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Record Information
Version1.0
Created at2020-12-09 01:39:54 UTC
Updated at2021-07-15 16:48:26 UTC
NP-MRD IDNP0004168
Secondary Accession NumbersNone
Natural Product Identification
Common NamePropeptin
Provided ByNPAtlasNPAtlas Logo
Description1-{2-[(2-{[2-({2-[(2-{[2-({2-[(2-{[2-({[15-(3-Carbamimidamidopropyl)-9-(carboxymethyl)-1,4,7,10,13,16,20,23-octahydroxy-12,25-bis[(4-hydroxyphenyl)methyl]-3,6-bis[(1H-indol-3-yl)methyl]-26-oxo-3H,6H,9H,12H,15H,18H,19H,22H,25H,26H,28H,29H,30H,30aH-pyrrolo[1,2-g]1,4,7,10,13,16,19,22,25-nonaazacyclooctacosan-18-yl](hydroxy)methylidene}amino)-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]-1-hydroxyethylidene}amino)-1-hydroxyethylidene]amino}-1-hydroxy-3-(1H-imidazol-5-yl)propylidene)amino]-1,3-dihydroxybutylidene}amino)-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-methylpentylidene)amino]-3-hydroxypropanoyl}pyrrolidine-2-carboxylic acid belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues. Propeptin is found in Microbispora sp. It was first documented in 2002 (PMID: 12014445). Based on a literature review very few articles have been published on 1-{2-[(2-{[2-({2-[(2-{[2-({2-[(2-{[2-({[15-(3-carbamimidamidopropyl)-9-(carboxymethyl)-1,4,7,10,13,16,20,23-octahydroxy-12,25-bis[(4-hydroxyphenyl)methyl]-3,6-bis[(1H-indol-3-yl)methyl]-26-oxo-3H,6H,9H,12H,15H,18H,19H,22H,25H,26H,28H,29H,30H,30aH-pyrrolo[1,2-g]1,4,7,10,13,16,19,22,25-nonaazacyclooctacosan-18-yl](hydroxy)methylidene}amino)-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]-1-hydroxyethylidene}amino)-1-hydroxyethylidene]amino}-1-hydroxy-3-(1H-imidazol-5-yl)propylidene)amino]-1,3-dihydroxybutylidene}amino)-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-methylpentylidene)amino]-3-hydroxypropanoyl}pyrrolidine-2-carboxylic acid.
Structure
Thumb
Synonyms
ValueSource
1-{2-[(2-{[2-({2-[(2-{[2-({2-[(2-{[2-({[15-(3-carbamimidamidopropyl)-9-(carboxymethyl)-1,4,7,10,13,16,20,23-octahydroxy-12,25-bis[(4-hydroxyphenyl)methyl]-3,6-bis[(1H-indol-3-yl)methyl]-26-oxo-3H,6H,9H,12H,15H,18H,19H,22H,25H,26H,28H,29H,30H,30ah-pyrrolo[1,2-g]1,4,7,10,13,16,19,22,25-nonaazacyclooctacosan-18-yl](hydroxy)methylidene}amino)-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]-1-hydroxyethylidene}amino)-1-hydroxyethylidene]amino}-1-hydroxy-3-(1H-imidazol-5-yl)propylidene)amino]-1,3-dihydroxybutylidene}amino)-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-methylpentylidene)amino]-3-hydroxypropanoyl}pyrrolidine-2-carboxylateGenerator
Chemical FormulaC113H142N26O27
Average Mass2296.5340 Da
Monoisotopic Mass2295.05377 Da
IUPAC Name(2R)-1-[(2S)-2-[(2S,3S)-2-[(2R)-2-[(2S,3R)-2-[(2R)-2-(2-{2-[(2R)-2-[(2R)-2-{[(3R,6S,9S,12R,15S,18R,25R,30aS)-15-(3-carbamimidamidopropyl)-9-(carboxymethyl)-12,25-bis[(4-hydroxyphenyl)methyl]-3,6-bis[(1H-indol-3-yl)methyl]-1,4,7,10,13,16,20,23,26-nonaoxo-triacontahydropyrrolo[1,2-g]1,4,7,10,13,16,19,22,25-nonaazacyclooctacosan-18-yl]formamido}-4-methylpentanamido]-3-phenylpropanamido]acetamido}acetamido)-3-(1H-imidazol-4-yl)propanamido]-3-hydroxybutanamido]-3-phenylpropanamido]-3-methylpentanamido]-3-hydroxypropanoyl]pyrrolidine-2-carboxylic acid
Traditional Name(2R)-1-[(2S)-2-[(2S,3S)-2-[(2R)-2-[(2S,3R)-2-[(2R)-2-(2-{2-[(2R)-2-[(2R)-2-{[(3R,6S,9S,12R,15S,18R,25R,30aS)-15-(3-carbamimidamidopropyl)-9-(carboxymethyl)-12,25-bis[(4-hydroxyphenyl)methyl]-3,6-bis(1H-indol-3-ylmethyl)-1,4,7,10,13,16,20,23,26-nonaoxo-icosahydro-2H-pyrrolo[1,2-g]1,4,7,10,13,16,19,22,25-nonaazacyclooctacosan-18-yl]formamido}-4-methylpentanamido]-3-phenylpropanamido]acetamido}acetamido)-3-(1H-imidazol-4-yl)propanamido]-3-hydroxybutanamido]-3-phenylpropanamido]-3-methylpentanamido]-3-hydroxypropanoyl]pyrrolidine-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CCC(C)C(NC(=O)C(CC1=CC=CC=C1)NC(=O)C(NC(=O)C(CC1=CNC=N1)NC(=O)CNC(=O)CNC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC(C)C)NC(=O)C1CC(=O)NCC(=O)NC(CC2=CC=C(O)C=C2)C(=O)N2CCCC2C(=O)NC(CC2=CNC3=CC=CC=C23)C(=O)NC(CC2=CNC3=CC=CC=C23)C(=O)NC(CC(O)=O)C(=O)NC(CC2=CC=C(O)C=C2)C(=O)NC(CCCNC(N)=N)C(=O)N1)C(C)O)C(=O)NC(CO)C(=O)N1CCCC1C(O)=O
InChI Identifier
InChI=1S/C113H142N26O27/c1-6-61(4)95(108(161)135-87(58-140)111(164)139-41-19-30-89(139)112(165)166)136-105(158)80(44-64-22-11-8-12-23-64)134-109(162)96(62(5)141)137-106(159)83(49-69-54-116-59-123-69)124-92(146)57-121-91(145)55-122-97(150)78(43-63-20-9-7-10-21-63)128-99(152)77(42-60(2)3)127-103(156)84-50-90(144)120-56-93(147)125-86(46-66-33-37-71(143)38-34-66)110(163)138-40-18-29-88(138)107(160)133-82(48-68-53-119-75-27-16-14-25-73(68)75)102(155)130-81(47-67-52-118-74-26-15-13-24-72(67)74)101(154)132-85(51-94(148)149)104(157)129-79(45-65-31-35-70(142)36-32-65)100(153)126-76(98(151)131-84)28-17-39-117-113(114)115/h7-16,20-27,31-38,52-54,59-62,76-89,95-96,118-119,140-143H,6,17-19,28-30,39-51,55-58H2,1-5H3,(H,116,123)(H,120,144)(H,121,145)(H,122,150)(H,124,146)(H,125,147)(H,126,153)(H,127,156)(H,128,152)(H,129,157)(H,130,155)(H,131,151)(H,132,154)(H,133,160)(H,134,162)(H,135,161)(H,136,158)(H,137,159)(H,148,149)(H,165,166)(H4,114,115,117)
InChI KeyVIRBPQIAVNKZST-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Microbispora sp.NPAtlas
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
  • Cyclic alpha peptide
  • Phenylalanine or derivatives
  • Histidine or derivatives
  • Leucine or derivatives
  • Isoleucine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Proline or derivatives
  • Macrolactam
  • Alpha-amino acid amide
  • Amphetamine or derivatives
  • 3-alkylindole
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Indole
  • Indole or derivatives
  • Imidazolyl carboxylic acid derivative
  • Pyrrolidine carboxylic acid or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • Fatty acyl
  • N-acyl-amine
  • Benzenoid
  • Substituted pyrrole
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Pyrrole
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Lactam
  • Guanidine
  • Carboxamide group
  • Carboximidamide
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Imine
  • Primary alcohol
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-7.4ChemAxon
pKa (Strongest Acidic)3.03ChemAxon
pKa (Strongest Basic)12.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count31ChemAxon
Hydrogen Donor Count29ChemAxon
Polar Surface Area813 ŲChemAxon
Rotatable Bond Count46ChemAxon
Refractivity601.66 m³·mol⁻¹ChemAxon
Polarizability231.19 ųChemAxon
Number of Rings12ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA008484
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID78444106
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139585465
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Esumi Y, Suzuki Y, Itoh Y, Uramoto M, Kimura K, Goto M, Yoshihama M, Ichikawa T: Propeptin, a new inhibitor of prolyl endopeptidase produced by microbispora II. Determination of chemical structure. J Antibiot (Tokyo). 2002 Mar;55(3):296-300. doi: 10.7164/antibiotics.55.296. [PubMed:12014445 ]