Np mrd loader

Record Information
Version2.0
Created at2022-09-02 17:12:37 UTC
Updated at2022-09-02 17:12:37 UTC
NP-MRD IDNP0159456
Secondary Accession NumbersNone
Natural Product Identification
Common Name[3,3a,4-trihydroxy-7-(2-imino-1h-purin-9-yl)-hexahydrofuro[2,3-c]pyran-5-yl][(2-amino-5-carbamimidamido-1-hydroxypentylidene)amino]acetic acid
DescriptionMiharamycin B belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. [3,3a,4-trihydroxy-7-(2-imino-1h-purin-9-yl)-hexahydrofuro[2,3-c]pyran-5-yl][(2-amino-5-carbamimidamido-1-hydroxypentylidene)amino]acetic acid is found in Streptomyces miharaensis. [3,3a,4-trihydroxy-7-(2-imino-1h-purin-9-yl)-hexahydrofuro[2,3-c]pyran-5-yl][(2-amino-5-carbamimidamido-1-hydroxypentylidene)amino]acetic acid was first documented in 2008 (PMID: 18833553). Based on a literature review very few articles have been published on Miharamycin B (PMID: 35606651).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC20H30N10O8
Average Mass538.5220 Da
Monoisotopic Mass538.22481 Da
IUPAC Name2-[3,3a,4-trihydroxy-7-(2-imino-2,9-dihydro-1H-purin-9-yl)-hexahydro-2H-furo[2,3-c]pyran-5-yl]-2-[(2-amino-5-carbamimidamido-1-hydroxypentylidene)amino]acetic acid
Traditional Name[3,3a,4-trihydroxy-7-(2-imino-1H-purin-9-yl)-hexahydrofuro[2,3-c]pyran-5-yl][(2-amino-5-carbamimidamido-1-hydroxypentylidene)amino]acetic acid
CAS Registry NumberNot Available
SMILES
NC(CCCNC(N)=N)C(O)=NC(C1OC(C2OCC(O)C2(O)C1O)N1C=NC2=CNC(=N)N=C12)C(O)=O
InChI Identifier
InChI=1S/C20H30N10O8/c21-7(2-1-3-25-18(22)23)15(33)28-10(17(34)35)11-12(32)20(36)9(31)5-37-13(20)16(38-11)30-6-27-8-4-26-19(24)29-14(8)30/h4,6-7,9-13,16,31-32,36H,1-3,5,21H2,(H,28,33)(H,34,35)(H4,22,23,25)(H2,24,26,29)
InChI KeyJOTXNJQBWBCEHD-UHFFFAOYSA-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
Streptomyces miharaensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Imidazopyrimidine
  • Purine
  • Furopyran
  • Aminopyrimidine
  • Amino saccharide
  • N-substituted imidazole
  • Oxane
  • N-acyl-amine
  • Pyran
  • Pyrimidine
  • Fatty amide
  • Fatty acyl
  • Tertiary alcohol
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Furan
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Amino acid
  • Amino acid or derivatives
  • Carboxamide group
  • Guanidine
  • Oxacycle
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Polyol
  • Amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Primary amine
  • Primary aliphatic amine
  • Alcohol
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • 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
logP-2.6ALOGPS
logP-8.4ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)2.84ChemAxon
pKa (Strongest Basic)12.21ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area300.8 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity146.56 m³·mol⁻¹ChemAxon
Polarizability51.74 ųChemAxon
Number of Rings4ChemAxon
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 ID175426
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound202590
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Marcelo F, Jimenez-Barbero J, Marrot J, Rauter AP, Sinay P, Bleriot Y: Stereochemical assignment and first synthesis of the core of miharamycin antibiotics. Chemistry. 2008;14(32):10066-73. doi: 10.1002/chem.200801826. [PubMed:18833553 ]
  2. Huang W, Fan S, Gao J, Luo S, Tang S, Liu J, Wang X: Total Synthesis of Complex Peptidyl Nucleoside Antibiotics: Asymmetric De Novo Syntheses of Miharamycin B and Its Biosynthetic Precursor. Angew Chem Int Ed Engl. 2022 Aug 1;61(31):e202204907. doi: 10.1002/anie.202204907. Epub 2022 Jun 21. [PubMed:35606651 ]
  3. LOTUS database [Link]