MiMeDB: Showing metabocard for L-Ascorbate 6-phosphate (MMDBc0030072)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:52:51 UTC

Update Date

2022-08-31 17:39:30 UTC

Metabolite ID

MMDBc0030072

Metabolite Identification

Common Name

L-Ascorbate 6-phosphate

Description

L-ascorbate 6-phosphate is a member of the chemical class known as Organophosphate Esters. These are organic compounds containing phosphoric acid ester functional group.

Structure

MOL SDF PDB SMILES InChI

      
  Mrv1533005191517022D          

 17 17  0  0  0  0            999 V2000
   -0.1120   -0.2517    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6229   -0.6262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2905   -1.1112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0355   -1.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5205   -2.5634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2104   -1.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2744   -2.5634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0444   -1.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8291   -0.8563    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.6229    0.1987    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3375    0.6112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0914    0.6112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0914    1.4363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8060    1.8488    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5205    2.2614    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.3934    2.5634    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.2185    1.1343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  2 10  1  1  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  2  0  0  0  0
M  CHG  3   9  -1  15  -1  16  -1
M  END
> <DATABASE_ID>
MMDBc0030072

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(OC(=O)C(O)=C1[O-])[C@@H](O)COP([O-])([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H9O9P/c7-2(1-14-16(11,12)13)5-3(8)4(9)6(10)15-5/h2,5,7-9H,1H2,(H2,11,12,13)/p-3/t2-,5+/m0/s1

> <INCHI_KEY>
KIENGQUGHPTFGC-JLAZNSOCSA-K

> <FORMULA>
C6H6O9P

> <MOLECULAR_WEIGHT>
253.08

> <EXACT_MASS>
252.976589511

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
18.60185543507159

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-3

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-4-hydroxy-2-[(1S)-1-hydroxy-2-(phosphonatooxy)ethyl]-5-oxo-2,5-dihydrofuran-3-olate

> <ALOGPS_LOGP>
-1.30

> <JCHEM_LOGP>
-2.037124907

> <ALOGPS_LOGS>
-0.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.425670518670561

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4779683342764827

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5772494233594445

> <JCHEM_POLAR_SURFACE_AREA>
162.24

> <JCHEM_REFRACTIVITY>
56.21190000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.53e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-ascorbate 6-phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-MAY-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAY-15         0                                  
HETATM    1  H   UNK     0      -0.209  -0.470   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       1.163  -1.169   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.409  -2.074   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.933  -3.539   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.838  -4.785   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.393  -3.539   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.512  -4.785   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.083  -2.074   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.548  -1.598   0.000  0.00  0.00           O-1
HETATM   10  C   UNK     0       1.163   0.371   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.497   1.141   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.171   1.141   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.171   2.681   0.000  0.00  0.00           O+0
HETATM   14  P   UNK     0      -1.504   3.451   0.000  0.00  0.00           P+0
HETATM   15  O   UNK     0      -2.838   4.221   0.000  0.00  0.00           O-1
HETATM   16  O   UNK     0      -0.734   4.785   0.000  0.00  0.00           O-1
HETATM   17  O   UNK     0      -2.275   2.117   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8   10                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8                                                            
CONECT   10    2   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

Synonyms

Value	Source
L-Ascorbate-6-phosphate	ChEBI
L-Ascorbate-6-phosphate(3-)	ChEBI
L-Ascorbic acid-6-phosphoric acid	Generator
L-Ascorbic acid-6-phosphoric acid(3-)	Generator
L-Ascorbic acid 6-phosphoric acid	Generator

Molecular Formula

C₆H₆O₉P

Average Mass

253.08

Monoisotopic Mass

252.976589511

IUPAC Name

(2R)-4-hydroxy-2-[(1S)-1-hydroxy-2-(phosphonatooxy)ethyl]-5-oxo-2,5-dihydrofuran-3-olate

Traditional Name

L-ascorbate 6-phosphate

CAS Registry Number

Not Available

SMILES

[H][C@@]1(OC(=O)C(O)=C1[O-])[C@@H](O)COP([O-])([O-])=O

InChI Identifier

InChI=1S/C6H9O9P/c7-2(1-14-16(11,12)13)5-3(8)4(9)6(10)15-5/h2,5,7-9H,1H2,(H2,11,12,13)/p-3/t2-,5+/m0/s1

InChI Key

KIENGQUGHPTFGC-JLAZNSOCSA-K

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

2-furanone
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous acid
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Carbonyl group
Alcohol
Organic oxygen compound
Organic anion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

carbohydrate acid derivative anion (CHEBI:61698 )
organophosphate oxoanion (CHEBI:61698 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	55.3 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-2	ChemAxon
logS	-0.74	ALOGPS
pKa (Strongest Acidic)	1.48	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	162.24 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	56.21 m³·mol⁻¹	ChemAxon
Polarizability	18.6 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	38	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26332326

KEGG Compound ID

Not Available

BioCyc ID

L-ASCORBATE-6-PHOSPHATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54735473

PDB ID

Not Available

ChEBI ID

61698

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for L-Ascorbate 6-phosphate (MMDBc0030072)

MOL for #<Metabolite:0x00007fecdef64618>

3D MOL for #<Metabolite:0x00007fecdef64618>

3D SDF for #<Metabolite:0x00007fecdef64618>

3D-SDF for #<Metabolite:0x00007fecdef64618>

PDB for #<Metabolite:0x00007fecdef64618>

3D PDB for #<Metabolite:0x00007fecdef64618>

SMILES for #<Metabolite:0x00007fecdef64618>

INCHI for #<Metabolite:0x00007fecdef64618>

Structure for #<Metabolite:0x00007fecdef64618>

3D Structure for #<Metabolite:0x00007fecdef64618>