MiMeDB: Showing metabocard for 1-Methylhistidine (MMDBc0000323)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 17:44:11 UTC

Update Date

2024-10-10 23:34:11 UTC

Metabolite ID

MMDBc0000323

Metabolite Identification

Common Name

1-Methylhistidine

Description

1-Methylhistidine, also known as 1-MHis, 1MH, tau-methylhistidine or tele-methylhistidine, belongs to the class of organic compounds known as histidine and derivatives. 1MH is also classified as a methylamino acid. Methylamino acids are primarily proteogenic amino acids (found in proteins) which have been methylated (in situ) on their side chains by various methyltransferase enzymes. Histidine can be methylated at either the N1 or N3 position of its imidazole ring, yielding the isomers 1-methylhistidine (1MH; also referred to as tau-methylhistidine, according to IUPAC) or 3-methylhistidine (3MH; pi-methylhistidine, according to IUPAC), respectively. There is considerable confusion with regard to the nomenclature of the methylated nitrogen atoms on the imidazole ring of histidine in histidine-containing proteins (such as actin and myosin) as well as histidine-containing peptides (such as anserine and ophidine/balenine). In particular, older literature (mostly prior to the year 2000) as well as most biochemists and nutrition scientists incorrectly number the imidazole nitrogen atom most proximal to the side chain beta-carbon as 1 or N1, while organic chemists correctly designate it as 3 or N3. As a result, biochemists and nutrition scientists historically designated anserine (Npi-methylated) as beta-alanyl-N1-methylhistidine (or beta-alanyl-1-methylhistidine), whereas according to standard IUPAC nomenclature, anserine is correctly named as beta-alanyl-N3-methylhistidine. As a result, for several decades, many papers incorrectly identified 1MH as a specific marker for dietary consumption or various pathophysiological effects when they really are referring to 3MH – and vice versa (PMID: 24137022 ). To help resolve this issue the IUPAC commission (PMID: 6743224 and IUPAC Compendium of Chemical Terminology, 2nd ed. (the 'Gold Book'). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997)) revised the nomenclature for histidine and introduced the terms pi (for prox or pros – near) and tau (for tele – far) to label the imidazole nitrogens in histidine. Therefore, the pi nitrogen is the nitrogen closest to the side chain beta carbon (atom #3 or N3) while the tau nitrogen is most distant from the side chain beta carbon (atom #1 or N1). IUPAC's goal is for the global community to refer to the molecule depicted here is as 'tau-methylhistidine' with the hope that the archaic term, 1-methylhistidine will eventually disappear. Unfortunately, this has not happened and confusion still persists. Older versions of the HMDB (prior to 2022) as well as current versions of some databases, such as PubChem, KEGG, and UniProt, indicate that an acceptable synonym for 1MH is pi-methylhistidine or otherwise somehow equate 1MH and 3MH. This is incorrect and it continues to sow confusion. Indeed, a key paper that identified METTL9 as the enzyme responsible for pi-methylation of histidine in most vertebrates also incorrectly labeled the METTL9 product as 1MH (PMID: 33563959 ). Similarly, a key paper that identified METTL18 as the enzyme responsible for tau-methylation of histidine incorrectly labelled the METTL18 product as 3MH (PMID: 33693809 ). Likewise, many members of the biochemical/nutrition community still incorrectly refer to 1MH as pi-methlyhistidine and 3MH as tau-methylhistidine. This has led to even more confusion. To maintain consistency for this compound description, all papers cited herein that incorrectly refer to 3MH as 1MH and vice versa, will have their conclusions re-stated and the citation will be marked with the phrase '3MH/1MH switch'. 1MH is a free amino acid arising from the proteolysis of 1MH-containing proteins and peptides. It is not synthesized on its own, nor can it be incorporated into proteins as an amino acid. However, it can be incorporated into certain dipeptides through the action of the enzyme known as carnosine synthase I. 1MH can only be generated from histidine residues through the action of methyltransferases as a protein post-translational modification event. Histidine methylation on the 1- or tau site of histidine-containing proteins is mediated by at least two enzymes: SETD3 (PMID: 30526847 ) and METTL18 (3MH/1MH switch - PMID: 33693809 ). SETD3, or SET domain-containing protein 3, is a protein-histidine N-methyltransferase that specifically mediates 1-methylhistidine (tau-methylhistidine) methylation of actin at 'His-73' (PMID: 30526847 ; 3MH/1MH switch - PMID: 30626964 ). SETD3 is a methyltransferase that uses S-adenosyl-L-methionine to transfer the methyl group to histidine at the tau position. Histidine methylation of actin His-73 is required for smooth muscle contraction of the laboring uterus during delivery (3MH/1MH switch - PMID: 30626964 ). It also reduces the nucleotide exchange rate on actin monomers and modestly accelerates actin filament assembly (3MH/1MH switch - PMID: 30626964 ). SETD3-mediated histidine methylation appears to occur in all higher eukaryotes with actin, from plants to insects to vertebrates. Within cells, SETD3 is found in the cytoplasm and nucleus. In contrast to SETD3, METTL18 is a nuclear methyltransferase protein that contains a functional nuclear localization signal and accumulates in nucleoli. Specifically, METTL18 is a seven β-strand (7BS) methyltransferase that uses S-adenosyl-L-methionine to transfer the methyl group to the tau position of His-245 on ribosomal protein L3, RPL3 (3MH/1MH switch - PMID: 33693809 ). METTL18 is highly conserved and found in essentially all eukaryotes (from yeast to humans). METTL18-mediated methylation of RPL3 is important for optimal ribosome biogenesis and function (3MH/1MH switch - PMID: 33693809 ). Other proteins that are known to have 1MH modifications include myosin and myosin kinase. In addition to these tau-His-methylated proteins, a specialized dipeptide called ophidine (balenine) that consists of beta-alanine and 1MH is also known (PMID: 24137022 ). This methylated analog of carnosine, which is naturally produced in the liver via the enzyme carnosine synthase I (PMID: 20097752 ), is especially abundant in the skeletal muscles and brains of whales and dolphins but almost completely absent in other vertebrates (PMID: 24137022 ). Ophidine, like its homologs anserine and carnosine, is believed to act as a pH buffer (for lactic acid generated by muscles), an antiglycating agent, and an antioxidant. Neither ophidine nor anserine are produced in humans, with humans being the only vertebrate not producing (or producing very little) methylated histidine versions of carnosine (PMID: 24137022 ). Because 1MH is so abundant in skeletal muscle tissues (being found in the main myofibrillar proteins actin and myosin), the urinary concentrations of 1-methylhistidine can be used as a biomarker for skeletal muscle protein breakdown, especially for those who have been subject to muscle injury (3MH/1MH switch - PMID: 16079625 ). During protein catabolism, 1-methylhistidine is released but cannot be reutilized. Therefore, the plasma concentration and urine excretion of 1-methylhistidine serve as sensitive markers of myofibrillar protein degradation (3MH/1MH switch - PMID: 32235743 ). Approximately 75% of 1-methylhistidine in the human body is estimated to originate from skeletal muscle (3MH/1MH switch - PMID: 32235743 ). In addition to the degradation of muscle proteins, the 1-methylhistidine level can be moderately affected by the degradation of intestinal proteins and meat intake. 1-Methylhistidine has been found to be associated with several diseases such as Alzheimer's disease, preeclampsia, obesity, kidney disease. The normal concentration of 1-methylhistidine in the urine of healthy adult humans has been detected and quantified in a range of 17.7-153.8 micromoles per millimole (umol/mmol) of creatinine, with most studies reporting the average urinary concentration between 25-40 umol/mmol of creatinine. The average concentration of 1-methylhistidine in human blood plasma has been detected and quantified at 12.7 micromolar (uM) with a range of 9.8-15.6 uM. As a general rule, urinary 3MH is associated with white meat intake (p< 0.001), whereas urinary 1MH is associated with red meat intake (p< 0.001) (3MH/1MH switch - PMID: 34091671 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Methyl-DL-histidine	ChEBI

Molecular Formula

C₇H₁₁N₃O₂

Average Mass

169.1811

Monoisotopic Mass

169.085126611

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C7H11N3O2/c1-10-3-5(9-4-10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)

InChI Key

BRMWTNUJHUMWMS-UHFFFAOYSA-N

Chemical Taxonomy

Functional Ontology

Physical Properties

Spectra

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	10.66	2.68			uM	Elderly (>65 years old)	Both	Alzheimer's disease	HMDB	17031479
Human Urine	Detected and Quantified	15.7	4.04			umol/mmol creatinine	Adult (>18 years old)	Both	Alzheimer's disease	HMDB	17031479
Human Cerebrospinal fluid (csf)	Detected and Quantified	2.6	1.13			uM	Adult (>18 years old)	Both	Alzheimer's disease	HMDB	17031479
Human Urine	Detected and Quantified	17.5	25.7			umol/mmol creatinine	Adult (>18 years old)	Both	Diabetes	HMDB	15899597
Human Blood	Detected and Quantified	50.7	12.9			uM	Adult (>18 years old)	Female	Early preeclampsia	HMDB	22494326
Human Blood	Detected and Quantified	28.8	18.2			uM	Adult (>18 years old)	Both	Kidney disease	HMDB	10838467
Human Blood	Detected and Quantified	83.1	21.7			uM	Adult (>18 years old)	Both	Kidney disease	HMDB	10838467
Human Blood	Detected and Quantified	70.3	40.0			uM	Adult (>18 years old)	Female	Late-onset preeclampsia	HMDB	23159745
Human Urine	Detected and Quantified	31	11			umol/mmol creatinine	Adult (>18 years old)	Both	Maple syrup urine disease	HMDB	19551947
Human Urine	Detected and Quantified	10.9	10.1			umol/mmol creatinine	Adult (>18 years old)	Both	Obesity	HMDB	15899597
Human Blood	Detected and Quantified	32.7	13.7			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23313728
Human Blood	Detected and Quantified	38.9	20.3			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23159745
Human Blood	Detected and Quantified	43.4	22.3			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23535240
Human Blood	Detected and Quantified	50.0	14.6			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	22494326
Human Urine	Detected and Quantified	40	2.6			umol/mmol creatinine	Adult (>18 years old)	Both	Propionic acidemia	HMDB	19551947
Human Urine	Detected and Quantified	4.635				umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	11052553
Human Urine	Detected and Quantified			10	17	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Urine	Detected and Quantified			11	16	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified	1.3	2.76			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	11052553
Human Urine	Detected and Quantified	1.334	2.759			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	11052553
Human Blood	Detected and Quantified	12.7	2.9			uM	Adult (>18 years old)	Both	Normal	HMDB	7061274
Human Blood	Detected and Quantified	14.4	2.3			uM	Adult (>18 years old)	Both	Normal	HMDB	7061274
Human Urine	Detected and Quantified	15.9	19.5			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	11052553
Human Urine	Detected and Quantified	15.9	19.5			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	11052553
Human Urine	Detected and Quantified	15.919	19.503			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	11052553
Human Urine	Detected and Quantified			18.55	145.2	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Blood	Detected and Quantified	19.6	2.6			uM	Adult (>18 years old)	Both	Normal	HMDB	7061274
Human Urine	Detected and Quantified	2.3	5.1			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	11052553
Human Urine	Detected and Quantified	2.340	5.0764			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	11052553
Human Blood	Detected and Quantified	20.2	4.0			uM	Adult (>18 years old)	Both	Normal	HMDB	7061274
Human Urine	Detected and Quantified	28.0954	31.826			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	11052553
Human Urine	Detected and Quantified	28.1	31.8			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	11052553
Human Urine	Detected and Quantified	30.0	43.0			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	15899597
Human Urine	Detected and Quantified	33.6	36.4			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	11052553
Human Urine	Detected and Quantified	33.624	36.360			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	11052553
Human Cerebrospinal fluid (csf)	Detected and Quantified	4.0	1.74			uM	Adult (>18 years old)	Both	Normal	HMDB	17031479
Human Urine	Detected and Quantified	4.6	2.7			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	11052553
Human Urine	Detected and Quantified	45.473	41.617			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	11052553
Human Urine	Detected and Quantified	45.5	41.6			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	11052553
Human Urine	Detected and Quantified	46.0833	53.432			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	11052553
Human Urine	Detected and Quantified	46.1	53.5			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	11052553
Human Urine	Detected and Quantified	47.06		17.31	146.8	umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Urine	Detected and Quantified	53.18		22.81	139.9	umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Blood	Detected and Quantified	7.7	1.9			uM	Adult (>18 years old)	Both	Normal	HMDB	7061274
Human Urine	Detected and Quantified	8.3		2.4	28.4	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	18.299	16.521			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	21.329	12.971			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified			17.74	153.77	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	David F. Putnam Composition and Concentrative Properties of Human Urine. NASA Contractor Report. July 1971
Human Blood	Detected and Quantified	4.0	8.0			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	9.1	7.2			uM	Children (1-13 years old)	Not Specified	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified			1.13	166.96	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified			1.36	175.22	umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified			1.92	47.39	umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified			2.036	184.27	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified			2.15	162.32	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified			2.60	151.46	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						NULL	Male	Normal	HMDB	22932811
Human Feces	Detected but not Quantified						Not Specified	Both	Normal	HMDB	25486321
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	17022649
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21736852
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	23269817
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

References

General References

Betto P, Ricciarello G, Pichini S, Dello Strologo L, Rizzoni G: High-performance liquid chromatography-electrochemical detection of 3-methylhistidine in human urine. J Chromatogr. 1992 Dec 23;584(2):256-60. doi: 10.1016/0378-4347(92)80583-c. [PubMed:1484110 ]
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Giesecke K, Magnusson I, Ahlberg M, Hagenfeldt L, Wahren J: Protein and amino acid metabolism during early starvation as reflected by excretion of urea and methylhistidines. Metabolism. 1989 Dec;38(12):1196-200. doi: 10.1016/0026-0495(89)90159-5. [PubMed:2593832 ]
Sjolin J, Stjernstrom H, Henneberg S, Hambraeus L, Friman G: Evaluation of urinary 3-methylhistidine excretion in infection by measurements of 1-methylhistidine and the creatinine ratios. Am J Clin Nutr. 1989 Jan;49(1):62-70. doi: 10.1093/ajcn/49.1.62. [PubMed:2912013 ]
Dohm GL, Williams RT, Kasperek GJ, van Rij AM: Increased excretion of urea and N tau -methylhistidine by rats and humans after a bout of exercise. J Appl Physiol Respir Environ Exerc Physiol. 1982 Jan;52(1):27-33. doi: 10.1152/jappl.1982.52.1.27. [PubMed:7061274 ]
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Dunnett M, Harris RC: High-performance liquid chromatographic determination of imidazole dipeptides, histidine, 1-methylhistidine and 3-methylhistidine in equine and camel muscle and individual muscle fibres. J Chromatogr B Biomed Sci Appl. 1997 Jan 10;688(1):47-55. doi: 10.1016/s0378-4347(97)88054-1. [PubMed:9029312 ]
Garlick PJ, McNurlan MA, Bark T, Lang CH, Gelato MC: Hormonal regulation of protein metabolism in relation to nutrition and disease. J Nutr. 1998 Feb;128(2 Suppl):356S-359S. doi: 10.1093/jn/128.2.356S. [PubMed:9478024 ]
Colombani PC, Kovacs E, Frey-Rindova P, Frey W, Langhans W, Arnold M, Wenk C: Metabolic effects of a protein-supplemented carbohydrate drink in marathon runners. Int J Sport Nutr. 1999 Jun;9(2):181-201. doi: 10.1123/ijsn.9.2.181. [PubMed:10362454 ]
Myint T, Fraser GE, Lindsted KD, Knutsen SF, Hubbard RW, Bennett HW: Urinary 1-methylhistidine is a marker of meat consumption in Black and in White California Seventh-day Adventists. Am J Epidemiol. 2000 Oct 15;152(8):752-5. doi: 10.1093/aje/152.8.752. [PubMed:11052553 ]
COCKS DH, DENNIS PO, NELSON TH: ISOLATION OF 3-METHYL HISTIDINE FROM WHALEMEAT EXTRACT AND THE PREPARATION OF SOME DERIVATIVES. Nature. 1964 Apr 11;202:184-5. doi: 10.1038/202184a0. [PubMed:14156296 ]
Tuma P, Samcova E, Balinova P: Determination of 3-methylhistidine and 1-methylhistidine in untreated urine samples by capillary electrophoresis. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jul 5;821(1):53-9. doi: 10.1016/j.jchromb.2005.04.006. [PubMed:15899597 ]
Chinkes DL: Methods for measuring tissue protein breakdown rate in vivo. Curr Opin Clin Nutr Metab Care. 2005 Sep;8(5):534-7. doi: 10.1097/01.mco.0000170754.25372.37. [PubMed:16079625 ]
Drozak J, Veiga-da-Cunha M, Vertommen D, Stroobant V, Van Schaftingen E: Molecular identification of carnosine synthase as ATP-grasp domain-containing protein 1 (ATPGD1). J Biol Chem. 2010 Mar 26;285(13):9346-9356. doi: 10.1074/jbc.M109.095505. Epub 2010 Jan 22. [PubMed:20097752 ]
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Boldyrev AA, Aldini G, Derave W: Physiology and pathophysiology of carnosine. Physiol Rev. 2013 Oct;93(4):1803-45. doi: 10.1152/physrev.00039.2012. [PubMed:24137022 ]
Mitry P, Wawro N, Rohrmann S, Giesbertz P, Daniel H, Linseisen J: Plasma concentrations of anserine, carnosine and pi-methylhistidine as biomarkers of habitual meat consumption. Eur J Clin Nutr. 2019 May;73(5):692-702. doi: 10.1038/s41430-018-0248-1. Epub 2018 Jul 17. [PubMed:30018457 ]
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Davydova E, Shimazu T, Schuhmacher MK, Jakobsson ME, Willemen HLDM, Liu T, Moen A, Ho AYY, Malecki J, Schroer L, Pinto R, Suzuki T, Gronsberg IA, Sohtome Y, Akakabe M, Weirich S, Kikuchi M, Olsen JV, Dohmae N, Umehara T, Sodeoka M, Siino V, McDonough MA, Eijkelkamp N, Schofield CJ, Jeltsch A, Shinkai Y, Falnes PO: The methyltransferase METTL9 mediates pervasive 1-methylhistidine modification in mammalian proteomes. Nat Commun. 2021 Feb 9;12(1):891. doi: 10.1038/s41467-020-20670-7. [PubMed:33563959 ]
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Showing metabocard for 1-Methylhistidine (MMDBc0000323)

MOL for #<Metabolite:0x00007fd5c44c1688>

3D MOL for #<Metabolite:0x00007fd5c44c1688>

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3D PDB for #<Metabolite:0x00007fd5c44c1688>

SMILES for #<Metabolite:0x00007fd5c44c1688>

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Structure for #<Metabolite:0x00007fd5c44c1688>

3D Structure for #<Metabolite:0x00007fd5c44c1688>