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Record Information
Version2.0
Created at2020-12-09 05:46:36 UTC
Updated at2021-07-15 16:59:30 UTC
NP-MRD IDNP0008126
Secondary Accession NumbersNone
Natural Product Identification
Common NameCitreamicin ε
Provided ByNPAtlasNPAtlas Logo
Description3,18,25,29-Tetrahydroxy-7-(hydroxymethyl)-24-methoxy-7,10-dimethyl-9,20-dioxa-6-azaheptacyclo[15.12.0.0²,¹⁴.0⁴,¹².0⁶,¹⁰.0¹⁹,²⁸.0²¹,²⁶]Nonacosa-1(17),2,4(12),13,18,21(26),22,24,28-nonaene-5,8,27-trione belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. Citreamicin ε is found in Streptomyces caelestis and Streptomyces vinaceus. Based on a literature review very few articles have been published on 3,18,25,29-tetrahydroxy-7-(hydroxymethyl)-24-methoxy-7,10-dimethyl-9,20-dioxa-6-azaheptacyclo[15.12.0.0²,¹⁴.0⁴,¹².0⁶,¹⁰.0¹⁹,²⁸.0²¹,²⁶]Nonacosa-1(17),2,4(12),13,18,21(26),22,24,28-nonaene-5,8,27-trione.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC30H25NO11
Average Mass575.5260 Da
Monoisotopic Mass575.14276 Da
IUPAC Name(7S,10S)-3,18,25,29-tetrahydroxy-7-(hydroxymethyl)-24-methoxy-7,10-dimethyl-9,20-dioxa-6-azaheptacyclo[15.12.0.0^{2,14}.0^{4,12}.0^{6,10}.0^{19,28}.0^{21,26}]nonacosa-1(17),2(14),3,12,18,21,23,25,28-nonaene-5,8,27-trione
Traditional Name(7S,10S)-3,18,25,29-tetrahydroxy-7-(hydroxymethyl)-24-methoxy-7,10-dimethyl-9,20-dioxa-6-azaheptacyclo[15.12.0.0^{2,14}.0^{4,12}.0^{6,10}.0^{19,28}.0^{21,26}]nonacosa-1(17),2(14),3,12,18,21,23,25,28-nonaene-5,8,27-trione
CAS Registry NumberNot Available
SMILES
COC1=C(O)C2=C(OC3=C(C(O)=C4C(CCC5=CC6=C(C(=O)N7C(C)(C6)OC(=O)C7(C)CO)C(O)=C45)=C3O)C2=O)C=C1
InChI Identifier
InChI=1S/C30H25NO11/c1-29(10-32)28(39)42-30(2)9-12-8-11-4-5-13-18(16(11)23(35)17(12)27(38)31(29)30)24(36)20-25(37)19-14(41-26(20)21(13)33)6-7-15(40-3)22(19)34/h6-8,32-36H,4-5,9-10H2,1-3H3
InChI KeyFJAZFAHKUIAABK-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
Streptomyces caelestisLOTUS Database
Streptomyces vinaceusNPAtlas
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentXanthones
Alternative Parents
Substituents
  • Naphthopyranone
  • Xanthone
  • Phenanthrene
  • Naphthopyran
  • Chromone
  • Isoquinolone
  • 1-naphthol
  • Alpha-amino acid or derivatives
  • Naphthalene
  • Tetrahydroisoquinoline
  • Phenol ether
  • Anisole
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Oxazolidinone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Tertiary carboxylic acid amide
  • Oxazolidine
  • Carboxamide group
  • Carboxylic acid ester
  • Lactam
  • Lactone
  • Polyol
  • Carboxylic acid derivative
  • Ether
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Primary alcohol
  • Organonitrogen compound
  • Organic oxide
  • Alcohol
  • Organic nitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • 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
logP2.82ALOGPS
logP4.84ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)7.55ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area183.29 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity146.31 m³·mol⁻¹ChemAxon
Polarizability59.2 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA010667
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24713927
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25147606
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References