MiMeDB: Showing metabocard for 3-Dehydro-L-gulonate 6-phosphate (MMDBc0029997)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:50:00 UTC

Update Date

2022-08-31 17:38:31 UTC

Metabolite ID

MMDBc0029997

Metabolite Identification

Common Name

3-Dehydro-L-gulonate 6-phosphate

Description

3-dehydro-L-gulonate 6-phosphate is a member of the chemical class known as Medium-chain Keto Acids and Derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 08131209242D          

 20 19  0  0  0  0            999 V2000
    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  1  0  0  0  0  0  0  0  0  0
    3.1895   -1.8414    0.0000 C   0  0  2  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
    4.6184   -1.8414    0.0000 C   0  0  1  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
    2.4750   -0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -2.6664    0.0000 O   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   -2.6664    0.0000 O   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
   -0.3829   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0809   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7441   -2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316   -1.8414    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -2.2539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.0164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -1.0164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  2  7  1  1  0  0  0
  3  8  1  1  0  0  0
  9  4  2  0  0  0  0
  5 10  1  6  0  0  0
 11  6  2  0  0  0  0
 12  6  1  0  0  0  0
 16  1  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  2  0  0  0  0
 17 16  1  0  0  0  0
  2 18  1  1  0  0  0
  3 19  1  1  0  0  0
  5 20  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029997

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H11O10P/c7-2(1-16-17(13,14)15)3(8)4(9)5(10)6(11)12/h2-3,5,7-8,10H,1H2,(H,11,12)(H2,13,14,15)/t2-,3+,5-/m0/s1

> <INCHI_KEY>
BDUIIKXSXFDPEC-LWKDLAHASA-N

> <FORMULA>
C6H11O10P

> <MOLECULAR_WEIGHT>
274.1193

> <EXACT_MASS>
274.008983084

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
20.668638996799046

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4R,5S)-2,4,5-trihydroxy-3-oxo-6-(phosphonooxy)hexanoic acid

> <ALOGPS_LOGP>
-2.13

> <JCHEM_LOGP>
-2.76594495

> <ALOGPS_LOGS>
-1.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.2586965219006627

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4695807225551283

> <JCHEM_PKA_STRONGEST_BASIC>
-3.581034897866549

> <JCHEM_POLAR_SURFACE_AREA>
181.82

> <JCHEM_REFRACTIVITY>
48.452299999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.64e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4R,5S)-2,4,5-trihydroxy-3-oxo-6-(phosphonooxy)hexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-AUG-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   18  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2   16                                                       
CONECT    2    1    3    7   18                                             
CONECT    3    2    4    8   19                                             
CONECT    4    3    5    9                                                  
CONECT    5    4    6   10   20                                             
CONECT    6    5   11   12                                                  
CONECT    7    2                                                            
CONECT    8    3                                                            
CONECT    9    4                                                            
CONECT   10    5                                                            
CONECT   11    6                                                            
CONECT   12    6                                                            
CONECT   13   17                                                            
CONECT   14   17                                                            
CONECT   15   17                                                            
CONECT   16    1   17                                                       
CONECT   17   13   14   15   16                                             
CONECT   18    2                                                            
CONECT   19    3                                                            
CONECT   20    5                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

Synonyms

Value	Source
6-O-Phosphono-L-xylo-hex-3-ulosonic acid	ChEBI
6-O-Phosphono-L-xylo-hex-3-ulosonate	Generator
3-Dehydro-L-gulonic acid 6-phosphoric acid	Generator

Molecular Formula

C₆H₁₁O₁₀P

Average Mass

274.1193

Monoisotopic Mass

274.008983084

IUPAC Name

(2S,4R,5S)-2,4,5-trihydroxy-3-oxo-6-(phosphonooxy)hexanoic acid

Traditional Name

(2S,4R,5S)-2,4,5-trihydroxy-3-oxo-6-(phosphonooxy)hexanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C6H11O10P/c7-2(1-16-17(13,14)15)3(8)4(9)5(10)6(11)12/h2-3,5,7-8,10H,1H2,(H,11,12)(H2,13,14,15)/t2-,3+,5-/m0/s1

InChI Key

BDUIIKXSXFDPEC-LWKDLAHASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentose phosphates

Alternative Parents

Substituents

Pentose phosphate
Hexose monosaccharide
Monosaccharide phosphate
Medium-chain keto acid
Beta-keto acid
Monoalkyl phosphate
Acyloin
Alpha-hydroxy acid
Beta-hydroxy ketone
Hydroxy acid
Keto acid
Alkyl phosphate
1,3-dicarbonyl compound
Organic phosphoric acid derivative
Phosphoric acid ester
Alpha-hydroxy ketone
Ketone
Secondary alcohol
Carboxylic acid
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

ketoaldonic acid derivative (CHEBI:49039 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	16.4 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-2.8	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.47	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	181.82 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	48.45 m³·mol⁻¹	ChemAxon
Polarizability	20.67 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_15) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-2690000000-f449fb1ab1b0ad581c58	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6v-6920000000-564500c3114af11aacc1	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9400000000-6b05c022383e0736c0f2	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0fi0-8920000000-4ee0d90515ba8a6ee947	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9300000000-c74e1e3fbf6cd7457258	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-7c6c3d1f837e7e96f4d7	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	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	40	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown
Bacteria	Tenericutes	1	Human

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

Not Available

KEGG Compound ID

C14899

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

49039

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 3-Dehydro-L-gulonate 6-phosphate (MMDBc0029997)

MOL for #<Metabolite:0x00007fece40b1958>

3D MOL for #<Metabolite:0x00007fece40b1958>

3D SDF for #<Metabolite:0x00007fece40b1958>

3D-SDF for #<Metabolite:0x00007fece40b1958>

PDB for #<Metabolite:0x00007fece40b1958>

3D PDB for #<Metabolite:0x00007fece40b1958>

SMILES for #<Metabolite:0x00007fece40b1958>

INCHI for #<Metabolite:0x00007fece40b1958>

Structure for #<Metabolite:0x00007fece40b1958>

3D Structure for #<Metabolite:0x00007fece40b1958>