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Record Information
Version2.0
Created at2020-12-09 01:24:24 UTC
Updated at2021-07-15 16:47:32 UTC
NP-MRD IDNP0003845
Secondary Accession NumbersNone
Natural Product Identification
Common NameDeacetylravidomycin M
Provided ByNPAtlasNPAtlas Logo
Description12-[(2S,3R,4S,5R,6S)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]Octadeca-1(10),2(7),3,5,11,13,15,17-octaen-8-one belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Deacetylravidomycin M is found in Streptomyces. Deacetylravidomycin M was first documented in 2001 (PMID: 11560373). Based on a literature review very few articles have been published on 12-[(2S,3R,4S,5R,6S)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]Octadeca-1(10),2(7),3,5,11,13,15,17-octaen-8-one.
Structure
Data?1624573916
SynonymsNot Available
Chemical FormulaC28H31NO8
Average Mass509.5550 Da
Monoisotopic Mass509.20497 Da
IUPAC Name12-[(2S,3R,4S,5R,6S)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadeca-1(10),2,4,6,11,13,15,17-octaen-8-one
Traditional Name12-[(2S,3R,4S,5R,6S)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadeca-1(10),2,4,6,11,13,15,17-octaen-8-one
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(OC(=O)C3=CC(C)=CC(OC)=C23)C2=C(C=CC(O)=C12)[C@@H]1O[C@@H](C)[C@H](O)[C@@H]([C@H]1O)N(C)C
InChI Identifier
InChI=1S/C28H31NO8/c1-12-9-16-20(18(10-12)34-5)15-11-19(35-6)22-17(30)8-7-14(21(22)26(15)37-28(16)33)27-25(32)23(29(3)4)24(31)13(2)36-27/h7-11,13,23-25,27,30-32H,1-6H3/t13-,23-,24-,25+,27-/m0/s1
InChI KeyXMWCTNFIDFLZBU-YIGMCNEPSA-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
Species Where Detected
Species NameSourceReference
Streptomyces sp. WK-6326KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthopyrans
Sub ClassNot Available
Direct ParentNaphthopyrans
Alternative Parents
Substituents
  • Naphthopyran
  • Coumarin
  • Isocoumarin
  • 1-naphthol
  • Benzopyran
  • Naphthalene
  • 2-benzopyran
  • 1-benzopyran
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Pyranone
  • Benzenoid
  • Oxane
  • Pyran
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Lactone
  • 1,2-aminoalcohol
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Organooxygen compound
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic nitrogen 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
logP2.67ALOGPS
logP2.07ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)8.29ChemAxon
pKa (Strongest Basic)8.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.92 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity136.64 m³·mol⁻¹ChemAxon
Polarizability55.19 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA012291
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID78439752
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102515295
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Arai M, Tomoda H, Matsumoto A, Takahashi Y, Woodruff BH, Ishiguro N, Kobayashi S, Omura S: Deacetylravidomycin M, a new inhibitor of IL-4 signal transduction, produced by Streptomyces sp. WK-6326. I. Taxonomy, fermentation, isolation and biological activities. J Antibiot (Tokyo). 2001 Jul;54(7):554-61. doi: 10.7164/antibiotics.54.554. [PubMed:11560373 ]