NP-MRD: Showing NP-Card for 4-hydroxyphenylpyruvic acid oxime (NP0008807)

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Record Information

Version

2.0

Created at

2020-12-09 06:18:23 UTC

Updated at

2021-07-15 17:01:28 UTC

NP-MRD ID

NP0008807

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxyphenylpyruvic acid oxime

Provided By

NPAtlas

Description

4-hydroxyphenylpyruvic acid oxime is found in Aspergillus. 4-hydroxyphenylpyruvic acid oxime was first documented in 2009 (PMID: 19824618). Based on a literature review very few articles have been published on 4-hydroxyphenylpyruvic acid oxime.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106303D          

 23 23  0  0  0  0            999 V2000
   -2.7395    0.5912   -2.7139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0846    0.7109   -1.6479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2921    1.8279   -1.5026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1422   -0.2712   -0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3698   -0.1170    0.6395 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0863   -0.0467    0.4706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7362    1.1622    0.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1267    1.2242    0.3546 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695    0.0892    0.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2462    0.1099   -0.0498 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2164   -1.1209    0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8475   -1.1657    0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8895   -1.2993   -0.7627 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9601   -2.2478    0.2242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5419    2.6110   -0.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6752   -0.9473    1.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7657    0.8055    1.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2266    2.0959    0.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6468    2.1636    0.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8176    0.0132    0.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7623   -2.0353   -0.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3517   -2.1103    0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4732   -2.0433    1.0680 H   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 13  2  0  0  0  0
 13 14  1  0  0  0  0
 12  6  1  0  0  0  0
  3 15  1  0  0  0  0
  5 16  1  0  0  0  0
  5 17  1  0  0  0  0
  7 18  1  0  0  0  0
  8 19  1  0  0  0  0
 10 20  1  0  0  0  0
 11 21  1  0  0  0  0
 12 22  1  0  0  0  0
 14 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0008807

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O\N=C(\C(=O)O[H])C([H])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C9H9NO4/c11-7-3-1-6(2-4-7)5-8(10-14)9(12)13/h1-4,11,14H,5H2,(H,12,13)/b10-8+

> <INCHI_KEY>
HOSMGQOSNROJPE-UHFFFAOYSA-N

> <FORMULA>
C9H9NO4

> <MOLECULAR_WEIGHT>
195.174

> <EXACT_MASS>
195.053157774

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.167230460505472

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-2-(N-hydroxyimino)-3-(4-hydroxyphenyl)propanoic acid

> <ALOGPS_LOGP>
1.02

> <JCHEM_LOGP>
1.6061282373333334

> <ALOGPS_LOGS>
-2.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.406951369592166

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3749579739255147

> <JCHEM_PKA_STRONGEST_BASIC>
-2.702041712296187

> <JCHEM_POLAR_SURFACE_AREA>
90.12

> <JCHEM_REFRACTIVITY>
48.5142

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-2-(N-hydroxyimino)-3-(4-hydroxyphenyl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -2.740   0.591  -2.714  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.085   0.711  -1.648  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.292   1.828  -1.503  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.142  -0.271  -0.597  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.370  -0.117   0.640  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.086  -0.047   0.471  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.736   1.162   0.528  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.127   1.224   0.355  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.869   0.089   0.126  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.246   0.110  -0.050  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.216  -1.121   0.070  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.848  -1.166   0.242  0.00  0.00           C+0
HETATM   13  N   UNK     0      -2.890  -1.299  -0.763  0.00  0.00           N+0
HETATM   14  O   UNK     0      -2.960  -2.248   0.224  0.00  0.00           O+0
HETATM   15  H   UNK     0      -1.542   2.611  -0.904  0.00  0.00           H+0
HETATM   16  H   UNK     0      -1.675  -0.947   1.331  0.00  0.00           H+0
HETATM   17  H   UNK     0      -1.766   0.806   1.146  0.00  0.00           H+0
HETATM   18  H   UNK     0       0.227   2.096   0.712  0.00  0.00           H+0
HETATM   19  H   UNK     0       2.647   2.164   0.397  0.00  0.00           H+0
HETATM   20  H   UNK     0       4.818   0.013   0.782  0.00  0.00           H+0
HETATM   21  H   UNK     0       2.762  -2.035  -0.107  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.352  -2.110   0.196  0.00  0.00           H+0
HETATM   23  H   UNK     0      -3.473  -2.043   1.068  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2   15                                                       
CONECT    4    2    5   13                                                  
CONECT    5    4    6   16   17                                             
CONECT    6    5    7   12                                                  
CONECT    7    6    8   18                                                  
CONECT    8    7    9   19                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   20                                                       
CONECT   11    9   12   21                                                  
CONECT   12   11    6   22                                                  
CONECT   13    4   14                                                       
CONECT   14   13   23                                                       
CONECT   15    3                                                            
CONECT   16    5                                                            
CONECT   17    5                                                            
CONECT   18    7                                                            
CONECT   19    8                                                            
CONECT   20   10                                                            
CONECT   21   11                                                            
CONECT   22   12                                                            
CONECT   23   14                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
4-Hydroxyphenylpyruvate oxime	Generator
2-(N-Hydroxyimino)-3-(4-hydroxyphenyl)propanoate	Generator

Chemical Formula

C₉H₉NO₄

Average Mass

195.1740 Da

Monoisotopic Mass

195.05316 Da

IUPAC Name

(2E)-2-(N-hydroxyimino)-3-(4-hydroxyphenyl)propanoic acid

Traditional Name

(2E)-2-(N-hydroxyimino)-3-(4-hydroxyphenyl)propanoic acid

CAS Registry Number

Not Available

SMILES

ON=C(CC1=CC=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C9H9NO4/c11-7-3-1-6(2-4-7)5-8(10-14)9(12)13/h1-4,11,14H,5H2,(H,12,13)

InChI Key

HOSMGQOSNROJPE-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
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, 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	¹³C NMR Spectrum (1D, 50 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, 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	¹³C NMR Spectrum (1D, 176 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, 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
Aspergillus	NPAtlas	19824618

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

3-phenylpropanoic-acid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Ketoxime
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxime
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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	1.02	ALOGPS
logP	1.61	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.12 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.51 m³·mol⁻¹	ChemAxon
Polarizability	18.17 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

NPAtlas ID

NPA004348

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

60745135

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72730734

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ingavat N, Dobereiner J, Wiyakrutta S, Mahidol C, Ruchirawat S, Kittakoop P: Aspergillusol A, an alpha-glucosidase inhibitor from the marine-derived fungus Aspergillus aculeatus. J Nat Prod. 2009 Nov;72(11):2049-52. doi: 10.1021/np9003883. [PubMed:19824618 ]

Showing NP-Card for 4-hydroxyphenylpyruvic acid oxime (NP0008807)

MOL for NP0008807 (4-hydroxyphenylpyruvic acid oxime)

3D MOL for NP0008807 (4-hydroxyphenylpyruvic acid oxime)

3D SDF for NP0008807 (4-hydroxyphenylpyruvic acid oxime)

3D-SDF for NP0008807 (4-hydroxyphenylpyruvic acid oxime)

PDB for NP0008807 (4-hydroxyphenylpyruvic acid oxime)

3D PDB for NP0008807 (4-hydroxyphenylpyruvic acid oxime)

SMILES for NP0008807 (4-hydroxyphenylpyruvic acid oxime)

INCHI for NP0008807 (4-hydroxyphenylpyruvic acid oxime)

Structure for NP0008807 (4-hydroxyphenylpyruvic acid oxime)

3D Structure for NP0008807 (4-hydroxyphenylpyruvic acid oxime)