NP-MRD: Showing NP-Card for 4-Nitrophenyl phosphate (NP0001036)

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Record Information

Version

1.0

Created at

2013-05-09 21:15:04 UTC

Updated at

2021-06-30 02:07:06 UTC

NP-MRD ID

NP0001036

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Nitrophenyl phosphate

Description

4-Nitrophenyl phosphate, also known as nitrophenylphosphoric acid, 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. These are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both an hydroxyl group and a nitro group on two different ring carbon atoms.

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>
NP0001036

> <DATABASE_NAME>
NP-MRD

> <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

View in JSmol View NMR Assignments

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

Chemical Formula

C₆H₆NO₆P

Average Mass

219.0887 Da

Monoisotopic Mass

218.99327 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Mus musculus	LOTUS Database	35616633

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 )

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
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

External Links

HMDB ID

HMDB0060272

DrugBank ID

DB04214

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

369

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

Good Scents ID

Not Available

References

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 ]
Fernandes AC, Soares DC, Saraiva EM, Meyer-Fernandes JR, Souto-Padron T: Different secreted phosphatase activities in Leishmania amazonensis. FEMS Microbiol Lett. 2013 Mar;340(2):117-28. doi: 10.1111/1574-6968.12080. Epub 2013 Feb 11. [PubMed:23305417 ]
Authors unspecified: Cancer Therapy Interactions With Foods and Dietary Supplements (PDQ(R)): Patient Version. 2002. [PubMed:34403226 ]
Authors unspecified: Thyroid Cancer Screening (PDQ(R)): Health Professional Version. 2002. [PubMed:28876831 ]
Authors unspecified: Childhood Cancer Genomics (PDQ(R)): Health Professional Version. 2002. [PubMed:27466641 ]
Authors unspecified: Adult Soft Tissue Sarcoma Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389481 ]
Authors unspecified: Testicular Cancer Screening (PDQ(R)): Health Professional Version. 2002. [PubMed:26389404 ]
Authors unspecified: Rectal Cancer Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389402 ]
Authors unspecified: Childhood Astrocytomas Treatment (PDQ(R)): Patient Version. 2002. [PubMed:26389391 ]
Authors unspecified: Colon Cancer Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389297 ]
Authors unspecified: Childhood Craniopharyngioma Treatment (PDQ(R)): Patient Version. 2002. [PubMed:26389237 ]

Showing NP-Card for 4-Nitrophenyl phosphate (NP0001036)

MOL for NP0001036 (4-Nitrophenyl phosphate)

3D MOL for NP0001036 (4-Nitrophenyl phosphate)

3D SDF for NP0001036 (4-Nitrophenyl phosphate)

3D-SDF for NP0001036 (4-Nitrophenyl phosphate)

PDB for NP0001036 (4-Nitrophenyl phosphate)

3D PDB for NP0001036 (4-Nitrophenyl phosphate)

SMILES for NP0001036 (4-Nitrophenyl phosphate)

INCHI for NP0001036 (4-Nitrophenyl phosphate)

Structure for NP0001036 (4-Nitrophenyl phosphate)

3D Structure for NP0001036 (4-Nitrophenyl phosphate)