NP-MRD: Showing NP-Card for 2,3,5-trihydroxy-4-(phosphonooxy)hexanedioic acid (NP0201394)

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Record Information

Version

2.0

Created at

2022-09-04 20:25:47 UTC

Updated at

2022-09-04 20:25:47 UTC

NP-MRD ID

NP0201394

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3,5-trihydroxy-4-(phosphonooxy)hexanedioic acid

Description

2,3,5-Trihydroxy-4-phosphonooxyadipic acid belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. 2,3,5-Trihydroxy-4-phosphonooxyadipic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 2,3,5-trihydroxy-4-(phosphonooxy)hexanedioic acid is found in Trypanosoma brucei. Based on a literature review very few articles have been published on 2,3,5-trihydroxy-4-phosphonooxyadipic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 28  0  0  0  0  0  0  0  0999 V2000
   -0.4305   -3.6072   -0.2981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9878   -2.5151   -0.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4710   -2.3156   -1.8551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1260   -1.4612    0.4550 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5910   -1.8290    1.6704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6813   -0.1110   -0.0453 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0146    0.8912    0.8263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1340    1.9659    0.1665 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.3190    1.2371   -0.4005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5729    3.0518    1.3857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4369    2.8825   -1.0861 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7450   -0.0198   -0.4514 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1277   -1.0228   -1.3292 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7255    0.1888    0.6613 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8631   -0.9881    1.3865 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.4909    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0784   -0.2273    0.2817 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1460    1.6621   -0.6855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1210   -2.9923   -2.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2390   -1.3576    0.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3476   -2.7901    1.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791    0.0836   -0.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4898    3.3636    1.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0008    3.6840   -0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8163    0.9297   -1.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8941   -0.7150   -1.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4496    1.0496    1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2778   -1.6482    0.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0397    2.1195   -0.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 18  1  0
 16 17  2  0
 12  6  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  8 11  1  0
  8  9  2  0
  6  4  1  0
  4  5  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
 13 26  1  0
 12 25  1  6
 14 27  1  1
 15 28  1  0
 18 29  1  0
  6 22  1  6
 10 23  1  0
 11 24  1  0
  4 20  1  1
  5 21  1  0
  3 19  1  0
M  END


  Mrv1652309042222252D          

 18 17  0  0  0  0            999 V2000
    0.1105    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.8250    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0201394

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(C(O)C(O)=O)C(OP(O)(O)=O)C(O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H11O11P/c7-1(2(8)5(10)11)4(3(9)6(12)13)17-18(14,15)16/h1-4,7-9H,(H,10,11)(H,12,13)(H2,14,15,16)

> <INCHI_KEY>
FJYQVOPLAANXAB-UHFFFAOYSA-N

> <FORMULA>
C6H11O11P

> <MOLECULAR_WEIGHT>
290.117

> <EXACT_MASS>
290.003898172

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
21.235440160790613

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3,5-trihydroxy-4-(phosphonooxy)hexanedioic acid

> <JCHEM_LOGP>
-3.213035803999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
2.9424151210441987

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.9511790781655947

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2550397439645975

> <JCHEM_POLAR_SURFACE_AREA>
202.04999999999998

> <JCHEM_REFRACTIVITY>
49.011300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2,3,5-trihydroxy-4-(phosphonooxy)hexanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0       0.206   5.390   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.127   4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.461   5.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.127   3.080   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.461   2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.206   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.540   3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.127   0.000   0.000  0.00  0.00           O+0
HETATM   10  P   UNK     0      -1.127  -1.540   0.000  0.00  0.00           P+0
HETATM   11  O   UNK     0      -1.127  -3.080   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.413  -1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.540  -1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.874   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.207  -0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    8   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
2,3,5-Trihydroxy-4-phosphonooxyhexanedioic acid	ChEBI
2,3,5-Trihydroxy-4-phosphonooxyhexanedioate	Generator
2,3,5-Trihydroxy-4-phosphonooxyadipate	Generator

Chemical Formula

C₆H₁₁O₁₁P

Average Mass

290.1170 Da

Monoisotopic Mass

290.00390 Da

IUPAC Name

2,3,5-trihydroxy-4-(phosphonooxy)hexanedioic acid

Traditional Name

2,3,5-trihydroxy-4-(phosphonooxy)hexanedioic acid

CAS Registry Number

Not Available

SMILES

OC(C(O)C(O)=O)C(OP(O)(O)=O)C(O)C(O)=O

InChI Identifier

InChI=1S/C6H11O11P/c7-1(2(8)5(10)11)4(3(9)6(12)13)17-18(14,15)16/h1-4,7-9H,(H,10,11)(H,12,13)(H2,14,15,16)

InChI Key

FJYQVOPLAANXAB-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glucuronic acid derivatives

Alternative Parents

Substituents

Glucuronic acid or derivatives
Hexose monosaccharide
Medium-chain hydroxy acid
Medium-chain fatty acid
Monoalkyl phosphate
Beta-hydroxy acid
Hydroxy fatty acid
Fatty acid
Alpha-hydroxy acid
Alkyl phosphate
Dicarboxylic acid or derivatives
Hydroxy acid
Fatty acyl
Monosaccharide
Organic phosphoric acid derivative
Phosphoric acid ester
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Polyol
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

triol (CHEBI:73968 )
alpha,omega-dicarboxylic acid (CHEBI:73968 )
phosphate monoester (CHEBI:73968 )

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	-3.2	ChemAxon
pKa (Strongest Acidic)	0.95	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	202.05 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	49.01 m³·mol⁻¹	ChemAxon
Polarizability	21.24 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29368116

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25244160

PDB ID

Not Available

ChEBI ID

73968

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,3,5-trihydroxy-4-(phosphonooxy)hexanedioic acid (NP0201394)

MOL for NP0201394 (2,3,5-trihydroxy-4-(phosphonooxy)hexanedioic acid)

3D MOL for NP0201394 (2,3,5-trihydroxy-4-(phosphonooxy)hexanedioic acid)

3D SDF for NP0201394 (2,3,5-trihydroxy-4-(phosphonooxy)hexanedioic acid)

3D-SDF for NP0201394 (2,3,5-trihydroxy-4-(phosphonooxy)hexanedioic acid)

PDB for NP0201394 (2,3,5-trihydroxy-4-(phosphonooxy)hexanedioic acid)

3D PDB for NP0201394 (2,3,5-trihydroxy-4-(phosphonooxy)hexanedioic acid)

SMILES for NP0201394 (2,3,5-trihydroxy-4-(phosphonooxy)hexanedioic acid)

INCHI for NP0201394 (2,3,5-trihydroxy-4-(phosphonooxy)hexanedioic acid)

Structure for NP0201394 (2,3,5-trihydroxy-4-(phosphonooxy)hexanedioic acid)

3D Structure for NP0201394 (2,3,5-trihydroxy-4-(phosphonooxy)hexanedioic acid)