NP-MRD: Showing NP-Card for 2-(4-bromophenyl)-2-oxoethyl (2r,3r)-3-hydroxy-2-methylbutanoate (NP0297845)

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Record Information

Version

2.0

Created at

2022-09-10 08:34:09 UTC

Updated at

2022-09-10 08:34:09 UTC

NP-MRD ID

NP0297845

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(4-bromophenyl)-2-oxoethyl (2r,3r)-3-hydroxy-2-methylbutanoate

Description

2-(4-Bromophenyl)-2-oxoethyl (2R,3R)-3-hydroxy-2-methylbutanoate belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 2-(4-bromophenyl)-2-oxoethyl (2r,3r)-3-hydroxy-2-methylbutanoate is found in Cuscuta obtusiflora and Ipomoea capillacea. Based on a literature review very few articles have been published on 2-(4-bromophenyl)-2-oxoethyl (2R,3R)-3-hydroxy-2-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 33  0  0  0  0  0  0  0  0999 V2000
   -5.2949    0.3040    1.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8831    0.8320    0.9767 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4802    1.2549    2.2401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9517   -0.2620    0.4511 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4166   -0.7228   -0.9009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5522    0.2152    0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3069    1.3896    0.8707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4755   -0.5316    0.0463 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8464    0.0032    0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8476   -0.9450   -0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5012   -2.0849   -0.7799 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2430   -0.5645   -0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6951    0.6743   -0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0225    1.0468   -0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9711    0.1696   -0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7870    0.7256   -0.4934 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.5558   -1.0708   -0.8954 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2320   -1.4458   -0.8742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6342    0.2646    2.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3041   -0.7560    0.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0136    0.8502    0.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8395    1.7138    0.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4041    2.2430    2.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0992   -1.1281    1.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0663    0.0467   -1.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0190   -1.6709   -0.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5125   -0.9297   -1.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9346    0.9389   -0.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0506    0.1836    1.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9912    1.4092    0.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3261    2.0399    0.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3174   -1.7540   -1.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9317   -2.4390   -1.2107 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
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  6
  3 23  1  0
  4 24  1  1
  5 25  1  0
  5 26  1  0
  5 27  1  0
  9 28  1  0
  9 29  1  0
 13 30  1  0
 14 31  1  0
 17 32  1  0
 18 33  1  0
M  END


  Mrv1652309102210342D          

 18 18  0  0  1  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  1  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
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    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
    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 Br  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
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0297845

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)[C@@H](C)C(=O)OCC(=O)C1=CC=C(Br)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H15BrO4/c1-8(9(2)15)13(17)18-7-12(16)10-3-5-11(14)6-4-10/h3-6,8-9,15H,7H2,1-2H3/t8-,9-/m1/s1

> <INCHI_KEY>
ZQBYIWXDRNSUCD-RKDXNWHRSA-N

> <FORMULA>
C13H15BrO4

> <MOLECULAR_WEIGHT>
315.163

> <EXACT_MASS>
314.015372

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
28.34061825587611

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-bromophenyl)-2-oxoethyl (2R,3R)-3-hydroxy-2-methylbutanoate

> <JCHEM_LOGP>
2.302849317666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.050597290776931

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.662622632245899

> <JCHEM_PKA_STRONGEST_BASIC>
-2.786781615041403

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
70.33220000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-bromophenyl)-2-oxoethyl (2R,3R)-3-hydroxy-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   16 Br   UNK     0      14.670 -10.010   0.000  0.00  0.00          Br+0
HETATM   17  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
2-(4-Bromophenyl)-2-oxoethyl (2R,3R)-3-hydroxy-2-methylbutanoic acid	Generator

Chemical Formula

C₁₃H₁₅BrO₄

Average Mass

315.1630 Da

Monoisotopic Mass

314.01537 Da

IUPAC Name

2-(4-bromophenyl)-2-oxoethyl (2R,3R)-3-hydroxy-2-methylbutanoate

Traditional Name

2-(4-bromophenyl)-2-oxoethyl (2R,3R)-3-hydroxy-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

C[C@@H](O)[C@@H](C)C(=O)OCC(=O)C1=CC=C(Br)C=C1

InChI Identifier

InChI=1S/C13H15BrO4/c1-8(9(2)15)13(17)18-7-12(16)10-3-5-11(14)6-4-10/h3-6,8-9,15H,7H2,1-2H3/t8-,9-/m1/s1

InChI Key

ZQBYIWXDRNSUCD-RKDXNWHRSA-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
Cuscuta obtusiflora	LOTUS Database	35616633
Ipomoea capillacea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Benzoyl
Aryl alkyl ketone
Beta-hydroxy acid
Bromobenzene
Fatty acid ester
Halobenzene
Alpha-acyloxy ketone
Hydroxy acid
Aryl halide
Aryl bromide
Benzenoid
Monocyclic benzene moiety
Fatty acyl
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organobromide
Organohalogen compound
Alcohol
Organic oxide
Hydrocarbon derivative
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	2.3	ChemAxon
pKa (Strongest Acidic)	13.66	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	70.33 m³·mol⁻¹	ChemAxon
Polarizability	28.34 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

10394344

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14033792

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(4-bromophenyl)-2-oxoethyl (2r,3r)-3-hydroxy-2-methylbutanoate (NP0297845)

MOL for NP0297845 (2-(4-bromophenyl)-2-oxoethyl (2r,3r)-3-hydroxy-2-methylbutanoate)

3D MOL for NP0297845 (2-(4-bromophenyl)-2-oxoethyl (2r,3r)-3-hydroxy-2-methylbutanoate)

3D SDF for NP0297845 (2-(4-bromophenyl)-2-oxoethyl (2r,3r)-3-hydroxy-2-methylbutanoate)

3D-SDF for NP0297845 (2-(4-bromophenyl)-2-oxoethyl (2r,3r)-3-hydroxy-2-methylbutanoate)

PDB for NP0297845 (2-(4-bromophenyl)-2-oxoethyl (2r,3r)-3-hydroxy-2-methylbutanoate)

3D PDB for NP0297845 (2-(4-bromophenyl)-2-oxoethyl (2r,3r)-3-hydroxy-2-methylbutanoate)

SMILES for NP0297845 (2-(4-bromophenyl)-2-oxoethyl (2r,3r)-3-hydroxy-2-methylbutanoate)

INCHI for NP0297845 (2-(4-bromophenyl)-2-oxoethyl (2r,3r)-3-hydroxy-2-methylbutanoate)

Structure for NP0297845 (2-(4-bromophenyl)-2-oxoethyl (2r,3r)-3-hydroxy-2-methylbutanoate)

3D Structure for NP0297845 (2-(4-bromophenyl)-2-oxoethyl (2r,3r)-3-hydroxy-2-methylbutanoate)