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Record Information
Version2.0
Created at2022-09-08 18:34:36 UTC
Updated at2022-09-08 18:34:36 UTC
NP-MRD IDNP0272075
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-3-(c-hydroxycarbonimidoyl)propanoic acid
DescriptionAla-Phe-Trp-Asn, also known as a-F-W-N or AFWN, 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. Ala-Phe-Trp-Asn is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-3-(c-hydroxycarbonimidoyl)propanoic acid is found in Trypanosoma brucei. Based on a literature review very few articles have been published on Ala-Phe-Trp-Asn.
Structure
Thumb
Synonyms
ValueSource
a-F-W-NChEBI
AFWNChEBI
L-Ala-L-phe-L-TRP-L-asnChEBI
Chemical FormulaC27H32N6O6
Average Mass536.5890 Da
Monoisotopic Mass536.23833 Da
IUPAC Name(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino}-3-(C-hydroxycarbonimidoyl)propanoic acid
Traditional Name(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino}-3-(C-hydroxycarbonimidoyl)propanoic acid
CAS Registry NumberNot Available
SMILES
C[C@H](N)C(O)=N[C@@H](CC1=CC=CC=C1)C(O)=N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=N[C@@H](CC(O)=N)C(O)=O
InChI Identifier
InChI=1S/C27H32N6O6/c1-15(28)24(35)31-20(11-16-7-3-2-4-8-16)25(36)32-21(26(37)33-22(27(38)39)13-23(29)34)12-17-14-30-19-10-6-5-9-18(17)19/h2-10,14-15,20-22,30H,11-13,28H2,1H3,(H2,29,34)(H,31,35)(H,32,36)(H,33,37)(H,38,39)/t15-,20-,21-,22-/m0/s1
InChI KeyPPSSXNJBIKWOLE-JNHSIYEJSA-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 Origin
Species NameSourceReference
Trypanosoma bruceiLOTUS Database
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
  • Asparagine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • Triptan
  • Alanine or derivatives
  • 3-alkylindole
  • N-substituted-alpha-amino acid
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • Indole
  • Indole or derivatives
  • Monocyclic benzene moiety
  • Fatty amide
  • Fatty acyl
  • Benzenoid
  • Substituted pyrrole
  • Pyrrole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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-2.2ChemAxon
pKa (Strongest Acidic)-1.2ChemAxon
pKa (Strongest Basic)12.65ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area220.96 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity153.07 m³·mol⁻¹ChemAxon
Polarizability55.04 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 IDNot Available
Chemspider ID28639283
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71464524
PDB IDNot Available
ChEBI ID73379
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]