NP-MRD: Showing NP-Card for Sedoheptulose 1,7-bisphosphate (NP0044494)

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Record Information

Version

2.0

Created at

2022-02-14 20:57:44 UTC

Updated at

2022-03-10 22:22:28 UTC

NP-MRD ID

NP0044494

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sedoheptulose 1,7-bisphosphate

Description

Sedoheptulose 1,7-bisphosphate belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Sedoheptulose 1,7-bisphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). These are monosaccharides comprising a phosphated group linked tot he carbohydrate unit. Sedoheptulose 1,7-bisphosphate is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 37  0  0  0  0  0  0  0  0999 V2000
    0.5638    0.9071    1.3821 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4066    0.6363    0.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7747    0.2909    1.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6608    0.1160    0.3078 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2240   -0.1394    0.7797 P   0  0  1  0  0  5  0  0  0  0  0  0
    6.0239   -0.6914   -0.3798 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9586    1.3615    1.1920 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4128   -1.1972    2.0755 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3220    0.5892   -0.8368 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6218    0.2370   -1.3191 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4581   -0.6295   -1.3035 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8650   -0.8394   -2.6246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744   -0.0043   -1.5144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8156    1.2695   -1.9519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8447   -0.3185   -0.4115 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9254   -1.7237   -0.3545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2754    0.2714   -0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0082   -0.5757    0.1722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9203    0.2432    1.2805 P   0  0  2  0  0  5  0  0  0  0  0  0
   -4.1038    1.4923    1.7258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9395   -0.8095    2.6933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4150    0.7092    0.8847 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326   -0.6750    1.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0052    1.0427    2.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3245    2.0973    0.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1968   -0.9168    2.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0421    1.4989   -1.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5960   -0.6092   -1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4850   -1.4418   -0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7761   -0.0355   -3.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280   -0.5803   -2.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8164    1.3107   -2.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6203    0.0129    0.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4906   -2.0756   -1.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3226    1.3041   -0.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5201    0.1840   -1.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7391   -0.2720    3.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0908    0.0040    0.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 17  1  0
 17 18  1  0
 19 18  1  6
 19 21  1  0
 19 22  1  0
 19 20  2  0
 15 13  1  0
 13 14  1  0
 13 11  1  0
 11 12  1  0
 11  9  1  0
  9 10  1  0
  9  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  5  4  1  6
  5  7  1  0
  5  8  1  0
  5  6  2  0
 16 34  1  0
 15 33  1  1
 17 35  1  0
 17 36  1  0
 21 37  1  0
 22 38  1  0
 13 31  1  6
 14 32  1  0
 11 29  1  1
 12 30  1  0
  9 27  1  6
 10 28  1  0
  3 23  1  0
  3 24  1  0
  7 25  1  0
  8 26  1  0
M  END


  Mrv1652309042000402D          

 22 21  0  0  1  0            999 V2000
   10.3733  -10.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0842  -11.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7949  -10.8218    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5058  -11.2406    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2165  -10.8345    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9274  -11.2533    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.6382  -10.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6626  -11.2152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0842  -12.0530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7949   -9.9967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5058  -12.0656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2165  -10.0094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9147  -12.0561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3526  -11.2596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0671  -10.8471    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.9481  -10.8027    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.0671  -10.0221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7816  -11.2596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2806  -11.6440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9481   -9.9777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2336  -11.2152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7346  -11.5996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
  2  1  1  0  0  0  0
  9  2  2  0  0  0  0
  3  2  1  0  0  0  0
  3 10  1  1  0  0  0
  4  3  1  0  0  0  0
  4 11  1  1  0  0  0
  5  4  1  0  0  0  0
  5 12  1  6  0  0  0
  6  5  1  0  0  0  0
  6 13  1  1  0  0  0
  7  6  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 16  1  0  0  0  0
 15 17  2  0  0  0  0
 15 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 16 21  1  0  0  0  0
 16 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044494

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H16O13P2/c8-3(1-19-21(13,14)15)5(10)7(12)6(11)4(9)2-20-22(16,17)18/h3,5-8,10-12H,1-2H2,(H2,13,14,15)(H2,16,17,18)/t3-,5-,6-,7-/m1/s1

> <INCHI_KEY>
OKHXOUGRECCASI-SHUUEZRQSA-N

> <FORMULA>
C7H16O13P2

> <MOLECULAR_WEIGHT>
370.1417

> <EXACT_MASS>
370.006613622

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
28.034589633912134

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(3S,4R,5R,6R)-3,4,5,6-tetrahydroxy-2-oxo-7-(phosphonooxy)heptyl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-1.52

> <JCHEM_LOGP>
-4.144498896666667

> <ALOGPS_LOGS>
-1.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.6639331088172806

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.0065590425670043

> <JCHEM_PKA_STRONGEST_BASIC>
-3.539513696987668

> <JCHEM_POLAR_SURFACE_AREA>
231.50999999999996

> <JCHEM_REFRACTIVITY>
65.2701

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.43e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sedoheptulose 1,7-bisphosphate

> <JCHEM_VEBER_RULE>
0

$$$$

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      19.363 -20.177   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.691 -20.959   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.017 -20.201   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.344 -20.982   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.671 -20.224   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.998 -21.006   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.325 -20.248   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      18.037 -20.935   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      20.691 -22.499   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      22.017 -18.661   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      23.344 -22.522   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      24.671 -18.684   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      25.974 -22.505   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      28.658 -21.018   0.000  0.00  0.00           O+0
HETATM   15  P   UNK     0      29.992 -20.248   0.000  0.00  0.00           P+0
HETATM   16  P   UNK     0      16.703 -20.165   0.000  0.00  0.00           P+0
HETATM   17  O   UNK     0      29.992 -18.708   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      31.326 -21.018   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      30.390 -21.735   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      16.703 -18.625   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      15.369 -20.935   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      16.305 -21.653   0.000  0.00  0.00           O+0
CONECT    1    8    2                                                       
CONECT    2    1    9    3                                                  
CONECT    3    2   10    4                                                  
CONECT    4    3   11    5                                                  
CONECT    5    4   12    6                                                  
CONECT    6    5   13    7                                                  
CONECT    7    6   14                                                       
CONECT    8    1   16                                                       
CONECT    9    2                                                            
CONECT   10    3                                                            
CONECT   11    4                                                            
CONECT   12    5                                                            
CONECT   13    6                                                            
CONECT   14    7   15                                                       
CONECT   15   14   17   18   19                                             
CONECT   16    8   20   21   22                                             
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   16                                                            
CONECT   22   16                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

View in JSmol

Synonyms

Value	Source
altro-Heptulose 1,7-biphosphate	ChEBI, HMDB
D-altro-Heptulose 1,7-biphosphate	ChEBI, KEGG
D-Sedoheptulose 1,7-bisphosphate	ChEBI, KEGG
altro-Heptulose 1,7-biphosphoric acid	Generator, HMDB
Sedoheptulose 1,7-bisphosphoric acid	Generator
D-altro-Heptulose 1,7-biphosphoric acid	Generator
D-Sedoheptulose 1,7-bisphosphoric acid	Generator
altro Heptulose 1,7-Bisphosphate	MeSH
D-Sedoheptulose 1,7-diphosphate	HMDB
D-altro-Heptulose 1,7-bisphosphate	HMDB
Sedoheptulose 1,7-bisphosphate	HMDB

Chemical Formula

C₇H₁₆O₁₃P₂

Average Mass

370.1417 Da

Monoisotopic Mass

370.00661 Da

IUPAC Name

{[(3S,4R,5R,6R)-3,4,5,6-tetrahydroxy-2-oxo-7-(phosphonooxy)heptyl]oxy}phosphonic acid

Traditional Name

sedoheptulose 1,7-bisphosphate

CAS Registry Number

815-91-8

SMILES

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

InChI Identifier

InChI=1S/C7H16O13P2/c8-3(1-19-21(13,14)15)5(10)7(12)6(11)4(9)2-20-22(16,17)18/h3,5-8,10-12H,1-2H2,(H2,13,14,15)(H2,16,17,18)/t3-,5-,6-,7-/m1/s1

InChI Key

OKHXOUGRECCASI-SHUUEZRQSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cannabis sativa	CannabisDB	Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharide phosphates

Alternative Parents

Substituents

Heptose monosaccharide
Monosaccharide phosphate
Glycerone phosphate
Monoalkyl phosphate
Acyloin
Beta-hydroxy ketone
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Alpha-hydroxy ketone
Ketone
Secondary alcohol
Polyol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

ketoheptose phosphate (CHEBI:17969 )
sedoheptulose derivative (CHEBI:17969 )

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	-4.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.01	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	231.51 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	65.27 m³·mol⁻¹	ChemAxon
Polarizability	28.03 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon