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Showing NP-Card for DL-3,4-dihydroxymandelic acid (NP0002848)

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Record Information
Version1.0
Created at2020-11-23 19:41:56 UTC
Updated at2021-08-12 19:52:19 UTC
NP-MRD IDNP0002848
Secondary Accession NumbersNone
Natural Product Identification
Common NameDL-3,4-dihydroxymandelic acid
Provided ByBMRBBMRB logo
Description It was first documented in 2008 (PMID: 17984079). Based on a literature review very few articles have been published on (2R)-2-(3,4-dihydroxyphenyl)-2-hydroxyacetic acid.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002848 (DL-3,4-dihydroxymandelic acid)


     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
   -1.9567    1.4300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4572    0.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9531    0.5688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8055   -0.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1537   -2.2442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4545   -0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3434    1.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0076    1.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2475    1.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5985    1.7139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1365   -0.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3764   -1.2779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7855   -1.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6049    1.9198    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1565   -1.5450    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9978   -3.4842    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1656    1.9754    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1186    3.4021    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8385    0.8698    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2654   -2.7738    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6744   -2.5814    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13  6  1  0
  3 14  1  0
  4 15  1  6
  5 16  1  0
  7 17  1  0
  8 18  1  0
 10 19  1  0
 12 20  1  0
 13 21  1  0
M  END
Download

3D MOL for NP0002848 (DL-3,4-dihydroxymandelic acid)

NP0002848
     RDKit          3D

 21 21  0  0  0  0  0  0  0  0999 V2000
   -2.1118    1.0083    2.0232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5099    0.4413    0.9835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6538   -0.3257    1.0384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7786    0.5723   -0.3199 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4211   -0.1492   -1.3151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3720    0.1406   -0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1053   -1.2145   -0.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1888   -1.6711    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2094   -0.7762    0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5135   -1.2188    0.2685 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9888    0.5905    0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0465    1.4753    0.2290 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860    1.0279   -0.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6936   -1.2058    0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7702    1.6533   -0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3573    0.3912   -2.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8758   -1.9754   -0.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -2.7352    0.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2972   -0.5850    0.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8419    2.4597    0.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4499    2.0964   -0.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13  6  1  0
  3 14  1  0
  4 15  1  6
  5 16  1  0
  7 17  1  0
  8 18  1  0
 10 19  1  0
 12 20  1  0
 13 21  1  0
M  END
Download

3D SDF for NP0002848 (DL-3,4-dihydroxymandelic acid)


     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
   -1.9567    1.4300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4572    0.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9531    0.5688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8055   -0.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1537   -2.2442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4545   -0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3434    1.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0076    1.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2475    1.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5985    1.7139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1365   -0.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3764   -1.2779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7855   -1.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6049    1.9198    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1565   -1.5450    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9978   -3.4842    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1656    1.9754    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1186    3.4021    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8385    0.8698    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2654   -2.7738    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6744   -2.5814    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13  6  1  0
  3 14  1  0
  4 15  1  6
  5 16  1  0
  7 17  1  0
  8 18  1  0
 10 19  1  0
 12 20  1  0
 13 21  1  0
M  END
> <DATABASE_ID>
NP0002848

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O5/c9-5-2-1-4(3-6(5)10)7(11)8(12)13/h1-3,7,9-11H,(H,12,13)/t7-/m1/s1

> <INCHI_KEY>
RGHMISIYKIHAJW-SSDOTTSWSA-N

> <FORMULA>
C8H8O5

> <MOLECULAR_WEIGHT>
184.147

> <EXACT_MASS>
184.037173358

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.52519608953186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2-(3,4-dihydroxyphenyl)-2-hydroxyacetic acid

> <JCHEM_LOGP>
0.28870500133333327

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.219357318675643

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9769258542306654

> <JCHEM_PKA_STRONGEST_BASIC>
-4.126018555289758

> <JCHEM_POLAR_SURFACE_AREA>
97.99

> <JCHEM_REFRACTIVITY>
42.6656

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3,4 dihydroxymandelic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002848 (DL-3,4-dihydroxymandelic acid)

NP0002848
     RDKit          3D

 21 21  0  0  0  0  0  0  0  0999 V2000
   -2.1118    1.0083    2.0232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5099    0.4413    0.9835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6538   -0.3257    1.0384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7786    0.5723   -0.3199 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4211   -0.1492   -1.3151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3720    0.1406   -0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1053   -1.2145   -0.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1888   -1.6711    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2094   -0.7762    0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5135   -1.2188    0.2685 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9888    0.5905    0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0465    1.4753    0.2290 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860    1.0279   -0.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6936   -1.2058    0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7702    1.6533   -0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3573    0.3912   -2.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8758   -1.9754   -0.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -2.7352    0.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2972   -0.5850    0.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8419    2.4597    0.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4499    2.0964   -0.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13  6  1  0
  3 14  1  0
  4 15  1  6
  5 16  1  0
  7 17  1  0
  8 18  1  0
 10 19  1  0
 12 20  1  0
 13 21  1  0
M  END
Download

PDB for NP0002848 (DL-3,4-dihydroxymandelic acid)

HEADER    PROTEIN                                 23-NOV-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-NOV-20         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    5                                                       
CONECT    3    4    6                                                       
CONECT    4    1    3    7                                                  
CONECT    5    2    6    9                                                  
CONECT    6    3    5   10                                                  
CONECT    7    4    8   11                                                  
CONECT    8    7   12   13                                                  
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    8                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for NP0002848 (DL-3,4-dihydroxymandelic acid)

COMPND    NP0002848
HETATM    1  O1  UNL     1      -2.112   1.008   2.023  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.510   0.441   0.984  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.654  -0.326   1.038  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.779   0.572  -0.320  1.00  0.00           C  
HETATM    5  O3  UNL     1      -2.421  -0.149  -1.315  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.372   0.141  -0.163  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.105  -1.214  -0.140  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.189  -1.671   0.004  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.209  -0.776   0.123  1.00  0.00           C  
HETATM   10  O4  UNL     1       3.513  -1.219   0.268  1.00  0.00           O  
HETATM   11  C7  UNL     1       1.989   0.591   0.105  1.00  0.00           C  
HETATM   12  O5  UNL     1       3.046   1.475   0.229  1.00  0.00           O  
HETATM   13  C8  UNL     1       0.686   1.028  -0.040  1.00  0.00           C  
HETATM   14  H1  UNL     1      -3.694  -1.206   0.536  1.00  0.00           H  
HETATM   15  H2  UNL     1      -1.770   1.653  -0.555  1.00  0.00           H  
HETATM   16  H3  UNL     1      -2.357   0.391  -2.155  1.00  0.00           H  
HETATM   17  H4  UNL     1      -0.876  -1.975  -0.231  1.00  0.00           H  
HETATM   18  H5  UNL     1       1.427  -2.735   0.026  1.00  0.00           H  
HETATM   19  H6  UNL     1       4.297  -0.585   0.360  1.00  0.00           H  
HETATM   20  H7  UNL     1       2.842   2.460   0.211  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.450   2.096  -0.061  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5    6   15
CONECT    5   16
CONECT    6    7    7   13
CONECT    7    8   17
CONECT    8    9    9   18
CONECT    9   10   11
CONECT   10   19
CONECT   11   12   13   13
CONECT   12   20
CONECT   13   21
END
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SMILES for NP0002848 (DL-3,4-dihydroxymandelic acid)

O[C@@H](C(O)=O)C1=CC(O)=C(O)C=C1
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INCHI for NP0002848 (DL-3,4-dihydroxymandelic acid)

InChI=1S/C8H8O5/c9-5-2-1-4(3-6(5)10)7(11)8(12)13/h1-3,7,9-11H,(H,12,13)/t7-/m1/s1
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View in JSmol
Synonyms
ValueSource
(2R)-2-(3,4-Dihydroxyphenyl)-2-hydroxyacetateGenerator
Chemical FormulaC8H8O5
Average Mass184.1470 Da
Monoisotopic Mass184.03717 Da
IUPAC Name(2R)-2-(3,4-dihydroxyphenyl)-2-hydroxyacetic acid
Traditional Name3,4 dihydroxymandelic acid
CAS Registry NumberNot Available
SMILES
O[C@@H](C(O)=O)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C8H8O5/c9-5-2-1-4(3-6(5)10)7(11)8(12)13/h1-3,7,9-11H,(H,12,13)/t7-/m1/s1
InChI KeyRGHMISIYKIHAJW-SSDOTTSWSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.29ChemAxon
pKa (Strongest Acidic)2.98ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.67 m³·mol⁻¹ChemAxon
Polarizability16.53 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5323127
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6950181
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]