NP-MRD: Showing NP-Card for p-hydroxyphenylpyruvic acid (NP0028355)

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Record Information

Version

2.0

Created at

2021-06-19 20:16:02 UTC

Updated at

2021-06-29 23:55:06 UTC

NP-MRD ID

NP0028355

Secondary Accession Numbers

None

Natural Product Identification

Common Name

p-hydroxyphenylpyruvic acid

Provided By

JEOL Database JEOL Logo

Description

2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid, also known as 4,alpha-dihydroxycinnamic acid or 4-hydroxy-enol-phenylpyruvate, belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid. 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid exists in all living organisms, ranging from bacteria to humans. In humans, 2-hydroxy-3-(4-hydroxyphenyl)propenoic acid is involved in the metabolic disorder called hawkinsinuria. 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. p-hydroxyphenylpyruvic acid is found in Ceratodictyon spongiosum. p-hydroxyphenylpyruvic acid was first documented in 2002 (Bugni, T. S., et al.). Based on a literature review very few articles have been published on 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122163D          

 21 21  0  0  0  0            999 V2000
    3.2990   -1.1204    1.9728 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4322   -0.4203    0.9893 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5354    0.3330    0.7838 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4938   -0.2272   -0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8741    0.6299   -1.1708 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3364   -0.9086   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2916   -0.8697   -1.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4080   -2.0496   -1.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4342   -2.0531   -2.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7730   -0.8745   -3.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7794   -0.9210   -3.9963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1055    0.3110   -2.7932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0792    0.3116   -1.8430 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0855    0.1406    1.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7658    0.9418   -0.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1237   -1.5859    0.6758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1558   -2.9812   -0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9658   -2.9725   -2.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8926   -0.0335   -4.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3657    1.2396   -3.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4267    1.2480   -1.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
  7  6  1  0  0  0  0
 12 13  1  0  0  0  0
  6  4  2  0  0  0  0
  4  2  1  0  0  0  0
 13  7  2  0  0  0  0
  2  1  2  0  0  0  0
 10 12  2  0  0  0  0
  2  3  1  0  0  0  0
  7  8  1  0  0  0  0
  4  5  1  0  0  0  0
  8  9  2  0  0  0  0
 10 11  1  0  0  0  0
  9 18  1  0  0  0  0
 12 20  1  0  0  0  0
 13 21  1  0  0  0  0
  8 17  1  0  0  0  0
  6 16  1  0  0  0  0
  3 14  1  0  0  0  0
  5 15  1  0  0  0  0
 11 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028355

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-5,10-11H,(H,12,13)/b8-5-

> <INCHI_KEY>
GQYBCIHRWMPOOF-YVMONPNESA-N

> <FORMULA>
C9H8O4

> <MOLECULAR_WEIGHT>
180.1574

> <EXACT_MASS>
180.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
17.252444159875566

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
1.28

> <JCHEM_LOGP>
1.313863257

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.314950242027475

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1638469545728034

> <JCHEM_PKA_STRONGEST_BASIC>
-5.970951493065994

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
47.00820000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,α-dihydroxycinnamic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  O   UNK     0       3.299  -1.120   1.973  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.432  -0.420   0.989  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.535   0.333   0.784  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.494  -0.227  -0.151  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.874   0.630  -1.171  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.336  -0.909  -0.151  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.292  -0.870  -1.186  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.408  -2.050  -1.479  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.434  -2.053  -2.427  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.773  -0.875  -3.078  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.779  -0.921  -3.996  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.105   0.311  -2.793  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.079   0.312  -1.843  0.00  0.00           C+0
HETATM   14  H   UNK     0       5.085   0.141   1.574  0.00  0.00           H+0
HETATM   15  H   UNK     0       3.766   0.942  -0.910  0.00  0.00           H+0
HETATM   16  H   UNK     0       1.124  -1.586   0.676  0.00  0.00           H+0
HETATM   17  H   UNK     0      -0.156  -2.981  -0.978  0.00  0.00           H+0
HETATM   18  H   UNK     0      -1.966  -2.973  -2.655  0.00  0.00           H+0
HETATM   19  H   UNK     0      -2.893  -0.034  -4.374  0.00  0.00           H+0
HETATM   20  H   UNK     0      -1.366   1.240  -3.290  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.427   1.248  -1.620  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    4    1    3                                                  
CONECT    3    2   14                                                       
CONECT    4    6    2    5                                                  
CONECT    5    4   15                                                       
CONECT    6    7    4   16                                                  
CONECT    7    6   13    8                                                  
CONECT    8    7    9   17                                                  
CONECT    9   10    8   18                                                  
CONECT   10    9   12   11                                                  
CONECT   11   10   19                                                       
CONECT   12   13   10   20                                                  
CONECT   13   12    7   21                                                  
CONECT   14    3                                                            
CONECT   15    5                                                            
CONECT   16    6                                                            
CONECT   17    8                                                            
CONECT   18    9                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   13                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Value	Source
4,alpha-Dihydroxycinnamic acid	ChEBI
4-Hydroxy-enol-phenylpyruvate	Kegg
4,a-Dihydroxycinnamate	Generator
4,a-Dihydroxycinnamic acid	Generator
4,alpha-Dihydroxycinnamate	Generator
4,Α-dihydroxycinnamate	Generator
4,Α-dihydroxycinnamic acid	Generator
4-Hydroxy-enol-phenylpyruvic acid	Generator
2-Hydroxy-3-(4-hydroxyphenyl)propenoate	Generator

Chemical Formula

C₉H₈O₄

Average Mass

180.1574 Da

Monoisotopic Mass

180.04226 Da

IUPAC Name

(2Z)-2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoic acid

Traditional Name

4,α-dihydroxycinnamic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C(\O[H])=C(/[H])C1=C([H])C([H])=C(O[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-5,10-11H,(H,12,13)/b8-5-

InChI Key

GQYBCIHRWMPOOF-YVMONPNESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, 5% D₂O/ CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, 5% D₂O/ CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, 5% D₂O/ CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, 5% D₂O/ CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, 5% D₂O/ CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, 5% D₂O/ CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, 5% D₂O/ CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, 5% D₂O/ CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, 5% D₂O/ CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, 5% D₂O/ CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, 5% D₂O/ CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 5% D₂O/ CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, 5% D₂O/ CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, 5% D₂O/ CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, 5% D₂O/ CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, 5% D₂O/ CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, 5% D₂O/ CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, 5% D₂O/ CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, 5% D₂O/ CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, 5% D₂O/ CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Ceratodictyon spongiosum	JEOL database	Bugni, T. S., et al, Phytochemistry 60, 361 (2002)
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpyruvic acid derivatives

Direct Parent

Phenylpyruvic acid derivatives

Alternative Parents

Not Available

Substituents

Not Available

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	1.28	ALOGPS
logP	1.31	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.16	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.01 m³·mol⁻¹	ChemAxon
Polarizability	17.25 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

HMDB0006915

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB024152

KNApSAcK ID

Not Available

Chemspider ID

552441

KEGG Compound ID

C05350

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

636708

PDB ID

Not Available

ChEBI ID

27683

Good Scents ID

Not Available

References

General References

Bugni, T. S., et al. (2002). Bugni, T. S., et al, Phytochemistry 60, 361 (2002). Phytochem..

Showing NP-Card for p-hydroxyphenylpyruvic acid (NP0028355)

MOL for NP0028355 (p-hydroxyphenylpyruvic acid)

3D MOL for NP0028355 (p-hydroxyphenylpyruvic acid)

3D SDF for NP0028355 (p-hydroxyphenylpyruvic acid)

3D-SDF for NP0028355 (p-hydroxyphenylpyruvic acid)

PDB for NP0028355 (p-hydroxyphenylpyruvic acid)

3D PDB for NP0028355 (p-hydroxyphenylpyruvic acid)

SMILES for NP0028355 (p-hydroxyphenylpyruvic acid)

INCHI for NP0028355 (p-hydroxyphenylpyruvic acid)

Structure for NP0028355 (p-hydroxyphenylpyruvic acid)

3D Structure for NP0028355 (p-hydroxyphenylpyruvic acid)