Np mrd loader

Record Information
Version2.0
Created at2024-05-01 21:42:24 UTC
Updated at2024-09-03 04:20:36 UTC
NP-MRD IDNP0332893
Natural Product DOIhttps://doi.org/10.57994/2173
Secondary Accession NumbersNone
Natural Product Identification
Common NameAsperustin H
DescriptionAsperustin H belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group. Asperustin H was first documented in 2024 (PMID: 38441877). Based on a literature review very few articles have been published on Asperustin H.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC23H24O9
Average Mass444.4360 Da
Monoisotopic Mass444.14203 Da
IUPAC Name(4R,6S,8S)-2,4,18-trihydroxy-15-(3-hydroxy-3-methylbutyl)-6-methoxy-7,9,13-trioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1,3(10),11,14(19),15,17-hexaen-20-one
Traditional Name(4R,6S,8S)-2,4,18-trihydroxy-15-(3-hydroxy-3-methylbutyl)-6-methoxy-7,9,13-trioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1,3(10),11,14(19),15,17-hexaen-20-one
CAS Registry NumberNot Available
SMILES
[H][C@]12O[C@@H](C[C@@]1(O)C1=C(O2)C=C2OC3=C(C(O)=CC=C3CCC(C)(C)O)C(=O)C2=C1O)OC
InChI Identifier
InChI=1S/C23H24O9/c1-22(2,27)7-6-10-4-5-11(24)15-18(25)16-12(30-20(10)15)8-13-17(19(16)26)23(28)9-14(29-3)32-21(23)31-13/h4-5,8,14,21,24,26-28H,6-7,9H2,1-3H3/t14-,21-,23+/m0/s1
InChI KeyZBBLSPVHCOHEAE-OAJKGFPOSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
NOESY NMR[1H, 1H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)ruanhl@hust.edu.cnHuazhong University of Science and TechnologyHan-Li Ruan2024-05-01View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)ruanhl@hust.edu.cnHuazhong University of Science and TechnologyHan-Li Ruan2024-05-01View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)ruanhl@hust.edu.cnHuazhong University of Science and TechnologyHan-Li Ruan2024-05-01View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)ruanhl@hust.edu.cnHuazhong University of Science and TechnologyHan-Li Ruan2024-05-01View Spectrum
1D_DEPT NMR13C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)ruanhl@hust.edu.cnHuazhong University of Science and TechnologyHan-Li Ruan2024-05-01View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)ruanhl@hust.edu.cnHuazhong University of Science and TechnologyHan-Li Ruan2024-05-01View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)ruanhl@hust.edu.cnHuazhong University of Science and TechnologyHan-Li Ruan2024-05-01View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
ustus NRRL 5856
      Not Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent4-prenylated xanthones
Alternative Parents
Substituents
  • 4-prenylated xanthone
  • Furanochromone
  • Chromone
  • Coumaran
  • Furofuran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Dihydropyranone
  • Alpha-branched alpha,beta-unsaturated-ketone
  • Benzenoid
  • Pyran
  • Beta-hydroxy ketone
  • Heteroaromatic compound
  • Vinylogous acid
  • Alpha,beta-unsaturated ketone
  • Tetrahydrofuran
  • Tertiary alcohol
  • Enone
  • Dihydrofuran
  • Acryloyl-group
  • Ketone
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • 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
logP3.86ChemAxon
pKa (Strongest Acidic)8.35ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area134.91 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity110.92 m³·mol⁻¹ChemAxon
Polarizability45.32 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Chang JL, Gan YT, Zhou YH, Peng XG, Xie ZY, Meng X, Li SM, Ruan HL: Asperustins A-J: Austocystins with Immunosuppressive and Cytotoxic Activities from Aspergillus ustus NRRL 5856. J Nat Prod. 2024 Apr 26;87(4):966-975. doi: 10.1021/acs.jnatprod.3c01243. Epub 2024 Mar 5. [PubMed:38441877 ]