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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:18:00 UTC

Update Date

2023-07-07 20:53:57 UTC

HMDB ID

HMDB0002643

Secondary Accession Numbers

HMDB02643

Metabolite Identification

Common Name

HPHPA

Description

3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid (HPHPA) is an organic acid detected in human urine. It is relatively abundant in adult human urine and it is normally relatively benign. It is thought that the presence of this acid is from nutritional sources (i.e. dietary phenylalanine or polyphenols). However, there has been a considerable degree of ambiguity in the origin and/or significance of this compound (PMID:11978597 ). Recently, it has been reported that HPHPA is actually an abnormal phenylalanine metabolite arising from bacterial metabolism in the gastrointestinal tract. Specifically, HPHPA appears to arise from the action of the anaerobic bacteria Clostridia sp. (PMID:20423563 ; PMID:24063620 ). Elevated levels of HPHPA have been reported in the urine of children with autism as well as in adult patients with schizophrenia. It has been proposed that HPHPA may be a bacterial metabolite of m-tyrosine, a tyrosine analog that causes symptoms of autism in experimental animals. Under certain conditions, HPHPA can act as a neurotoxin and a metabotoxin. A neurotoxin causes damage to nerve cells and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of HPHPA are associated with autism and schizophrenia. The mechanism by which HPHPA exerts its toxic effects is not clear. It may function as a catecholamine analog and disrupt catecholamine signalling, especially in younger individuals. Alternately, HPHPA may function as an amino acid analog to tyrosine and phenylalanine. High plasma concentrations of phenylalanine (and possibly HPHPA) are known to influence the blood-brain barrier transport of large neutral amino acids. This altered transport is believed to interfere with the function of different cerebral enzyme systems in the developing brain. Studies have shown that higher levels of HPHPA are associated with overgrowth of Clostridia in the gut, including Clostridium difficile, Clostridium sporogenes, Clostridium botulinum, Clostridium calortolerans, Clostridium mangenoyi, Clostridium ghoni, Clostridium bifermentans, Clostridium sordelli. (PMID:20423563 ; PMID:24063620 )

Structure

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

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0    8667.3138667.399   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.6488666.630   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8669.9828667.399   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8671.3128666.630   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8669.9828668.937   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8667.3138668.937   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8661.9838667.399   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8665.9838666.631   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.6498667.401   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.3158666.631   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8663.3158665.091   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.6498664.321   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.9838665.091   0.000  0.00  0.00           C+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    1                                                            
CONECT    7   10                                                            
CONECT    8    9   13    1                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11    7                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(3-Hydroxyphenyl)hydracrylic acid	ChEBI
3'-Hydroxyphenylhydracrylic acid	ChEBI
3-(m-Hydroxyphenyl)hydracrylic acid	ChEBI
3-Hydroxyphenyl-hydracrylic acid	ChEBI
b-(m-Hydroxyphenyl)hydracrylic acid	ChEBI
beta-(m-Hydroxyphenyl)hydracrylic acid	ChEBI
HPHPA	ChEBI
(3-Hydroxyphenyl)hydracrylate	Generator
3'-Hydroxyphenylhydracrylate	Generator
3-(3-Hydroxyphenyl)-3-hydroxypropionate	Generator
3-(3-Hydroxyphenyl)hydracrylate	Generator
3-(m-Hydroxyphenyl)hydracrylate	Generator
3-Hydroxy-3-(3-hydroxyphenyl)propionate	Generator
3-Hydroxyphenyl-hydracrylate	Generator
b-(m-Hydroxyphenyl)hydracrylate	Generator
beta-(m-Hydroxyphenyl)hydracrylate	Generator
Β-(m-hydroxyphenyl)hydracrylate	Generator
Β-(m-hydroxyphenyl)hydracrylic acid	Generator
3-(3-Hydroxyphenyl)-3-hydroxypropanoate	Generator
HPHPA CPD	HMDB
beta-(Meta-hydroxyphenyl)hydracrylic acid	HMDB
MHPHA	HMDB
3-Hydroxy-3-(3'-hydroxyphenyl)propanoic acid	HMDB
3-Hydroxy-3-(3-hydroxyphenyl)propanoic acid	HMDB

Chemical Formula

C₉H₁₀O₄

Average Molecular Weight

182.1733

Monoisotopic Molecular Weight

182.057908808

IUPAC Name

3-hydroxy-3-(3-hydroxyphenyl)propanoic acid

Traditional Name

mhpha

CAS Registry Number

3247-75-4

SMILES

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

InChI Identifier

InChI=1S/C9H10O4/c10-7-3-1-2-6(4-7)8(11)5-9(12)13/h1-4,8,10-11H,5H2,(H,12,13)

InChI Key

KHTAGVZHYUZYMF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

3-phenylpropanoic-acid
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Phenol
Monocyclic benzene moiety
Hydroxy acid
Benzenoid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:86369 )
dihydroxy monocarboxylic acid (CHEBI:86369 )

Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Nervous system disorder

Nerve damage (PMID: 31434538)

Central nervous system disorder

Psychiatric disorder

Schizophrenia (HMDB: HMDB0002643)

Psychological development disorder

Autism (HMDB: HMDB0002643)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 20423563)

Source

Endogenous

Endogenous (HMDB: HMDB0002643)

Plant

Plant (HMDB: HMDB0002643)

Microbe

Microbe (HMDB: HMDB0002643)
Clostridium difficile (HMDB: HMDB0002643)
Clostridium sporogenes (HMDB: HMDB0002643)
Clostridium bifermentans (HMDB: HMDB0002643)
Clostridium calortolerans (HMDB: HMDB0002643)
Clostridium ghoni (HMDB: HMDB0002643)
Clostridium mangenoyi (HMDB: HMDB0002643)
Clostridium botulinium (HMDB: HMDB0002643)

Exogenous

Exogenous (HMDB: HMDB0002643)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0002643)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0002643)

Tea

Tea products (HMDB: HMDB0002643)

Fat and oil

Olive oil (HMDB: HMDB0002643)

Fruit

Fruits (HMDB: HMDB0002643)

Citrus

Citrus (HMDB: HMDB0002643)

Vegetable

Vegetables (HMDB: HMDB0002643)

Legumes (HMDB: HMDB0002643)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0002643)

Nut

Nuts (HMDB: HMDB0002643)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0002643)

Process

Not Available

Role

Indirect biological role

Metabotoxin

Metabotoxin (HMDB: HMDB0002643)

Biological role

Waste product (PMID: 35448883)

Industrial application

Pharmaceutical industry

Biomarker

Autism (MarkerDB: MDB00000394)

Physical Properties

State

Solid

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
Water Solubility	6.31 g/L	ALOGPS
logP	0.68	ALOGPS
logP	0.68	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.94	ChemAxon
pKa (Strongest Basic)	-3.2	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	3	ChemAxon
Refractivity	45.31 m³·mol⁻¹	ChemAxon
Polarizability	17.31 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	142.174	31661259
DarkChem	[M-H]-	135.538	31661259
DeepCCS	[M+H]+	134.775	30932474
DeepCCS	[M-H]-	132.148	30932474
DeepCCS	[M-2H]-	168.02	30932474
DeepCCS	[M+Na]+	143.525	30932474
AllCCS	[M+H]+	140.0	32859911
AllCCS	[M+H-H2O]+	135.8	32859911
AllCCS	[M+NH4]+	144.0	32859911
AllCCS	[M+Na]+	145.1	32859911
AllCCS	[M-H]-	136.8	32859911
AllCCS	[M+Na-2H]-	137.6	32859911
AllCCS	[M+HCOO]-	138.5	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. Predicted by Afia on May 17, 2022.	2.68 minutes	32390414
Predicted by Siyang on May 30, 2022	9.2554 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.91 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	83.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1105.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	275.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	97.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	70.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	277.2 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	294.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	230.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	631.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	192.4 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	927.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	200.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	211.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	477.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	282.8 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	182.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid	OC(CC(O)=O)C1=CC(O)=CC=C1	3552.6	Standard polar	33892256
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid	OC(CC(O)=O)C1=CC(O)=CC=C1	1757.6	Standard non polar	33892256
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid	OC(CC(O)=O)C1=CC(O)=CC=C1	1874.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid,1TMS,isomer #1	C[Si](C)(C)OC(CC(=O)O)C1=CC=CC(O)=C1	1848.1	Semi standard non polar	33892256
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)CC(O)C1=CC=CC(O)=C1	1879.1	Semi standard non polar	33892256
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid,1TMS,isomer #3	C[Si](C)(C)OC1=CC=CC(C(O)CC(=O)O)=C1	1889.4	Semi standard non polar	33892256
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC(O[Si](C)(C)C)C1=CC=CC(O)=C1	1844.3	Semi standard non polar	33892256
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid,2TMS,isomer #2	C[Si](C)(C)OC1=CC=CC(C(CC(=O)O)O[Si](C)(C)C)=C1	1846.8	Semi standard non polar	33892256
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)CC(O)C1=CC=CC(O[Si](C)(C)C)=C1	1835.8	Semi standard non polar	33892256
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1	1844.4	Semi standard non polar	33892256
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CC(=O)O)C1=CC=CC(O)=C1	2106.3	Semi standard non polar	33892256
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC(O)C1=CC=CC(O)=C1	2115.5	Semi standard non polar	33892256
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=CC(C(O)CC(=O)O)=C1	2134.7	Semi standard non polar	33892256
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O)=C1	2318.2	Semi standard non polar	33892256
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC(C(CC(=O)O)O[Si](C)(C)C(C)(C)C)=C1	2366.0	Semi standard non polar	33892256
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CC(O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2335.5	Semi standard non polar	33892256
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2533.0	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 - HPHPA GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-6900000000-1c85dbbfd5980c188548	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - HPHPA GC-MS (3 TMS) - 70eV, Positive	splash10-014i-3094000000-b60bebf30bd58b1783a1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - HPHPA GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - HPHPA 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 - HPHPA 10V, Positive-QTOF	splash10-0159-0900000000-db4168cb272b787d7521	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - HPHPA 20V, Positive-QTOF	splash10-01ba-1900000000-bf141ae9daa7c4c192b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - HPHPA 40V, Positive-QTOF	splash10-01b9-6900000000-6baa657777aef17afbb5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - HPHPA 10V, Negative-QTOF	splash10-001i-1900000000-9e5b5607972b5e60f0ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - HPHPA 20V, Negative-QTOF	splash10-07ci-3900000000-d464d54fbcadeb4e4444	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - HPHPA 40V, Negative-QTOF	splash10-052f-9400000000-4de7b48574933f1a2830	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - HPHPA 10V, Positive-QTOF	splash10-01c1-1900000000-79d8859d77850e029ca4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - HPHPA 20V, Positive-QTOF	splash10-00kb-3900000000-36acb66d08cbc9708189	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - HPHPA 40V, Positive-QTOF	splash10-014j-9100000000-0eae14fd6f9433582771	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - HPHPA 10V, Negative-QTOF	splash10-001i-1900000000-ae7a51ac5fc753f2380d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - HPHPA 20V, Negative-QTOF	splash10-014i-3900000000-95ac6fbe6696a0e175df	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - HPHPA 40V, Negative-QTOF	splash10-014l-7900000000-52680aaff3251da70f1f	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
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 500 MHz, H₂O, experimental)	2012-12-05	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.18(0.01-3.37) umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details
Urine	Detected and Quantified	0.20(0.05-1.57) umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.01-3.37 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	69.556 +/- 56.735 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	5.121 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22932811	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22827565	details
Urine	Detected and Quantified	91.5 +/- 90.4 umol/mmol creatinine	Children (1-13 years old)	Male	Normal	20423563	details
Urine	Detected and Quantified	5.9 (1.4-22.1) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	4.2 (0.9-15.3) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	16 (0.8-83) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	2702744	details
Urine	Detected and Quantified	0.55-54.93 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	David F. Putnam C...	details
Urine	Detected and Quantified	0.3-12.7 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	20423563	details
Urine	Detected and Quantified	39.8 +/- 50.2 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	20423563	details
Urine	Detected and Quantified	85.5 +/- 55.9 umol/mmol creatinine	Children (1-13 years old)	Female	Normal	20423563	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	192.4 +/- 90.4 umol/mmol creatinine	Children (1-13 years old)	Male	Autism	20423563	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Hypertension (mild)	20013882	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Hypertension (mild)	20013882	details
Urine	Detected and Quantified	3.326 +/- 2.352 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	57.84 +/- 80.919 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	16.197 +/- 9.854 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Autism
Shaw W: Increased urinary excretion of a 3-(3-hydroxyphenyl)-3-hydroxypropionic acid (HPHPA), an abnormal phenylalanine metabolite of Clostridia spp. in the gastrointestinal tract, in urine samples from patients with autism and schizophrenia. Nutr Neurosci. 2010 Jun;13(3):135-43. doi: 10.1179/147683010X12611460763968. [PubMed:20423563 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

209850 (Autism)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023037

KNApSAcK ID

Not Available

Chemspider ID

93013

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6729

PubChem Compound

102959

PDB ID

Not Available

ChEBI ID

86369

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000394

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Kumps A, Duez P, Mardens Y: Metabolic, nutritional, iatrogenic, and artifactual sources of urinary organic acids: a comprehensive table. Clin Chem. 2002 May;48(5):708-17. [PubMed:11978597 ]
Shaw W: Increased urinary excretion of a 3-(3-hydroxyphenyl)-3-hydroxypropionic acid (HPHPA), an abnormal phenylalanine metabolite of Clostridia spp. in the gastrointestinal tract, in urine samples from patients with autism and schizophrenia. Nutr Neurosci. 2010 Jun;13(3):135-43. doi: 10.1179/147683010X12611460763968. [PubMed:20423563 ]
Kesli R, Gokcen C, Bulug U, Terzi Y: Investigation of the relation between anaerobic bacteria genus clostridium and late-onset autism etiology in children. J Immunoassay Immunochem. 2014;35(1):101-9. doi: 10.1080/15321819.2013.792834. [PubMed:24063620 ]

Enzymes

Enzyme Details

1. Sulfotransferase family cytosolic 2B member 1

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:: SULT2B1
Uniprot ID:: O00204
Molecular weight:: 39598.595

Reactions

HPHPA → 3-(3-hydroxyphenyl)-3-(sulfooxy)propanoic acid	details

Enzyme Details

2. 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

HPHPA → 6-[3-(2-carboxy-1-hydroxyethyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details
HPHPA → 3,4,5-trihydroxy-6-{[3-hydroxy-3-(3-hydroxyphenyl)propanoyl]oxy}oxane-2-carboxylic acid	details

Enzyme Details

3. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

HPHPA → 3-hydroxy-3-[3-(sulfooxy)phenyl]propanoic acid	details

Showing metabocard for HPHPA (HMDB0002643)

MOL for HMDB0002643 (HPHPA)

3D MOL for HMDB0002643 (HPHPA)

3D SDF for HMDB0002643 (HPHPA)

3D-SDF for HMDB0002643 (HPHPA)

PDB for HMDB0002643 (HPHPA)

3D PDB for HMDB0002643 (HPHPA)

SMILES for HMDB0002643 (HPHPA)

INCHI for HMDB0002643 (HPHPA)

Structure for HMDB0002643 (HPHPA)

3D Structure for HMDB0002643 (HPHPA)

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

Reactions

Reactions