NP-MRD: Showing NP-Card for armin (NP0197944)

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Record Information

Version

2.0

Created at

2022-09-04 16:18:21 UTC

Updated at

2022-09-04 16:18:21 UTC

NP-MRD ID

NP0197944

Secondary Accession Numbers

None

Natural Product Identification

Common Name

armin

Description

Ethyl 4-nitrophenyl ethylphosphonate, also known as p-nitrophenyl-O-ethyl ethylphosphonic acid, belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group. armin is found in Artemisia armeniaca. Ethyl 4-nitrophenyl ethylphosphonate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -4.6346   -1.3931    0.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2134   -1.9027   -0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5220   -0.9524   -0.8133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3460   -0.1287   -0.0171 P   0  0  2  0  0  5  0  0  0  0  0  0
   -1.9076    0.1455    1.4709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2819    1.5290   -0.7946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0657    2.5189    0.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1002   -0.8107    0.2251 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4124   -0.5341    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1243    0.1872    1.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4744    0.4506    1.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2078    0.0136   -0.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6415    0.1859   -0.1499 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.2725   -0.4395   -1.0455 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3370    0.9688    0.7150 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.5595   -0.7150   -1.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1776   -0.9528   -0.9307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6439   -0.2688   -0.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7864   -1.5658    1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4041   -1.8696   -0.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3787   -2.7944   -0.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6854   -2.2243    0.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8030    1.5068   -1.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655    1.9085   -0.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9015    1.9117    0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5487    3.2769   -0.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4053    2.9449    0.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5603    0.5641    1.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0176    1.0300    1.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1570   -1.0667   -1.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7516   -1.5241   -1.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  3  1  6
  4  5  2  0
  4  6  1  0
  6  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 16  1  0
 16 17  2  0
 12 13  1  0
 13 15  1  0
 13 14  2  0
 17  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
 10 28  1  0
 11 29  1  0
 16 30  1  0
 17 31  1  0
M  CHG  2  13   1  15  -1
M  END


  Mrv1572004221606212D          

 17 17  0  0  0  0            999 V2000
   -1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    3.1895    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
    0.0000   -0.0000    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
    0.0000    0.8250    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    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
   -0.0000    2.4750    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 11  2  0  0  0  0
 13 11  2  0  0  0  0
 15  3  1  0  0  0  0
 16 10  1  0  0  0  0
 17  4  1  0  0  0  0
 17 14  2  0  0  0  0
 17 15  1  0  0  0  0
 17 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197944

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOP(=O)(CC)OC1=CC=C(C=C1)N(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H14NO5P/c1-3-15-17(14,4-2)16-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3

> <INCHI_KEY>
XXUJMEYKYHETBZ-UHFFFAOYSA-N

> <FORMULA>
C10H14NO5P

> <MOLECULAR_WEIGHT>
259.198

> <EXACT_MASS>
259.060959553

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.95722543304042

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 4-nitrophenyl ethylphosphonate

> <ALOGPS_LOGP>
2.12

> <JCHEM_LOGP>
2.221320763666667

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-8.034933694944797

> <JCHEM_POLAR_SURFACE_AREA>
81.35000000000001

> <JCHEM_REFRACTIVITY>
62.86590000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
armin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   5.954   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.770   5.954   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.770   3.286   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   17  P   UNK     0      -0.000   4.620   0.000  0.00  0.00           P+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1   15                                                       
CONECT    4    2   17                                                       
CONECT    5    7    9                                                       
CONECT    6    8    9                                                       
CONECT    7    5   10                                                       
CONECT    8    6   10                                                       
CONECT    9    5    6   11                                                  
CONECT   10    7    8   16                                                  
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   17                                                            
CONECT   15    3   17                                                       
CONECT   16   10   17                                                       
CONECT   17    4   14   15   16                                             
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
p-Nitrophenyl-O-ethyl ethylphosphonate	Kegg
p-Nitrophenyl-O-ethyl ethylphosphonic acid	Generator
Ethyl 4-nitrophenyl ethylphosphonic acid	Generator
Ethyl 4-nitrophenyl ethylphosphonate	KEGG
Armin	MeSH
Armine	MeSH
Ethyl-P-nitrophenyl ethylphosphonate	MeSH

Chemical Formula

C₁₀H₁₄NO₅P

Average Mass

259.1980 Da

Monoisotopic Mass

259.06096 Da

IUPAC Name

ethyl 4-nitrophenyl ethylphosphonate

Traditional Name

armin

CAS Registry Number

Not Available

SMILES

CCOP(=O)(CC)OC1=CC=C(C=C1)N(=O)=O

InChI Identifier

InChI=1S/C10H14NO5P/c1-3-15-17(14,4-2)16-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3

InChI Key

XXUJMEYKYHETBZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Artemisia armeniaca	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Nitrobenzenes

Direct Parent

Nitrobenzenes

Alternative Parents

Substituents

Nitrobenzene
Phenoxy compound
Nitroaromatic compound
Phosphonic acid diester
Phosphonic acid ester
Organophosphonic acid derivative
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
Organophosphorus compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organic phosphonate (CHEBI:32353 )
phosphonic ester (CHEBI:32353 )

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	2.12	ALOGPS
logP	2.22	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	-8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	81.35 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	62.87 m³·mol⁻¹	ChemAxon
Polarizability	23.96 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C13048

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

66067

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for armin (NP0197944)

MOL for NP0197944 (armin)

3D MOL for NP0197944 (armin)

3D SDF for NP0197944 (armin)

3D-SDF for NP0197944 (armin)

PDB for NP0197944 (armin)

3D PDB for NP0197944 (armin)

SMILES for NP0197944 (armin)

INCHI for NP0197944 (armin)

Structure for NP0197944 (armin)

3D Structure for NP0197944 (armin)