Showing metabocard for L-3,4-Dihydroxybutan-2-one 4-phosphate (MMDBc0031764)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 01:48:23 UTC
Update Date2022-08-31 18:24:28 UTC
Metabolite IDMMDBc0031764
Metabolite Identification
Common NameL-3,4-Dihydroxybutan-2-one 4-phosphate
DescriptionL-3,4-Dihydroxybutan-2-one 4-phosphate is an intermediate involved in riboflavin metabolism. It is a substrate for the enzyme 6,7-dimethyl-8-ribityllumazine synthase which atalyzes the formation of 6,7-dimethyl-8-ribityllumazine by condensation of 5-amino-6-(D-ribitylamino)uracil with 3,4-dihydroxy-2-butanone 4-phosphate. This is the penultimate step in the biosynthesis of riboflavin.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f5abca584f8>


  Mrv1652303082008142D          

 11 10  0  0  0  0            999 V2000
    9.6785   -3.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3942   -4.1072    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9668   -4.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6785   -2.8722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1093   -3.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3942   -4.9307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8250   -4.1072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5394   -2.8697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2539   -4.1072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5394   -3.6947    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.7530   -4.4916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7 10  1  0  0  0  0
 10  8  2  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f5abca584f8>

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3D SDF for #<Metabolite:0x00007f5abca584f8>

  Mrv1652303082008142D          

 11 10  0  0  0  0            999 V2000
    9.6785   -3.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3942   -4.1072    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9668   -4.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6785   -2.8722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1093   -3.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3942   -4.9307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8250   -4.1072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5394   -2.8697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2539   -4.1072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5394   -3.6947    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.7530   -4.4916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7 10  1  0  0  0  0
 10  8  2  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031764

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H9O6P/c1-3(5)4(6)2-10-11(7,8)9/h4,6H,2H2,1H3,(H2,7,8,9)/t4-/m0/s1

> <INCHI_KEY>
OKYHYXLCTGGOLM-BYPYZUCNSA-N

> <FORMULA>
C4H9O6P

> <MOLECULAR_WEIGHT>
184.0844

> <EXACT_MASS>
184.013674532

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.379791410155622

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S)-2-hydroxy-3-oxobutoxy]phosphonic acid

> <ALOGPS_LOGP>
-1.62

> <JCHEM_LOGP>
-1.3126799933333335

> <ALOGPS_LOGS>
-0.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.415057530560526

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.388886854275381

> <JCHEM_PKA_STRONGEST_BASIC>
-3.847198471680728

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
34.8075

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.49e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-hydroxy-3-oxobutoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f5abca584f8>
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PDB for #<Metabolite:0x00007f5abca584f8>
HEADER    PROTEIN                                 08-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-MAR-20         0                                  
HETATM    1  C   UNK     0      18.067  -6.899   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.403  -7.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.738  -7.667   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      18.067  -5.361   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      20.737  -6.899   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      19.403  -9.204   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      22.073  -7.667   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      23.407  -5.357   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      24.741  -7.667   0.000  0.00  0.00           O+0
HETATM   10  P   UNK     0      23.407  -6.897   0.000  0.00  0.00           P+0
HETATM   11  O   UNK     0      23.806  -8.384   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    2    7                                                       
CONECT    6    2                                                            
CONECT    7    5   10                                                       
CONECT    8   10                                                            
CONECT    9   10                                                            
CONECT   10    7    8    9   11                                             
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for #<Metabolite:0x00007f5abca584f8>
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SMILES for #<Metabolite:0x00007f5abca584f8>
CC(=O)[C@@H](O)COP(O)(O)=O
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INCHI for #<Metabolite:0x00007f5abca584f8>
InChI=1S/C4H9O6P/c1-3(5)4(6)2-10-11(7,8)9/h4,6H,2H2,1H3,(H2,7,8,9)/t4-/m0/s1
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Synonyms
ValueSource
(3S)-3-Hydroxy-4-(phosphonooxy)butan-2-oneChEBI
(S)-3-Hydroxy-4-(phosphonooxy)-2-butanoneChEBI
1-Deoxy-L-glycero-tetrulose 4-phosphateChEBI
3,4-DHBPChEBI
3,4-Dihydroxy-2-butanone-4-phosphateChEBI
1-Deoxy-L-glycero-tetrulose 4-phosphoric acidGenerator
3,4-Dihydroxy-2-butanone-4-phosphoric acidGenerator
L-3,4-Dihydroxybutan-2-one 4-phosphoric acidGenerator
L-3,4-Dihydroxybutan-2-one 4-phosphateChEBI
(2S)-2-Hydroxy-3-oxobutoxyphosphonateGenerator
Molecular FormulaC4H9O6P
Average Mass184.0844
Monoisotopic Mass184.013674532
IUPAC Name[(2S)-2-hydroxy-3-oxobutoxy]phosphonic acid
Traditional Name(2S)-2-hydroxy-3-oxobutoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CC(=O)[C@@H](O)COP(O)(O)=O
InChI Identifier
InChI=1S/C4H9O6P/c1-3(5)4(6)2-10-11(7,8)9/h4,6H,2H2,1H3,(H2,7,8,9)/t4-/m0/s1
InChI KeyOKYHYXLCTGGOLM-BYPYZUCNSA-N