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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2017-09-12 19:17:59 UTC

Update Date

2023-02-21 17:31:24 UTC

HMDB ID

HMDB0125090

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,4,6-trihydroxybenzaldehyde

Description

2,4,6-trihydroxybenzaldehyde is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-1λ⁴-chromen-1-ylium. It is generated by unspecified-gutmicro enzyme via an anthocyanidin-c-ring-fission-pattern3 reaction. This anthocyanidin-c-ring-fission-pattern3 occurs in human gut microbiota.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Phloroglucinol aldehyde	MeSH
Phloroglucinaldehyde	HMDB
2,4,6-Trihydroxybenzaldehyde	HMDB

Chemical Formula

C₇H₆O₄

Average Molecular Weight

154.121

Monoisotopic Molecular Weight

154.026608673

IUPAC Name

2,4,6-trihydroxybenzaldehyde

Traditional Name

2,4,6-trihydroxybenzaldehyde

CAS Registry Number

Not Available

SMILES

OC1=CC(O)=C(C=O)C(O)=C1

InChI Identifier

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

InChI Key

BTQAJGSMXCDDAJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylphloroglucinols and derivatives. These are phloroglucinol derivatives characterized by the presence of a COR group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

Benzenetriols and derivatives

Direct Parent

Acylphloroglucinols and derivatives

Alternative Parents

Substituents

Acylphloroglucinol derivative
Hydroxybenzaldehyde
Benzaldehyde
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aryl-aldehyde
Monocyclic benzene moiety
Vinylogous acid
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aldehyde
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Source

Endogenous

Endogenous (HMDB: HMDB0125090)

Exogenous

Food

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0125090)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0125090)

Tea

Tea products (HMDB: HMDB0125090)

Fat and oil

Olive oil (HMDB: HMDB0125090)

Fruit

Fruits (HMDB: HMDB0125090)

Vegetable

Vegetables (HMDB: HMDB0125090)

Legumes (HMDB: HMDB0125090)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0125090)

Nut

Nuts (HMDB: HMDB0125090)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0125090)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.7	ALOGPS
logP	2.08	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	7.48	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	38.58 m³·mol⁻¹	ChemAxon
Polarizability	13.72 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	131.731	31661259
DarkChem	[M-H]-	128.548	31661259
DeepCCS	[M+H]+	131.949	30932474
DeepCCS	[M-H]-	128.284	30932474
DeepCCS	[M-2H]-	166.062	30932474
DeepCCS	[M+Na]+	141.601	30932474
AllCCS	[M+H]+	132.8	32859911
AllCCS	[M+H-H2O]+	128.3	32859911
AllCCS	[M+NH4]+	137.0	32859911
AllCCS	[M+Na]+	138.2	32859911
AllCCS	[M-H]-	126.7	32859911
AllCCS	[M+Na-2H]-	128.0	32859911
AllCCS	[M+HCOO]-	129.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	2.98 minutes	32390414
Predicted by Siyang on May 30, 2022	12.0712 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.67 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1446.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	398.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	104.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	256.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	237.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	534.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	558.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	308.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	860.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	314.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1187.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	310.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	487.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	737.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	301.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	370.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,4,6-trihydroxybenzaldehyde	OC1=CC(O)=C(C=O)C(O)=C1	2761.9	Standard polar	33892256
2,4,6-trihydroxybenzaldehyde	OC1=CC(O)=C(C=O)C(O)=C1	1588.0	Standard non polar	33892256
2,4,6-trihydroxybenzaldehyde	OC1=CC(O)=C(C=O)C(O)=C1	1905.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,4,6-trihydroxybenzaldehyde,1TMS,isomer #1	C[Si](C)(C)OC1=CC(O)=C(C=O)C(O)=C1	1665.3	Semi standard non polar	33892256
2,4,6-trihydroxybenzaldehyde,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC(O)=C1C=O	1713.6	Semi standard non polar	33892256
2,4,6-trihydroxybenzaldehyde,2TMS,isomer #1	C[Si](C)(C)OC1=CC(O)=C(C=O)C(O[Si](C)(C)C)=C1	1745.4	Semi standard non polar	33892256
2,4,6-trihydroxybenzaldehyde,2TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC(O[Si](C)(C)C)=C1C=O	1765.1	Semi standard non polar	33892256
2,4,6-trihydroxybenzaldehyde,3TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C(C=O)C(O[Si](C)(C)C)=C1	1821.4	Semi standard non polar	33892256
2,4,6-trihydroxybenzaldehyde,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O)=C(C=O)C(O)=C1	1967.6	Semi standard non polar	33892256
2,4,6-trihydroxybenzaldehyde,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(O)=C1C=O	2003.2	Semi standard non polar	33892256
2,4,6-trihydroxybenzaldehyde,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O)=C(C=O)C(O[Si](C)(C)C(C)(C)C)=C1	2277.4	Semi standard non polar	33892256
2,4,6-trihydroxybenzaldehyde,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C=O	2287.3	Semi standard non polar	33892256
2,4,6-trihydroxybenzaldehyde,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C(C=O)C(O[Si](C)(C)C(C)(C)C)=C1	2542.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4,6-trihydroxybenzaldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-0900000000-83f920215849ad33c980	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4,6-trihydroxybenzaldehyde GC-MS (3 TMS) - 70eV, Positive	splash10-05fs-5195000000-81758c0a5095482e1f81	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4,6-trihydroxybenzaldehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4,6-trihydroxybenzaldehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-trihydroxybenzaldehyde 10V, Positive-QTOF	splash10-0a4i-0900000000-cc80043e99ca874aba37	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-trihydroxybenzaldehyde 20V, Positive-QTOF	splash10-0a4i-0900000000-c126cd4664e481f2b435	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-trihydroxybenzaldehyde 40V, Positive-QTOF	splash10-00kr-9800000000-20c69d3efa67e1877d29	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-trihydroxybenzaldehyde 10V, Negative-QTOF	splash10-0udi-0900000000-da2a5f55d9a392f94254	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-trihydroxybenzaldehyde 20V, Negative-QTOF	splash10-0udi-0900000000-c3647c4ae22b2ee216ac	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-trihydroxybenzaldehyde 40V, Negative-QTOF	splash10-00lu-9300000000-2fa60b158e9215b8fd16	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-trihydroxybenzaldehyde 10V, Negative-QTOF	splash10-0udi-0900000000-4cbc094fef1beac3f21d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-trihydroxybenzaldehyde 20V, Negative-QTOF	splash10-0fb9-4900000000-35033c5a9b0195c367e2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-trihydroxybenzaldehyde 40V, Negative-QTOF	splash10-0006-9000000000-b944b156748264eaaade	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-trihydroxybenzaldehyde 10V, Positive-QTOF	splash10-0a4i-0900000000-6d08afcd803576ccc189	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-trihydroxybenzaldehyde 20V, Positive-QTOF	splash10-05p9-3900000000-d15e961e0d93ec88f677	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-trihydroxybenzaldehyde 40V, Positive-QTOF	splash10-0udi-9000000000-7c28e06ae78ff8ee8752	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB084007

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

68099

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

2,4,6-trihydroxybenzaldehyde → 6-(2-formyl-3,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details
2,4,6-trihydroxybenzaldehyde → 6-(4-formyl-3,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for 2,4,6-trihydroxybenzaldehyde (HMDB0125090)

MOL for HMDB0125090 (2,4,6-trihydroxybenzaldehyde)

3D MOL for HMDB0125090 (2,4,6-trihydroxybenzaldehyde)

3D SDF for HMDB0125090 (2,4,6-trihydroxybenzaldehyde)

3D-SDF for HMDB0125090 (2,4,6-trihydroxybenzaldehyde)

PDB for HMDB0125090 (2,4,6-trihydroxybenzaldehyde)

3D PDB for HMDB0125090 (2,4,6-trihydroxybenzaldehyde)

SMILES for HMDB0125090 (2,4,6-trihydroxybenzaldehyde)

INCHI for HMDB0125090 (2,4,6-trihydroxybenzaldehyde)

Structure for HMDB0125090 (2,4,6-trihydroxybenzaldehyde)

3D Structure for HMDB0125090 (2,4,6-trihydroxybenzaldehyde)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions