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Record Information
Version1.0
Created at2021-01-06 02:28:11 UTC
Updated at2021-07-15 17:26:32 UTC
NP-MRD IDNP0017822
Secondary Accession NumbersNone
Natural Product Identification
Common NameJessenipeptin
Provided ByNPAtlasNPAtlas Logo
Description Jessenipeptin is found in Pseudomonas sp. QS1027. It was first documented in 2018 (PMID: 29592954). Based on a literature review very few articles have been published on (3R)-N-[(2Z)-1-[(2R)-2-{[(1R,2R)-1-{[(1R)-1-{[(1R)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1R)-1-{[(1R)-1-{[(1R)-1-{[(1R)-1-{[(1R)-1-{[(1Z)-1-{[(3S,6R,9S,12S,15R,16R)-9-(2-aminoethyl)-3-benzyl-5,8,11,14-tetrahydroxy-6-(hydroxymethyl)-12,16-dimethyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl]-C-hydroxycarbonimidoyl}prop-1-en-1-yl]-C-hydroxycarbonimidoyl}-3-methylbutyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}-2-methylpropyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}-2-hydroxyethyl]-C-hydroxycarbonimidoyl}-2-methylpropyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}-2-methylpropyl]-C-hydroxycarbonimidoyl}-2-methylbutyl]-C-hydroxycarbonimidoyl}pyrrolidin-1-yl]-1-oxobut-2-en-2-yl]-3-hydroxydecanimidic acid.
Structure
Thumb
Synonyms
ValueSource
(3R)-N-[(2Z)-1-[(2R)-2-{[(1R,2R)-1-{[(1R)-1-{[(1R)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1R)-1-{[(1R)-1-{[(1R)-1-{[(1R)-1-{[(1R)-1-{[(1Z)-1-{[(3S,6R,9S,12S,15R,16R)-9-(2-aminoethyl)-3-benzyl-5,8,11,14-tetrahydroxy-6-(hydroxymethyl)-12,16-dimethyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl]-C-hydroxycarbonimidoyl}prop-1-en-1-yl]-C-hydroxycarbonimidoyl}-3-methylbutyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}-2-methylpropyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}-2-hydroxyethyl]-C-hydroxycarbonimidoyl}-2-methylpropyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}-2-methylpropyl]-C-hydroxycarbonimidoyl}-2-methylbutyl]-C-hydroxycarbonimidoyl}pyrrolidin-1-yl]-1-oxobut-2-en-2-yl]-3-hydroxydecanimidateGenerator
Chemical FormulaC91H148N20O24
Average Mass1906.3010 Da
Monoisotopic Mass1905.09754 Da
IUPAC Name(3R)-N-[(2Z)-1-[(2R)-2-{[(1R,2R)-1-{[(1R)-1-{[(1R)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1R)-1-{[(1R)-1-{[(1R)-1-{[(1R)-1-{[(1R)-1-{[(1Z)-1-{[(3S,6R,9S,12S,15R,16R)-9-(2-aminoethyl)-3-benzyl-6-(hydroxymethyl)-12,16-dimethyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetraazacyclohexadecan-15-yl]carbamoyl}prop-1-en-1-yl]carbamoyl}-3-methylbutyl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}ethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-methylpropyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-methylbutyl]carbamoyl}pyrrolidin-1-yl]-1-oxobut-2-en-2-yl]-3-hydroxydecanamide
Traditional Name(3R)-N-[(2Z)-1-[(2R)-2-{[(1R,2R)-1-{[(1R)-1-{[(1R)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1R)-1-{[(1R)-1-{[(1R)-1-{[(1R)-1-{[(1R)-1-{[(1Z)-1-{[(3S,6R,9S,12S,15R,16R)-9-(2-aminoethyl)-3-benzyl-6-(hydroxymethyl)-12,16-dimethyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetraazacyclohexadecan-15-yl]carbamoyl}prop-1-en-1-yl]carbamoyl}-3-methylbutyl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}ethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-methylpropyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-methylbutyl]carbamoyl}pyrrolidin-1-yl]-1-oxobut-2-en-2-yl]-3-hydroxydecanamide
CAS Registry NumberNot Available
SMILES
CCCCCCC[C@@H](O)CC(=O)N\C(=C/C)C(=O)N1CCC[C@@H]1C(=O)N[C@H]([C@H](C)CC)C(=O)N[C@H](C(C)C)C(=O)N[C@H](C)C(=O)N[C@H](C)C(=O)N[C@@H](C)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CO)C(=O)N[C@H](C)C(=O)N[C@H](C(C)C)C(=O)N[C@H](C)C(=O)N[C@H](CC(C)C)C(=O)N\C(=C/C)C(=O)N[C@@H]1[C@@H](C)OC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@@H](CO)NC(=O)[C@H](CCN)NC(=O)[C@H](C)NC1=O
InChI Identifier
InChI=1S/C91H148N20O24/c1-21-25-26-27-31-35-58(114)42-67(115)99-60(24-4)90(133)111-39-32-36-66(111)84(127)109-71(49(13)22-2)88(131)108-69(47(9)10)86(129)96-51(15)74(117)93-50(14)73(116)94-54(18)77(120)107-70(48(11)12)87(130)105-64(43-112)82(125)95-55(19)78(121)106-68(46(7)8)85(128)97-53(17)76(119)102-62(40-45(5)6)81(124)100-59(23-3)79(122)110-72-56(20)135-91(134)63(41-57-33-29-28-30-34-57)103-83(126)65(44-113)104-80(123)61(37-38-92)101-75(118)52(16)98-89(72)132/h23-24,28-30,33-34,45-56,58,61-66,68-72,112-114H,21-22,25-27,31-32,35-44,92H2,1-20H3,(H,93,117)(H,94,116)(H,95,125)(H,96,129)(H,97,128)(H,98,132)(H,99,115)(H,100,124)(H,101,118)(H,102,119)(H,103,126)(H,104,123)(H,105,130)(H,106,121)(H,107,120)(H,108,131)(H,109,127)(H,110,122)/b59-23-,60-24-/t49-,50-,51-,52+,53-,54+,55-,56-,58-,61+,62-,63+,64-,65-,66-,68-,69-,70-,71-,72-/m1/s1
InChI KeyRCRYELMDBHQIMX-JRGFPVMHSA-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
Pseudomonas sp. QS1027NPAtlas
Chemical Taxonomy
ClassificationNot classified
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-3.4ChemAxon
pKa (Strongest Acidic)10.34ChemAxon
pKa (Strongest Basic)9.45ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count22ChemAxon
Polar Surface Area657.12 ŲChemAxon
Rotatable Bond Count49ChemAxon
Refractivity492.02 m³·mol⁻¹ChemAxon
Polarizability202.18 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA024767
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound145720625
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Arp J, Gotze S, Mukherji R, Mattern DJ, Garcia-Altares M, Klapper M, Brock DA, Brakhage AA, Strassmann JE, Queller DC, Bardl B, Willing K, Peschel G, Stallforth P: Synergistic activity of cosecreted natural products from amoebae-associated bacteria. Proc Natl Acad Sci U S A. 2018 Apr 10;115(15):3758-3763. doi: 10.1073/pnas.1721790115. Epub 2018 Mar 28. [PubMed:29592954 ]