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Showing NP-Card for Phloroglucinol (NP0332247)

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Record Information
Version2.0
Created at2023-12-21 00:01:09 UTC
Updated at2024-09-03 04:18:34 UTC
NP-MRD IDNP0332247
Natural Product DOIhttps://doi.org/10.57994/1434
Secondary Accession NumbersNone
Natural Product Identification
Common NamePhloroglucinol
Description1,3,5-Trihydroxybenzene, also known as 1,3,5-benzenetriol or benzene-1,3,5-triol, belongs to the class of organic compounds known as phloroglucinols and derivatives. Phloroglucinols and derivatives are compounds containing a phloroglucinol (benzene-1,3,5-triol) moiety, which consists of a benzene ring bearing one hydroxyl group at positions 1,3, and 5. It is an organic compound that is used in the synthesis of pharmaceuticals and explosives. This molecule exists in two forms, or tautomers, 1,3,5-trihydroxybenzene, which has phenol-like, and 1,3,5-cyclohexanetrione (phloroglucin), which has ketone-like character. 1,3,5-Trihydroxybenzene has been found to be a metabolite in Pseudomonas (PMID: 15826166 ). 1,3,5-Trihydroxybenzene is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 1,3,5-Trihydroxybenzene is found, on average, in the highest concentration within garden onions. 1,3,5-Trihydroxybenzene has also been detected, but not quantified in, several different foods, such as carobs, highbush blueberries, soft-necked garlics, tarragons, and tea. This could make 1,3,5-trihydroxybenzene a potential biomarker for the consumption of these foods. These two tautomers are in equilibrium. Phloroglucinol is a useful intermediate because it is polyfunctional. Phloroglucinol was first documented in 2005 (PMID: 15826166). Phloroglucinol is a benzenetriol (PMID: 25456733) (PMID: 25640118).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0332247 (Phloroglucinol)


  Mrv1652309042000362D          

  9  9  0  0  0  0            999 V2000
    1.4294    1.2376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    0.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0007    1.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0007   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294    1.2364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0007   -1.2376    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
  2  4  2  0  0  0  0
  3  7  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
Download

3D MOL for NP0332247 (Phloroglucinol)

     RDKit          3D

 15 15  0  0  0  0  0  0  0  0999 V2000
   -1.3930    2.4261   -0.3178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6924    1.2257   -0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3330    0.0128   -0.3239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6436   -1.1751   -0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3003   -2.3950   -0.3353 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7087   -1.2198    0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3421   -0.0019    0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7228   -0.0034    0.4817 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6611    1.1929    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7948    2.8047    0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3857    0.0117   -0.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7265   -2.8837    0.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2610   -2.1441    0.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3906    0.0026   -0.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1831    2.1465    0.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9  2  1  0
  1 10  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  8 14  1  0
  9 15  1  0
M  END
Download

3D SDF for NP0332247 (Phloroglucinol)


  Mrv1652309042000362D          

  9  9  0  0  0  0            999 V2000
    1.4294    1.2376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    0.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0007    1.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0007   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294    1.2364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0007   -1.2376    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
  2  4  2  0  0  0  0
  3  7  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332247

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H

> <INCHI_KEY>
QCDYQQDYXPDABM-UHFFFAOYSA-N

> <FORMULA>
C6H6O3

> <MOLECULAR_WEIGHT>
126.11

> <EXACT_MASS>
126.031694058

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.685180476962078

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
benzene-1,3,5-triol

> <ALOGPS_LOGP>
0.25

> <JCHEM_LOGP>
1.0625498509999998

> <ALOGPS_LOGS>
-0.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.455560067223022

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.126324331505472

> <JCHEM_PKA_STRONGEST_BASIC>
-5.370308771902201

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
32.0007

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.58e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phloroglucinol

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0332247 (Phloroglucinol)

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PDB for NP0332247 (Phloroglucinol)
HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0       2.668   2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   1.538   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.001   2.308   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.002   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   1.538   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.668   2.308   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.001  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2    7                                                       
CONECT    4    2    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    3    6    8                                                  
CONECT    8    7                                                            
CONECT    9    5                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for NP0332247 (Phloroglucinol)
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SMILES for NP0332247 (Phloroglucinol)
OC1=CC(O)=CC(O)=C1
Download
INCHI for NP0332247 (Phloroglucinol)
InChI=1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H
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Synonyms
ValueSource
1,3,5-BenzenetriolChEBI
Benzene-1,3,5-triolChEBI
S-TrihydroxybenzeneChEBI
Dilospan SKegg
1,3, 5-TrihydroxybenzeneHMDB
1,3,5-Benzenetriol (acd/name 4.0)HMDB
1,3,5-Trihydroxy-benzeneHMDB
1,3,5-TrihydroxycyclohexatrieneHMDB
1,3,5-TriolHMDB
3,5-DihydroxyphenolHMDB
5-BenzenetriolHMDB
5-HydroxyresorcinolHMDB
5-OxyresorcinolHMDB
5-OxyresorcinolphloroglucinHMDB
Benzene, trihydroxyHMDB
Benzene-S-triolHMDB
FloroglucinHMDB
FloroglucinolHMDB
PhloroglucinHMDB
PhloroglucineHMDB
Phloroglucinol (1,3,5-benzenetriol)HMDB
Spasfon-lyocHMDB
Sym-trihydroxybenzeneHMDB
1,3,5-TrihydroxybenzeneChEBI
SpassirexMeSH
Chemical FormulaC6H6O3
Average Mass126.1100 Da
Monoisotopic Mass126.03169 Da
IUPAC Namebenzene-1,3,5-triol
Traditional Namephloroglucinol
CAS Registry NumberNot Available
SMILES
OC1=CC(O)=CC(O)=C1
InChI Identifier
InChI=1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H
InChI KeyQCDYQQDYXPDABM-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phloroglucinols and derivatives. Phloroglucinols and derivatives are compounds containing a phloroglucinol (benzene-1,3,5-triol) moiety, which consists of a benzene ring bearing one hydroxyl group at positions 1,3, and 5.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassPhenols  
Sub ClassBenzenetriols and derivatives  
Direct ParentPhloroglucinols and derivatives  
Alternative Parents
Substituents
  • Phloroglucinol derivative
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Polyol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.25ALOGPS
logP1.06ChemAxon
logS-0.55ALOGPS
pKa (Strongest Acidic)9.13ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32 m³·mol⁻¹ChemAxon
Polarizability11.69 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013675  
DrugBank IDDB12944  
Phenol Explorer Compound ID658  
FoodDB IDFDB013879  
KNApSAcK IDC00002665  
Chemspider ID352  
KEGG Compound IDC02183  
BioCyc IDCPD-16  
BiGG IDNot Available
Wikipedia LinkPhloroglucinol  
METLIN IDNot Available
PubChem Compound359  
PDB ID13X  
ChEBI ID16204  
Good Scents IDNot Available
References
General References
  1. Achkar J, Xian M, Zhao H, Frost JW: Biosynthesis of phloroglucinol. J Am Chem Soc. 2005 Apr 20;127(15):5332-3. doi: 10.1021/ja042340g. [PubMed:15826166  ] 
  2. Kim RK, Suh Y, Yoo KC, Cui YH, Hwang E, Kim HJ, Kang JS, Kim MJ, Lee YY, Lee SJ: Phloroglucinol suppresses metastatic ability of breast cancer cells by inhibition of epithelial-mesenchymal cell transition. Cancer Sci. 2015 Jan;106(1):94-101. doi: 10.1111/cas.12562. Epub 2014 Dec 3. [PubMed:25456733  ] 
  3. Jegou C, Kervarec N, Cerantola S, Bihannic I, Stiger-Pouvreau V: NMR use to quantify phlorotannins: the case of Cystoseira tamariscifolia, a phloroglucinol-producing brown macroalga in Brittany (France). Talanta. 2015 Apr;135:1-6. doi: 10.1016/j.talanta.2014.11.059. Epub 2014 Dec 12. [PubMed:25640118  ]