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Record Information
Version2.0
Created at2020-12-09 03:08:15 UTC
Updated at2021-07-15 16:53:43 UTC
NP-MRD IDNP0006059
Secondary Accession NumbersNone
Natural Product Identification
Common NameBischloroanthrabenzoxocinone
Provided ByNPAtlasNPAtlas Logo
Description Bischloroanthrabenzoxocinone is found in Streptomyces. Bischloroanthrabenzoxocinone was first documented in 2005 (PMID: 16180833). Based on a literature review very few articles have been published on 8,10-dichloro-3,7,9-trihydroxy-21-methoxy-12,12,17,23-tetramethyl-18,25-dioxahexacyclo[15.7.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0¹⁹,²⁴]Pentacosa-2,4(13),6(11),7,9,14,19(24),20,22-nonaen-5-one.
Structure
Data?1624574601
SynonymsNot Available
Chemical FormulaC28H24Cl2O7
Average Mass543.3900 Da
Monoisotopic Mass542.08991 Da
IUPAC Name(1S,17S)-8,10-dichloro-3,7,9-trihydroxy-21-methoxy-12,12,17,23-tetramethyl-18,25-dioxahexacyclo[15.7.1.0^{2,15}.0^{4,13}.0^{6,11}.0^{19,24}]pentacosa-2,4(13),6,8,10,14,19,21,23-nonaen-5-one
Traditional Name(1S,17S)-8,10-dichloro-3,7,9-trihydroxy-21-methoxy-12,12,17,23-tetramethyl-18,25-dioxahexacyclo[15.7.1.0^{2,15}.0^{4,13}.0^{6,11}.0^{19,24}]pentacosa-2,4(13),6,8,10,14,19,21,23-nonaen-5-one
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(C3OC(C)(CC4=C3C(O)=C3C(=O)C5=C(C(Cl)=C(O)C(Cl)=C5O)C(C)(C)C3=C4)O2)C(C)=C1
InChI Identifier
InChI=1S/C28H24Cl2O7/c1-10-6-12(35-5)8-14-15(10)26-16-11(9-28(4,36-14)37-26)7-13-17(22(16)31)23(32)18-19(27(13,2)3)20(29)25(34)21(30)24(18)33/h6-8,26,31,33-34H,9H2,1-5H3
InChI KeyZGJMIZXNGYVIRM-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
StreptomycesNPAtlas
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as naphthopyranones. These 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
  • Anthracene
  • Benzopyran
  • Isochromane
  • 2-benzopyran
  • Anisole
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Ketal
  • Pyranone
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Ketone
  • Ether
  • Oxacycle
  • Acetal
  • Polyol
  • Organohalogen compound
  • Organic oxygen compound
  • Aldehyde
  • Hydrocarbon derivative
  • Organochloride
  • Organooxygen compound
  • Organic oxide
  • 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
logP5.64ALOGPS
logP7.81ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)5.09ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.45 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity150.41 m³·mol⁻¹ChemAxon
Polarizability55.45 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA002681
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9752254
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11577486
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Herath KB, Jayasuriya H, Guan Z, Schulman M, Ruby C, Sharma N, MacNaul K, Menke JG, Kodali S, Galgoci A, Wang J, Singh SB: Anthrabenzoxocinones from Streptomyces sp. as liver X receptor ligands and antibacterial agents. J Nat Prod. 2005 Sep;68(9):1437-40. doi: 10.1021/np050176k. [PubMed:16180833 ]