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Record Information
Version1.0
Created at2020-09-22 23:34:35 UTC
Updated at2021-08-10 02:55:16 UTC
NP-MRD IDNP0001564
Secondary Accession NumbersNone
Natural Product Identification
Common NameDiperamycin
Provided ByNPAtlasNPAtlas Logo
DescriptionDiperamycin belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. Diperamycin 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. Diperamycin is found in Streptomyces and Streptomyces griseoaurantiacus. It was first documented in 1998 (PMID: 10048567). Based on a literature review very few articles have been published on diperamycin.
Structure
Data?1628564116
SynonymsNot Available
Chemical FormulaC38H64N8O14
Average Mass856.9720 Da
Monoisotopic Mass856.45420 Da
IUPAC Name(2S)-N-[(6S,9S,16S,17S,20S,23R)-7,21-dihydroxy-6-(methoxymethyl)-17,20-dimethyl-2,5,8,15,19,22-hexaoxo-18-oxa-1,4,7,13,14,21,27-heptaazatricyclo[21.4.0.0^{9,14}]heptacosan-16-yl]-2-[(2S,5R,6R)-5-hexyl-2-hydroxy-6-methyloxan-2-yl]-2-hydroxypropanamide
Traditional Name(2S)-N-[(6S,9S,16S,17S,20S,23R)-7,21-dihydroxy-6-(methoxymethyl)-17,20-dimethyl-2,5,8,15,19,22-hexaoxo-18-oxa-1,4,7,13,14,21,27-heptaazatricyclo[21.4.0.0^{9,14}]heptacosan-16-yl]-2-[(2S,5R,6R)-5-hexyl-2-hydroxy-6-methyloxan-2-yl]-2-hydroxypropanamide
CAS Registry NumberNot Available
SMILES
[H]ON1C(=O)[C@]2([H])N(N([H])C([H])([H])C([H])([H])C2([H])[H])C(=O)C([H])([H])N([H])C(=O)[C@@]([H])(N(O[H])C(=O)[C@@]2([H])N(N([H])C([H])([H])C([H])([H])C2([H])[H])C(=O)[C@@]([H])(N([H])C(=O)[C@](O[H])(C([H])([H])[H])[C@@]2(O[H])O[C@]([H])(C([H])([H])[H])[C@]([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C([H])([H])C2([H])[H])[C@@]([H])(OC(=O)[C@]1([H])C([H])([H])[H])C([H])([H])[H])C([H])([H])OC([H])([H])[H]
InChI Identifier
InChI=1S/C38H64N8O14/c1-7-8-9-10-13-25-16-17-38(55,60-23(25)3)37(5,54)36(53)42-30-24(4)59-35(52)22(2)45(56)32(49)26-14-11-18-40-43(26)29(47)20-39-31(48)28(21-58-6)46(57)33(50)27-15-12-19-41-44(27)34(30)51/h22-28,30,40-41,54-57H,7-21H2,1-6H3,(H,39,48)(H,42,53)/t22-,23+,24-,25+,26+,27-,28-,30-,37+,38-/m0/s1
InChI KeyIHQIMVZJVJTKSV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
StreptomycesNPAtlas
Streptomyces griseoaurantiacusLOTUS Database
Species Where Detected
Species NameSourceReference
Streptomyces griseoaurantiacus MK393-AF2KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassDepsipeptides
Direct ParentCyclic depsipeptides
Alternative Parents
Substituents
  • Cyclic depsipeptide
  • Macrolide lactam
  • Alpha-amino acid ester
  • Macrolactam
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • 1,2-diazinane
  • Oxane
  • Tertiary alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid ester
  • Carboxylic acid hydrazide
  • Hemiacetal
  • Hydroxamic acid
  • Lactam
  • Lactone
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP0.39ALOGPS
logP-1.2ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)7.28ChemAxon
pKa (Strongest Basic)4.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area289.18 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity229.93 m³·mol⁻¹ChemAxon
Polarizability88.13 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA011960
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00016125
Chemspider ID8051681
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID65799
Good Scents IDNot Available
References
General References
  1. Matsumoto N, Momose I, Umekita M, Kinoshita N, Chino M, Iinuma H, Sawa T, Hamada M, Takeuchi T: Diperamycin, a new antimicrobial antibiotic produced by Streptomyces griseoaurantiacus MK393-AF2. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities. J Antibiot (Tokyo). 1998 Dec;51(12):1087-92. doi: 10.7164/antibiotics.51.1087. [PubMed:10048567 ]