NP-MRD: Showing NP-Card for 4-fluoro-3,5,6-trihydroxy-2-oxohexanoic acid (NP0288388)

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Record Information

Version

2.0

Created at

2022-09-09 18:04:07 UTC

Updated at

2022-09-09 18:04:08 UTC

NP-MRD ID

NP0288388

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-fluoro-3,5,6-trihydroxy-2-oxohexanoic acid

Description

4-Fluoro-3,5,6-trihydroxy-2-oxohexanoic acid belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. 4-Fluoro-3,5,6-trihydroxy-2-oxohexanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241503392D          

 13 12  0  0  0  0            999 V2000
    1.0461    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0288388

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC(O)C(F)C(O)C(=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H9FO6/c7-3(2(9)1-8)4(10)5(11)6(12)13/h2-4,8-10H,1H2,(H,12,13)

> <INCHI_KEY>
LMCANDWMUCRYHX-UHFFFAOYSA-N

> <FORMULA>
C6H9FO6

> <MOLECULAR_WEIGHT>
196.13

> <EXACT_MASS>
196.038316173

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
15.648752141533652

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-fluoro-3,5,6-trihydroxy-2-oxohexanoic acid

> <ALOGPS_LOGP>
-1.63

> <JCHEM_LOGP>
-1.599097927

> <ALOGPS_LOGS>
-0.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.968431027483522

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.833248665908776

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9799577772143673

> <JCHEM_POLAR_SURFACE_AREA>
115.05999999999999

> <JCHEM_REFRACTIVITY>
35.9624

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.89e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-fluoro-3,5,6-trihydroxy-2-oxohexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0       1.953   2.667   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.620   1.127   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    6  F   UNK     0       5.954   4.977   0.000  0.00  0.00           F+0
HETATM    7  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.287   1.127   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.621   4.977   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol

Synonyms

Value	Source
4-Fluoro-3,5,6-trihydroxy-2-oxohexanoate	Generator

Chemical Formula

C₆H₉FO₆

Average Mass

196.1300 Da

Monoisotopic Mass

196.03832 Da

IUPAC Name

4-fluoro-3,5,6-trihydroxy-2-oxohexanoic acid

Traditional Name

4-fluoro-3,5,6-trihydroxy-2-oxohexanoic acid

CAS Registry Number

Not Available

SMILES

OCC(O)C(F)C(O)C(=O)C(O)=O

InChI Identifier

InChI=1S/C6H9FO6/c7-3(2(9)1-8)4(10)5(11)6(12)13/h2-4,8-10H,1H2,(H,12,13)

InChI Key

LMCANDWMUCRYHX-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Medium-chain keto acids and derivatives

Direct Parent

Medium-chain keto acids and derivatives

Alternative Parents

Substituents

Medium-chain keto acid
Beta-hydroxy acid
Halogenated fatty acid
Hydroxy fatty acid
Fatty acyl
Alpha-keto acid
Acyloin
Hydroxy acid
Monosaccharide
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Halohydrin
Fluorohydrin
Monocarboxylic acid or derivatives
Polyol
Carboxylic acid derivative
Carboxylic acid
Organohalogen compound
Alcohol
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Primary alcohol
Alkyl halide
Alkyl fluoride
Organofluoride
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	-1.6	ALOGPS
logP	-1.6	ChemAxon
logS	-0.6	ALOGPS
pKa (Strongest Acidic)	2.83	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	35.96 m³·mol⁻¹	ChemAxon
Polarizability	15.65 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86127892

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-fluoro-3,5,6-trihydroxy-2-oxohexanoic acid (NP0288388)

MOL for NP0288388 (4-fluoro-3,5,6-trihydroxy-2-oxohexanoic acid)

3D MOL for NP0288388 (4-fluoro-3,5,6-trihydroxy-2-oxohexanoic acid)

3D SDF for NP0288388 (4-fluoro-3,5,6-trihydroxy-2-oxohexanoic acid)

3D-SDF for NP0288388 (4-fluoro-3,5,6-trihydroxy-2-oxohexanoic acid)

PDB for NP0288388 (4-fluoro-3,5,6-trihydroxy-2-oxohexanoic acid)

3D PDB for NP0288388 (4-fluoro-3,5,6-trihydroxy-2-oxohexanoic acid)

SMILES for NP0288388 (4-fluoro-3,5,6-trihydroxy-2-oxohexanoic acid)

INCHI for NP0288388 (4-fluoro-3,5,6-trihydroxy-2-oxohexanoic acid)

Structure for NP0288388 (4-fluoro-3,5,6-trihydroxy-2-oxohexanoic acid)

3D Structure for NP0288388 (4-fluoro-3,5,6-trihydroxy-2-oxohexanoic acid)