NP-MRD: Showing NP-Card for 5-(2-hydroxy-3,5-dimethylphenyl)-3-(c-hydroxycarbonimidoylmethyl)-5-oxopentanoic acid (NP0298495)

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Record Information

Version

2.0

Created at

2022-09-10 09:46:36 UTC

Updated at

2022-09-10 09:46:36 UTC

NP-MRD ID

NP0298495

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(2-hydroxy-3,5-dimethylphenyl)-3-(c-hydroxycarbonimidoylmethyl)-5-oxopentanoic acid

Description

Phenatic acid A, also known as phenatate a, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Based on a literature review very few articles have been published on Phenatic acid A.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 40  0  0  0  0  0  0  0  0999 V2000
   -4.3372   -3.3789    1.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3611   -2.3485    1.1578 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2708   -1.6989    0.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630   -2.4035    0.9923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3160   -0.2310    0.7968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7617    0.2202   -0.5330 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1638    1.6049   -0.9096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4953    2.7092   -0.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8532    3.1799    0.8470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3983    3.2951   -0.8569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3378   -0.1368   -0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3570    0.3809    0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208    1.0890    1.1751 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0581    0.0690   -0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4173   -0.6994   -1.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7351   -1.0171   -1.3573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0762   -1.8562   -2.5434 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7223   -0.5800   -0.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3595    0.1943    0.5529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4007    0.7093    1.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0455    0.5181    0.8007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6659    1.3016    1.8972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7111   -2.8843    1.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7708    0.2131    1.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3510    0.0953    0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3290   -0.4320   -1.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2755    1.6663   -0.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0654    1.6716   -2.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6810    3.8106   -0.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2112   -1.2496   -0.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0878    0.2383   -1.8089 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6681   -1.0890   -1.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0428   -2.3986   -2.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2643   -2.5899   -2.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1472   -1.2360   -3.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7771   -0.8001   -0.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3002    0.0494    1.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1009    0.6038    2.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6853    1.7558    1.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3522    1.6542    2.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 21 14  1  0
 14 15  2  0
 14 12  1  0
 12 13  2  0
 12 11  1  0
 11  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
 15 16  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 22 40  1  0
 15 32  1  0
 11 30  1  0
 11 31  1  0
  6 26  1  6
  5 24  1  0
  5 25  1  0
  4 23  1  0
  2  1  1  0
  7 27  1  0
  7 28  1  0
 10 29  1  0
M  END


  Mrv1652309102211462D          

 21 21  0  0  0  0            999 V2000
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    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   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3802    3.2287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  8 21  2  0  0  0  0
  2 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0298495

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(C)=C(O)C(=C1)C(=O)CC(CC(O)=N)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H19NO5/c1-8-3-9(2)15(21)11(4-8)12(17)5-10(6-13(16)18)7-14(19)20/h3-4,10,21H,5-7H2,1-2H3,(H2,16,18)(H,19,20)

> <INCHI_KEY>
QMGAPCUMGLSWCA-UHFFFAOYSA-N

> <FORMULA>
C15H19NO5

> <MOLECULAR_WEIGHT>
293.319

> <EXACT_MASS>
293.126322716

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
29.493054490737183

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(2-hydroxy-3,5-dimethylphenyl)-3-[(C-hydroxycarbonimidoyl)methyl]-5-oxopentanoic acid

> <JCHEM_LOGP>
-0.051732791804309064

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.09851821642326

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.5569561957302351

> <JCHEM_PKA_STRONGEST_BASIC>
12.673324626231265

> <JCHEM_POLAR_SURFACE_AREA>
118.68

> <JCHEM_REFRACTIVITY>
87.5922

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-(2-hydroxy-3,5-dimethylphenyl)-3-(C-hydroxycarbonimidoylmethyl)-5-oxopentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       9.336   5.390   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       6.668   5.390   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.043   6.027   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.003   5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   21                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    8    2                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Value	Source
Phenatate a	Generator

Chemical Formula

C₁₅H₁₉NO₅

Average Mass

293.3190 Da

Monoisotopic Mass

293.12632 Da

IUPAC Name

5-(2-hydroxy-3,5-dimethylphenyl)-3-[(C-hydroxycarbonimidoyl)methyl]-5-oxopentanoic acid

Traditional Name

5-(2-hydroxy-3,5-dimethylphenyl)-3-(C-hydroxycarbonimidoylmethyl)-5-oxopentanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H19NO5/c1-8-3-9(2)15(21)11(4-8)12(17)5-10(6-13(16)18)7-14(19)20/h3-4,10,21H,5-7H2,1-2H3,(H2,16,18)(H,19,20)

InChI Key

QMGAPCUMGLSWCA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Butyrophenone
Xylenol
Benzoyl
M-xylene
Xylene
O-cresol
Aryl alkyl ketone
P-cresol
Medium-chain fatty acid
Amino fatty acid
Branched fatty acid
Hydroxy fatty acid
Phenol
Monocyclic benzene moiety
Fatty acyl
Fatty amide
Fatty acid
Benzenoid
Vinylogous acid
Carboxamide group
Primary carboxylic acid amide
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organic nitrogen compound
Organonitrogen compound
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	-0.052	ChemAxon
pKa (Strongest Acidic)	-0.56	ChemAxon
pKa (Strongest Basic)	12.67	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	118.68 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	87.59 m³·mol⁻¹	ChemAxon
Polarizability	29.49 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

9544775

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11369858

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(2-hydroxy-3,5-dimethylphenyl)-3-(c-hydroxycarbonimidoylmethyl)-5-oxopentanoic acid (NP0298495)

MOL for NP0298495 (5-(2-hydroxy-3,5-dimethylphenyl)-3-(c-hydroxycarbonimidoylmethyl)-5-oxopentanoic acid)

3D MOL for NP0298495 (5-(2-hydroxy-3,5-dimethylphenyl)-3-(c-hydroxycarbonimidoylmethyl)-5-oxopentanoic acid)

3D SDF for NP0298495 (5-(2-hydroxy-3,5-dimethylphenyl)-3-(c-hydroxycarbonimidoylmethyl)-5-oxopentanoic acid)

3D-SDF for NP0298495 (5-(2-hydroxy-3,5-dimethylphenyl)-3-(c-hydroxycarbonimidoylmethyl)-5-oxopentanoic acid)

PDB for NP0298495 (5-(2-hydroxy-3,5-dimethylphenyl)-3-(c-hydroxycarbonimidoylmethyl)-5-oxopentanoic acid)

3D PDB for NP0298495 (5-(2-hydroxy-3,5-dimethylphenyl)-3-(c-hydroxycarbonimidoylmethyl)-5-oxopentanoic acid)

SMILES for NP0298495 (5-(2-hydroxy-3,5-dimethylphenyl)-3-(c-hydroxycarbonimidoylmethyl)-5-oxopentanoic acid)

INCHI for NP0298495 (5-(2-hydroxy-3,5-dimethylphenyl)-3-(c-hydroxycarbonimidoylmethyl)-5-oxopentanoic acid)

Structure for NP0298495 (5-(2-hydroxy-3,5-dimethylphenyl)-3-(c-hydroxycarbonimidoylmethyl)-5-oxopentanoic acid)

3D Structure for NP0298495 (5-(2-hydroxy-3,5-dimethylphenyl)-3-(c-hydroxycarbonimidoylmethyl)-5-oxopentanoic acid)