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Record Information
Version2.0
Created at2022-09-08 05:29:34 UTC
Updated at2022-09-08 05:29:34 UTC
NP-MRD IDNP0262611
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s)-2-[(2s)-2-[(2e)-3-methoxy-n-methylbut-2-enamido]-3-(4-methoxyphenyl)-n-methylpropanamido]-n,4-dimethyl-n-[(2s,3s)-3-methyl-1-oxo-1-[(2s)-2-(1,3-thiazol-2-yl)pyrrolidin-1-yl]pentan-2-yl]pentanamide
DescriptionLyngbyapeptin A belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. (2s)-2-[(2s)-2-[(2e)-3-methoxy-n-methylbut-2-enamido]-3-(4-methoxyphenyl)-n-methylpropanamido]-n,4-dimethyl-n-[(2s,3s)-3-methyl-1-oxo-1-[(2s)-2-(1,3-thiazol-2-yl)pyrrolidin-1-yl]pentan-2-yl]pentanamide was first documented in 2010 (PMID: 20704304). Based on a literature review very few articles have been published on Lyngbyapeptin A.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC37H55N5O6S
Average Mass697.9400 Da
Monoisotopic Mass697.38731 Da
IUPAC Name(2S)-2-[(2S)-2-[(2E)-3-methoxy-N-methylbut-2-enamido]-3-(4-methoxyphenyl)-N-methylpropanamido]-N,4-dimethyl-N-[(2S,3S)-3-methyl-1-oxo-1-[(2S)-2-(1,3-thiazol-2-yl)pyrrolidin-1-yl]pentan-2-yl]pentanamide
Traditional Name(2S)-2-[(2S)-2-[(2E)-3-methoxy-N-methylbut-2-enamido]-3-(4-methoxyphenyl)-N-methylpropanamido]-N,4-dimethyl-N-[(2S,3S)-3-methyl-1-oxo-1-[(2S)-2-(1,3-thiazol-2-yl)pyrrolidin-1-yl]pentan-2-yl]pentanamide
CAS Registry NumberNot Available
SMILES
CC[C@H](C)[C@H](N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC1=CC=C(OC)C=C1)N(C)C(=O)\C=C(/C)OC)C(=O)N1CCC[C@H]1C1=NC=CS1
InChI Identifier
InChI=1S/C37H55N5O6S/c1-11-25(4)33(37(46)42-19-12-13-29(42)34-38-18-20-49-34)41(8)36(45)30(21-24(2)3)40(7)35(44)31(39(6)32(43)22-26(5)47-9)23-27-14-16-28(48-10)17-15-27/h14-18,20,22,24-25,29-31,33H,11-13,19,21,23H2,1-10H3/b26-22+/t25-,29-,30-,31-,33-/m0/s1
InChI KeyHTBQLUDZPAANPB-WMQQFFOQSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • Leucine or derivatives
  • Isoleucine or derivatives
  • Amphetamine or derivatives
  • Phenoxy compound
  • Anisole
  • N-acylpyrrolidine
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • N-acyl-amine
  • Benzenoid
  • Azole
  • Heteroaromatic compound
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Thiazole
  • Vinylogous ester
  • Carboxamide group
  • Azacycle
  • Ether
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP3.99ChemAxon
pKa (Strongest Acidic)17.88ChemAxon
pKa (Strongest Basic)2.12ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area112.59 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity192.82 m³·mol⁻¹ChemAxon
Polarizability75.25 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00034372
Chemspider ID8525202
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10349747
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Matthew S, Salvador LA, Schupp PJ, Paul VJ, Luesch H: Cytotoxic halogenated macrolides and modified peptides from the apratoxin-producing marine cyanobacterium Lyngbya bouillonii from Guam. J Nat Prod. 2010 Sep 24;73(9):1544-52. doi: 10.1021/np1004032. [PubMed:20704304 ]
  2. LOTUS database [Link]