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Record Information
Version2.0
Created at2022-09-06 22:50:42 UTC
Updated at2022-09-06 22:50:42 UTC
NP-MRD IDNP0239279
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3z)-7,16,18-trichloro-11,22-dihydroxy-4,19,19-trimethyl-8-methylidene-20-oxatetracyclo[11.7.1.1¹⁰,¹⁴.0¹,¹⁶]docosa-3,10,12,14(22)-tetraene-15,21-dione
DescriptionNapyradiomycin C-2 belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. (3z)-7,16,18-trichloro-11,22-dihydroxy-4,19,19-trimethyl-8-methylidene-20-oxatetracyclo[11.7.1.1¹⁰,¹⁴.0¹,¹⁶]docosa-3,10,12,14(22)-tetraene-15,21-dione is found in Streptomyces ruber. Based on a literature review very few articles have been published on Napyradiomycin C-2.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC25H27Cl3O5
Average Mass513.8400 Da
Monoisotopic Mass512.09241 Da
IUPAC Name(3Z)-7,16,18-trichloro-11,22-dihydroxy-4,19,19-trimethyl-8-methylidene-20-oxatetracyclo[11.7.1.1^{10,14}.0^{1,16}]docosa-3,10,12,14(22)-tetraene-15,21-dione
Traditional Name(3Z)-7,16,18-trichloro-11,22-dihydroxy-4,19,19-trimethyl-8-methylidene-20-oxatetracyclo[11.7.1.1^{10,14}.0^{1,16}]docosa-3,10,12,14(22)-tetraene-15,21-dione
CAS Registry NumberNot Available
SMILES
C\C1=C\CC23OC(C)(C)C(Cl)CC2(Cl)C(=O)C2=C(O)C(CC(=C)C(Cl)CC1)=C(O)C=C2C3=O
InChI Identifier
InChI=1S/C25H27Cl3O5/c1-12-5-6-16(26)13(2)9-14-17(29)10-15-19(20(14)30)22(32)24(28)11-18(27)23(3,4)33-25(24,8-7-12)21(15)31/h7,10,16,18,29-30H,2,5-6,8-9,11H2,1,3-4H3/b12-7-
InChI KeyTUASWIIAAPWHMO-GHXNOFRVSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces ruberLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthopyrans
Sub ClassNaphthopyranones
Direct ParentNaphthopyranones
Alternative Parents
Substituents
  • Naphthopyranone
  • Naphthoquinone
  • Naphthalene
  • Tetralin
  • Quinone
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Oxane
  • Pyran
  • Benzenoid
  • Alpha-chloroketone
  • Alpha-haloketone
  • Vinylogous acid
  • Ketone
  • Ether
  • Dialkyl ether
  • Oxacycle
  • Alkyl halide
  • Hydrocarbon derivative
  • Organic oxide
  • Alkyl chloride
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen 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
logP6.31ChemAxon
pKa (Strongest Acidic)7.01ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity130.26 m³·mol⁻¹ChemAxon
Polarizability49.42 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4943389
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92029308
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]