MiMeDB: Showing metabocard for 2-Hydroxy-3-keto-5-methylthiopentenyl-1-phosphate (MMDBc0048267)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 21:55:06 UTC

Update Date

2022-09-01 02:14:31 UTC

Metabolite ID

MMDBc0048267

Metabolite Identification

Common Name

2-Hydroxy-3-keto-5-methylthiopentenyl-1-phosphate

Description

DTXSID60274260 belongs to the class of organic compounds known as phosphate esters. These are organic compounds containing phosphoric acid ester functional group, with the general structure R1P(=O)(R2)OR3. R1,R2 = O,N, or halogen atom; R3 = organyl group. Based on a literature review very few articles have been published on DTXSID60274260.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304292223552D          

 15 14  0  0  0  0            999 V2000
   -0.9059    1.9520    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.1270    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  2  0  0  0  0
  2  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  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
M  END
> <DATABASE_ID>
MMDBc0048267

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(OP(O)(O)=O)=C(O)C(=O)CCSC

> <INCHI_IDENTIFIER>
InChI=1S/C6H11O6PS/c1-14-3-2-5(7)6(8)4-12-13(9,10)11/h4,8H,2-3H2,1H3,(H2,9,10,11)

> <INCHI_KEY>
YIEMFVNCENFBSD-UHFFFAOYSA-N

> <FORMULA>
C6H11O6PS

> <MOLECULAR_WEIGHT>
242.18

> <EXACT_MASS>
242.001396246

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
20.685732498781107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{[2-hydroxy-5-(methylsulfanyl)-3-oxopent-1-en-1-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-0.23

> <JCHEM_LOGP>
0.15778081366666724

> <ALOGPS_LOGS>
-1.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.40082136178022

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3641115734153981

> <JCHEM_PKA_STRONGEST_BASIC>
-4.556270321103455

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
52.74170000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[2-hydroxy-5-(methylsulfanyl)-3-oxopent-1-en-1-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  H   UNK     0      -1.691   3.644   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      -1.691   2.104   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.025   1.334   0.000  0.00  0.00           O+0
HETATM    4  P   UNK     0      -4.358   2.104   0.000  0.00  0.00           P+0
HETATM    5  O   UNK     0      -5.692   2.874   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -5.128   0.770   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -3.588   3.437   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.357  -0.206   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.976   3.644   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   14  S   UNK     0       4.977   1.334   0.000  0.00  0.00           S+0
HETATM   15  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6    7                                             
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    4                                                            
CONECT    8    2    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

Synonyms

Value	Source
2-Hydroxy-3-keto-5-methylthiopentenyl-1-phosphate	ChEBI
2-Hydroxy-5-(methylthio)-3-oxopent-1-enyl phosphate	ChEBI
2-Hydroxy-3-keto-5-methylthiopentenyl-1-phosphoric acid	Generator
2-Hydroxy-5-(methylthio)-3-oxopent-1-enyl phosphoric acid	Generator

Molecular Formula

C₆H₁₁O₆PS

Average Mass

242.18

Monoisotopic Mass

242.001396246

IUPAC Name

{[2-hydroxy-5-(methylsulfanyl)-3-oxopent-1-en-1-yl]oxy}phosphonic acid

Traditional Name

[2-hydroxy-5-(methylsulfanyl)-3-oxopent-1-en-1-yl]oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H]C(OP(O)(O)=O)=C(O)C(=O)CCSC

InChI Identifier

InChI=1S/C6H11O6PS/c1-14-3-2-5(7)6(8)4-12-13(9,10)11/h4,8H,2-3H2,1H3,(H2,9,10,11)

InChI Key

YIEMFVNCENFBSD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphate esters. These are organic compounds containing phosphoric acid ester functional group, with the general structure R1P(=O)(R2)OR3. R1,R2 = O,N, or halogen atom; R3 = organyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Phosphate esters

Alternative Parents

Substituents

Phosphoric acid ester
Alpha-branched alpha,beta-unsaturated-ketone
Alpha,beta-unsaturated ketone
Acryloyl-group
Enone
Alpha-hydroxy ketone
Ketone
Dialkylthioether
Sulfenyl compound
Thioether
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Carbonyl group
Organic oxide
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

aliphatic sulfide (CHEBI:50605 )
oxoalkyl phosphate (CHEBI:50605 )
hydroxyalkyl phosphate (CHEBI:50605 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	6.16 g/L	ALOGPS
logP	-0.23	ALOGPS
logP	0.16	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.36	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	52.74 m³·mol⁻¹	ChemAxon
Polarizability	20.69 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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
MMDBr0008244	2-Hydroxy-3-keto-5-methylthiopentenyl-1-phosphate	5-(methylsulfanyl)-2,3-dioxopentyl phosphate	Not Available		VMH	30371894

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	Firmicutes	42	Human feces; Human	Metabolic reconstruction
Bacteria	Proteobacteria	35	Human feces; Human	Metabolic reconstruction

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

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

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

PDB ID

Not Available

ChEBI ID

50605

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for 2-Hydroxy-3-keto-5-methylthiopentenyl-1-phosphate (MMDBc0048267)

MOL for #<Metabolite:0x00007fdb44e30450>

3D MOL for #<Metabolite:0x00007fdb44e30450>

3D SDF for #<Metabolite:0x00007fdb44e30450>

3D-SDF for #<Metabolite:0x00007fdb44e30450>

PDB for #<Metabolite:0x00007fdb44e30450>

3D PDB for #<Metabolite:0x00007fdb44e30450>

SMILES for #<Metabolite:0x00007fdb44e30450>

INCHI for #<Metabolite:0x00007fdb44e30450>

Structure for #<Metabolite:0x00007fdb44e30450>

3D Structure for #<Metabolite:0x00007fdb44e30450>