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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:32:18 UTC

Update Date

2021-09-26 22:55:40 UTC

HMDB ID

HMDB0246521

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Methylumbelliferyl phosphate

Description

[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]phosphonic acid belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Based on a literature review very few articles have been published on [(4-methyl-2-oxo-2H-chromen-7-yl)oxy]phosphonic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-methylumbelliferyl phosphate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Methylumbelliferyl phosphate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 05041406302D          

 17 18  0  0  0  0            999 V2000
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  6  1  1  0  0  0  0
  6  4  2  0  0  0  0
  7  2  1  0  0  0  0
  7  5  2  0  0  0  0
  8  3  1  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  2  0  0  0  0
 10  4  1  0  0  0  0
 11 10  2  0  0  0  0
 15  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16  7  1  0  0  0  0
 17 12  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  2  0  0  0  0
 17 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246521

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(=O)OC2=C1C=CC(OP(O)(O)=O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C10H9O6P/c1-6-4-10(11)15-9-5-7(2-3-8(6)9)16-17(12,13)14/h2-5H,1H3,(H2,12,13,14)

> <INCHI_KEY>
BCHIXGBGRHLSBE-UHFFFAOYSA-N

> <FORMULA>
C10H9O6P

> <MOLECULAR_WEIGHT>
256.1486

> <EXACT_MASS>
256.013674532

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
21.960898686778666

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]phosphonic acid

> <ALOGPS_LOGP>
0.95

> <JCHEM_LOGP>
1.125323753

> <ALOGPS_LOGS>
-2.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.740423916855905

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7821348283439256

> <JCHEM_PKA_STRONGEST_BASIC>
-6.950903323325436

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
58.68440000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4-methyl-2-oxochromen-7-yl)oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         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  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+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
CONECT    1    6                                                            
CONECT    2    3    7                                                       
CONECT    3    2    8                                                       
CONECT    4    6   10                                                       
CONECT    5    7    9                                                       
CONECT    6    1    4    8                                                  
CONECT    7    2    5   16                                                  
CONECT    8    3    6    9                                                  
CONECT    9    5    8   15                                                  
CONECT   10    4   11   15                                                  
CONECT   11   10                                                            
CONECT   12   17                                                            
CONECT   13   17                                                            
CONECT   14   17                                                            
CONECT   15    9   10                                                       
CONECT   16    7   17                                                       
CONECT   17   12   13   14   16                                             
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0246521
HETATM    1  C1  UNL     1      -3.639   0.976   0.602  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.680   0.106  -0.130  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.105  -0.818  -1.059  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.197  -1.614  -1.727  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.594  -2.470  -2.587  1.00  0.00           O  
HETATM    6  O2  UNL     1      -0.919  -1.479  -1.465  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.425  -0.632  -0.602  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.938  -0.562  -0.393  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.421   0.347   0.526  1.00  0.00           C  
HETATM   10  O3  UNL     1       2.758   0.499   0.811  1.00  0.00           O  
HETATM   11  P1  UNL     1       4.020  -0.375   0.106  1.00  0.00           P  
HETATM   12  O4  UNL     1       3.702  -1.832  -0.075  1.00  0.00           O  
HETATM   13  O5  UNL     1       5.417  -0.285   1.079  1.00  0.00           O  
HETATM   14  O6  UNL     1       4.450   0.295  -1.398  1.00  0.00           O  
HETATM   15  C8  UNL     1       0.532   1.160   1.212  1.00  0.00           C  
HETATM   16  C9  UNL     1      -0.832   1.091   1.004  1.00  0.00           C  
HETATM   17  C10 UNL     1      -1.317   0.190   0.092  1.00  0.00           C  
HETATM   18  H1  UNL     1      -3.408   0.952   1.681  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.667   0.591   0.384  1.00  0.00           H  
HETATM   20  H3  UNL     1      -3.581   2.036   0.278  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.170  -0.888  -1.237  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.622  -1.201  -0.934  1.00  0.00           H  
HETATM   23  H6  UNL     1       5.249  -0.900   1.859  1.00  0.00           H  
HETATM   24  H7  UNL     1       4.055   1.202  -1.511  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.899   1.876   1.935  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.529   1.736   1.549  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   17
CONECT    3    4   21
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8    8   17
CONECT    8    9   22
CONECT    9   10   15   15
CONECT   10   11
CONECT   11   12   12   13   14
CONECT   13   23
CONECT   14   24
CONECT   15   16   25
CONECT   16   17   17   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
[(4-Methyl-2-oxo-2H-chromen-7-yl)oxy]phosphonate	Generator
4-Methylumbelliferone phosphate	ChEMBL
4-Methylumbelliferone phosphoric acid	Generator
4-Methylumbelliferyl phosphoric acid	Generator

Chemical Formula

C₁₀H₉O₆P

Average Molecular Weight

256.1486

Monoisotopic Molecular Weight

256.013674532

IUPAC Name

[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]phosphonic acid

Traditional Name

(4-methyl-2-oxochromen-7-yl)oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)OC2=C1C=CC(OP(O)(O)=O)=C2

InChI Identifier

InChI=1S/C10H9O6P/c1-6-4-10(11)15-9-5-7(2-3-8(6)9)16-17(12,13)14/h2-5H,1H3,(H2,12,13,14)

InChI Key

BCHIXGBGRHLSBE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Aryl phosphate
Aryl phosphomonoester
Benzopyran
1-benzopyran
Pyranone
Organic phosphoric acid derivative
Phosphoric acid ester
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Organoheterocyclic compound
Oxacycle
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.95	ALOGPS
logP	1.13	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	1.78	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.68 m³·mol⁻¹	ChemAxon
Polarizability	21.96 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	145.353	30932474
DeepCCS	[M-H]-	142.995	30932474
DeepCCS	[M-2H]-	175.897	30932474
DeepCCS	[M+Na]+	151.446	30932474
AllCCS	[M+H]+	154.2	32859911
AllCCS	[M+H-H2O]+	150.4	32859911
AllCCS	[M+NH4]+	157.7	32859911
AllCCS	[M+Na]+	158.7	32859911
AllCCS	[M-H]-	149.9	32859911
AllCCS	[M+Na-2H]-	149.7	32859911
AllCCS	[M+HCOO]-	149.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Methylumbelliferyl phosphate	CC1=CC(=O)OC2=C1C=CC(OP(O)(O)=O)=C2	3315.0	Standard polar	33892256
4-Methylumbelliferyl phosphate	CC1=CC(=O)OC2=C1C=CC(OP(O)(O)=O)=C2	2173.3	Standard non polar	33892256
4-Methylumbelliferyl phosphate	CC1=CC(=O)OC2=C1C=CC(OP(O)(O)=O)=C2	2499.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Methylumbelliferyl phosphate,1TMS,isomer #1	CC1=CC(=O)OC2=CC(OP(=O)(O)O[Si](C)(C)C)=CC=C12	2344.3	Semi standard non polar	33892256
4-Methylumbelliferyl phosphate,1TMS,isomer #1	CC1=CC(=O)OC2=CC(OP(=O)(O)O[Si](C)(C)C)=CC=C12	2383.2	Standard non polar	33892256
4-Methylumbelliferyl phosphate,1TMS,isomer #1	CC1=CC(=O)OC2=CC(OP(=O)(O)O[Si](C)(C)C)=CC=C12	2908.6	Standard polar	33892256
4-Methylumbelliferyl phosphate,2TMS,isomer #1	CC1=CC(=O)OC2=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=CC=C12	2353.4	Semi standard non polar	33892256
4-Methylumbelliferyl phosphate,2TMS,isomer #1	CC1=CC(=O)OC2=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=CC=C12	2441.2	Standard non polar	33892256
4-Methylumbelliferyl phosphate,2TMS,isomer #1	CC1=CC(=O)OC2=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=CC=C12	2597.0	Standard polar	33892256
4-Methylumbelliferyl phosphate,1TBDMS,isomer #1	CC1=CC(=O)OC2=CC(OP(=O)(O)O[Si](C)(C)C(C)(C)C)=CC=C12	2601.9	Semi standard non polar	33892256
4-Methylumbelliferyl phosphate,1TBDMS,isomer #1	CC1=CC(=O)OC2=CC(OP(=O)(O)O[Si](C)(C)C(C)(C)C)=CC=C12	2589.1	Standard non polar	33892256
4-Methylumbelliferyl phosphate,1TBDMS,isomer #1	CC1=CC(=O)OC2=CC(OP(=O)(O)O[Si](C)(C)C(C)(C)C)=CC=C12	3057.1	Standard polar	33892256
4-Methylumbelliferyl phosphate,2TBDMS,isomer #1	CC1=CC(=O)OC2=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C12	2807.8	Semi standard non polar	33892256
4-Methylumbelliferyl phosphate,2TBDMS,isomer #1	CC1=CC(=O)OC2=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C12	2865.7	Standard non polar	33892256
4-Methylumbelliferyl phosphate,2TBDMS,isomer #1	CC1=CC(=O)OC2=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C12	2885.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methylumbelliferyl phosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0571-3890000000-729a8d6a8a3530f56524	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methylumbelliferyl phosphate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylumbelliferyl phosphate 10V, Positive-QTOF	splash10-0a4i-0090000000-eee7442828ef70a8de15	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylumbelliferyl phosphate 20V, Positive-QTOF	splash10-0a4i-0190000000-29739e501b3fcd36ca97	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylumbelliferyl phosphate 40V, Positive-QTOF	splash10-017j-3910000000-fd0b6229fa7803b941d7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylumbelliferyl phosphate 10V, Negative-QTOF	splash10-0a6r-5090000000-0e65e5c7c52bd826062f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylumbelliferyl phosphate 20V, Negative-QTOF	splash10-004i-9030000000-fe59b48209f68ee977f2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylumbelliferyl phosphate 40V, Negative-QTOF	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58627

KEGG Compound ID

Not Available

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

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 4-Methylumbelliferyl phosphate (HMDB0246521)

MOL for HMDB0246521 (4-Methylumbelliferyl phosphate)

3D MOL for HMDB0246521 (4-Methylumbelliferyl phosphate)

3D SDF for HMDB0246521 (4-Methylumbelliferyl phosphate)

3D-SDF for HMDB0246521 (4-Methylumbelliferyl phosphate)

PDB for HMDB0246521 (4-Methylumbelliferyl phosphate)

3D PDB for HMDB0246521 (4-Methylumbelliferyl phosphate)

SMILES for HMDB0246521 (4-Methylumbelliferyl phosphate)

INCHI for HMDB0246521 (4-Methylumbelliferyl phosphate)

Structure for HMDB0246521 (4-Methylumbelliferyl phosphate)

3D Structure for HMDB0246521 (4-Methylumbelliferyl phosphate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra