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Record Information
Version2.0
Created at2020-12-09 05:40:40 UTC
Updated at2021-07-15 16:59:18 UTC
NP-MRD IDNP0008053
Secondary Accession NumbersNone
Natural Product Identification
Common NamePestalazine A
Provided ByNPAtlasNPAtlas Logo
Description(1R,4R,7S)-4-benzyl-9-(3-{[(2S,5R)-3,6-dihydroxy-5-(2-methylpropyl)-2,5-dihydropyrazin-2-yl]methyl}-1H-indol-7-yl)-6-hydroxy-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]Hexadeca-5,10,12,14-tetraen-3-one belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Pestalazine A is found in Pestalotiopsis and Pestalotiopsis theae. Based on a literature review very few articles have been published on (1R,4R,7S)-4-benzyl-9-(3-{[(2S,5R)-3,6-dihydroxy-5-(2-methylpropyl)-2,5-dihydropyrazin-2-yl]methyl}-1H-indol-7-yl)-6-hydroxy-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]Hexadeca-5,10,12,14-tetraen-3-one.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC37H38N6O4
Average Mass630.7490 Da
Monoisotopic Mass630.29545 Da
IUPAC Name(1R,4R,7S,9R)-4-benzyl-9-(3-{[(2S,5R)-5-(2-methylpropyl)-3,6-dioxopiperazin-2-yl]methyl}-1H-indol-7-yl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10,12,14-triene-3,6-dione
Traditional Name(1R,4R,7S,9R)-4-benzyl-9-(3-{[(2S,5R)-5-(2-methylpropyl)-3,6-dioxopiperazin-2-yl]methyl}-1H-indol-7-yl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10,12,14-triene-3,6-dione
CAS Registry NumberNot Available
SMILES
CC(C)C[C@H]1NC(=O)[C@H](CC2=CNC3=C2C=CC=C3C23C[C@@H]4N([C@H]2NC2=CC=CC=C32)C(=O)[C@@H](CC2=CC=CC=C2)NC4=O)NC1=O
InChI Identifier
InChI=1S/C37H38N6O4/c1-20(2)15-27-32(44)40-28(33(45)39-27)17-22-19-38-31-23(22)11-8-13-25(31)37-18-30-34(46)41-29(16-21-9-4-3-5-10-21)35(47)43(30)36(37)42-26-14-7-6-12-24(26)37/h3-14,19-20,27-30,36,38,42H,15-18H2,1-2H3,(H,39,45)(H,40,44)(H,41,46)/t27-,28+,29-,30+,36-,37?/m1/s1
InChI KeyYBZQMAQAADAOGH-KWTBDXKOSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
PestalotiopsisNPAtlas
Pseudopestalotiopsis theaeFungi
Species Where Detected
Species NameSourceReference
Pestalotiopsis theaeKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassPyrroloindoles
Direct ParentPyrroloindoles
Alternative Parents
Substituents
  • Pyrroloindole
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • Indole
  • Dihydroindole
  • Dioxopiperazine
  • 2,5-dioxopiperazine
  • Secondary aliphatic/aromatic amine
  • N-alkylpiperazine
  • Monocyclic benzene moiety
  • 1,4-diazinane
  • Piperazine
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrolidine
  • Pyrrole
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Secondary amine
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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
logP3.75ALOGPS
logP3.46ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)10.8ChemAxon
pKa (Strongest Basic)1.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area135.43 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity187.34 m³·mol⁻¹ChemAxon
Polarizability68.51 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA016710
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID78438270
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139587750
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References