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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:20:30 UTC

Update Date

2021-09-26 22:53:36 UTC

HMDB ID

HMDB0245251

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-Naphthyl dihydrogen phosphate

Description

2-Naphthyl dihydrogen phosphate, also known as phosphoric acid mono-2-naphthyl ester or beta-naphthyl phosphate, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Based on a literature review a significant number of articles have been published on 2-Naphthyl dihydrogen phosphate. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2-naphthyl dihydrogen phosphate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2-Naphthyl dihydrogen 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

  Mrv1652309112100202D          

 15 16  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    2.1434   -0.4125    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
    3.5724   -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
    2.8579   -1.6500    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4618    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
  1 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245251

> <DATABASE_NAME>
hmdb

> <SMILES>
OP(O)(=O)OC1=CC2=CC=CC=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H9O4P/c11-15(12,13)14-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,(H2,11,12,13)

> <INCHI_KEY>
CQTZJAKSNDFPOB-UHFFFAOYSA-N

> <FORMULA>
C10H9O4P

> <MOLECULAR_WEIGHT>
224.152

> <EXACT_MASS>
224.023845768

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
20.122601467100704

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(naphthalen-2-yloxy)phosphonic acid

> <ALOGPS_LOGP>
1.57

> <JCHEM_LOGP>
2.0052921053333335

> <ALOGPS_LOGS>
-2.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.743790722531692

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7865009652116761

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
55.361999999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.31e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
naphthalen-2-yloxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   12  P   UNK     0       8.002   1.540   0.000  0.00  0.00           P+0
HETATM   13  O   UNK     0       8.002   3.080   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       9.542   1.540   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.462   1.540   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9    1                                                       
CONECT   11    6   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Naphthyl phosphate	ChEBI
beta-Naphthyl dihydrogen phosphate	ChEBI
beta-Naphthyl phosphate	ChEBI
Phosphoric acid mono-2-naphthyl ester	ChEBI
Phosphoric acid mono-beta-naphthyl ester	ChEBI
2-Naphthyl phosphoric acid	Generator
b-Naphthyl dihydrogen phosphate	Generator
b-Naphthyl dihydrogen phosphoric acid	Generator
beta-Naphthyl dihydrogen phosphoric acid	Generator
Β-naphthyl dihydrogen phosphate	Generator
Β-naphthyl dihydrogen phosphoric acid	Generator
b-Naphthyl phosphate	Generator
b-Naphthyl phosphoric acid	Generator
beta-Naphthyl phosphoric acid	Generator
Β-naphthyl phosphate	Generator
Β-naphthyl phosphoric acid	Generator
Phosphate mono-2-naphthyl ester	Generator
Phosphate mono-b-naphthyl ester	Generator
Phosphate mono-beta-naphthyl ester	Generator
Phosphate mono-β-naphthyl ester	Generator
Phosphoric acid mono-b-naphthyl ester	Generator
Phosphoric acid mono-β-naphthyl ester	Generator
2-Naphthyl dihydrogen phosphoric acid	Generator
beta-Naphthyl phosphate, calcium (1:1) salt	HMDB
beta-Naphthyl phosphate, calcium salt	HMDB
beta-Naphthyl phosphate, disodium salt	HMDB
beta-Naphthyl phosphate, monosodium salt	HMDB

Chemical Formula

C₁₀H₉O₄P

Average Molecular Weight

224.152

Monoisotopic Molecular Weight

224.023845768

IUPAC Name

(naphthalen-2-yloxy)phosphonic acid

Traditional Name

naphthalen-2-yloxyphosphonic acid

CAS Registry Number

Not Available

SMILES

OP(O)(=O)OC1=CC2=CC=CC=C2C=C1

InChI Identifier

InChI=1S/C10H9O4P/c11-15(12,13)14-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,(H2,11,12,13)

InChI Key

CQTZJAKSNDFPOB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Aryl phosphate
Aryl phosphomonoester
Naphthalene
Phosphoric acid ester
Organic phosphoric acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	1.57	ALOGPS
logP	2.01	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	1.79	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	55.36 m³·mol⁻¹	ChemAxon
Polarizability	20.12 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]+	137.277	30932474
DeepCCS	[M-H]-	134.944	30932474
DeepCCS	[M-2H]-	169.385	30932474
DeepCCS	[M+Na]+	143.646	30932474
AllCCS	[M+H]+	150.2	32859911
AllCCS	[M+H-H2O]+	146.4	32859911
AllCCS	[M+NH4]+	153.7	32859911
AllCCS	[M+Na]+	154.7	32859911
AllCCS	[M-H]-	143.2	32859911
AllCCS	[M+Na-2H]-	143.4	32859911
AllCCS	[M+HCOO]-	143.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Naphthyl dihydrogen phosphate	OP(O)(=O)OC1=CC2=CC=CC=C2C=C1	3220.4	Standard polar	33892256
2-Naphthyl dihydrogen phosphate	OP(O)(=O)OC1=CC2=CC=CC=C2C=C1	1886.7	Standard non polar	33892256
2-Naphthyl dihydrogen phosphate	OP(O)(=O)OC1=CC2=CC=CC=C2C=C1	2130.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Naphthyl dihydrogen phosphate,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OC1=CC=C2C=CC=CC2=C1	1975.4	Semi standard non polar	33892256
2-Naphthyl dihydrogen phosphate,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OC1=CC=C2C=CC=CC2=C1	2039.4	Standard non polar	33892256
2-Naphthyl dihydrogen phosphate,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OC1=CC=C2C=CC=CC2=C1	2611.8	Standard polar	33892256
2-Naphthyl dihydrogen phosphate,2TMS,isomer #1	C[Si](C)(C)OP(=O)(OC1=CC=C2C=CC=CC2=C1)O[Si](C)(C)C	1983.4	Semi standard non polar	33892256
2-Naphthyl dihydrogen phosphate,2TMS,isomer #1	C[Si](C)(C)OP(=O)(OC1=CC=C2C=CC=CC2=C1)O[Si](C)(C)C	2159.7	Standard non polar	33892256
2-Naphthyl dihydrogen phosphate,2TMS,isomer #1	C[Si](C)(C)OP(=O)(OC1=CC=C2C=CC=CC2=C1)O[Si](C)(C)C	2327.6	Standard polar	33892256
2-Naphthyl dihydrogen phosphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OC1=CC=C2C=CC=CC2=C1	2240.5	Semi standard non polar	33892256
2-Naphthyl dihydrogen phosphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OC1=CC=C2C=CC=CC2=C1	2256.2	Standard non polar	33892256
2-Naphthyl dihydrogen phosphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OC1=CC=C2C=CC=CC2=C1	2767.6	Standard polar	33892256
2-Naphthyl dihydrogen phosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OC1=CC=C2C=CC=CC2=C1)O[Si](C)(C)C(C)(C)C	2432.5	Semi standard non polar	33892256
2-Naphthyl dihydrogen phosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OC1=CC=C2C=CC=CC2=C1)O[Si](C)(C)C(C)(C)C	2584.8	Standard non polar	33892256
2-Naphthyl dihydrogen phosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OC1=CC=C2C=CC=CC2=C1)O[Si](C)(C)C(C)(C)C	2614.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Naphthyl dihydrogen phosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-006w-3930000000-929cce76a394547a62d3	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Naphthyl dihydrogen 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 - 2-Naphthyl dihydrogen phosphate 10V, Positive-QTOF	splash10-004i-0090000000-fe0aa9904d7dc4fea0da	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Naphthyl dihydrogen phosphate 20V, Positive-QTOF	splash10-004i-0490000000-ba6435b5fcabbe04c42a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Naphthyl dihydrogen phosphate 40V, Positive-QTOF	splash10-0fvi-3900000000-961e449a446941631654	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Naphthyl dihydrogen phosphate 10V, Negative-QTOF	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Naphthyl dihydrogen phosphate 20V, Negative-QTOF	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Naphthyl dihydrogen phosphate 40V, Negative-QTOF	splash10-004i-9010000000-b74440d0af422b7eb199	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

75001

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

83133

PDB ID

Not Available

ChEBI ID

91043

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 2-Naphthyl dihydrogen phosphate (HMDB0245251)

MOL for HMDB0245251 (2-Naphthyl dihydrogen phosphate)

3D MOL for HMDB0245251 (2-Naphthyl dihydrogen phosphate)

3D SDF for HMDB0245251 (2-Naphthyl dihydrogen phosphate)

3D-SDF for HMDB0245251 (2-Naphthyl dihydrogen phosphate)

PDB for HMDB0245251 (2-Naphthyl dihydrogen phosphate)

3D PDB for HMDB0245251 (2-Naphthyl dihydrogen phosphate)

SMILES for HMDB0245251 (2-Naphthyl dihydrogen phosphate)

INCHI for HMDB0245251 (2-Naphthyl dihydrogen phosphate)

Structure for HMDB0245251 (2-Naphthyl dihydrogen phosphate)

3D Structure for HMDB0245251 (2-Naphthyl dihydrogen phosphate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra