MiMeDB: Showing metabocard for 4-nitrophenylphosphate (MMDBc0032108)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 02:02:42 UTC

Update Date

2024-04-30 19:54:26 UTC

Metabolite ID

MMDBc0032108

Metabolite Identification

Common Name

4-nitrophenylphosphate

Description

NULL

Structure

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

4NP
  Mrv1652305261923592D          

 14 14  0  0  0  0            999 V2000
    1.1586    1.1720    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.1586    0.3470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1586    1.9970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3336    1.1720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9836    1.1720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441   -0.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441   -0.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2704   -1.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9848   -0.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9848   -0.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2704    0.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6993   -1.3030    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -1.6993   -2.1280    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.4138   -0.8905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  CHG  2  12   1  13  -1
M  END
> <DATABASE_ID>
MMDBc0032108

> <DATABASE_NAME>
MIME

> <SMILES>
OP(O)(=O)OC1=CC=C(C=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H6NO6P/c8-7(9)5-1-3-6(4-2-5)13-14(10,11)12/h1-4H,(H2,10,11,12)

> <INCHI_KEY>
XZKIHKMTEMTJQX-UHFFFAOYSA-N

> <FORMULA>
C6H6NO6P

> <MOLECULAR_WEIGHT>
219.0887

> <EXACT_MASS>
218.993273441

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
16.61297419464198

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4-nitrophenoxy)phosphonic acid

> <ALOGPS_LOGP>
0.50

> <JCHEM_LOGP>
0.9557995379999997

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.732966687481505

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7670475440101345

> <JCHEM_PKA_STRONGEST_BASIC>
-9.694907407591746

> <JCHEM_POLAR_SURFACE_AREA>
109.9

> <JCHEM_REFRACTIVITY>
45.23230000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-nitrophenyl phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 4NP                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  P   UNK     0       2.163   2.188   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0       2.163   0.648   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       2.163   3.728   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.623   2.188   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.703   2.188   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.829  -0.122   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.829  -1.662   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.505  -2.432   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.838  -1.662   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.838  -0.122   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.505   0.648   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -3.172  -2.432   0.000  0.00  0.00           N+1
HETATM   13  O   UNK     0      -3.172  -3.972   0.000  0.00  0.00           O-1
HETATM   14  O   UNK     0      -4.506  -1.662   0.000  0.00  0.00           O+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    2    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11    6   10                                                       
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

Synonyms

Value	Source
Nitrophenylphosphate	ChEBI
p-Nitrophenyl dihydrogen phosphate	ChEBI
p-Nitrophenyl phosphate	ChEBI
Phosphoric acid, mono(4-nitrophenyl) ester	ChEBI
Phosphoric acid, mono(p-nitrophenyl) ester	ChEBI
Nitrophenylphosphoric acid	Generator
p-Nitrophenyl dihydrogen phosphoric acid	Generator
p-Nitrophenyl phosphoric acid	Generator
Phosphate, mono(4-nitrophenyl) ester	Generator
Phosphate, mono(p-nitrophenyl) ester	Generator
4-Nitrophenyl phosphoric acid	Generator
Disodium nitrophenylphosphate	HMDB
Diammonium nitrophenylphosphate	HMDB
Sodium nitrophenylphosphate	HMDB
Dipotassium nitrophenylphosphate	HMDB
Magnesium nitrophenylphosphate	HMDB
Monosodium nitrophenylphosphate	HMDB
4-Nitrophenylphosphate	HMDB
p-Nitrophenol phosphate	HMDB

Molecular Formula

C₆H₆NO₆P

Average Mass

219.0887

Monoisotopic Mass

218.993273441

IUPAC Name

(4-nitrophenoxy)phosphonic acid

Traditional Name

4-nitrophenyl phosphate

CAS Registry Number

Not Available

SMILES

OP(O)(=O)OC1=CC=C(C=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C6H6NO6P/c8-7(9)5-1-3-6(4-2-5)13-14(10,11)12/h1-4H,(H2,10,11,12)

InChI Key

XZKIHKMTEMTJQX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenyl phosphates. These are aromatic organooxygen compounds containing a phosphate group, which is O-esterified with a phenyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Phenyl phosphates

Alternative Parents

Substituents

Phenyl phosphate
Nitrobenzene
Phenoxy compound
Nitroaromatic compound
Monocyclic benzene moiety
Benzenoid
C-nitro compound
Organic nitro compound
Organic oxoazanium
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aryl phosphate (CHEBI:17440 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.03 g/L	ALOGPS
logP	0.5	ALOGPS
logP	0.96	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	1.77	ChemAxon
pKa (Strongest Basic)	-9.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	109.9 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	45.23 m³·mol⁻¹	ChemAxon
Polarizability	16.61 Å³	ChemAxon
Number of Rings	1	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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01pt-1953000000-f98c304b3a6ab9cd2c5d	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01pt-1953000000-f98c304b3a6ab9cd2c5d	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0hn0-3920000000-657f264f7fae01826457	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-3090000000-f21aa9ac1a47ee6f3125	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-c63df6191601e73b27fb	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-1dd228dda161ae54601f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-7aa2269324d3d40f4c38	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-90c742e07486b602e9c0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-9000000000-d99bb72e9136380d8698	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-9000000000-027da95acd3eda7ca243	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-9000000000-261d7b5a3ed6f38c7b78	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00dl-9550000000-2caf54e289b4f89bf43f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-004i-9000000000-027da95acd3eda7ca243	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-2090000000-bf49b02fd8accd28c0ea	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dl-1690000000-65b1343789f97a63c59f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001j-8910000000-0c83bc1df690856d218a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0159-5090000000-4730832a25320a38eaf9	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02u0-9170000000-08a8302b031ef8d35763	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002b-9000000000-d53bff0ab80eab337c47	2015-09-15	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)		2016-10-22	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

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
MMDBp0191763	Alkaline phosphatase, placental type	Unknown	P05187	Homo sapiens
MMDBp0191766	Intestinal-type alkaline phosphatase	Unknown	P09923	Homo sapiens
MMDBp0191769	Alkaline phosphatase, tissue-nonspecific isozyme	Unknown	P05186	Homo sapiens
MMDBp0191772	Alkaline phosphatase, placental-like	Unknown	P10696	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0002611	Water	4-Nitrophenol	Alkaline phosphatase, liver/bone/kidney	4-Nitrophenyl Phosphate Phosphohydrolase Gamma-Hexachlorocyclohexane Degradation	VMH	11797369 1730777 388794
MMDBr0014132	4-nitrophenylphosphate	4-Nitrophenol	4-nitrophenylphosphatase	Dephosphorylation	RHEA	34755880

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	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown
Eukaryota/Fungi	Ascomycota	3	Human feces; Human saliva	Unknown

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
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0060272

DrugBank ID

DB04214

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C03360

BioCyc ID

CPD-194

BiGG ID

Not Available

Wikipedia Link

Para-Nitrophenylphosphate

METLIN ID

Not Available

PubChem Compound

378

PDB ID

4NP

ChEBI ID

17440

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]

Showing metabocard for 4-nitrophenylphosphate (MMDBc0032108)

MOL for #<Metabolite:0x00007fa4d9734a08>

3D MOL for #<Metabolite:0x00007fa4d9734a08>

3D SDF for #<Metabolite:0x00007fa4d9734a08>

3D-SDF for #<Metabolite:0x00007fa4d9734a08>

PDB for #<Metabolite:0x00007fa4d9734a08>

3D PDB for #<Metabolite:0x00007fa4d9734a08>

SMILES for #<Metabolite:0x00007fa4d9734a08>

INCHI for #<Metabolite:0x00007fa4d9734a08>

Structure for #<Metabolite:0x00007fa4d9734a08>

3D Structure for #<Metabolite:0x00007fa4d9734a08>