
3.69

> <JCHEM_LOGP>
0.8634119172855441

> <ALOGPS_LOGS>
-4.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.329946598060896

> <JCHEM_PKA_STRONGEST_BASIC>
9.256705557285647

> <JCHEM_POLAR_SURFACE_AREA>
49.769999999999996

> <JCHEM_REFRACTIVITY>
87.6532

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.69e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       4.001  -6.930   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   10 Br   UNK     0      12.003  -5.390   0.000  0.00  0.00          Br+0
HETATM   11  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      17.338 -11.550   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      16.004 -13.860   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   20 Br   UNK     0       9.336 -10.010   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   12   19                                                       
CONECT   19   18    8   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
3-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}prop-2-enoate	Generator

Chemical Formula

C₁₄H₁₇Br₂NO₃

Average Mass

407.1020 Da

Monoisotopic Mass

404.95752 Da

IUPAC Name

3-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}prop-2-enoic acid

Traditional Name

3-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

CN(C)CCCOC1=C(Br)C=C(C=CC(O)=O)C=C1Br

InChI Identifier

InChI=1S/C14H17Br2NO3/c1-17(2)6-3-7-20-14-11(15)8-10(9-12(14)16)4-5-13(18)19/h4-5,8-9H,3,6-7H2,1-2H3,(H,18,19)

InChI Key

CEJAIYZSSZZLIZ-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acids

Direct Parent

Cinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Phenoxy compound
Phenol ether
Styrene
Alkyl aryl ether
Bromobenzene
Halobenzene
Aryl bromide
Aryl halide
Monocyclic benzene moiety
Benzenoid
Amino acid or derivatives
Amino acid
Tertiary aliphatic amine
Tertiary amine
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organohalogen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Amine
Organic oxide
Organopnictogen compound
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	3.69	ALOGPS
logP	0.86	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	2.33	ChemAxon
pKa (Strongest Basic)	9.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	87.65 m³·mol⁻¹	ChemAxon
Polarizability	34.91 Å³	ChemAxon
Number of Rings	1	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

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

72994280

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3,5-Dibromo-4-[3-(dimethylamino)propoxy]cinnamic acid (NP0141324)

MOL for NP0141324 (3,5-Dibromo-4-[3-(dimethylamino)propoxy]cinnamic acid)

3D MOL for NP0141324 (3,5-Dibromo-4-[3-(dimethylamino)propoxy]cinnamic acid)

3D SDF for NP0141324 (3,5-Dibromo-4-[3-(dimethylamino)propoxy]cinnamic acid)

3D-SDF for NP0141324 (3,5-Dibromo-4-[3-(dimethylamino)propoxy]cinnamic acid)

PDB for NP0141324 (3,5-Dibromo-4-[3-(dimethylamino)propoxy]cinnamic acid)

3D PDB for NP0141324 (3,5-Dibromo-4-[3-(dimethylamino)propoxy]cinnamic acid)

SMILES for NP0141324 (3,5-Dibromo-4-[3-(dimethylamino)propoxy]cinnamic acid)

INCHI for NP0141324 (3,5-Dibromo-4-[3-(dimethylamino)propoxy]cinnamic acid)

Structure for NP0141324 (3,5-Dibromo-4-[3-(dimethylamino)propoxy]cinnamic acid)

3D Structure for NP0141324 (3,5-Dibromo-4-[3-(dimethylamino)propoxy]cinnamic acid)