Normetanephrine (BioDeep_00000003684)
Secondary id: BioDeep_00000402919, BioDeep_00001869059
human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019 Volatile Flavor Compounds
代谢物信息卡片
(+/-)-alpha-(aminomethyl)-4-hydroxy-3-methoxy-benzenemethanol
化学式: C9H13NO3 (183.0895388)
中文名称: 去甲变肾上腺素, 去甲肾上腺素
谱图信息:
最多检出来源 Homo sapiens(blood) 0.02%
Reviewed
Last reviewed on 2024-09-14.
Cite this Page
Normetanephrine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China.
https://query.biodeep.cn/s/normetanephrine (retrieved
2024-11-21) (BioDeep RN: BioDeep_00000003684). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
分子结构信息
SMILES: COC1=C(C=CC(=C1)C(CN)O)O
InChI: InChI=1S/C9H13NO3/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,11-12H,5,10H2,1H3
描述信息
Normetanephrine, also known as normetadrenaline or N111, 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. Normetanephrine is a solid that is soluble in water. Normetanephrine is a metabolite of norepinephrine created by action of catechol-O-methyl transferase on norepinephrine. Within humans, normetanephrine participates in a number of enzymatic reactions. In particular, normetanephrine can be converted into 3-methoxy-4-hydroxyphenylglycolaldehyde through its interaction with the enzyme amine oxidase [flavin-containing] A. It is also involved in the metabolic disorder called transient tyrosinemia of the newborn. This compound is excreted in the urine and is found in certain tissues. It is a marker for catecholamine-secreting tumors such as pheochromocytoma (PMID: 30538672).
A methylated metabolite of norepinephrine that is excreted in the urine and found in certain tissues. It is a marker for tumors. [HMDB]
同义名列表
18 个代谢物同义名
(+/-)-alpha-(aminomethyl)-4-hydroxy-3-methoxy-benzenemethanol; alpha-(Aminomethyl)-4-hydroxy-3-methoxy-benzenemethanol; 4-(2-Amino-1-hydroxyethyl)-2-methoxyphenol; m-O-Methylnorepinephrine; 3-O-Methyl-noradrenaline; 3-Methoxy-noradrenaline; 3 Methoxynoradrenaline; 3-Methoxynoradrenaline; (+/-)-normetanephrine; O-Methylnoradrenaline; DL-N-Normetanephrine; DL-Normetanephrine; L-Normetanephrine; Normetadrenaline; NORMETANEPHRINE; N111; Normetanephrine; Normetanephrine
数据库引用编号
22 个数据库交叉引用编号
- ChEBI: CHEBI:89951
- ChEBI: CHEBI:6277
- KEGG: C05589
- PubChem: 688100
- PubChem: 1237
- HMDB: HMDB0000819
- Metlin: METLIN66
- ChEMBL: CHEMBL1559460
- ChEMBL: CHEMBL774
- Wikipedia: Normetanephrine
- MeSH: Normetanephrine
- KNApSAcK: C00037562
- foodb: FDB022265
- chemspider: 1200
- CAS: 97-31-4
- PMhub: MS000010908
- PubChem: 7914
- 3DMET: B05079
- NIKKAJI: J342.886I
- RefMet: Normetanephrine
- BioNovoGene_Lab2019: BioNovoGene_Lab2019-254
- LOTUS: LTS0219122
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(1)
- noradrenaline and adrenaline degradation:
H2O + O2 + noradrenaline ⟶ 3,4-dihydroxyphenylglycolaldehyde + H+ + ammonia + hydrogen peroxide
Plant Reactome(0)
INOH(1)
- Tyrosine metabolism ( Tyrosine metabolism ):
4-Hydroxy-phenyl-acetaldehyde + H2O + NAD+ ⟶ 4-Hydroxy-phenyl-acetic acid + NADH
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(24)
- Tyrosine Metabolism:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Alkaptonuria:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Hawkinsinuria:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Tyrosinemia Type I:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Disulfiram Action Pathway:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Tyrosinemia, Transient, of the Newborn:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Dopamine beta-Hydroxylase Deficiency:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Monoamine Oxidase-A Deficiency (MAO-A):
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Tyrosine Metabolism:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Alkaptonuria:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Hawkinsinuria:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Tyrosinemia Type I:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Tyrosinemia, Transient, of the Newborn:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Dopamine beta-Hydroxylase Deficiency:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Monoamine Oxidase-A Deficiency (MAO-A):
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Tyrosine Metabolism:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Tyrosine Metabolism:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Tyrosine Metabolism:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Alkaptonuria:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Hawkinsinuria:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Tyrosinemia Type I:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Tyrosinemia, Transient, of the Newborn:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Dopamine beta-Hydroxylase Deficiency:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid - Monoamine Oxidase-A Deficiency (MAO-A):
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
PharmGKB(0)
2 个相关的物种来源信息
- 9606 - Homo sapiens: -
- 4107 - Solanum: 10.1016/S0031-9422(01)00232-1
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
- Joanna Kokoszka, Marta Opalinska, Katarzyna Sitarz, Magdalena Kolasa, Monika Szewczyk, Jolanta Bugajska, Joanna Berska, Krystyna Sztefko, Alicja Hubalewska-Dydejczyk. 24-hours urine metanephrines excretion in patients diagnosed with adrenal incidentaloma: impact of commonly used drugs on clinical decision.
Polish archives of internal medicine.
2024 Jan; ?(?):. doi:
10.20452/pamw.16646. [PMID: 38164744] - Leonardo Rossi, Carlo Enrico Ambrosini, Liborio Torregrossa, Maria Margherita de Santi, Raffaella Guazzo, Tommaso Simoncini, Alessandra Bacca, Benard Gjeloshi, Francesco Pignatelli, Mattia Iachini, Elisa Loguercio, Chiara Becucci, Gabriele Materazzi. An adrenal cortical adenoma with neuroendocrine-type granules mimicking pheochromocytoma.
Ultrastructural pathology.
2023 May; 47(3):236-240. doi:
10.1080/01913123.2023.2201314. [PMID: 37040538] - Yuhang Deng, Qingxiang Liu, Zhenni Liu, Haijian Zhao, Weiyan Zhou, Chuanbao Zhang. Commutability Assessment of Processed Human Plasma Samples for Normetanephrine and Metanephrine Measurements Based on the Candidate Reference Measurement Procedure.
Annals of laboratory medicine.
2022 Sep; 42(5):575-584. doi:
10.3343/alm.2022.42.5.575. [PMID: 35470275] - Hanna Remde, Christina Pamporaki, Marcus Quinkler, Svenja Nölting, Aleksander Prejbisz, Henri J L M Timmers, Jimmy Masjkur, Carmina T Fuss, Martin Fassnacht, Graeme Eisenhofer, Timo Deutschbein. Improved Diagnostic Accuracy of Clonidine Suppression Testing Using an Age-Related Cutoff for Plasma Normetanephrine.
Hypertension (Dallas, Tex. : 1979).
2022 06; 79(6):1257-1264. doi:
10.1161/hypertensionaha.122.19019. [PMID: 35378989] - Hongyu Zeng, Xiaoqing Zhang, Qianna Zhen, Yifan He, Haoran Wang, Yang Zhu, Qi Sun, Min Ding. Dual-Template Magnetic Molecularly Imprinted Polymer for Simultaneous Determination of Spot Urine Metanephrines and 3-Methoxytyramine for the Diagnosis of Pheochromocytomas and Paragangliomas.
Molecules (Basel, Switzerland).
2022 May; 27(11):. doi:
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Analytical and bioanalytical chemistry.
2022 May; 414(11):3541-3549. doi:
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Endocrine-related cancer.
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Journal of veterinary diagnostic investigation : official publication of the American Association of Veterinary Laboratory Diagnosticians, Inc.
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Endokrynologia Polska.
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Clinical biochemistry.
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Clinical cardiology.
2021 Nov; 44(11):1567-1574. doi:
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Scandinavian journal of clinical and laboratory investigation.
2021 Nov; 81(7):564-572. doi:
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American journal of clinical pathology.
2021 Sep; 156(4):691-699. doi:
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Endocrine-related cancer.
2021 09; 28(11):695-703. doi:
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Clinical chemistry.
2021 08; 67(8):1090-1097. doi:
10.1093/clinchem/hvab064. [PMID: 34096581] - Mirko Peitzsch, Talia Novos, Denise Kaden, Max Kurlbaum, Antonius E van Herwaarden, Daniel Müller, Jo Adaway, Eric Grouzmann, Brett McWhinney, Kirsten Hoad, Gerald Woollard, Ido Kema, Christopher Boot, Martin Fassnacht, Fred Sweep, Tze P Loh, Andrea R Horvath, Graeme Eisenhofer. Harmonization of LC-MS/MS Measurements of Plasma Free Normetanephrine, Metanephrine, and 3-Methoxytyramine.
Clinical chemistry.
2021 08; 67(8):1098-1112. doi:
10.1093/clinchem/hvab060. [PMID: 33993248] - Zhan Wang, Hua Fan, Jinghua Fan, Samuel Seery, Wenda Wang, Yushi Zhang. Solitary vaginal paraganglioma with mature sacrococcygeal teratoma: a rare case report.
BMC endocrine disorders.
2021 Jul; 21(1):145. doi:
10.1186/s12902-021-00806-6. [PMID: 34233670] - Nanditha Ananthakrishnan, Saravanan Sanniyasi, Daniel Ravikumar. Malignant pheochromocytoma: pain, palpitation, perspiration and perplexities.
BMJ case reports.
2021 Jun; 14(6):. doi:
10.1136/bcr-2020-239991. [PMID: 34167972] - Kanae Koyama, Noriyoshi Miura, Ryuta Watanabe, Yuichiro Sawada, Terutaka Noda, Kenichi Nishimura, Seiji Asai, Tetsuya Fukumoto, Yutaka Yanagihara, Yuki Miyauchi, Tadahiko Kikugawa, Takashi Saika. Predictors of Hypotension after Adrenalectomy for Pheochromocytoma.
Acta medica Okayama.
2021 Jun; 75(3):345-349. doi:
10.18926/amo/62229. [PMID: 34176938] - Songlin Yu, Danchen Wang, Jialei Yu, Yicong Yin, Shaowei Xie, Qian Cheng, Xi Wang, Wei Liu, Ling Qiu, Xinqi Cheng. Plasma or serum, which is the better choice for the measurement of metanephrines?.
Scandinavian journal of clinical and laboratory investigation.
2021 May; 81(3):250-253. doi:
10.1080/00365513.2021.1904280. [PMID: 33787416] - 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] - Ralitsa Robeva, Miroslava Nedyalkova, Georgi Kirilov, Atanaska Elenkova, Sabina Zacharieva, Błażej Kudłak, Natalia Jatkowska, Vasil Simeonov. Multivariate Statistical Approach for Nephrines in Women with Obesity.
Molecules (Basel, Switzerland).
2021 Mar; 26(5):. doi:
10.3390/molecules26051393. [PMID: 33807567] - Alina Maria Mehedințeanu, Veronica Sfredel, Puiu Olivian Stovicek, Michael Schenker, Georgică Costinel Târtea, Octavian Istrătoaie, Ana-Maria Ciurea, Cristin Constantin Vere. Assessment of Epinephrine and Norepinephrine in Gastric Carcinoma.
International journal of molecular sciences.
2021 Feb; 22(4):. doi:
10.3390/ijms22042042. [PMID: 33670813] - Hanna Barchanska, Ji Tang, Xiangyu Fang, Magdalena Danek, Joanna Płonka, Marcin Sajdak. Profiling and fingerprinting strategies to assess exposure of edible plants to herbicides.
Food chemistry.
2021 Jan; 335(?):127658. doi:
10.1016/j.foodchem.2020.127658. [PMID: 32731124] - Meiling Jian, Honglang Huang, Kecheng Li, Liangmin Chuan, Lin Li, Li Jiang. A 3-min UPLC-MS/MS method for the simultaneous determination of plasma catecholamines and their metabolites: Method verification and diagnostic efficiency.
Clinical biochemistry.
2021 Jan; 87(?):67-73. doi:
10.1016/j.clinbiochem.2020.10.009. [PMID: 33096053] - Graeme Eisenhofer, Timo Deutschbein, Georgiana Constantinescu, Katharina Langton, Christina Pamporaki, Bruna Calsina, Maria Monteagudo, Mirko Peitzsch, Stephanie Fliedner, Henri J L M Timmers, Nicole Bechmann, Maria Fankhauser, Svenja Nölting, Felix Beuschlein, Anthony Stell, Martin Fassnacht, Aleksander Prejbisz, Jacques W M Lenders, Mercedes Robledo. Plasma metanephrines and prospective prediction of tumor location, size and mutation type in patients with pheochromocytoma and paraganglioma.
Clinical chemistry and laboratory medicine.
2020 10; 59(2):353-363. doi:
10.1515/cclm-2020-0904. [PMID: 33001846] - Neethu Sunil V, Kevin John, Sultan Nawahirsha, Ramya Iyyadurai. Micturition syncope: a rare presentation of bladder paraganglioma.
BMJ case reports.
2020 Sep; 13(9):. doi:
10.1136/bcr-2020-235353. [PMID: 32878856] - Emilia Sbardella, Zoe Maunsell, Christine J H May, Michael Tadman, Tim James, Bahram Jafar-Mohammadi, Andrea M Isidori, Ashley B Grossman, Brian Shine. Random 'spot' urinary metanephrines compared with 24-h-urinary and plasma results in phaeochromocytomas and paragangliomas.
European journal of endocrinology.
2020 Aug; 183(2):129-139. doi:
10.1530/eje-19-0809. [PMID: 32413848] - Dallas Fowler, Helen Irving, Peter Borzi, Peter Trnka, Tony Huynh. A Rare and Unusual Cause of Unilateral Ureteric Obstruction in a Child.
Clinical chemistry.
2020 08; 66(8):1006-1009. doi:
10.1093/clinchem/hvaa059. [PMID: 32746464] - Kaijuan Wang, Xiaojing Gao, Hongying Cong, Wei Zhang, Xiaocui Shi, Shuming Dai, Zhou Zhou. Stability and reference intervals of spot urinary fractionated metanephrines and methoxytyramine by tandem mass spectrometry as a screening method for pheochromocytoma and paraganglioma.
Endocrine.
2020 07; 69(1):188-195. doi:
10.1007/s12020-020-02267-8. [PMID: 32222878] - Kanako Bokuda, Midori Yatabe, Yasufumi Seki, Atsuhiro Ichihara. Clinical factors affecting spot urine fractionated metanephrines in patients suspected pheochromocytoma/paraganglioma.
Hypertension research : official journal of the Japanese Society of Hypertension.
2020 06; 43(6):543-549. doi:
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Clinical endocrinology.
2020 06; 92(6):518-524. doi:
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Clinical chemistry and laboratory medicine.
2020 04; 58(5):753-757. doi:
10.1515/cclm-2019-0020. [PMID: 31348754] - Johns T Johnson, Kripa Elizabeth Cherian, Nitin Kapoor, Thomas Vizhalil Paul. Micturition syncope secondary to urinary bladder paraganglioma.
BMJ case reports.
2020 Mar; 13(3):. doi:
10.1136/bcr-2019-233556. [PMID: 32169989] - Gao Jing Ong, Thanh Ha Nguyen, Jeanette Stansborough, Sven Y Surikow, John D Horowitz. Incremental "Therapeutic" Myocardial Exposure to Catecholamines: Incidence and Impact in Takotsubo Syndrome.
Cardiovascular drugs and therapy.
2020 02; 34(1):95-100. doi:
10.1007/s10557-019-06918-5. [PMID: 32076930] - Mirko Peitzsch, Elizabeth R Butch, Elizabeth Lovorn, Anastasios Mangelis, Wayne L Furman, Victor M Santana, Barbara Hero, Frank Berthold, Barry L Shulkin, Angela Huebner, Graeme Eisenhofer. Biochemical testing for neuroblastoma using plasma free 3-O-methyldopa, 3-methoxytyramine, and normetanephrine.
Pediatric blood & cancer.
2020 02; 67(2):e28081. doi:
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European journal of mass spectrometry (Chichester, England).
2020 Feb; 26(1):46-54. doi:
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PloS one.
2020; 15(2):e0228787. doi:
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Endocrine journal.
2019 Dec; 66(12):1063-1072. doi:
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Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2019 Oct; 1129(?):121805. doi:
10.1016/j.jchromb.2019.121805. [PMID: 31670057] - Jessica Omassoli, Neil E Hill, David R Woods, Simon K Delves, Joanne L Fallowfield, Stephen J Brett, Duncan Wilson, Richard W Corbett, Adrian J Allsopp, Michael J Stacey. Variation in renal responses to exercise in the heat with progressive acclimatisation.
Journal of science and medicine in sport.
2019 Sep; 22(9):1004-1009. doi:
10.1016/j.jsams.2019.04.010. [PMID: 31085130] - Jessica Boyd, Alexander A Leung, Hossein Sm Sadrzadeh, Christina Pamporaki, Karel Pacak, Timo Deutschbein, Stephanie Fliedner, Gregory A Kline. A high rate of modestly elevated plasma normetanephrine in a population referred for suspected PPGL when measured in a seated position.
European journal of endocrinology.
2019 Sep; 181(3):301-309. doi:
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Journal of bone and mineral metabolism.
2019 Jul; 37(4):694-702. doi:
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