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Record Information
Version1.0
Created at2020-12-09 00:33:05 UTC
Updated at2021-07-15 16:46:07 UTC
NP-MRD IDNP0003320
Secondary Accession NumbersNone
Natural Product Identification
Common NameRubiginone I
Provided ByNPAtlasNPAtlas Logo
Description(4S,5R,6R)-4,11-dihydroxy-13-methoxy-5-methyl-3,18-dioxo-19-oxapentacyclo[8.8.1.0¹,¹⁰.0²,⁷.0¹²,¹⁷]Nonadeca-2(7),8,12(17),13,15-pentaen-6-yl acetate belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane. Rubiginone I is found in Streptomyces sp. and Streptomyces sp. Go N1/5. It was first documented in 2000 (PMID: 10866213). Based on a literature review very few articles have been published on (4S,5R,6R)-4,11-dihydroxy-13-methoxy-5-methyl-3,18-dioxo-19-oxapentacyclo[8.8.1.0¹,¹⁰.0²,⁷.0¹²,¹⁷]Nonadeca-2(7),8,12(17),13,15-pentaen-6-yl acetate.
Structure
Data?1624573783
Synonyms
ValueSource
(4S,5R,6R)-4,11-Dihydroxy-13-methoxy-5-methyl-3,18-dioxo-19-oxapentacyclo[8.8.1.0,.0,.0,]nonadeca-2(7),8,12(17),13,15-pentaen-6-yl acetic acidGenerator
Chemical FormulaC22H20O8
Average Mass412.3940 Da
Monoisotopic Mass412.11582 Da
IUPAC Name(1R,4S,5R,6R,10R,11R)-4,11-dihydroxy-13-methoxy-5-methyl-3,18-dioxo-19-oxapentacyclo[8.8.1.0^{1,10}.0^{2,7}.0^{12,17}]nonadeca-2(7),8,12(17),13,15-pentaen-6-yl acetate
Traditional Name(1R,4S,5R,6R,10R,11R)-4,11-dihydroxy-13-methoxy-5-methyl-3,18-dioxo-19-oxapentacyclo[8.8.1.0^{1,10}.0^{2,7}.0^{12,17}]nonadeca-2(7),8,12(17),13,15-pentaen-6-yl acetate
CAS Registry NumberNot Available
SMILES
COC1=CC=CC2=C1C(O)C13OC1(C2=O)C1=C(C=C3)[C@H](OC(C)=O)[C@H](C)[C@H](O)C1=O
InChI Identifier
InChI=1S/C22H20O8/c1-9-16(24)17(25)15-12(18(9)29-10(2)23)7-8-21-20(27)14-11(5-4-6-13(14)28-3)19(26)22(15,21)30-21/h4-9,16,18,20,24,27H,1-3H3/t9-,16+,18-,20?,21?,22?/m1/s1
InChI KeyNONBUEJWSJNYAK-GHCOXSAKSA-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 sp.NPAtlas
Streptomyces sp. Go N1/5Bacteria
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.
KingdomOrganic compounds
Super ClassBenzenoids
ClassTetralins
Sub ClassNot Available
Direct ParentTetralins
Alternative Parents
Substituents
  • Tetralin
  • Anisole
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Cyclohexenone
  • Carboxylic acid ester
  • Ketone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • 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
logP1.3ALOGPS
logP0.29ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)12.54ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area122.66 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity103.05 m³·mol⁻¹ChemAxon
Polarizability40.5 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA019432
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8494925
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10319461
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Puder C, Zeeck A, Beil W: New biologically active rubiginones from Streptomyces sp. J Antibiot (Tokyo). 2000 Apr;53(4):329-36. doi: 10.7164/antibiotics.53.329. [PubMed:10866213 ]