Phloroglucinol (BioCAD00000016206)

feces

Metabolite Card

Formula: C6H6O3 (126.0317)
SMILES: OC1=CC(O)=CC(O)=C1

Synonyms [en]

phloroglucinol; 1,3,5-trihydroxybenzene; 1,3,5-benzenetriol; Benzene-1,3,5-triol; 5-Oxyresorcinolphloroglucin; 5-Oxyresorcinol

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Phloroglucinol. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000016206). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Phloroglucinol is a benzenetriol. 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. These two tautomers are in equilibrium. Phloroglucinol is a useful intermediate because it is polyfunctional. 1,3,5-Trihydroxybenzene has been found to be a metabolite in Pseudomonas (PMID: 15826166).

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 108-73-6
  • PubChem: 359
  • ChEBI: ChEBI:16204
  • HMDB: HMDB0013675
  • KEGG: C02183
  • BioCyc: CPD-16
  • NCBI MeSH: Phloroglucinol
  • Wikipedia: Phloroglucinol
  • DrugBank: DB12944
  • RefMet: RM0188159
  • MoNA: FiehnHILIC000684
  • MoNA: FiehnHILIC001445
  • MoNA: FiehnHILIC002253
  • MoNA: FiehnLib000826
  • MoNA: HMDB0013675_c_ms_100047
  • MoNA: MoNA_0006912
  • MoNA: MoNA_0006913
  • MoNA: MoNA_0006914
  • MoNA: MoNA_0006915
  • MoNA: MoNA_0006916
  • MoNA: MoNA_0006917
  • MoNA: MoNA_0008634
  • MoNA: MoNA_0008635
  • MoNA: MoNA_0008636
  • MoNA: MoNA_0008637
  • MoNA: MoNA_0008639
  • MoNA: MoNA_0008911
  • MoNA: MoNA_0008912
  • MoNA: MoNA_0009314
  • MoNA: MoNA_0009315
  • MoNA: MoNA_0009316
  • Metlin: METLIN_65724
  • Coconut NaturalProduct: CNP0299558.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02901 3.7.1.4 phloretin acylhydrolase (phloroglucinol-forming)
KEGG:R04297 1.97.1.2 1,2,3,5-tetrahydroxybenzene:1,2,3-trihydroxybenzene hydroxytransferase
KEGG:R05308 1.3.1.57 dihydrophloroglucinol:NADP+ oxidoreductase
KEGG:R10967 2.3.1.253 malonyl-CoA:malonyl-CoA malonyltransferase (decarboxylating, phloroglucinol-forming)
KEGG:R12087 2.3.1.272 2-acetylphloroglucinol C-acetyltransferase
KEGG:R13082 3.7.1.4 3-hydroxyphloretin acylhydrolase (phloroglucinol-forming)
KEGG:R13085 C22552 + 2 C00001<=>C01161 + C02183 + C00011 + 2 C00080
KEGG:R13086 C22553<=>C00642 + C02183
Rhea:RHEA:10081 1.3.1.57 dihydrophloroglucinol + NADP+ => 1,3,5-trihydroxybenzene + NADPH
Rhea:RHEA:10082 1.3.1.57 1,3,5-trihydroxybenzene + NADPH => dihydrophloroglucinol + NADP+
Rhea:RHEA:10083 1.3.1.57 dihydrophloroglucinol + NADP+ <=> 1,3,5-trihydroxybenzene + NADPH
Rhea:RHEA:21001 1.97.1.2 1,2,3,5-tetrahydroxybenzene + 1,2,3-trihydroxybenzene => 1,2,3,5-tetrahydroxybenzene + 1,3,5-trihydroxybenzene
Rhea:RHEA:21002 1.97.1.2 1,2,3,5-tetrahydroxybenzene + 1,3,5-trihydroxybenzene => 1,2,3,5-tetrahydroxybenzene + 1,2,3-trihydroxybenzene
Rhea:RHEA:21003 1.97.1.2 1,2,3,5-tetrahydroxybenzene + 1,2,3-trihydroxybenzene <=> 1,2,3,5-tetrahydroxybenzene + 1,3,5-trihydroxybenzene
Rhea:RHEA:23397 3.7.1.4 phloretin + H2O => phloretate + 1,3,5-trihydroxybenzene + H+
Rhea:RHEA:23398 3.7.1.4 phloretate + 1,3,5-trihydroxybenzene + H+ => phloretin + H2O
Rhea:RHEA:23399 3.7.1.4 phloretin + H2O <=> phloretate + 1,3,5-trihydroxybenzene + H+
Rhea:RHEA:48237 2.3.1.272 2 2-acetylphloroglucinol => 2,4-diacetylphloroglucinol + 1,3,5-trihydroxybenzene + H+
Rhea:RHEA:48238 2.3.1.272 2,4-diacetylphloroglucinol + 1,3,5-trihydroxybenzene + H+ => 2 2-acetylphloroglucinol
Rhea:RHEA:48239 2.3.1.272 2 2-acetylphloroglucinol <=> 2,4-diacetylphloroglucinol + 1,3,5-trihydroxybenzene + H+
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Organism Source

Taxonomy Source

  1. Acacia arabica [ncbi taxid: 658885]
  2. Alkanna cappadocica [ncbi taxid: 2650392]
  3. Allium cepa [ncbi taxid: 4679]
  4. Alliun cepa [ncbi taxid: ]
  5. Alpinia blepharocalyx [ncbi taxid: 105668]
  6. Artemisia dentata [ncbi taxid: ]
  7. Atalantia racemosa [ncbi taxid: 159026]
  8. Buddleja cordata [ncbi taxid: 168492]
  9. Buphane fischeri [ncbi taxid: ]
  10. Crambe tatarica [ncbi taxid: 71346]
  11. Cystophora retroflexa [ncbi taxid: 97144]
  12. Cystoseira tamariscifolia [ncbi taxid: ]
  13. Diospyros eriantha [ncbi taxid: 1009467]
  14. Dryopteris crassirhizoma [ncbi taxid: 97234]
  15. Ecklonia cava [ncbi taxid: 105407]
  16. Ecklonia stolonifera [ncbi taxid: ]
  17. Eisenia bicyclis [ncbi taxid: 6395]
  18. Eucalyptus calophylla [ncbi taxid: ]
  19. Fritillaria ningguoensis [ncbi taxid: ]
  20. Haematoxylon brasiletto [ncbi taxid: ]
  21. Hoffmannia strigillosa [ncbi taxid: ]
  22. Homo sapiens [ncbi taxid: 9606]
  23. Humulus lupulus [ncbi taxid: 3486]
  24. Hypericum perforatum [ncbi taxid: 65561]
  25. Juniperus rigida var. conferta [ncbi taxid: 13102]
  26. Lemaireocereus griseus [ncbi taxid: ]
  27. Lychnis dioica [ncbi taxid: ]
  28. Mallotus philippinensis [ncbi taxid: ]
  29. Malus pumila [ncbi taxid: 283210]
  30. Millettia erythrocalyx [ncbi taxid: 1679271]
  31. Mycobacterium leprae [ncbi taxid: 1769]
  32. Negombata magnifica [ncbi taxid: 344322]
  33. Ononis vaginalis [ncbi taxid: 798051]
  34. Posidonia oceanica [ncbi taxid: 55489]
  35. Prorocentrum micans [ncbi taxid: 2945]
  36. Pteris semipinnata [ncbi taxid: 265705]
  37. Rapanea lancifolia [ncbi taxid: ]
  38. Salvia hispanica [ncbi taxid: 49212]
  39. Scorzonera pseudodivaricata [ncbi taxid: ]
  40. Sequoia gigantea [ncbi taxid: ]
  41. Sequoia sempervirens [ncbi taxid: 28980]
  42. Spatholobus suberectus [ncbi taxid: 455371]
  43. Streptomyces nigra 452T [ncbi taxid: ]
  44. Syncarpia hillii [ncbi taxid: 271921]
  45. Xenoacremonium recifei [ncbi taxid: 1036759]

Pathway Synthetic

pathway id name
BioCyc:CLOSTSYMB_P3-PWY gallate degradation III (anaerobic)
BioCyc:ANTHRA_P3-PWY gallate degradation III (anaerobic)
BioCyc:CLOSSAC_P3-PWY gallate degradation III (anaerobic)
BioCyc:META_PWY-5765 1,3,5-trimethoxybenzene biosynthesis
BioCyc:META_PWY-6241 thyroid hormone biosynthesis
BioCyc:META_PWY-723 alkylnitronates degradation
BioCyc:ARA_PWY-5765 1,3,5-trimethoxybenzene biosynthesis
BioCyc:META_P3-PWY gallate degradation III (anaerobic)
BioCyc:SCO_P3-PWY gallate degradation III (anaerobic)
PlantCyc:CSATIVA_PK_PWY-5765 1,3,5-trimethoxybenzene biosynthesis
PlantCyc:PLANT_PWY-5765 1,3,5-trimethoxybenzene biosynthesis
PlantCyc:SWEETCHERRY_PWY-5765 1,3,5-trimethoxybenzene biosynthesis
PlantCyc:FVESCA_VESCA_PWY-5765 1,3,5-trimethoxybenzene biosynthesis
PlantCyc:PPERSICA_PWY-5765 1,3,5-trimethoxybenzene biosynthesis
PlantCyc:MDOMESTICA_PWY-5765 1,3,5-trimethoxybenzene biosynthesis
PlantCyc:EUROPEANPEAR_PWY-5765 1,3,5-trimethoxybenzene biosynthesis
PlantCyc:ARA_PWY-5765 1,3,5-trimethoxybenzene biosynthesis
PlantCyc:HOP_PWY-5765 1,3,5-trimethoxybenzene biosynthesis
PlantCyc:RCHINENSIS_PWY-5765 1,3,5-trimethoxybenzene biosynthesis
PlantCyc:RMULTIFLORA_PWY-5765 1,3,5-trimethoxybenzene biosynthesis
View All Pathways