NP-MRD: Showing NP-Card for 5-(methylthio)-2,3-dioxopentyl phosphate (NP0338672)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-11 16:53:42 UTC

Updated at

2024-09-11 16:53:42 UTC

NP-MRD ID

NP0338672

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(methylthio)-2,3-dioxopentyl phosphate

Description

5-(Methylthio)-2,3-dioxopentyl phosphate, also known as 1-phospho-2,3-diketo-5-S-methylthiopentane or 2,3-diketo-5-methylthio-1-phosphopentane, belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. 5-(Methylthio)-2,3-dioxopentyl phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5-(Methylthio)-2,3-dioxopentyl phosphate has been detected, but not quantified in, several different foods, such as atlantic herrings, narrowleaf cattails, tartary buckwheats, allium (onion), and nectarines. This could make 5-(methylthio)-2,3-dioxopentyl phosphate a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305171807392D          

 14 13  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 S   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
    3.9039    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  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
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763    1.8414    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.1908    2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638    2.5559    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 11  1  0  0  0  0
 14 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0338672

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSCCC(=O)C(=O)COP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H11O6PS/c1-14-3-2-5(7)6(8)4-12-13(9,10)11/h2-4H2,1H3,(H2,9,10,11)

> <INCHI_KEY>
HKEAOVFNWRDVAJ-UHFFFAOYSA-N

> <FORMULA>
C6H11O6PS

> <MOLECULAR_WEIGHT>
242.187

> <EXACT_MASS>
242.001395286

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
21.009206917920018

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{[5-(methylsulfanyl)-2,3-dioxopentyl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-0.08

> <JCHEM_LOGP>
0.5128286950000003

> <ALOGPS_LOGS>
-1.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.143880429984992

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1140333449772122

> <JCHEM_PKA_STRONGEST_BASIC>
-9.360354692322906

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
51.197100000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.99e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-pdmsp

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAY-18         0                                  
HETATM    1  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       4.620   2.667   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.621   4.977   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      11.288   3.437   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.622   2.667   0.000  0.00  0.00           O+0
HETATM   11  P   UNK     0      13.956   3.437   0.000  0.00  0.00           P+0
HETATM   12  O   UNK     0      15.289   4.207   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      14.726   2.104   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      13.186   4.771   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
1-Phospho-2,3-diketo-5-S-methylthiopentane	ChEBI
2,3-Diketo-5-methylthio-1-phosphopentane	ChEBI
2,3-Diketo-5-methylthiopentyl-1-phosphate	ChEBI
5-Methylthio-1-(phosphonooxy)pentane-2,3-dione	ChEBI
5-(Methylsulfanyl)-2,3-dioxopentyl phosphate	Kegg
2,3-Diketo-5-methylthiopentyl-1-phosphoric acid	Generator
5-(Methylsulfanyl)-2,3-dioxopentyl phosphoric acid	Generator
5-(Methylsulphanyl)-2,3-dioxopentyl phosphate	Generator
5-(Methylsulphanyl)-2,3-dioxopentyl phosphoric acid	Generator
5-(Methylthio)-2,3-dioxopentyl phosphoric acid	Generator
1-PDMSP	HMDB
5-(Methylthio)-1-(phosphonooxy)-2,3-pentanedione	HMDB
DK-MTP-1-p	HMDB
5-(Methylthio)-2,3-dioxopentyl phosphate	ChEBI

Chemical Formula

C₆H₁₁O₆PS

Average Mass

242.1870 Da

Monoisotopic Mass

242.00140 Da

IUPAC Name

{[5-(methylsulfanyl)-2,3-dioxopentyl]oxy}phosphonic acid

Traditional Name

1-pdmsp

CAS Registry Number

Not Available

SMILES

CSCCC(=O)C(=O)COP(O)(O)=O

InChI Identifier

InChI=1S/C6H11O6PS/c1-14-3-2-5(7)6(8)4-12-13(9,10)11/h2-4H2,1H3,(H2,9,10,11)

InChI Key

HKEAOVFNWRDVAJ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Monoalkyl phosphates

Alternative Parents

Substituents

Monoalkyl phosphate
Monosaccharide
Alpha-diketone
Ketone
Dialkylthioether
Sulfenyl compound
Thioether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

aliphatic sulfide (CHEBI:50604 )
alpha-diketone (CHEBI:50604 )
oxoalkyl phosphate (CHEBI:50604 )

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	-0.08	ALOGPS
logP	0.51	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.11	ChemAxon
pKa (Strongest Basic)	-9.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	51.2 m³·mol⁻¹	ChemAxon
Polarizability	21.01 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