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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:11:46 UTC
Update Date2020-02-26 21:38:03 UTC
HMDB IDHMDB0013020
Secondary Accession Numbers
  • HMDB13020
Metabolite Identification
Common NameNeuromedin C
DescriptionNeuromedin c is a neuropeptide derived from the same precursor polypeptide as neurotensin, and with similar but subtly distinct expression and effect. Neurotensin is a 13 amino acid neuropeptide that is implicated in the regulation of luteinizing hormone and prolactin release and has significant interaction with the dopaminergic system. Neurotensin was first isolated from extracts of bovine hypothalamus based on its ability to cause a visible vasodilation in the exposed cutaneous regions of anesthetized rats. This structure shows neuromedin C.
Structure
Data?1582753083
Synonyms
ValueSource
NMCHMDB
GRP (18-27)HMDB
Canine gastrin-releasing peptide 10HMDB
Gastrin releasing peptide 10HMDB
GRP-10HMDB
Bombesin decapeptideHMDB
Gly-asn-his-TRP-ala-val-gly-his-leu-met-NH2HMDB
NMC PeptideHMDB
Gastrin releasing peptide (18-27)HMDB
(2R)-2-[(2-Amino-1-hydroxyethylidene)amino]-N-[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-[({[(1S)-1-[(1-{[(1R)-1-(C-hydroxycarbonimidoyl)-3-(methylsulfanyl)propyl]-C-hydroxycarbonimidoyl}-3-methylbutyl)-C-hydroxycarbonimidoyl]-2-(1H-imidazol-5-yl)ethyl]-C-hydroxycarbonimidoyl}methyl)-C-hydroxycarbonimidoyl]-2-methylpropyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}-2-(1H-indol-3-yl)ethyl]-C-hydroxycarbonimidoyl}-2-(1H-imidazol-5-yl)ethyl]butanediimidateGenerator
(2R)-2-[(2-Amino-1-hydroxyethylidene)amino]-N-[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-[({[(1S)-1-[(1-{[(1R)-1-(C-hydroxycarbonimidoyl)-3-(methylsulphanyl)propyl]-C-hydroxycarbonimidoyl}-3-methylbutyl)-C-hydroxycarbonimidoyl]-2-(1H-imidazol-5-yl)ethyl]-C-hydroxycarbonimidoyl}methyl)-C-hydroxycarbonimidoyl]-2-methylpropyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}-2-(1H-indol-3-yl)ethyl]-C-hydroxycarbonimidoyl}-2-(1H-imidazol-5-yl)ethyl]butanediimidateGenerator
(2R)-2-[(2-Amino-1-hydroxyethylidene)amino]-N-[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-[({[(1S)-1-[(1-{[(1R)-1-(C-hydroxycarbonimidoyl)-3-(methylsulphanyl)propyl]-C-hydroxycarbonimidoyl}-3-methylbutyl)-C-hydroxycarbonimidoyl]-2-(1H-imidazol-5-yl)ethyl]-C-hydroxycarbonimidoyl}methyl)-C-hydroxycarbonimidoyl]-2-methylpropyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}-2-(1H-indol-3-yl)ethyl]-C-hydroxycarbonimidoyl}-2-(1H-imidazol-5-yl)ethyl]butanediimidic acidGenerator
Neuromedin CMeSH
Chemical FormulaC50H73N17O11S
Average Molecular Weight1120.287
Monoisotopic Molecular Weight1119.539616953
IUPAC Name(2R)-2-(2-aminoacetamido)-N-[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-[({[(1S)-1-[(1-{[(1R)-1-carbamoyl-3-(methylsulfanyl)propyl]carbamoyl}-3-methylbutyl)carbamoyl]-2-(1H-imidazol-5-yl)ethyl]carbamoyl}methyl)carbamoyl]-2-methylpropyl]carbamoyl}ethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-(1H-imidazol-5-yl)ethyl]butanediamide
Traditional Name(2R)-2-(2-aminoacetamido)-N-[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-[({[(1S)-1-[(1-{[(1R)-1-carbamoyl-3-(methylsulfanyl)propyl]carbamoyl}-3-methylbutyl)carbamoyl]-2-(3H-imidazol-4-yl)ethyl]carbamoyl}methyl)carbamoyl]-2-methylpropyl]carbamoyl}ethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-(3H-imidazol-4-yl)ethyl]succinamide
CAS Registry Number81608-30-2
SMILES
CSCC[C@@H](NC(=O)C(CC(C)C)NC(=O)[C@H](CC1=CN=CN1)NC(=O)CNC(=O)[C@H](NC(=O)[C@H](C)NC(=O)[C@@H](CC1=CNC2=C1C=CC=C2)NC(=O)[C@H](CC1=CN=CN1)NC(=O)[C@@H](CC(N)=O)NC(=O)CN)C(C)C)C(N)=O
InChI Identifier
InChI=1S/C50H73N17O11S/c1-25(2)13-34(46(74)63-33(43(53)71)11-12-79-6)64-47(75)36(15-29-20-54-23-58-29)62-41(70)22-57-50(78)42(26(3)4)67-44(72)27(5)60-45(73)35(14-28-19-56-32-10-8-7-9-31(28)32)65-48(76)37(16-30-21-55-24-59-30)66-49(77)38(17-39(52)68)61-40(69)18-51/h7-10,19-21,23-27,33-38,42,56H,11-18,22,51H2,1-6H3,(H2,52,68)(H2,53,71)(H,54,58)(H,55,59)(H,57,78)(H,60,73)(H,61,69)(H,62,70)(H,63,74)(H,64,75)(H,65,76)(H,66,77)(H,67,72)/t27-,33+,34?,35+,36-,37-,38+,42+/m0/s1
InChI KeyRWBLWXCGQLZKLK-FHOLMIEWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
KingdomOrganic compounds
Super ClassOrganic Polymers
ClassPolypeptides
Sub ClassNot Available
Direct ParentPolypeptides
Alternative Parents
Substituents
  • Polypeptide
  • Alpha peptide
  • Histidine or derivatives
  • Leucine or derivatives
  • Asparagine or derivatives
  • Methionine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Valine or derivatives
  • Alpha-amino acid amide
  • Triptan
  • Alanine or derivatives
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Benzenoid
  • Fatty acyl
  • Fatty amide
  • Substituted pyrrole
  • N-acyl-amine
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Pyrrole
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Organoheterocyclic compound
  • Azacycle
  • Dialkylthioether
  • Carboxylic acid derivative
  • Sulfenyl compound
  • Thioether
  • Organic nitrogen compound
  • Amine
  • Organosulfur compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Primary amine
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP0.17ALOGPS
logP-5.8ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)11.5ChemAxon
pKa (Strongest Basic)7.9ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area447.25 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity287.45 m³·mol⁻¹ChemAxon
Polarizability112.96 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f7x-6921237000-1c6ef9aad67106f77defSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0016-9520131000-f0b04f769d012e3b8d6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001c-7930123000-80bd0eadf16a1d23ff7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kk-9400001001-61504f08135f7b942f4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9100000001-265cab6d89ef346c855fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000001011-4e4363692473c92620b0Spectrum
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 IDFDB029248
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481581
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available