NP-MRD: Showing NP-Card for D-Fructose-1,6-bisphosphate (NP0002596)

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Record Information

Version

2.0

Created at

2020-11-23 18:24:54 UTC

Updated at

2021-08-12 19:51:36 UTC

NP-MRD ID

NP0002596

Secondary Accession Numbers

None

Natural Product Identification

Common Name

D-Fructose-1,6-bisphosphate

Provided By

BMRB

Description

Fructose 1,6-bisphosphate, also known as fosfructose, 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. Fructose 1,6-bisphosphate exists in all living organisms, ranging from bacteria to humans. In humans, fructose 1,6-bisphosphate is involved in the metabolic disorder called the glycogen storage disease type 1A (gsd1a) or von gierke disease pathway. Fructose 1,6-bisphosphate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. D-Fructose-1,6-bisphosphate is found in Mus musculus. D-Fructose-1,6-bisphosphate was first documented in 1993 (PMID: 8412001). Based on a literature review a small amount of articles have been published on Fructose 1,6-bisphosphate (PMID: 14693576) (PMID: 11916152).

Structure

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


     RDKit          2D

 34 34  0  0  0  0  0  0  0  0999 V2000
   -6.2611   -0.7208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9219   -0.0451    0.0000 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.5826    0.6305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5975    1.2941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2462   -1.3844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7486   -1.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2510   -1.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1963   -1.9475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0183   -0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1802   -1.6414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0832    0.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1481    1.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5955    1.0260    0.0000 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.9895    2.4733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2014   -0.4213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0428    0.6319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0790    0.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3403    1.2886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235   -0.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7059    1.3953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4981    2.1281    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7755    2.5488    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8473    0.0278    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8332   -2.9665    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4916   -3.0340    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396   -3.1220    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6754    1.0486    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1396   -0.7013    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2578   -1.4862    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4252   -0.8185    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4283    1.8883    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8005    0.9454    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8228   -0.1015    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7777    2.5736    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  0
  8  9  1  0
  9 10  1  6
  9 11  1  0
 11 12  1  0
 13 12  1  1
 13 14  2  0
 13 15  1  0
 13 16  1  0
  9 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  7  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  6
  6 24  1  0
  7 25  1  1
 10 26  1  0
 11 27  1  1
 11 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  1
 18 32  1  0
 19 33  1  6
 20 34  1  0
M  END

NP0002596
     RDKit          3D

 34 34  0  0  0  0  0  0  0  0999 V2000
   -3.8118   -0.7675    1.3222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3553   -0.4407   -0.0438 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.1647   -1.7818   -0.6527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5102    0.7892    0.1694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1843    0.1481   -1.0931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0852   -0.6965   -1.2132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1311   -0.3969   -0.0933 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1361   -0.9027   -0.2855 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0522    0.1250   -0.2177 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2662    0.6955   -1.4811 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3474   -0.2519    0.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0484   -1.2278   -0.2601 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6785   -1.0585    0.1966 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.7419   -0.4588    1.5925 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4611   -2.5450    0.2495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3813    1.1469    0.6913 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9714    2.3902    0.6208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0006    1.1121    0.0466 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9737    1.6734    0.8381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8044   -2.5871   -0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3659    0.4271    0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3773   -1.7578   -1.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5445   -0.4655   -2.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4898   -0.7977    0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6105    1.6232   -1.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1550   -0.5166    1.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9891    0.6631    0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0836    0.9169   -0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5215   -2.9253   -0.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505    0.7102    1.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5016    2.9607    1.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9338    1.5362   -0.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9792    2.6526    0.6354 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
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 19  7  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
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  7 25  1  1
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 11 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  1
 18 32  1  0
 19 33  1  6
 20 34  1  0
M  END


     RDKit          2D

 34 34  0  0  0  0  0  0  0  0999 V2000
   -6.2611   -0.7208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9219   -0.0451    0.0000 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.5826    0.6305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5975    1.2941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2462   -1.3844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7486   -1.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2510   -1.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1963   -1.9475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0183   -0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1802   -1.6414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0832    0.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1481    1.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5955    1.0260    0.0000 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.9895    2.4733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2014   -0.4213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0428    0.6319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0790    0.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3403    1.2886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235   -0.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7059    1.3953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4981    2.1281    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7755    2.5488    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8473    0.0278    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8332   -2.9665    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4916   -3.0340    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396   -3.1220    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6754    1.0486    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1396   -0.7013    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2578   -1.4862    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4252   -0.8185    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4283    1.8883    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8005    0.9454    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8228   -0.1015    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7777    2.5736    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  0
  8  9  1  0
  9 10  1  6
  9 11  1  0
 11 12  1  0
 13 12  1  1
 13 14  2  0
 13 15  1  0
 13 16  1  0
  9 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  7  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  6
  6 24  1  0
  7 25  1  1
 10 26  1  0
 11 27  1  1
 11 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  1
 18 32  1  0
 19 33  1  6
 20 34  1  0
M  END
> <DATABASE_ID>
NP0002596

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6-/m1/s1

> <INCHI_KEY>
RNBGYGVWRKECFJ-ARQDHWQXSA-N

> <FORMULA>
C6H14O12P2

> <MOLECULAR_WEIGHT>
340.1157

> <EXACT_MASS>
339.996048936

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
25.7026361336695

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.51

> <JCHEM_LOGP>
-3.0051313806666666

> <ALOGPS_LOGS>
-1.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.4935700215596834

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8894221949103738

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686727898823656

> <JCHEM_POLAR_SURFACE_AREA>
203.43999999999997

> <JCHEM_REFRACTIVITY>
58.10660000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.61e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

NP0002596
     RDKit          3D

 34 34  0  0  0  0  0  0  0  0999 V2000
   -3.8118   -0.7675    1.3222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3553   -0.4407   -0.0438 P   0  0  0  0  0  5  0  0  0  0  0  0
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   -3.1843    0.1481   -1.0931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0852   -0.6965   -1.2132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1311   -0.3969   -0.0933 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1361   -0.9027   -0.2855 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0522    0.1250   -0.2177 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2662    0.6955   -1.4811 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3474   -0.2519    0.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0484   -1.2278   -0.2601 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6785   -1.0585    0.1966 P   0  0  0  0  0  5  0  0  0  0  0  0
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    0.9714    2.3902    0.6208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0006    1.1121    0.0466 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9737    1.6734    0.8381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8044   -2.5871   -0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3659    0.4271    0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3773   -1.7578   -1.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5445   -0.4655   -2.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4898   -0.7977    0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6105    1.6232   -1.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1550   -0.5166    1.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9891    0.6631    0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0836    0.9169   -0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5215   -2.9253   -0.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505    0.7102    1.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5016    2.9607    1.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9338    1.5362   -0.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9792    2.6526    0.6354 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  0
  8  9  1  0
  9 10  1  6
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 13 16  1  0
  9 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  7  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  1
 10 26  1  0
 11 27  1  0
 11 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  1
 18 32  1  0
 19 33  1  6
 20 34  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  C   UNK     0    8669.2598667.744   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8670.5948666.977   0.000  0.00  0.00           O+0
HETATM    3  P   UNK     0    8671.9338667.744   0.000  0.00  0.00           P+0
HETATM    4  O   UNK     0    8671.1578669.083   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8673.2688666.977   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8672.7018669.083   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8669.1018665.984   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8668.3028664.269   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8664.9568664.284   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8664.0838667.744   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8662.7438666.977   0.000  0.00  0.00           O+0
HETATM   12  P   UNK     0    8661.4068667.744   0.000  0.00  0.00           P+0
HETATM   13  O   UNK     0    8662.1798669.083   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8660.0658666.973   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8660.6368669.083   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8666.6638667.898   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    8665.4178666.993   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8665.8938665.528   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8667.4338665.528   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8667.9088666.993   0.000  0.00  0.00           C+0
CONECT    1    2   20                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3                                                            
CONECT    7   20                                                            
CONECT    8   19                                                            
CONECT    9   18                                                            
CONECT   10   11   17                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16   17   20                                                       
CONECT   17   18   16   10                                                  
CONECT   18   17   19    9                                                  
CONECT   19   18   20    8                                                  
CONECT   20   19   16    1    7                                             
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    NP0002596
HETATM    1  O1  UNL     1      -3.812  -0.767   1.322  1.00  0.00           O  
HETATM    2  P1  UNL     1      -4.355  -0.441  -0.044  1.00  0.00           P  
HETATM    3  O2  UNL     1      -5.165  -1.782  -0.653  1.00  0.00           O  
HETATM    4  O3  UNL     1      -5.510   0.789   0.169  1.00  0.00           O  
HETATM    5  O4  UNL     1      -3.184   0.148  -1.093  1.00  0.00           O  
HETATM    6  C1  UNL     1      -2.085  -0.697  -1.213  1.00  0.00           C  
HETATM    7  C2  UNL     1      -1.131  -0.397  -0.093  1.00  0.00           C  
HETATM    8  O5  UNL     1       0.136  -0.903  -0.286  1.00  0.00           O  
HETATM    9  C3  UNL     1       1.052   0.125  -0.218  1.00  0.00           C  
HETATM   10  O6  UNL     1       1.266   0.696  -1.481  1.00  0.00           O  
HETATM   11  C4  UNL     1       2.347  -0.252   0.439  1.00  0.00           C  
HETATM   12  O7  UNL     1       3.048  -1.228  -0.260  1.00  0.00           O  
HETATM   13  P2  UNL     1       4.679  -1.058   0.197  1.00  0.00           P  
HETATM   14  O8  UNL     1       4.742  -0.459   1.592  1.00  0.00           O  
HETATM   15  O9  UNL     1       5.415   0.008  -0.896  1.00  0.00           O  
HETATM   16  O10 UNL     1       5.461  -2.545   0.250  1.00  0.00           O  
HETATM   17  C5  UNL     1       0.381   1.147   0.691  1.00  0.00           C  
HETATM   18  O11 UNL     1       0.971   2.390   0.621  1.00  0.00           O  
HETATM   19  C6  UNL     1      -1.001   1.112   0.047  1.00  0.00           C  
HETATM   20  O12 UNL     1      -1.974   1.673   0.838  1.00  0.00           O  
HETATM   21  H1  UNL     1      -4.804  -2.587  -0.197  1.00  0.00           H  
HETATM   22  H2  UNL     1      -6.366   0.427   0.492  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.377  -1.758  -1.244  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.545  -0.466  -2.165  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.490  -0.798   0.887  1.00  0.00           H  
HETATM   26  H6  UNL     1       1.610   1.623  -1.356  1.00  0.00           H  
HETATM   27  H7  UNL     1       2.155  -0.517   1.492  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.989   0.663   0.428  1.00  0.00           H  
HETATM   29  H9  UNL     1       5.084   0.917  -0.650  1.00  0.00           H  
HETATM   30  H10 UNL     1       5.522  -2.925  -0.662  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.350   0.710   1.699  1.00  0.00           H  
HETATM   32  H12 UNL     1       0.502   2.961   1.281  1.00  0.00           H  
HETATM   33  H13 UNL     1      -0.934   1.536  -0.970  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.979   2.653   0.635  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4    5
CONECT    3   21
CONECT    4   22
CONECT    5    6
CONECT    6    7   23   24
CONECT    7    8   19   25
CONECT    8    9
CONECT    9   10   11   17
CONECT   10   26
CONECT   11   12   27   28
CONECT   12   13
CONECT   13   14   14   15   16
CONECT   15   29
CONECT   16   30
CONECT   17   18   19   31
CONECT   18   32
CONECT   19   20   33
CONECT   20   34
END

NP0002596
     RDKit          3D

34 34  0  0  0  0  0  0  0  0999 V2000
   -3.8118   -0.7675    1.3222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3553   -0.4407   -0.0438 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.1647   -1.7818   -0.6527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5102    0.7892    0.1694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1843    0.1481   -1.0931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0852   -0.6965   -1.2132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1311   -0.3969   -0.0933 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1361   -0.9027   -0.2855 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0522    0.1250   -0.2177 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2662    0.6955   -1.4811 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3474   -0.2519    0.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0484   -1.2278   -0.2601 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6785   -1.0585    0.1966 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.7419   -0.4588    1.5925 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4155    0.0075   -0.8960 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4611   -2.5450    0.2495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3813    1.1469    0.6913 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9714    2.3902    0.6208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0006    1.1121    0.0466 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9737    1.6734    0.8381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8044   -2.5871   -0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3659    0.4271    0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3773   -1.7578   -1.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5445   -0.4655   -2.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4898   -0.7977    0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6105    1.6232   -1.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1550   -0.5166    1.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9891    0.6631    0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0836    0.9169   -0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5215   -2.9253   -0.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505    0.7102    1.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5016    2.9607    1.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9338    1.5362   -0.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9792    2.6526    0.6354 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  0
  8  9  1  0
  9 10  1  6
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 13 16  1  0
  9 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  7  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  1
 10 26  1  0
 11 27  1  0
 11 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  1
 18 32  1  0
 19 33  1  6
 20 34  1  0
M  END

View in JSmol

Synonyms

Value	Source
1,6-Di-O-phosphono-beta-D-fructofuranose	ChEBI
BETA FRUCTOSE 1,6-diphosphATE	ChEBI
beta-D-Fructose 1,6-bisphosphate	ChEBI
Fosfructose	ChEBI
1,6-Di-O-phosphono-b-D-fructofuranose	Generator
1,6-Di-O-phosphono-β-D-fructofuranose	Generator
b FRUCTOSE 1,6-diphosphate	Generator
b FRUCTOSE 1,6-diphosphoric acid	Generator
beta FRUCTOSE 1,6-diphosphoric acid	Generator
Β fructose 1,6-diphosphate	Generator
Β fructose 1,6-diphosphoric acid	Generator
b-D-Fructose 1,6-bisphosphate	Generator
b-D-Fructose 1,6-bisphosphoric acid	Generator
beta-D-Fructose 1,6-bisphosphoric acid	Generator
Β-D-fructose 1,6-bisphosphate	Generator
Β-D-fructose 1,6-bisphosphoric acid	Generator
Fructose 1,6-bisphosphoric acid	Generator
SR-FDP	MeSH, HMDB
Fructose 1,6-diphosphate	MeSH, HMDB
Fructose-1,6-diphosphate, (L)-isomer	MeSH, HMDB
Fructose-1,6-diphosphate, (alpha-D)-isomer	MeSH, HMDB
Fructose-1,6-diphosphate, barium (1:2) salt	MeSH, HMDB
Fructose-1,6-diphosphate, sodium salt, monohydrate	MeSH, HMDB
Fructose-1,6-diphosphate, tetrasodium salt	MeSH, HMDB
Strontium fructose-1,6-diphosphate	MeSH, HMDB
Fructose-1,6-diphosphate, calcium salt	MeSH, HMDB
Fructose-1,6-diphosphate, disodium salt	MeSH, HMDB
Fructose-1,6-diphosphate, trisodium salt	MeSH, HMDB
Fructose 1,6-bisphosphate	MeSH
Fructose-1,6-diphosphate, 2-(18)O-labeled	MeSH, HMDB
Fructose-1,6-diphosphate, calcium (1:2) salt	MeSH, HMDB
Fructose-1,6-diphosphate, monosodium salt	MeSH, HMDB
Strontium fructose 1,6-diphosphate	MeSH, HMDB
Fructose-1,6-diphosphate magnesium salt	MeSH, HMDB
Fructose-1,6-diphosphate, (beta-D)-isomer	MeSH, HMDB
Fructose-1,6-diphosphate, tetrapotassium salt	MeSH, HMDB
Fructose-1,6-diphosphate	MeSH, HMDB
D-Fructose 1,6-biphosphate	HMDB
D-Fructose 1,6-bisphosphate	HMDB
D-Fructose 1,6-diphosphate	HMDB
Diphosphofructose	HMDB
Fructose 1,6-bis(dihydrogen phosphate)	HMDB
beta-D-Fructofuranose 1,6-bisphosphate	HMDB
beta-D-Fructofuranose 1,6-diphosphate	HMDB
beta-D-Fructose 1,6-diphosphate	HMDB
β-D-Fructofuranose 1,6-bisphosphate	HMDB, Generator
β-D-Fructofuranose 1,6-diphosphate	HMDB
β-D-Fructose 1,6-diphosphate	HMDB
b-D-Fructofuranose 1,6-bisphosphate	Generator
b-D-Fructofuranose 1,6-bisphosphoric acid	Generator
beta-D-Fructofuranose 1,6-bisphosphoric acid	Generator
Β-D-fructofuranose 1,6-bisphosphoric acid	Generator

Chemical Formula

C₆H₁₄O₁₂P₂

Average Mass

340.1157 Da

Monoisotopic Mass

339.99605 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@H](O)[C@@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=O

InChI Identifier

InChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6-/m1/s1

InChI Key

RNBGYGVWRKECFJ-ARQDHWQXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 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
Arabidopsis thaliana	KNApSAcK Database	22123792
Cannabis sativa	CannabisDB	Not Available
Mus musculus	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

Not Available

Substituents

Not Available

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	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.5	ALOGPS
logP	-3	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	0.89	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.44 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	58.11 m³·mol⁻¹	ChemAxon
Polarizability	25.7 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0001058

DrugBank ID

DB04551

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

FRUCTOSE-16-DIPHOSPHATE

BiGG ID

Not Available

Wikipedia Link

Fructose 1,6-bisphosphate

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

Good Scents ID

Not Available

References

General References

Nakai A, Shigematsu Y, Liu YY, Kikawa Y, Sudo M: Urinary sugar phosphates and related organic acids in fructose-1,6-diphosphatase deficiency. J Inherit Metab Dis. 1993;16(2):408-14. [PubMed:8412001 ]
Riedel BJ, Gal J, Ellis G, Marangos PJ, Fox AW, Royston D: Myocardial protection using fructose-1,6-diphosphate during coronary artery bypass graft surgery: a randomized, placebo-controlled clinical trial. Anesth Analg. 2004 Jan;98(1):20-9, table of contents. doi: 10.1213/01.ane.0000094336.97693.90. [PubMed:14693576 ]
Acan NL, Ozer N: Modification of human erythrocyte pyruvate kinase by an active site-directed reagent: bromopyruvate. J Enzyme Inhib. 2001 Nov;16(5):457-64. doi: 10.1080/14756360109162395. [PubMed:11916152 ]

Showing NP-Card for D-Fructose-1,6-bisphosphate (NP0002596)

MOL for NP0002596 (D-Fructose-1,6-bisphosphate)

3D MOL for NP0002596 (D-Fructose-1,6-bisphosphate)

3D SDF for NP0002596 (D-Fructose-1,6-bisphosphate)

3D-SDF for NP0002596 (D-Fructose-1,6-bisphosphate)

PDB for NP0002596 (D-Fructose-1,6-bisphosphate)

3D PDB for NP0002596 (D-Fructose-1,6-bisphosphate)

SMILES for NP0002596 (D-Fructose-1,6-bisphosphate)

INCHI for NP0002596 (D-Fructose-1,6-bisphosphate)

Structure for NP0002596 (D-Fructose-1,6-bisphosphate)

3D Structure for NP0002596 (D-Fructose-1,6-bisphosphate)