3-hydroxymandelic acid profile

3-Hydroxymandelic acid (3-HMA) is an aromatic alpha-hydroxy acid that has been investigated for its potential therapeutic benefits. It is a metabolite of L-dopa, a precursor to dopamine, and is found in various biological systems. 3-HMA has been shown to exhibit antioxidant and anti-inflammatory properties. Its synthesis is often achieved through chemical reactions involving mandelic acid as a starting material. Research on 3-HMA is driven by its potential role in neurological disorders, particularly Parkinson's disease, where it is believed to have neuroprotective effects. Furthermore, 3-HMA has been studied for its potential applications in the treatment of cancer and inflammatory conditions. The compound's ability to modulate dopamine levels and its antioxidant properties make it a promising target for further research in the development of novel therapeutic agents.'

3-hydroxymandelic acid : A 2-hydroxy monocarboxylic acid that is mandelic acid substituted by a hydroxy group at position 3'. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	86957
CHEBI ID	86553
SCHEMBL ID	1840382
MeSH ID	M0081931

Synonym
m-hydroxymandelic acid
17119-15-2
3-hydroxymandelic acid, >=97.0% (t)
3-hydroxymandelic acid
BMSE000573
dl-hydroxy(m-hydroxyphenyl)acetic acid
alpha,3-dihydroxybenzeneacetic acid
hydroxy(3-hydroxyphenyl)acetic acid
3-hydroxyphenylglycolic acid
2-hydroxy-2-(3-hydroxyphenyl)acetic acid
A811304
AKOS009157988
einecs 241-182-3
537k5qmu5f ,
unii-537k5qmu5f
meta-hydroxymandelic acid
FT-0615846
mhma
SCHEMBL1840382
mandelic acid, m-hydroxy-
hydroxy(3-hydroxyphenyl)acetic acid #
3-hydroxymandelate
3-hydroxymandelic acid, (+/-)-
2-hydroxy-2-(3-hydroxyphenyl)ethanoic acid
CHEBI:86553
AS-64759
mfcd00042723
J-010698
m-hydroxy-(6ci,7ci,8ci)mandelate
m-hydroxy-(6ci,7ci,8ci)mandelic acid
m-hydroxymandelate
dl-3-hydroxymandelate
HY-W015326
CS-W016042
DTXSID70864737
Q10395567
(+/-)-3-hydroxymandelic acid
2-hydroxy-2-(3-hydroxyphenyl)aceticacid
3-hydroxymandelicacid
SB85224
benzeneacetic acid, ?,3-dihydroxy-
PD099469

Excerpt	Relevance	Reference
" When m-synephrine hydrochloride was administered orally to humans in normal dosage regimens four main metabolites were excreted in urine: (i) unconjugated m-hydroxymandelic acid (MHMA, 30%), (ii) m-hydroxyphenylglycol (MHPG) sulphate (6%), (iii) m-synephrine sulphate (47%) and (iv) m-synephrine glucuronide (12%)."	( The mammalian metabolism of R-(-)-m-synephrine. Crowley, JR; Ibrahim, KE; Midgley, JM; Williams, CM, 1983)	0.27

Role	Description
human metabolite	Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
2-hydroxy monocarboxylic acid
phenols	Organic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	7 (70.00)	18.7374
1990's	3 (30.00)	18.2507
2000's	0 (0.00)	29.6817
2010's	0 (0.00)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	10 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	1.97	1	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
4-hydroxymandelic acid 4-hydroxymandelic acid: RN given refers to cpd without isomeric designation. 4-hydroxymandelic acid : A 2-hydroxy carboxylic acid that is mandelic acid bearing a phenolic hydroxy substituent at position 4.	2.88	4	2-hydroxy carboxylic acid; phenols	metabolite
3,4-dihydroxyphenylacetic acid 3,4-Dihydroxyphenylacetic Acid: A deaminated metabolite of LEVODOPA.. (3,4-dihydroxyphenyl)acetic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine.. dihydroxyphenylacetic acid : A dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents.	1.96	1	catechols; dihydroxyphenylacetic acid	human metabolite
vanilmandelic acid Vanilmandelic Acid: A 3-O-methyl ether of 3,4-dihydroxymandelic acid. It is an end-stage metabolite of CATECHOLAMINES; EPINEPHRINE; and NOREPINEPHRINE.. vanillylmandelic acid : An aromatic ether that is the 3-O-methyl ether of 3,4-dihydroxymandelic acid.	2.66	3	2-hydroxy monocarboxylic acid; aromatic ether; phenols	human metabolite
mandelic acid SAMMA: mandelic acid condensation polymer	1.98	1	2-hydroxy monocarboxylic acid; benzenes	antibacterial agent; human xenobiotic metabolite
atrolactic acid atrolactic acid: see also 3-isomer; RN given refers to parent cpd without isomeric designation; structure	1.98	1	2-hydroxy monocarboxylic acid
homovanillic acid Homovanillic Acid: A 3-O-methyl ETHER of (3,4-dihydroxyphenyl)acetic acid.. homovanillate : A hydroxy monocarboxylic acid anion which is obtained by deprotonation of the carboxy group of homovanillic acid.. homovanillic acid : A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.	2.37	2	guaiacols; monocarboxylic acid	human metabolite; mouse metabolite
3-phenyllactic acid 3-phenyllactic acid: alpha-hydroxy analog of phenylalanine; RN given refers to cpd without isomeric designation. 3-phenyllactic acid : A 2-hydroxy monocarboxylic acid that is lactic acid in which one of the methyl hydrogens is substituted by a phenyl group.	1.98	1	2-hydroxy monocarboxylic acid	human metabolite
norfenefrine norfenefrine: RN given refers to cpd without isomeric designation; structure	2.65	3	phenols
octopamine Octopamine: An alpha-adrenergic sympathomimetic amine, biosynthesized from tyramine in the CNS and platelets and also in invertebrate nervous systems. It is used to treat hypotension and as a cardiotonic. The natural D(-) form is more potent than the L(+) form in producing cardiovascular adrenergic responses. It is also a neurotransmitter in some invertebrates.. octopamine : A member of the class of phenylethanolamines that is phenol which is substituted at the para- position by a 2-amino-1-hydroxyethyl group. A biogenic phenylethanolamine which has been found to act as a neurotransmitter, neurohormone or neuromodulator in invertebrates.	2.88	4	phenylethanolamines; tyramines	neurotransmitter
phenylephrine Phenylephrine: An alpha-1 adrenergic agonist used as a mydriatic, nasal decongestant, and cardiotonic agent.. phenylephrine : A member of the class of the class of phenylethanolamines that is (1R)-2-(methylamino)-1-phenylethan-1-ol carrying an additional hydroxy substituent at position 3 on the phenyl ring.	1.96	1	phenols; phenylethanolamines; secondary amino compound	alpha-adrenergic agonist; cardiotonic drug; mydriatic agent; nasal decongestant; protective agent; sympathomimetic agent; vasoconstrictor agent
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	1.96	1	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
styrene glycol styrene glycol: RN given refers to cpd without isomeric designation	1.97	1	benzenes
synephrine [no description available]	2.36	2	ethanolamines; phenethylamine alkaloid; phenols	alpha-adrenergic agonist; plant metabolite
methoxyhydroxyphenylglycol Methoxyhydroxyphenylglycol: Synthesized from endogenous epinephrine and norepinephrine in vivo. It is found in brain, blood, CSF, and urine, where its concentrations are used to measure catecholamine turnover.	1.96	1	methoxybenzenes; phenols
3-hydroxybenzeneacetic acid 3-hydroxybenzeneacetic acid: metabolite of L-dopa; structure. 3-hydroxyphenylacetic acid : A monocarboxylic acid that is phenylacetic acid in which the hydrogen at position 3 on the benzene ring is replaced by a hydroxy group.	1.96	1	monocarboxylic acid; phenols	human xenobiotic metabolite
3,4-dihydroxymandelic acid 3,4-dihydroxymandelic acid: metabolite of L-dopa; RN given refers to parent cpd without isomeric designation. 3,4-dihydroxymandelic acid : A catechol that is the 3,4-dihydroxy derivative of mandelic acid; a metabolite of L-dopa.	1.98	1	2-hydroxy monocarboxylic acid; catechols	antioxidant; drug metabolite; human metabolite; mouse metabolite
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	1.98	1	cyclodextrin
3-tyrosine 3-tyrosine: RN given refers to cpd with unspecified isomeric designation. L-m-tyrosine : A hydroxyphenylalanine that is L-phenylalanine with a substituent hydroxy group at position 3.	1.96	1	hydroxyphenylalanine; L-alpha-amino acid zwitterion; L-phenylalanine derivative; non-proteinogenic L-alpha-amino acid; phenols	plant metabolite

Condition	Relationship Strength	Studies
BH4 Deficiency [description not available]	1.96	1
Phenylketonurias A group of autosomal recessive disorders marked by a deficiency of the hepatic enzyme PHENYLALANINE HYDROXYLASE or less frequently by reduced activity of DIHYDROPTERIDINE REDUCTASE (i.e., atypical phenylketonuria). Classical phenylketonuria is caused by a severe deficiency of phenylalanine hydroxylase and presents in infancy with developmental delay; SEIZURES; skin HYPOPIGMENTATION; ECZEMA; and demyelination in the central nervous system. (From Adams et al., Principles of Neurology, 6th ed, p952).	1.96	1
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	2.37	2
Blood Pressure, High [description not available]	1.96	1
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	1.96	1
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	1.96	1

3-hydroxymandelic acid

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Roles (1)

Drug Classes (2)

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Research Demand Index: 24.31

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