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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:11:44 UTC
Update Date2021-09-14 15:46:17 UTC
HMDB IDHMDB0013018
Secondary Accession Numbers
  • HMDB13018
Metabolite Identification
Common NameNeuromedin B
DescriptionNMB acts by binding to its high affinity cell surface receptor, neuromedin B receptor (NMBR). This receptor is a G protein-coupled receptor with seven transmembrane spanning regions, hence the receptor is also denoted as a 7 transmembrane receptor (7-TMR). Upon binding several intracellular signaling pathways are triggered (see Figure 2). Neuromedin B (NMB) is a bombesin-related peptide in mammals. It was originally purified from pig spinal cord, and later shown to be present in human central nervous system and gastrointestinal tract.
Structure
Data?1582753083
Synonyms
ValueSource
Gly-asn-leu-TRP-ala-THR-gly-his-phe-met-NH2MeSH
Glycyl-arginyl-leucyl-tryptophyl-alanyl-threonyl-glycyl-histidyl-phenylalanyl-methioninamideMeSH
(2R)-2-[(2-Amino-1-hydroxyethylidene)amino]-N-[(1S)-1-{[(1R)-1-{[(1R)-1-{[(1S,2R)-2-hydroxy-1-[({[(1S)-1-{[(1R)-1-{[(1S)-1-(C-hydroxycarbonimidoyl)-3-(methylsulfanyl)propyl]-C-hydroxycarbonimidoyl}-2-phenylethyl]-C-hydroxycarbonimidoyl}-2-(1H-imidazol-5-yl)ethyl]-C-hydroxycarbonimidoyl}methyl)-C-hydroxycarbonimidoyl]propyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}-2-(1H-indol-3-yl)ethyl]-C-hydroxycarbonimidoyl}-3-methylbutyl]butanediimidateGenerator
(2R)-2-[(2-Amino-1-hydroxyethylidene)amino]-N-[(1S)-1-{[(1R)-1-{[(1R)-1-{[(1S,2R)-2-hydroxy-1-[({[(1S)-1-{[(1R)-1-{[(1S)-1-(C-hydroxycarbonimidoyl)-3-(methylsulphanyl)propyl]-C-hydroxycarbonimidoyl}-2-phenylethyl]-C-hydroxycarbonimidoyl}-2-(1H-imidazol-5-yl)ethyl]-C-hydroxycarbonimidoyl}methyl)-C-hydroxycarbonimidoyl]propyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}-2-(1H-indol-3-yl)ethyl]-C-hydroxycarbonimidoyl}-3-methylbutyl]butanediimidateGenerator
(2R)-2-[(2-Amino-1-hydroxyethylidene)amino]-N-[(1S)-1-{[(1R)-1-{[(1R)-1-{[(1S,2R)-2-hydroxy-1-[({[(1S)-1-{[(1R)-1-{[(1S)-1-(C-hydroxycarbonimidoyl)-3-(methylsulphanyl)propyl]-C-hydroxycarbonimidoyl}-2-phenylethyl]-C-hydroxycarbonimidoyl}-2-(1H-imidazol-5-yl)ethyl]-C-hydroxycarbonimidoyl}methyl)-C-hydroxycarbonimidoyl]propyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}-2-(1H-indol-3-yl)ethyl]-C-hydroxycarbonimidoyl}-3-methylbutyl]butanediimidic acidGenerator
Neuromedin bMeSH
Chemical FormulaC52H73N15O12S
Average Molecular Weight1132.294
Monoisotopic Molecular Weight1131.528383565
IUPAC Name(2S)-2-[(2R)-2-[(2S)-2-{2-[(2S,3R)-2-[(2R)-2-[(2R)-2-[(2S)-2-[(2R)-2-(2-aminoacetamido)-3-(C-hydroxycarbonimidoyl)propanamido]-4-methylpentanamido]-3-(1H-indol-3-yl)propanamido]propanamido]-3-hydroxybutanamido]acetamido}-3-(1H-imidazol-4-yl)propanamido]-3-phenylpropanamido]-4-(methylsulfanyl)butanimidic acid
Traditional Name(2S)-2-[(2R)-2-[(2S)-2-{2-[(2S,3R)-2-[(2R)-2-[(2R)-2-[(2S)-2-[(2R)-2-(2-aminoacetamido)-3-(C-hydroxycarbonimidoyl)propanamido]-4-methylpentanamido]-3-(1H-indol-3-yl)propanamido]propanamido]-3-hydroxybutanamido]acetamido}-3-(1H-imidazol-4-yl)propanamido]-3-phenylpropanamido]-4-(methylsulfanyl)butanimidic acid
CAS Registry Number87096-84-2
SMILES
CSCC[C@H](NC(=O)[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1=CNC=N1)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](C)NC(=O)[C@@H](CC1=CNC2=CC=CC=C12)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(O)=N)NC(=O)CN)[C@@H](C)O)C(O)=N
InChI Identifier
InChI=1S/C52H73N15O12S/c1-27(2)17-36(64-51(78)40(21-41(54)69)61-42(70)22-53)48(75)66-38(19-31-23-57-34-14-10-9-13-33(31)34)47(74)60-28(3)46(73)67-44(29(4)68)52(79)58-25-43(71)62-39(20-32-24-56-26-59-32)50(77)65-37(18-30-11-7-6-8-12-30)49(76)63-35(45(55)72)15-16-80-5/h6-14,23-24,26-29,35-40,44,57,68H,15-22,25,53H2,1-5H3,(H2,54,69)(H2,55,72)(H,56,59)(H,58,79)(H,60,74)(H,61,70)(H,62,71)(H,63,76)(H,64,78)(H,65,77)(H,66,75)(H,67,73)/t28-,29-,35+,36+,37-,38-,39+,40-,44+/m1/s1
InChI KeyYPFNACALNKVZNK-ICQOWDAWSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Phenylalanine or derivatives
  • Histidine or derivatives
  • Methionine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Triptan
  • Alanine or derivatives
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Aralkylamine
  • Monocyclic benzene moiety
  • Fatty amide
  • N-acyl-amine
  • Substituted pyrrole
  • Fatty acyl
  • Benzenoid
  • Pyrrole
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Dialkylthioether
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thioether
  • Azacycle
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Organonitrogen compound
  • Amine
  • Organooxygen compound
  • Organosulfur compound
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP0.39ALOGPS
logP-8.2ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)-1.8ChemAxon
pKa (Strongest Basic)13.12ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area440.78 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity312.78 m³·mol⁻¹ChemAxon
Polarizability116.85 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-359.12230932474
DeepCCS[M+Na]+332.89730932474
AllCCS[M+H]+335.532859911
AllCCS[M+H-H2O]+336.332859911
AllCCS[M+NH4]+334.832859911
AllCCS[M+Na]+334.532859911
AllCCS[M-H]-264.832859911
AllCCS[M+Na-2H]-270.332859911
AllCCS[M+HCOO]-276.232859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neuromedin B 10V, Positive-QTOFsplash10-08n9-7920237000-da6c4f78ebfc9ab5eed02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neuromedin B 20V, Positive-QTOFsplash10-06rx-9410132000-2469dd578db8202607de2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neuromedin B 40V, Positive-QTOFsplash10-052o-9631123000-4f532b6c9caa4069271c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neuromedin B 10V, Negative-QTOFsplash10-01pk-9400001001-539d33d517831778e9632017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neuromedin B 20V, Negative-QTOFsplash10-0002-9100010001-4ebc6f640bf1f436fca12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neuromedin B 40V, Negative-QTOFsplash10-0002-9100001001-cffa904c0adcabff32a82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neuromedin B 10V, Positive-QTOFsplash10-001i-3900000000-387a6c951d7b7b1d3b5d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neuromedin B 20V, Positive-QTOFsplash10-0006-9000100010-590c45ad1ab41f94d8c82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neuromedin B 40V, Positive-QTOFsplash10-03di-9500010001-120c9086c573f8af80242021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neuromedin B 10V, Negative-QTOFsplash10-001i-6900011001-b6f6660b62cb99c25b4c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neuromedin B 20V, Negative-QTOFsplash10-052e-9000000000-3bb64b0e27fce00632852021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neuromedin B 40V, Negative-QTOFsplash10-0007-9100000001-4210bb774b10511956292021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029246
KNApSAcK IDNot Available
Chemspider ID30776675
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNeuromedin B
METLIN IDNot Available
PubChem Compound53481579
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available