Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2021-01-06 00:28:12 UTC
Updated at2021-07-15 17:19:34 UTC
NP-MRD IDNP0015294
Secondary Accession NumbersNone
Natural Product Identification
Common NamePelianthinarubin A
Provided ByNPAtlasNPAtlas Logo
Description[(1S)-1-carboxy-2-{1-[(3S,7R)-3-carboxy-9,10-dioxo-4,12-diazatetracyclo[6.5.2.0⁴,¹⁵.0¹¹,¹⁴]Pentadeca-1(13),8(15),11(14)-trien-7-yl]-1H-imidazol-4-yl}ethyl]trimethylazanium belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Pelianthinarubin A is found in Mycena pelianthina. It was first documented in 2002 (PMID: 28267306). Based on a literature review very few articles have been published on [(1S)-1-carboxy-2-{1-[(3S,7R)-3-carboxy-9,10-dioxo-4,12-diazatetracyclo[6.5.2.0⁴,¹⁵.0¹¹,¹⁴]Pentadeca-1(13),8(15),11(14)-trien-7-yl]-1H-imidazol-4-yl}ethyl]trimethylazanium (PMID: 27002340) (PMID: 26389440) (PMID: 26389428) (PMID: 26389376).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC23H26N5O6
Average Mass468.4890 Da
Monoisotopic Mass468.18776 Da
IUPAC Name[(1S)-1-carboxy-2-{1-[(3S,7R)-3-carboxy-9,10-dioxo-4,12-diazatetracyclo[6.5.2.0^{4,15}.0^{11,14}]pentadeca-1(13),8(15),11(14)-trien-7-yl]-1H-imidazol-4-yl}ethyl]trimethylazanium
Traditional Name[(1S)-1-carboxy-2-{1-[(3S,7R)-3-carboxy-9,10-dioxo-4,12-diazatetracyclo[6.5.2.0^{4,15}.0^{11,14}]pentadeca-1(13),8(15),11(14)-trien-7-yl]imidazol-4-yl}ethyl]trimethylazanium
CAS Registry NumberNot Available
SMILES
C[N+](C)(C)[C@@H](CC1=CN(C=N1)[C@@H]1CCN2[C@@H](CC3=CNC4=C3C2=C1C(=O)C4=O)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C23H25N5O6/c1-28(2,3)15(23(33)34)7-12-9-26(10-25-12)13-4-5-27-14(22(31)32)6-11-8-24-18-16(11)19(27)17(13)20(29)21(18)30/h8-10,13-15H,4-7H2,1-3H3,(H2-,24,29,30,31,32,33,34)/p+1/t13-,14+,15+/m1/s1
InChI KeyCUYHMRHBVJBMGH-ILXRZTDVSA-O
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Mycena pelianthina
Chemical Taxonomy
Description Belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine 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 ParentHistidine and derivatives
Alternative Parents
Substituents
  • Histidine or derivatives
  • Quinoline-2-carboxylic acid
  • Pyrroloquinoline
  • Pyrrolo[4,3,2-de]quinoline
  • L-alpha-amino acid
  • Alpha-amino acid
  • Indole or derivatives
  • Aryl ketone
  • Aralkylamine
  • Tetrahydropyridine
  • N-substituted imidazole
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Heteroaromatic compound
  • Vinylogous amide
  • Quaternary ammonium salt
  • Pyrrole
  • Imidazole
  • Azole
  • Amino acid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ketone
  • Azacycle
  • Organoheterocyclic compound
  • Enamine
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic cation
  • 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
logP0.22ALOGPS
logP-4.6ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)1.89ChemAxon
pKa (Strongest Basic)6.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area145.59 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity132.37 m³·mol⁻¹ChemAxon
Polarizability46.81 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
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 ID78443803
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139589605
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Pulte A, Wagner S, Kogler H, Spiteller P: Pelianthinarubins A and B, Red Pyrroloquinoline Alkaloids from the Fruiting Bodies of the Mushroom Mycena pelianthina. J Nat Prod. 2016 Apr 22;79(4):873-8. doi: 10.1021/acs.jnatprod.5b00942. Epub 2016 Mar 22. [PubMed:27002340 ]
  2. Authors unspecified: Medicinal Mushrooms (PDQ(R)): Patient Version. 2002. [PubMed:28267306 ]
  3. Authors unspecified: Nutrition in Cancer Care (PDQ(R)): Patient Version. 2002. [PubMed:26389440 ]
  4. Authors unspecified: Lung Cancer Screening (PDQ(R)): Patient Version. 2002. [PubMed:26389428 ]
  5. Authors unspecified: Colorectal Cancer Prevention (PDQ(R)): Patient Version. 2002. [PubMed:26389376 ]