NP-MRD: Showing NP-Card for 3,5-dihydroxybenzoic acid (NP0023601)

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Record Information

Version

1.0

Created at

2021-01-06 08:39:33 UTC

Updated at

2024-05-04 00:30:13 UTC

NP-MRD ID

NP0023601

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,5-dihydroxybenzoic acid

Provided By

NPAtlas

Description

3,5-Dihydroxybenzoic acid, also known as alpha-resorcylic acid or a-resorcylate, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3,5-Dihydroxybenzoic acid is found, on average, in the highest concentration within beer. 3,5-Dihydroxybenzoic acid has also been detected, but not quantified in, several different foods, such as grape wine, nuts, peanuts (Arachis hypogaea), and pulses. This could make 3,5-dihydroxybenzoic acid a potential biomarker for the consumption of these foods. 3,5-Dihydroxybenzoic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 3,5-dihydroxybenzoic acid is found in Aspergillus oryzae, Botrytis sp., Conyza canadensis , Penicillium, Persea americana, Secamone afzelii and Viburnum cylindricum. It was first documented in 1997 (PMID: 9439700). Based on a literature review a small amount of articles have been published on 3,5-Dihydroxybenzoic acid (PMID: 22770225) (PMID: 11959959) (PMID: 15282102) (PMID: 34352962).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120433D          

 17 17  0  0  0  0            999 V2000
    2.8985   -1.3783    0.4555 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3296   -0.2765    0.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1066    0.8529    0.1799 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8881   -0.1662    0.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0678   -1.2759    0.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3001   -1.1365    0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1296   -2.2537    0.4963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8715    0.1262    0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0581    1.2205    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6328    2.4593   -0.0851 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3026    1.0830    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4315    1.0705   -0.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5321   -2.2429    0.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7242   -3.1727    0.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9529    0.1570    0.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8345    2.9814    0.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9470    1.9518    0.0134 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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11  4  1  0  0  0  0
  3 12  1  0  0  0  0
  5 13  1  0  0  0  0
  7 14  1  0  0  0  0
  8 15  1  0  0  0  0
 10 16  1  0  0  0  0
 11 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023601

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O4/c8-5-1-4(7(10)11)2-6(9)3-5/h1-3,8-9H,(H,10,11)

> <INCHI_KEY>
UYEMGAFJOZZIFP-UHFFFAOYSA-N

> <FORMULA>
C7H6O4

> <MOLECULAR_WEIGHT>
154.121

> <EXACT_MASS>
154.026608673

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.87553214865925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,5-dihydroxybenzoic acid

> <ALOGPS_LOGP>
1.29

> <JCHEM_LOGP>
1.0236980806666667

> <ALOGPS_LOGS>
-1.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.285381966170803

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6141076332493496

> <JCHEM_PKA_STRONGEST_BASIC>
-5.714022330881936

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
37.275999999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5-dihydroxybenzoic 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       2.898  -1.378   0.456  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.330  -0.277   0.310  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.107   0.853   0.180  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.888  -0.166   0.277  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.068  -1.276   0.404  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.300  -1.137   0.368  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.130  -2.254   0.496  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.871   0.126   0.203  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.058   1.220   0.077  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.633   2.459  -0.085  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.303   1.083   0.113  0.00  0.00           C+0
HETATM   12  H   UNK     0       3.432   1.071  -0.762  0.00  0.00           H+0
HETATM   13  H   UNK     0       0.532  -2.243   0.531  0.00  0.00           H+0
HETATM   14  H   UNK     0      -1.724  -3.173   0.617  0.00  0.00           H+0
HETATM   15  H   UNK     0      -2.953   0.157   0.184  0.00  0.00           H+0
HETATM   16  H   UNK     0      -1.835   2.981   0.777  0.00  0.00           H+0
HETATM   17  H   UNK     0       0.947   1.952   0.013  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2   12                                                       
CONECT    4    2    5   11                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6   14                                                       
CONECT    8    6    9   15                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   16                                                       
CONECT   11    9    4   17                                                  
CONECT   12    3                                                            
CONECT   13    5                                                            
CONECT   14    7                                                            
CONECT   15    8                                                            
CONECT   16   10                                                            
CONECT   17   11                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
alpha-Resorcylic acid	ChEBI
a-Resorcylate	Generator
a-Resorcylic acid	Generator
alpha-Resorcylate	Generator
Α-resorcylate	Generator
Α-resorcylic acid	Generator
3,5-Dihydroxybenzoate	Generator
3,5-Dihydroxy-benzoic acid	HMDB
3,5-Dihydroxybenzoic acid (acd/name 4.0)	HMDB
5-Carboxyresorcinol	HMDB
Benzoate	HMDB
Benzoic acid	HMDB
alpha-Resorcylic acid, copper (2+) salt	HMDB
alpha-Resorcylic acid, sodium salt	HMDB
3,5-DHBA	HMDB
3,5-Dihydroxybenzoic acid	HMDB

Chemical Formula

C₇H₆O₄

Average Mass

154.1210 Da

Monoisotopic Mass

154.02661 Da

IUPAC Name

3,5-dihydroxybenzoic acid

Traditional Name

3,5-dihydroxybenzoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC(O)=CC(O)=C1

InChI Identifier

InChI=1S/C7H6O4/c8-5-1-4(7(10)11)2-6(9)3-5/h1-3,8-9H,(H,10,11)

InChI Key

UYEMGAFJOZZIFP-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-02	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-02	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-02	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-02	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-02	View Spectrum

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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-02	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Arachis hypogaea	KNApSAcK Database	22123792
Aspergillus oryzae	LOTUS Database	35616633
Botrytis sp.	-	KNApSAcK
Cicer arietinum	KNApSAcK Database	22123792
Conyza canadensis	KNApSAcK Database	22123792
Erigeron canadensis	Plant	KNApSAcK
Penicillium	NPAtlas	9439700
Persea americana	LOTUS Database	35616633
Pterocarpus santalinus	KNApSAcK Database	22123792
Rubus niveus	KNApSAcK Database	22123792
Secamone afzelii	LOTUS Database	35616633
Viburnum cylindricum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hydroxybenzoic acid derivatives

Alternative Parents

Substituents

Hydroxybenzoic acid
Benzoic acid
Resorcinol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

resorcinols (CHEBI:39912 )
dihydroxybenzoic acid (CHEBI:39912 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	237.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	411.00 to 412.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	50980 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.860	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	1.29	ALOGPS
logP	1.02	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.61	ChemAxon
pKa (Strongest Basic)	-5.7	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	1	ChemAxon
Refractivity	37.28 m³·mol⁻¹	ChemAxon
Polarizability	13.88 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA005829

HMDB ID

HMDB0013677

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

Not Available

BioCyc ID

CPD0-1274

BiGG ID

Not Available

Wikipedia Link

3,5-Dihydroxybenzoic_acid

METLIN ID

Not Available

PubChem Compound

7424

PDB ID

Not Available

ChEBI ID

39912

Good Scents ID

rw1184651

References

General References

Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]
Alvi KA, Nair B, Gallo C, Baker D: Screening of microbial extracts for tyrosine kinase inhibitors J Antibiot (Tokyo). 1997 Mar;50(3):264-6. [PubMed:9439700 ]
Elemans JA, Boerakker MJ, Holder SJ, Rowan AE, Cho WD, Percec V, Nolte RJ: Plastic- and liquid-crystalline architectures from dendritic receptor molecules. Proc Natl Acad Sci U S A. 2002 Apr 16;99(8):5093-8. doi: 10.1073/pnas.072018999. [PubMed:11959959 ]
Ross AB, Aman P, Kamal-Eldin A: Identification of cereal alkylresorcinol metabolites in human urine-potential biomarkers of wholegrain wheat and rye intake. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Sep 25;809(1):125-30. doi: 10.1016/j.jchromb.2004.06.015. [PubMed:15282102 ]
Velazquez-Mujica J, Losco L, Aksoyler D, Chen HC: Perforator-to-perforator anastomosis as a salvage procedure during harvest of a perforator flap. Arch Plast Surg. 2021 Jul;48(4):467-469. doi: 10.5999/aps.2020.02194. Epub 2021 Jul 15. [PubMed:34352962 ]

Showing NP-Card for 3,5-dihydroxybenzoic acid (NP0023601)

MOL for NP0023601 (3,5-dihydroxybenzoic acid)

3D MOL for NP0023601 (3,5-dihydroxybenzoic acid)

3D SDF for NP0023601 (3,5-dihydroxybenzoic acid)

3D-SDF for NP0023601 (3,5-dihydroxybenzoic acid)

PDB for NP0023601 (3,5-dihydroxybenzoic acid)

3D PDB for NP0023601 (3,5-dihydroxybenzoic acid)

SMILES for NP0023601 (3,5-dihydroxybenzoic acid)

INCHI for NP0023601 (3,5-dihydroxybenzoic acid)

Structure for NP0023601 (3,5-dihydroxybenzoic acid)

3D Structure for NP0023601 (3,5-dihydroxybenzoic acid)