NP-MRD: Showing NP-Card for L-Sorbose-1-phosphate (NP0062914)

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Record Information

Version

2.0

Created at

2022-04-28 07:26:40 UTC

Updated at

2022-04-28 07:26:40 UTC

NP-MRD ID

NP0062914

Secondary Accession Numbers

None

Natural Product Identification

Common Name

L-Sorbose-1-phosphate

Description

Sorbose 1-phosphate, also known as L-sorbose 1P, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Sorbose 1-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Sorbose 1-phosphate exists in all living organisms, ranging from bacteria to humans. L-Sorbose-1-phosphate is found in Chlamydomonas reinhardtii and Escherichia coli. L-Sorbose-1-phosphate was first documented in 1984 (PMID: 6361004). The L-stereoisomer of sorbose 1-phosphate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 28  0  0  0  0  0  0  0  0999 V2000
    0.2647   -0.7391   -2.0022 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3563    0.1313   -1.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4440    0.0576   -0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2114   -1.0647   -0.4346 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4896   -1.2463    0.6445 P   0  0  1  0  0  5  0  0  0  0  0  0
    3.3043   -2.4656    1.5169 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8931   -1.5294   -0.2902 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6816    0.0980    1.6383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6198    1.2294   -1.1638 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5555    1.0776   -2.2206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3978    1.4180    0.0874 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6355    1.5910    1.2076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4188    0.3338    0.3402 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2298    0.1018   -0.7540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8217   -0.9243    0.8930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8906   -1.7521    1.2774 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0158    0.0175    0.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0771    0.9913   -0.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0581   -0.7869   -0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3695    0.7206    1.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1204    2.2166   -1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3289    0.2976   -2.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9955    2.3667   -0.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2357    1.7218    1.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0983    0.7420    1.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1371   -0.1702   -0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2379   -0.6696    1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2100   -1.4908    0.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2321   -2.2739    0.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  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 29  1  0
 15 27  1  0
 15 28  1  0
 13 25  1  1
 14 26  1  0
 11 23  1  6
 12 24  1  0
  9 21  1  6
 10 22  1  0
  3 17  1  0
  3 18  1  0
  7 19  1  0
  8 20  1  0
M  END

  
  Mrv0541 02231220512D          

 16 15  0  0  1  0            999 V2000
    0.4775    0.1786    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1921   -0.2336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2370   -0.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4775    1.0031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9100    0.1786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1921   -1.0581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9516    0.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2370   -1.0581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6246   -0.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9100    1.0031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6661   -0.2336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3392    0.1786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3808    0.1786    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0987   -0.2336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3808    1.0031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1678   -0.6184    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  1  1  0  0  0
  2  5  1  0  0  0  0
  2  6  1  1  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  1  0  0  0
  7 11  1  0  0  0  0
  9 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0062914

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h3,5-8,10-11H,1-2H2,(H2,12,13,14)/t3-,5+,6+/m0/s1

> <INCHI_KEY>
ZKLLSNQJRLJIGT-OTWZMJIISA-N

> <FORMULA>
C6H13O9P

> <MOLECULAR_WEIGHT>
260.1358

> <EXACT_MASS>
260.029718526

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
20.882231149367016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.80

> <JCHEM_LOGP>
-3.3905979233333325

> <ALOGPS_LOGS>
-1.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.208664456329444

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1785942950504693

> <JCHEM_PKA_STRONGEST_BASIC>
-2.97450105916879

> <JCHEM_POLAR_SURFACE_AREA>
164.75

> <JCHEM_REFRACTIVITY>
48.4347

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.34e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sorbose 1-phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       0.891   0.333   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.225  -0.436   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.442  -0.436   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.891   1.872   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.565   0.333   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.225  -1.975   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.776   0.333   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.442  -1.975   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.899  -0.436   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.565   1.872   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -3.110  -0.436   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.233   0.333   0.000  0.00  0.00           O+0
HETATM   13  P   UNK     0      -4.444   0.333   0.000  0.00  0.00           P+0
HETATM   14  O   UNK     0      -5.784  -0.436   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -4.444   1.872   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -4.047  -1.154   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1                                                            
CONECT    5    2    9   10                                                  
CONECT    6    2                                                            
CONECT    7    3   11                                                       
CONECT    8    3                                                            
CONECT    9    5   12                                                       
CONECT   10    5                                                            
CONECT   11    7   13                                                       
CONECT   12    9                                                            
CONECT   13   11   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Value	Source
1-O-Phosphono-L-sorbose	ChEBI
L-Sorbose 1P	ChEBI
L-Xylo-hex-2-ulose 1-(dihydrogen phosphate)	ChEBI
L-Xylo-hexulose 1-phosphate	ChEBI
L-Sorbose 1-phosphate	Kegg
L-Xylo-hex-2-ulose 1-(dihydrogen phosphoric acid)	Generator
L-Xylo-hexulose 1-phosphoric acid	Generator
L-Sorbose 1-phosphoric acid	Generator
Sorbose 1-phosphoric acid	Generator

Chemical Formula

C₆H₁₃O₉P

Average Mass

260.1358 Da

Monoisotopic Mass

260.02972 Da

IUPAC Name

{[(3S,4R,5S)-3,4,5,6-tetrahydroxy-2-oxohexyl]oxy}phosphonic acid

Traditional Name

sorbose 1-phosphate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h3,5-8,10-11H,1-2H2,(H2,12,13,14)/t3-,5+,6+/m0/s1

InChI Key

ZKLLSNQJRLJIGT-OTWZMJIISA-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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Chlamydomonas reinhardtii	LOTUS Database	35616633
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Escherichia coli	Bacteria	KNApSAcK
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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

Octose monosaccharide
Monosaccharide phosphate
Glycerone phosphate
Monoalkyl phosphate
Sugar acid
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
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

sorbose 1-phosphate (CHEBI:38342 )

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	-1.8	ALOGPS
logP	-3.4	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	1.18	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.75 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	48.43 m³·mol⁻¹	ChemAxon
Polarizability	20.88 Å³	ChemAxon
Number of Rings	0	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

HMDB0006797

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439837

PDB ID

Not Available

ChEBI ID

38342

Good Scents ID

Not Available

References

General References

Sprenger GA, Lengeler JW: L-Sorbose metabolism in Klebsiella pneumoniae and Sor+ derivatives of Escherichia coli K-12 and chemotaxis toward sorbose. J Bacteriol. 1984 Jan;157(1):39-45. doi: 10.1128/jb.157.1.39-45.1984. [PubMed:6361004 ]

Showing NP-Card for L-Sorbose-1-phosphate (NP0062914)

MOL for NP0062914 (L-Sorbose-1-phosphate)

3D MOL for NP0062914 (L-Sorbose-1-phosphate)

3D SDF for NP0062914 (L-Sorbose-1-phosphate)

3D-SDF for NP0062914 (L-Sorbose-1-phosphate)

PDB for NP0062914 (L-Sorbose-1-phosphate)

3D PDB for NP0062914 (L-Sorbose-1-phosphate)

SMILES for NP0062914 (L-Sorbose-1-phosphate)

INCHI for NP0062914 (L-Sorbose-1-phosphate)

Structure for NP0062914 (L-Sorbose-1-phosphate)

3D Structure for NP0062914 (L-Sorbose-1-phosphate)