NP-MRD: Showing NP-Card for Fructose-1P (NP0000751)

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Record Information

Version

1.0

Created at

2017-03-23 03:12:34 UTC

Updated at

2021-10-07 20:38:22 UTC

NP-MRD ID

NP0000751

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Fructose-1P

Description

Fructose 1-phosphate, also known as D-fructose-1-p, belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. Metabolism of fructose thus essentially results in intermediates of glycolysis. The final product of glycolysis (pyruvate) may then undergo gluconeogenesis, enter the TCA cycle or be stored as fatty acids. Fructose 1-phosphate exists in all living organisms, ranging from bacteria to humans. Within humans, fructose 1-phosphate participates in a number of enzymatic reactions. In particular, fructose 1-phosphate can be biosynthesized from D-fructose through the action of the enzyme ketohexokinase. In addition, fructose 1-phosphate can be converted into dihydroxyacetone phosphate and glyceraldehyde; which is catalyzed by the enzyme fructose-bisphosphate aldolase a. Because fructokinase has a high Vmax fructose entering cells is quickly phosphorylated to fructose 1-phosphate. In humans, fructose 1-phosphate is involved in fructose intolerance, hereditary. Hypoglycemia results from inhibition of glycogenolysis and gluconeogenesis. It is generated mainly by hepatic fructokinase but is also generated in smaller amounts in the small intestinal mucosa and proximal epithelium of the renal tubule. Aldolase B converts it into glyceraldehyde and dihydroxyacetone phosphate (DHAP). Symptoms of hereditary fructose intolerance are apathy, drowsiness, sweatiness and tremulousness.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
   -4.2181   -2.8058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7951   -1.3667    0.0000 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.3720    0.0724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2342   -0.9436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3559   -1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2700   -0.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841    0.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3267    1.2516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7315   -0.9083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1444   -0.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4976   -1.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8508   -3.3203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1021    1.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5977    0.9801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6630    1.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2341    2.9048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4068    1.1583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5873    0.5142    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2352   -1.8409    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3048    0.3310    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2551    2.4645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6312   -0.2058    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9554   -1.5093    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0398   -2.2157    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2899   -3.7434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3724    2.5702    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4447    2.2181    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3276    2.2213    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3185    4.0929    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  6
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15  7  1  0
  3 17  1  0
  4 18  1  0
  6 19  1  1
  6 20  1  0
  8 21  1  0
 10 22  1  6
 11 23  1  6
 11 24  1  0
 12 25  1  0
 13 26  1  1
 14 27  1  0
 15 28  1  6
 16 29  1  0
M  END

HMDB0001076
     RDKit          3D
Fructose 1-phosphate
 29 29  0  0  0  0  0  0  0  0999 V2000
    4.3041    1.6591    0.4839 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5075    0.4289    0.1577 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.3646   -0.5874    1.4974 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1975   -0.4441   -1.1259 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9290    0.8658   -0.2985 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1903   -0.3132   -0.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1681   -0.0742   -0.9315 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1625   -0.1913   -2.3181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0110   -1.0657   -0.4336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6936   -0.4994    0.6534 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8768   -1.3521    0.9887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3782   -2.4685    1.6789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0842    0.8388    0.0352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5701    1.7309    0.9729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7014    1.2502   -0.4612 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7506    2.2165   -1.4410 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1392   -1.5049    1.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7154   -1.1845   -0.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0335   -0.6601    0.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7265   -1.1144   -0.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2301    0.6022   -2.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0332   -0.2811    1.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6096   -0.8292    1.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3181   -1.7401    0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8493   -3.0290    1.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7877    0.6929   -0.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2683    2.6620    0.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1417    1.6104    0.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0667    2.7813   -1.3231 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
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15  7  1  0
  3 17  1  0
  4 18  1  0
  6 19  1  0
  6 20  1  0
  8 21  1  0
 10 22  1  1
 11 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  6
 14 27  1  0
 15 28  1  1
 16 29  1  0
M  END


     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
   -4.2181   -2.8058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7951   -1.3667    0.0000 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.3720    0.0724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2342   -0.9436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3559   -1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2700   -0.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841    0.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3267    1.2516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7315   -0.9083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1444   -0.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4976   -1.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8508   -3.3203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1021    1.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5977    0.9801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6630    1.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2341    2.9048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4068    1.1583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5873    0.5142    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2352   -1.8409    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3048    0.3310    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2551    2.4645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6312   -0.2058    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9554   -1.5093    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0398   -2.2157    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2899   -3.7434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3724    2.5702    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4447    2.2181    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3276    2.2213    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3185    4.0929    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  6
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15  7  1  0
  3 17  1  0
  4 18  1  0
  6 19  1  1
  6 20  1  0
  8 21  1  0
 10 22  1  6
 11 23  1  6
 11 24  1  0
 12 25  1  0
 13 26  1  1
 14 27  1  0
 15 28  1  6
 16 29  1  0
M  END
> <DATABASE_ID>
NP0000751

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@](O)(COP(O)(O)=O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C6H13O9P/c7-1-3-4(8)5(9)6(10,15-3)2-14-16(11,12)13/h3-5,7-10H,1-2H2,(H2,11,12,13)/t3-,4-,5+,6-/m1/s1

> <INCHI_KEY>
RHKKZBWRNHGJEZ-ARQDHWQXSA-N

> <FORMULA>
C6H13O9P

> <MOLECULAR_WEIGHT>
260.1358

> <EXACT_MASS>
260.029718526

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
21.063454724506986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}phosphonic acid

> <ALOGPS_LOGP>
-2.11

> <JCHEM_LOGP>
-2.881565349333333

> <ALOGPS_LOGS>
-0.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.189865965130803

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1613270396969364

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9814292193362135

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
47.2337

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.34e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001076
     RDKit          3D
Fructose 1-phosphate
 29 29  0  0  0  0  0  0  0  0999 V2000
    4.3041    1.6591    0.4839 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5075    0.4289    0.1577 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.3646   -0.5874    1.4974 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1975   -0.4441   -1.1259 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9290    0.8658   -0.2985 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1903   -0.3132   -0.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1681   -0.0742   -0.9315 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1625   -0.1913   -2.3181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0110   -1.0657   -0.4336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6936   -0.4994    0.6534 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8768   -1.3521    0.9887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3782   -2.4685    1.6789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0842    0.8388    0.0352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5701    1.7309    0.9729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7014    1.2502   -0.4612 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7506    2.2165   -1.4410 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1392   -1.5049    1.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7154   -1.1845   -0.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0335   -0.6601    0.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7265   -1.1144   -0.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2301    0.6022   -2.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0332   -0.2811    1.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6096   -0.8292    1.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3181   -1.7401    0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8493   -3.0290    1.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7877    0.6929   -0.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2683    2.6620    0.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1417    1.6104    0.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0667    2.7813   -1.3231 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
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15  7  1  0
  3 17  1  0
  4 18  1  0
  6 19  1  0
  6 20  1  0
  8 21  1  0
 10 22  1  1
 11 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  6
 14 27  1  0
 15 28  1  1
 16 29  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0      16.341 -17.116   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      17.485 -16.086   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.950 -16.562   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      20.196 -15.657   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      21.442 -16.562   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      22.726 -17.179   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      22.472 -15.417   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      23.979 -15.737   0.000  0.00  0.00           O+0
HETATM    9  P   UNK     0      25.009 -14.593   0.000  0.00  0.00           P+0
HETATM   10  O   UNK     0      26.154 -15.623   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      23.865 -13.563   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      26.040 -13.449   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      20.966 -18.026   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      21.871 -19.272   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      19.426 -18.026   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      18.521 -19.272   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   13                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13    5   14   15                                                  
CONECT   14   13                                                            
CONECT   15    3   13   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0001076
HETATM    1  O1  UNL     1       4.304   1.659   0.484  1.00  0.00           O  
HETATM    2  P1  UNL     1       3.508   0.429   0.158  1.00  0.00           P  
HETATM    3  O2  UNL     1       3.365  -0.587   1.497  1.00  0.00           O  
HETATM    4  O3  UNL     1       4.197  -0.444  -1.126  1.00  0.00           O  
HETATM    5  O4  UNL     1       1.929   0.866  -0.299  1.00  0.00           O  
HETATM    6  C1  UNL     1       1.190  -0.313  -0.323  1.00  0.00           C  
HETATM    7  C2  UNL     1      -0.168  -0.074  -0.931  1.00  0.00           C  
HETATM    8  O5  UNL     1      -0.162  -0.191  -2.318  1.00  0.00           O  
HETATM    9  O6  UNL     1      -1.011  -1.066  -0.434  1.00  0.00           O  
HETATM   10  C3  UNL     1      -1.694  -0.499   0.653  1.00  0.00           C  
HETATM   11  C4  UNL     1      -2.877  -1.352   0.989  1.00  0.00           C  
HETATM   12  O7  UNL     1      -2.378  -2.468   1.679  1.00  0.00           O  
HETATM   13  C5  UNL     1      -2.084   0.839   0.035  1.00  0.00           C  
HETATM   14  O8  UNL     1      -2.570   1.731   0.973  1.00  0.00           O  
HETATM   15  C6  UNL     1      -0.701   1.250  -0.461  1.00  0.00           C  
HETATM   16  O9  UNL     1      -0.751   2.217  -1.441  1.00  0.00           O  
HETATM   17  H1  UNL     1       3.139  -1.505   1.220  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.715  -1.185  -0.740  1.00  0.00           H  
HETATM   19  H3  UNL     1       1.034  -0.660   0.729  1.00  0.00           H  
HETATM   20  H4  UNL     1       1.727  -1.114  -0.882  1.00  0.00           H  
HETATM   21  H5  UNL     1       0.230   0.602  -2.748  1.00  0.00           H  
HETATM   22  H6  UNL     1      -1.033  -0.281   1.504  1.00  0.00           H  
HETATM   23  H7  UNL     1      -3.610  -0.829   1.621  1.00  0.00           H  
HETATM   24  H8  UNL     1      -3.318  -1.740   0.059  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.849  -3.029   1.045  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.788   0.693  -0.823  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.268   2.662   0.766  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.142   1.610   0.438  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.067   2.781  -1.323  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4    5
CONECT    3   17
CONECT    4   18
CONECT    5    6
CONECT    6    7   19   20
CONECT    7    8    9   15
CONECT    8   21
CONECT    9   10
CONECT   10   11   13   22
CONECT   11   12   23   24
CONECT   12   25
CONECT   13   14   15   26
CONECT   14   27
CONECT   15   16   28
CONECT   16   29
END

HMDB0001076
     RDKit          3D
Fructose 1-phosphate
 29 29  0  0  0  0  0  0  0  0999 V2000
    4.3041    1.6591    0.4839 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5075    0.4289    0.1577 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.3646   -0.5874    1.4974 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1975   -0.4441   -1.1259 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9290    0.8658   -0.2985 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1903   -0.3132   -0.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1681   -0.0742   -0.9315 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1625   -0.1913   -2.3181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0110   -1.0657   -0.4336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6936   -0.4994    0.6534 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8768   -1.3521    0.9887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3782   -2.4685    1.6789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0842    0.8388    0.0352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5701    1.7309    0.9729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7014    1.2502   -0.4612 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7506    2.2165   -1.4410 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1392   -1.5049    1.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7154   -1.1845   -0.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0335   -0.6601    0.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7265   -1.1144   -0.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2301    0.6022   -2.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0332   -0.2811    1.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6096   -0.8292    1.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3181   -1.7401    0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8493   -3.0290    1.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7877    0.6929   -0.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2683    2.6620    0.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1417    1.6104    0.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0667    2.7813   -1.3231 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
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15  7  1  0
  3 17  1  0
  4 18  1  0
  6 19  1  0
  6 20  1  0
  8 21  1  0
 10 22  1  1
 11 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  6
 14 27  1  0
 15 28  1  1
 16 29  1  0
M  END

View in JSmol

Synonyms

Value	Source
beta-D-Fructose 1-phosphate	ChEBI
b-D-Fructose 1-phosphate	Generator
b-D-Fructose 1-phosphoric acid	Generator
beta-D-Fructose 1-phosphoric acid	Generator
Β-D-fructose 1-phosphate	Generator
Β-D-fructose 1-phosphoric acid	Generator
Fructose 1-phosphoric acid	Generator
D-Fructose 1-phosphate	HMDB
D-Fructose-1-p	HMDB
D-Fructose-1-phosphate	HMDB
Fructose-1-p	HMDB
Fructose-1-phosphate	HMDB
b-D-Fructofuranose 1-phosphate	HMDB
b-D-Fructofuranose 1-phosphoric acid	HMDB
beta-D-Fructofuranose 1-phosphoric acid	HMDB
Β-D-fructofuranose 1-phosphate	HMDB
Β-D-fructofuranose 1-phosphoric acid	HMDB

Chemical Formula

C₆H₁₂O₆

Average Mass

180.1559 Da

Monoisotopic Mass

180.06339 Da

IUPAC Name

{[(2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}phosphonic acid

Traditional Name

[(2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxyphosphonic acid

CAS Registry Number

57-48-7

SMILES

[H][C@@](O)(CO)[C@@]([H])(O)[C@]([H])(O)C(=O)CO

InChI Identifier

InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5-,6-/m1/s1

InChI Key

BJHIKXHVCXFQLS-UYFOZJQFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Actinidia hemsleyana	LOTUS Database	35616633
Allium cepa	LOTUS Database	35616633
Allium suworowii	LOTUS Database	35616633
Aloe vera	LOTUS Database	35616633
Alstroemeria revoluta	LOTUS Database	35616633
Anethum graveolens	LOTUS Database	35616633
Annona squamosa	LOTUS Database	35616633
Arabidopsis thaliana	LOTUS Database	35616633
Arbutus unedo	LOTUS Database	35616633
Aristolochia arcuata	LOTUS Database	35616633
Aristolochia baetica	LOTUS Database	35616633
Ascoseira mirabilis	LOTUS Database	35616633
Astragalus hamosus	LOTUS Database	35616633
Bryum capillare	LOTUS Database	35616633
Cajanus cajan	LOTUS Database	35616633
Cannabis sativa	LOTUS Database	35616633
Carum carvi	LOTUS Database	35616633
Centaurea jacea	LOTUS Database	35616633
Colchicum schimperi	LOTUS Database	35616633
Coriandrum sativum	LOTUS Database	35616633
Cucurbita foetidissima	LOTUS Database	35616633
Dovyalis caffra	LOTUS Database	35616633
Euphorbia helioscopia	LOTUS Database	35616633
Evernia prunastri	LOTUS Database	35616633
Foeniculum vulgare	LOTUS Database	35616633
Fragaria x ananassa	LOTUS Database	35616633
Gastrodia elata	LOTUS Database	35616633
Gentiana orbicularis	LOTUS Database	35616633
Glycine max	LOTUS Database	35616633
Glycyrrhiza glabra	LOTUS Database	35616633
Helianthus annuus	LOTUS Database	35616633
Hypericum perforatum	LOTUS Database	35616633
Inga spectabilis	LOTUS Database	35616633
Levisticum officinale	LOTUS Database	35616633
Ligularia intermedia	LOTUS Database	35616633
Maclura pomifera	LOTUS Database	35616633
Marsdenia tomentosa	LOTUS Database	35616633
Medicago sativa	LOTUS Database	35616633
Momordica cochinchinensis	LOTUS Database	35616633
Mus musculus	LOTUS Database	35616633
Nicotiana tabacum	LOTUS Database	35616633
Olea europaea	LOTUS Database	35616633
Olearia paniculata	LOTUS Database	35616633
Panax ginseng	LOTUS Database	35616633
Panax quinquefolius	LOTUS Database	35616633
Passiflora oerstedii	LOTUS Database	35616633
Phaseolus coccineus	LOTUS Database	35616633
Phyllostachys edulis	LOTUS Database	35616633
Piper retrofractum	LOTUS Database	35616633
Pisum sativum	LOTUS Database	35616633
Planchonella vitiensis	LOTUS Database	35616633
Plinia cauliflora	LOTUS Database	35616633
Prunus avium	Plant	KNApSAcK
Prunus domestica	LOTUS Database	35616633
Prunus laurocerasus	LOTUS Database	35616633
Psidium guajava	LOTUS Database	35616633
Pycnandra acuminata	LOTUS Database	35616633
Pyrus communis	LOTUS Database	35616633
Rehmannia glutinosa	LOTUS Database	35616633
Salacia oblonga	LOTUS Database	35616633
Salacia reticulata	LOTUS Database	35616633
Salsola collina	LOTUS Database	35616633
Schleichera oleosa	LOTUS Database	35616633
Streptomyces murinus	LOTUS Database	35616633
Tamarix aphylla	LOTUS Database	35616633
Tecoma stans	LOTUS Database	35616633
Tetrapleura tetraptera	LOTUS Database	35616633
Theobroma cacao	LOTUS Database	35616633
Theonella swinhoei	-	KNApSAcK
Tillandsia usneoides	LOTUS Database	35616633
Torilis japonica	LOTUS Database	35616633
Tragopogon pratensis	LOTUS Database	35616633
Tulipa turkestanica	LOTUS Database	35616633
Turnera diffusa	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633
Xylocarpus granatum	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Escherichia coli	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexose phosphates

Alternative Parents

Substituents

Hexose phosphate
Pentose phosphate
Pentose-5-phosphate
C-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
Pentose monosaccharide
Monoalkyl phosphate
Organic phosphoric acid derivative
Alkyl phosphate
Phosphoric acid ester
Tetrahydrofuran
Secondary alcohol
Hemiacetal
Organoheterocyclic compound
Oxacycle
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	399 g/l	Tetko, I. V., Gasteiger, J., Todeschini, R., Mauri, A., Livingstone, D., Ertl, P., Palyulin, V.A., Radchenko, E.V., Zefirov, N.S., Makarenko, A.S., Tanchuk, V.Y. & Prokopenko, V. V. (2005). Virtual computational chemistry laboratory-design and description. Journal of computer-aided molecular design, 19(6), 453-463. (http://www.vcclab.org/lab/alogps/)
LogP	-2.23	Tetko, I. V., Gasteiger, J., Todeschini, R., Mauri, A., Livingstone, D., Ertl, P., Palyulin, V.A., Radchenko, E.V., Zefirov, N.S., Makarenko, A.S., Tanchuk, V.Y. & Prokopenko, V. V. (2005). Virtual computational chemistry laboratory-design and description. Journal of computer-aided molecular design, 19(6), 453-463. (http://www.vcclab.org/lab/alogps/)

Predicted Properties

Property	Value	Source
logP	-2.1	ALOGPS
logP	-2.9	ChemAxon
logS	-0.89	ALOGPS
pKa (Strongest Acidic)	1.16	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	47.23 m³·mol⁻¹	ChemAxon
Polarizability	21.06 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0001076

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

139419

Good Scents ID

Not Available

References

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
Alvarez E, Roncero I, Chowen JA, Vazquez P, Blazquez E: Evidence that glucokinase regulatory protein is expressed and interacts with glucokinase in rat brain. J Neurochem. 2002 Jan;80(1):45-53. doi: 10.1046/j.0022-3042.2001.00677.x. [PubMed:11796742 ]
Malaisse WJ: [Metabolic interactions between glucose and fructose]. Bull Mem Acad R Med Belg. 2002;157(7-9):349-52; discussion 352-3. [PubMed:12647375 ]
Watford M: Small amounts of dietary fructose dramatically increase hepatic glucose uptake through a novel mechanism of glucokinase activation. Nutr Rev. 2002 Aug;60(8):253-7. doi: 10.1301/002966402320289377. [PubMed:12199300 ]

Showing NP-Card for Fructose-1P (NP0000751)

MOL for NP0000751 (Fructose-1P)

3D MOL for NP0000751 (Fructose-1P)

3D SDF for NP0000751 (Fructose-1P)

3D-SDF for NP0000751 (Fructose-1P)

PDB for NP0000751 (Fructose-1P)

3D PDB for NP0000751 (Fructose-1P)

SMILES for NP0000751 (Fructose-1P)

INCHI for NP0000751 (Fructose-1P)

Structure for NP0000751 (Fructose-1P)

3D Structure for NP0000751 (Fructose-1P)