NP-MRD: Showing NP-Card for 3,4,5-trihydroxy-2-propylbenzoic acid (NP0230415)

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Record Information

Version

2.0

Created at

2022-09-06 10:51:33 UTC

Updated at

2022-09-06 10:51:34 UTC

NP-MRD ID

NP0230415

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4,5-trihydroxy-2-propylbenzoic acid

Description

Propyl gallic acid belongs to the class of organic compounds known as gallic acids. These are organic compounds that contain a 3,4,5-trihydroxybenzoic acid moiety. 3,4,5-trihydroxy-2-propylbenzoic acid is found in Zea mays. 3,4,5-trihydroxy-2-propylbenzoic acid was first documented in 2021 (PMID: 35053178). Based on a literature review a small amount of articles have been published on propyl gallic acid (PMID: 35508903) (PMID: 35235324) (PMID: 34980732).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062212512D          

 15 15  0  0  0  0            999 V2000
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    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
    2.1434    2.0625    0.0000 O   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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
   -0.7145   -0.4125    0.0000 O   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    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0230415

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC1=C(C=C(O)C(O)=C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O5/c1-2-3-5-6(10(14)15)4-7(11)9(13)8(5)12/h4,11-13H,2-3H2,1H3,(H,14,15)

> <INCHI_KEY>
QULIOZDJZXKLNY-UHFFFAOYSA-N

> <FORMULA>
C10H12O5

> <MOLECULAR_WEIGHT>
212.201

> <EXACT_MASS>
212.068473486

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.59349481034606

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4,5-trihydroxy-2-propylbenzoic acid

> <JCHEM_LOGP>
2.1226914783333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.220144101222385

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.791421983833578

> <JCHEM_PKA_STRONGEST_BASIC>
-5.996725381569331

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
53.50010000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-2-propylbenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   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  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    4   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
Propyl gallate	Generator

Chemical Formula

C₁₀H₁₂O₅

Average Mass

212.2010 Da

Monoisotopic Mass

212.06847 Da

IUPAC Name

3,4,5-trihydroxy-2-propylbenzoic acid

Traditional Name

3,4,5-trihydroxy-2-propylbenzoic acid

CAS Registry Number

Not Available

SMILES

CCCC1=C(C=C(O)C(O)=C1O)C(O)=O

InChI Identifier

InChI=1S/C10H12O5/c1-2-3-5-6(10(14)15)4-7(11)9(13)8(5)12/h4,11-13H,2-3H2,1H3,(H,14,15)

InChI Key

QULIOZDJZXKLNY-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
Zea mays	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gallic acids. These are organic compounds that contain a 3,4,5-trihydroxybenzoic acid moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Gallic acids

Alternative Parents

Substituents

Gallic acid
Benzenetriol
Benzoic acid
Pyrogallol derivative
Phenylpropane
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Carboxylic acid derivative
Carboxylic acid
Polyol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
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	2.12	ChemAxon
pKa (Strongest Acidic)	3.79	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	53.5 m³·mol⁻¹	ChemAxon
Polarizability	20.59 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

14385392

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Propyl gallate

METLIN ID

Not Available

PubChem Compound

18688975

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kiselevsky DB, Il'ina AV, Lunkov AP, Varlamov VP, Samuilov VD: Investigation of the Antioxidant Properties of the Quaternized Chitosan Modified with a Gallic Acid Residue Using Peroxidase that Produces Reactive Oxygen Species. Biochemistry (Mosc). 2022 Feb;87(2):141-149. doi: 10.1134/S0006297922020067. [PubMed:35508903 ]
Zhu Z, Marshall M, Harris R, Collins E, Bowen KH: Photoelectron Spectroscopic and Computational Study of the Deprotonated Gallic Acid and Propyl Gallate Anions. J Am Soc Mass Spectrom. 2022 Aug 3;33(8):1355-1361. doi: 10.1021/jasms.2c00017. Epub 2022 Mar 2. [PubMed:35235324 ]
Tanaka Y, Tsuneoka M: Gallic Acid Derivatives Propyl Gallate and Epigallocatechin Gallate Reduce rRNA Transcription via Induction of KDM2A Activation. Biomolecules. 2021 Dec 25;12(1):30. doi: 10.3390/biom12010030. [PubMed:35053178 ]
Sun Y, Kotani A, Machida K, Yamamoto K, Hakamata H: Determination of Phenolic Compounds in Beverages by Three-Flow Channel Isocratic HPLC with Electrochemical Detections Using a Column-Switching Technique. Chem Pharm Bull (Tokyo). 2022;70(1):43-49. doi: 10.1248/cpb.c21-00552. [PubMed:34980732 ]
LOTUS database [Link]

Showing NP-Card for 3,4,5-trihydroxy-2-propylbenzoic acid (NP0230415)

MOL for NP0230415 (3,4,5-trihydroxy-2-propylbenzoic acid)

3D MOL for NP0230415 (3,4,5-trihydroxy-2-propylbenzoic acid)

3D SDF for NP0230415 (3,4,5-trihydroxy-2-propylbenzoic acid)

3D-SDF for NP0230415 (3,4,5-trihydroxy-2-propylbenzoic acid)

PDB for NP0230415 (3,4,5-trihydroxy-2-propylbenzoic acid)

3D PDB for NP0230415 (3,4,5-trihydroxy-2-propylbenzoic acid)

SMILES for NP0230415 (3,4,5-trihydroxy-2-propylbenzoic acid)

INCHI for NP0230415 (3,4,5-trihydroxy-2-propylbenzoic acid)

Structure for NP0230415 (3,4,5-trihydroxy-2-propylbenzoic acid)

3D Structure for NP0230415 (3,4,5-trihydroxy-2-propylbenzoic acid)