| Record Information |
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| Version | 5.0 |
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| Status | Detected but not Quantified |
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| Creation Date | 2021-09-11 13:49:33 UTC |
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| Update Date | 2021-09-26 23:08:31 UTC |
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| HMDB ID | HMDB0254491 |
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| Secondary Accession Numbers | None |
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| Metabolite Identification |
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| Common Name | Met-glu-his-phe-arg-trp-gly |
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| Description | Met-glu-his-phe-arg-trp-gly, also known as MSH-acth (4-10) or acth-MSH (4-10), belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Based on a literature review very few articles have been published on Met-glu-his-phe-arg-trp-gly. This compound has been identified in human blood as reported by (PMID: 31557052 ). Met-glu-his-phe-arg-trp-gly is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Met-glu-his-phe-arg-trp-gly is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources. |
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| Structure | CSCCC(N)C(=O)NC(CCC(O)=O)C(=O)NC(CC1=CN=CN1)C(=O)NC(CC1=CC=CC=C1)C(=O)NC(CCCN=C(N)N)C(=O)NC(CC1=CNC2=CC=CC=C12)C(=O)NCC(O)=O InChI=1S/C44H59N13O10S/c1-68-17-15-29(45)38(62)53-32(13-14-36(58)59)41(65)57-35(20-27-22-48-24-52-27)43(67)55-33(18-25-8-3-2-4-9-25)42(66)54-31(12-7-16-49-44(46)47)40(64)56-34(39(63)51-23-37(60)61)19-26-21-50-30-11-6-5-10-28(26)30/h2-6,8-11,21-22,24,29,31-35,50H,7,12-20,23,45H2,1H3,(H,48,52)(H,51,63)(H,53,62)(H,54,66)(H,55,67)(H,56,64)(H,57,65)(H,58,59)(H,60,61)(H4,46,47,49) |
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| Synonyms | | Value | Source |
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| MSH-ACTH (4-10) | HMDB | | ACTH (4-10), (D-arg)-isomer | HMDB | | ACTH(4-10) | HMDB | | ACTH-MSH (4-10) | HMDB | | Human acth (4-10) | HMDB | | 4-10-SEMAX | HMDB | | Corticotropin (4-10) | HMDB | | Corticotropin 4-10 | HMDB | | Porcine acth (4-10) | HMDB | | ACTH (4-10) | HMDB | | ACTH (4-10), (D-met)-isomer | HMDB | | ACTH (4-10), (D-alpha glu)-isomer | HMDB | | ACTH (4-10), zinc phosphate (1:1) salt | HMDB |
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| Chemical Formula | C44H59N13O10S |
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| Average Molecular Weight | 962.1 |
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| Monoisotopic Molecular Weight | 961.422856326 |
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| IUPAC Name | 4-[2-amino-4-(methylsulfanyl)butanamido]-4-({1-[(1-{[1-({1-[(carboxymethyl)carbamoyl]-2-(1H-indol-3-yl)ethyl}carbamoyl)-4-[(diaminomethylidene)amino]butyl]carbamoyl}-2-phenylethyl)carbamoyl]-2-(1H-imidazol-5-yl)ethyl}carbamoyl)butanoic acid |
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| Traditional Name | 4-[2-amino-4-(methylsulfanyl)butanamido]-4-{[1-({1-[(1-{[1-(carboxymethylcarbamoyl)-2-(1H-indol-3-yl)ethyl]carbamoyl}-4-[(diaminomethylidene)amino]butyl)carbamoyl]-2-phenylethyl}carbamoyl)-2-(3H-imidazol-4-yl)ethyl]carbamoyl}butanoic acid |
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| CAS Registry Number | Not Available |
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| SMILES | CSCCC(N)C(=O)NC(CCC(O)=O)C(=O)NC(CC1=CN=CN1)C(=O)NC(CC1=CC=CC=C1)C(=O)NC(CCCN=C(N)N)C(=O)NC(CC1=CNC2=CC=CC=C12)C(=O)NCC(O)=O |
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| InChI Identifier | InChI=1S/C44H59N13O10S/c1-68-17-15-29(45)38(62)53-32(13-14-36(58)59)41(65)57-35(20-27-22-48-24-52-27)43(67)55-33(18-25-8-3-2-4-9-25)42(66)54-31(12-7-16-49-44(46)47)40(64)56-34(39(63)51-23-37(60)61)19-26-21-50-30-11-6-5-10-28(26)30/h2-6,8-11,21-22,24,29,31-35,50H,7,12-20,23,45H2,1H3,(H,48,52)(H,51,63)(H,53,62)(H,54,66)(H,55,67)(H,56,64)(H,57,65)(H,58,59)(H,60,61)(H4,46,47,49) |
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| InChI Key | HAAUASBAIUJHAN-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Amino acids, peptides, and analogues |
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| Direct Parent | Oligopeptides |
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| Alternative Parents | |
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| Substituents | - Alpha-oligopeptide
- Phenylalanine or derivatives
- Histidine or derivatives
- Glutamic acid or derivatives
- Methionine or derivatives
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid amide
- Triptan
- N-substituted-alpha-amino acid
- Alpha-amino acid or derivatives
- Amphetamine or derivatives
- 3-alkylindole
- Indole
- Indole or derivatives
- Imidazolyl carboxylic acid derivative
- N-acyl-amine
- Dicarboxylic acid or derivatives
- Benzenoid
- Fatty acyl
- Fatty amide
- Substituted pyrrole
- Monocyclic benzene moiety
- Pyrrole
- Heteroaromatic compound
- Imidazole
- Azole
- Secondary carboxylic acid amide
- Guanidine
- Carboxamide group
- Amino acid or derivatives
- Amino acid
- Azacycle
- Organoheterocyclic compound
- Dialkylthioether
- Organic 1,3-dipolar compound
- Carboxylic acid
- Propargyl-type 1,3-dipolar organic compound
- Sulfenyl compound
- Carboximidamide
- Thioether
- Hydrocarbon derivative
- Amine
- Carbonyl group
- Organic nitrogen compound
- Organic oxygen compound
- Organic oxide
- Primary amine
- Organosulfur compound
- Organooxygen compound
- Primary aliphatic amine
- Organonitrogen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Not Available | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Molecular Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Experimental Chromatographic Properties | Not Available |
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| Predicted Molecular Properties | |
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| Predicted Chromatographic Properties | Predicted Collision Cross Sections| Predictor | Adduct Type | CCS Value (Å2) | Reference |
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| DeepCCS | [M-2H]- | 326.412 | 30932474 | | DeepCCS | [M+Na]+ | 300.432 | 30932474 |
Predicted Retention Times Underivatized| Chromatographic Method | Retention Time | Reference |
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| Predicted by Siyang on May 30, 2022 | 13.7381 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 7.8 minutes | 32390414 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 1203.7 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 179.7 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 171.1 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 189.5 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 139.4 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 408.3 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 | 447.2 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 1415.9 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 944.7 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 465.3 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 | 1154.4 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 307.9 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 366.1 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 382.9 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 883.2 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 | 214.0 seconds | 40023050 |
Predicted Kovats Retention IndicesNot Available |
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| MS/MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Met-glu-his-phe-arg-trp-gly 10V, Positive-QTOF | splash10-03di-0100000009-7de9bfd410149cc2461a | 2021-10-12 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Met-glu-his-phe-arg-trp-gly 20V, Positive-QTOF | splash10-0006-0000000095-afab2bdd69055fb23fa6 | 2021-10-12 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Met-glu-his-phe-arg-trp-gly 40V, Positive-QTOF | splash10-03di-3900000220-7f204ed10bb09f1a5597 | 2021-10-12 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Met-glu-his-phe-arg-trp-gly 10V, Negative-QTOF | splash10-03di-1000000019-c50d6830aa5f444d4c41 | 2021-10-12 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Met-glu-his-phe-arg-trp-gly 20V, Negative-QTOF | splash10-03dj-2000000191-f9340767c3022d49741e | 2021-10-12 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Met-glu-his-phe-arg-trp-gly 40V, Negative-QTOF | splash10-000i-3391211121-b588ff437bd577643e00 | 2021-10-12 | Wishart Lab | View Spectrum |
NMR Spectra| Spectrum Type | Description | Deposition Date | Source | View |
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| Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum |
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