Vanillylmandelic acid (VMA) (BioDeep_00000003208)

 

Secondary id: BioDeep_00000265254, BioDeep_00000400103, BioDeep_00000402980

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


(2S)-2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid

化学式: C9H10O5 (198.052821)
中文名称: 3-甲氧基-4-羟基扁桃酸, 香草扁桃酸, DL-4-羟基-3-甲氧基苯乙醇酸, 香草扁桃酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.49%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

Vanillylmandelic acid (VMA). BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/vanillylmandelic_acid_(vma) (retrieved 2024-11-03) (BioDeep RN: BioDeep_00000003208). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: COc(c1)c(O)ccc1C(O)C(O)=O
InChI: InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)

描述信息

Vanillylmandelic acid, also known as vanillylmandelate or VMA, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Vanillylmandelic acid is a sweet and vanilla tasting compound. Vanillylmandelic acid (VMA) is a chemical intermediate in the synthesis of artificial vanilla flavorings and is an end-stage metabolite of the catecholamines (dopamine, epinephrine, and norepinephrine). Vanillylmandelic acid exists in all living organisms, ranging from bacteria to plants to humans. Within humans, vanillylmandelic acid participates in a number of enzymatic reactions. In particular, vanillylmandelic acid can be biosynthesized from 3-methoxy-4-hydroxyphenylglycolaldehyde through its interaction with the enzyme aldehyde dehydrogenase. In addition, vanillylmandelic acid and pyrocatechol can be biosynthesized from 3,4-dihydroxymandelic acid and guaiacol through the action of the enzyme catechol O-methyltransferase. Urinary VMA is elevated in patients with tumors that secrete catecholamines. Urinary VMA tests may also be used to diagnose neuroblastomas, and to monitor treatment of these conditions. VMA urinalysis tests can be used to diagnose an adrenal gland tumor called pheochromocytoma, a tumor of catecholamine-secreting chromaffin cells. Vanillylmandelic acid (VMA) is produced in the liver and is a major product of norepinephrine and epinephrine metabolism excreted in the urine.
Vanillylmandelic acid is one of the products of the catabolism of catecholamines (epinephrine, norepinephrine and dopamine). High levels of vanillylmandelic acid can indicate an adrenal gland tumor (pheochromocytoma) or another type of tumor that produces catecholamines. (WebMD) [HMDB]
D000890 - Anti-Infective Agents > D000892 - Anti-Infective Agents, Urinary > D008333 - Mandelic Acids
Acquisition and generation of the data is financially supported in part by CREST/JST.
KEIO_ID H056
Vanillylmandelic acid is the endproduct of epinephrine and norepinephrine metabolism. Vanillylmandelic acid can be used as an indication of the disorder in neurotransmitter metabolism as well. Vanillylmandelic acid has antioxidant activity towards DPPH radical with an IC50 value of 33 μM[1].

同义名列表

63 个代谢物同义名

(2S)-2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid; (alphaS)-alpha,4-Dihydroxy-3-methoxybenzeneacetic acid; 2-(4’-Hydroxy-3’-methoxyphenyl)-2-hydroxyethanoic acid; 2-(4-Hydroxy-3-methoxyphenyl)-2-hydroxyethanoic acid; 2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid; (S)-hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid; (αS)-α,4-Dihydroxy-3-methoxybenzeneacetic acid; alpha,4-Dihydroxy-3-methoxybenzeneacetic acid; 3-Methoxy-4-hydroxyphenylhydroxyacetic acid; Atrolactic acid monosodium salt, (S)-isomer; α,4-Dihydroxy-3-methoxybenzeneacetic acid; (4-Hydroxy-3-methoxyphenyl)glycolic acid; 3-Methoxy-4-hydroxyphenylhydroxyacetate; L-(+)-3-Methoxy-4-hydroxymandelic acid; (4-Hydroxy-3-methoxyphenyl)glycolate; (S)-4-Hydroxy-3-methoxymandelic acid; 4-Hydroxy-3-methoxy-DL-mandelic acid; (+)-4-Hydroxy-3-methoxymandelic acid; DL-3-Methoxy-4-hydroxymandelic acid; dl-4-hydroxy-3-methoxymandelic acid; 4’-Hydroxy-3’-methoxymandelic acid; 4-Hydroxy-3-methoxy-mandelic acid; 3-Methoxy-4-hydroxy-mandelic acid; 4-Hydroxy 3-methoxymandelic acid; 4-Hydroxy-3-methoxymandelic acid; 3-Methoxy-4-hydroxymandelic acid; 4-Hydroxy-3-methoxy-DL-mandelate; DL-3-Methoxy-4-hydroxymandelate; DL-4-Hydroxy-3-methoxymandelate; 4-Hydroxy-3-methoxy-mandelate; Atrolactic acid, (+-)-isomer; 4-Hydroxy-3-methoxymandelate; 3-Methoxy-4-hydroxymandelate; Hydroxymethoxymandelic acid; Hydroxymethylmandelic acid; DL-Vanillylmandelic acid; DL-Vanillomandelic acid; Vainillylmandelic acid; (+)-Vanilmandelic acid; Vanillyl mandelic acid; Vanillylmandellic acid; Vanillyl-mandelic acid; Vanillinmandelic acid; Vanillylmandelic acid; Vanilylmandelic acid; DL-Vanillylmandelate; Vanillomandelic acid; Vanillymandelic acid; 2-Phenyllactic acid; Vanyl-mandelic acid; DL-Vanillomandelate; Vanilmandelic acid; Vanylmandelic acid; Vanillylmandelate; Vanillinmandelate; Vanillomandelate; Atrolactic acid; Vanilmandelate; Lopac-H-0131; VMA CPD; HMMA; VMA; Vanillylmandelic acid



数据库引用编号

28 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

27 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(2)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(24)

PharmGKB(0)

4 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Jinmin Li, Xiangyang Liu, Mo Chen, Jiachen Wang, Xinning Wang. Values of serum CA125, NSE and 24-hour urine VMA in diagnosis and prediction of treatment of paediatric neuroblastoma. International journal of clinical practice. 2021 Dec; 75(12):e14932. doi: 10.1111/ijcp.14932. [PMID: 34606672]
  • Narae Hwang, Eunbin Chong, Hyeonju Oh, Hee Won Cho, Ji Won Lee, Ki Woong Sung, Soo-Youn Lee. Application of an LC-MS/MS Method for the Simultaneous Quantification of Homovanillic Acid and Vanillylmandelic Acid for the Diagnosis and Follow-Up of Neuroblastoma in 357 Patients. Molecules (Basel, Switzerland). 2021 Jun; 26(11):. doi: 10.3390/molecules26113470. [PMID: 34200415]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • E A Soler Arias, R H Trigo, D D Miceli, P N Vidal, M F Hernandez Blanco, V A Castillo. Urinary vanillylmandelic acid:creatinine ratio in dogs with pheochromocytoma. Domestic animal endocrinology. 2021 01; 74(?):106559. doi: 10.1016/j.domaniend.2020.106559. [PMID: 32980593]
  • Valeriy D Zaytsev, Aleksei A Furletov, Vladimir V Apyari, Alexey V Garshev, Stanislava G Dmitrienko, Yury A Zolotov. Label-free silver triangular nanoplates for spectrophotometric determination of catecholamines and their metabolites. Mikrochimica acta. 2020 10; 187(11):610. doi: 10.1007/s00604-020-04576-1. [PMID: 33057848]
  • Meng Wei, Mujie Ye, Kuiran Dong, Rui Dong. Mass screening for neuroblastoma in infants. Discovery medicine. 2020 Sep; 30(160):63-70. doi: NULL. [PMID: 33382962]
  • Heiko Brennenstuhl, Sven F Garbade, Jürgen G Okun, Patrik Feyh, Georg F Hoffmann, Claus-Dieter Langhans, Thomas Opladen. Semi-quantitative detection of a vanillactic acid/vanillylmandelic acid ratio in urine is a reliable diagnostic marker for aromatic L-amino acid decarboxylase deficiency. Molecular genetics and metabolism. 2020 Sep; 131(1-2):163-170. doi: 10.1016/j.ymgme.2020.07.001. [PMID: 32675002]
  • Blanka Fodor, Elina Üveges, Ibolya Molnár-Perl. Direct sample preparation and simultaneous perfluoroacylation - Trimethylsilylation of biogenic monoamines along with their acidic metabolites for a single step analysis by GC-MS. Analytica chimica acta. 2020 Aug; 1127(?):9-19. doi: 10.1016/j.aca.2020.06.032. [PMID: 32800142]
  • Ji-Na Hao, Dechao Niu, Jinlou Gu, Shaoliang Lin, Yongsheng Li, Jianlin Shi. Structure Engineering of a Lanthanide-Based Metal-Organic Framework for the Regulation of Dynamic Ranges and Sensitivities for Pheochromocytoma Diagnosis. Advanced materials (Deerfield Beach, Fla.). 2020 Jun; 32(23):e2000791. doi: 10.1002/adma.202000791. [PMID: 32337783]
  • Christopher W Farnsworth, Dennis J Dietzen, Stephen M Roper. Atypical Findings on a Urine Organic Acid Profile. The journal of applied laboratory medicine. 2020 03; 5(2):388-393. doi: 10.1093/jalm/jfz002. [PMID: 32445368]
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  • Ying Shen, Huijun Li, Jie Lu, Xia Luo, Qing Guan, Liming Cheng. Analytical validation and clinical application of urinary vanillylmandelic acid and homovanillic acid by LC-MS/MS for diagnosis of neuroblastoma. Biomedical chromatography : BMC. 2019 Jun; 33(6):e4484. doi: 10.1002/bmc.4484. [PMID: 30632178]
  • Marcela Valko-Rokytovská, Beáta Hubková, Anna Birková, Jana Mašlanková, Marek Stupák, Marianna Zábavníková, Beáta Čižmárová, Mária Mareková. Specific Urinary Metabolites in Malignant Melanoma. Medicina (Kaunas, Lithuania). 2019 May; 55(5):. doi: 10.3390/medicina55050145. [PMID: 31100919]
  • Eduardo Martínez-Morillo, Nuria Valdés Gallego, Edwin Eguia Ángeles, Juan Carlos Fernández Fernández, Belén Prieto García, Francisco V Álvarez. Performance of plasma free metanephrines in diagnosis of pheochromocytomas and paragangliomas in the population of Asturias. Endocrinologia, diabetes y nutricion. 2019 May; 66(5):312-319. doi: 10.1016/j.endinu.2018.08.009. [PMID: 30391255]
  • Nausheen Alam, Nousheen Wasi, Sadaf Naeem, Sadia Suri Kashif, Tuba Siddiqui, Lubna Bashir, Shazia Naz, Rahila Ikram. Methylphenidate increases the urinary excretion of vanillylmandelic acid in rats that is attenuated by buspirone co-administration. Pakistan journal of pharmaceutical sciences. 2019 Mar; 32(2 (Supplementary)):895-898. doi: . [PMID: 31103989]
  • Nick Flynn, Amanda LeFebvre, Boo Messahel, Sarah L Hogg. Olive ingestion causing a false suspicion of relapsed neuroblastoma: A case of 'oliveblastoma?'. Pediatric blood & cancer. 2018 10; 65(10):e27248. doi: 10.1002/pbc.27248. [PMID: 29923309]
  • Hizuru Amano, Hiroo Uchida, Yujiro Tanaka, Takahisa Tainaka, Makiko Mori, Eiji Oguma, Hiroshi Kishimoto, Hiroshi Kawashima, Yuki Arakawa, Ryoji Hanada, Katsuyoshi Koh. Excellent prognosis of patients with intermediate-risk neuroblastoma and residual tumor postchemotherapy. Journal of pediatric surgery. 2018 Sep; 53(9):1761-1765. doi: 10.1016/j.jpedsurg.2017.10.061. [PMID: 29195808]
  • Xiangqi Liu, Zhenzhen Zhang, Binbin Zhang, Yijie Zheng, Chao Zheng, Baihui Liu, Shan Zheng, Kuiran Dong, Rui Dong. Circulating tumor cells detection in neuroblastoma patients by EpCAM-independent enrichment and immunostaining-fluorescence in situ hybridization. EBioMedicine. 2018 Sep; 35(?):244-250. doi: 10.1016/j.ebiom.2018.08.005. [PMID: 30104180]
  • Eric Grouzmann, Catherine Centeno, Philippe J Eugster. Quantification of vanillylmandelic acid, homovanillic acid and 5-hydroxyindoleacetic acid in urine using a dilute-and-shoot and ultra-high pressure liquid chromatography tandem mass spectrometry method. Clinical chemistry and laboratory medicine. 2018 08; 56(9):1533-1541. doi: 10.1515/cclm-2017-1120. [PMID: 29708876]
  • Binamra Basnet, Aditya Bhushan, Rehan Khan, Guresh Kumar, Vinod Kumar Sharma, Alpana Sharma, Somesh Gupta. Plasma & urinary catecholamines & urinary vanillylmandelic acid levels in patients with generalized vitiligo. The Indian journal of medical research. 2018 04; 147(4):384-390. doi: 10.4103/ijmr.ijmr_657_16. [PMID: 29998874]
  • Dariusz Pawlak, Tomasz Domaniewski, Beata Znorko, Ewa Oksztulska-Kolanek, Paweł Lipowicz, Michał Doroszko, Malgorzata Karbowska, Krystyna Pawlak. The impact of peripheral serotonin on leptin-brain serotonin axis, bone metabolism and strength in growing rats with experimental chronic kidney disease. Bone. 2017 Dec; 105(?):1-10. doi: 10.1016/j.bone.2017.08.004. [PMID: 28797891]
  • David Bonifačić, Merica Aralica, Vlatka Sotošek Tokmadžić, Valentino Rački, Lidija Tuškan-Mohar, Natalia Kučić. Values of vanillylmandelic acid and homovanillic acid in the urine as potential prognostic biomarkers in ischaemic stroke patients. Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals. 2017 Dec; 22(8):790-797. doi: 10.1080/1354750x.2017.1351001. [PMID: 28675313]
  • Petra Maria Gaum, Monika Gube, Thomas Schettgen, Franziska Maria Putschögl, Thomas Kraus, Bruno Fimm, Jessica Lang. Polychlorinated biphenyls and depression: cross-sectional and longitudinal investigation of a dopamine-related Neurochemical path in the German HELPcB surveillance program. Environmental health : a global access science source. 2017 10; 16(1):106. doi: 10.1186/s12940-017-0316-3. [PMID: 29017568]
  • Kirk L Pappan, Adam D Kennedy, Pilar L Magoulas, Neil A Hanchard, Qin Sun, Sarah H Elsea. Clinical Metabolomics to Segregate Aromatic Amino Acid Decarboxylase Deficiency From Drug-Induced Metabolite Elevations. Pediatric neurology. 2017 Oct; 75(?):66-72. doi: 10.1016/j.pediatrneurol.2017.06.014. [PMID: 28823629]
  • Matthew Carter, Abdul Abdi, Fareeha Naz, Farouq Thabet, Arpita Vyas. A Mercury Toxicity Case Complicated by Hyponatremia and Abnormal Endocrinological Test Results. Pediatrics. 2017 Aug; 140(2):. doi: 10.1542/peds.2016-1402. [PMID: 28701428]
  • Fady Hannah-Shmouni, Karel Pacak, Constantine A Stratakis. Metanephrines for Evaluating Palpitations and Flushing. JAMA. 2017 Jul; 318(4):385-386. doi: 10.1001/jama.2017.5926. [PMID: 28742886]
  • Jiaoyang Cai, Ci Pan, Yanjing Tang, Jing Chen, Min Zhou, Benshang Li, Huiliang Xue, Shuhong Shen, Yijin Gao, AnAn Zhang, Jingyan Tang. Multivariate analysis of risk factors for patients with stage 4 neuroblastoma who were older than 18 months at diagnosis: a report from a single institute in Shanghai, China. Journal of cancer research and clinical oncology. 2017 Jul; 143(7):1327-1335. doi: 10.1007/s00432-017-2379-5. [PMID: 28283783]
  • Zlatuse D Clark, Jeaneah M Cutler, Igor Y Pavlov, Frederick G Strathmann, Elizabeth L Frank. Simple dilute-and-shoot method for urinary vanillylmandelic acid and homovanillic acid by liquid chromatography tandem mass spectrometry. Clinica chimica acta; international journal of clinical chemistry. 2017 May; 468(?):201-208. doi: 10.1016/j.cca.2017.03.004. [PMID: 28263737]
  • Hai Jiang, Wenpei Bai, Wenjuan Wang, Jing Zhang, Ke Wang, Yao Liu, Shuya Liu, Jing Jia, Lihua Qin. Changes in cardiovascular function based on adrenalin and norepinephrine metabolism in ovariectomized rats. Experimental gerontology. 2017 05; 91(?):15-24. doi: 10.1016/j.exger.2017.02.009. [PMID: 28219672]
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