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Record Information
Version1.0
Created at2022-09-04 02:59:04 UTC
Updated at2022-09-04 02:59:04 UTC
NP-MRD IDNP0186971
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,3ar,5ar,9as,11ar)-1-[(1s)-1-[(2s,5r,6s)-6-hydroxy-5-methyloxan-2-yl]ethyl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-one
DescriptionAstraeusin K epimer belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1r,3ar,5ar,9as,11ar)-1-[(1s)-1-[(2s,5r,6s)-6-hydroxy-5-methyloxan-2-yl]ethyl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-one is found in Astraeus odoratus. It was first documented in 2017 (PMID: 29114677). Based on a literature review a significant number of articles have been published on Astraeusin K epimer (PMID: 30585226) (PMID: 33334897) (PMID: 33879791) (PMID: 29272779).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC30H48O3
Average Mass456.7110 Da
Monoisotopic Mass456.36035 Da
IUPAC Name(2S,7R,11R,14R,15R)-14-[(1S)-1-[(2S,5R,6S)-6-hydroxy-5-methyloxan-2-yl]ethyl]-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-one
Traditional Name(2S,7R,11R,14R,15R)-14-[(1S)-1-[(2S,5R,6S)-6-hydroxy-5-methyloxan-2-yl]ethyl]-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-one
CAS Registry NumberNot Available
SMILES
C[C@@H]([C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C(C)(C)[C@@H]1CC3)[C@@H]1CC[C@@H](C)[C@@H](O)O1
InChI Identifier
InChI=1S/C30H48O3/c1-18-8-10-23(33-26(18)32)19(2)20-12-16-30(7)22-9-11-24-27(3,4)25(31)14-15-28(24,5)21(22)13-17-29(20,30)6/h18-20,23-24,26,32H,8-17H2,1-7H3/t18-,19+,20-,23+,24+,26+,28-,29-,30+/m1/s1
InChI KeyHYEBEDUHRUQRHO-VQGVFSKOSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Astraeus odoratusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • 14-alpha-methylsteroid
  • 3-oxo-5-alpha-steroid
  • Oxosteroid
  • 3-oxosteroid
  • Steroid
  • Oxane
  • Cyclic ketone
  • Ketone
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP6.69ChemAxon
pKa (Strongest Acidic)12.19ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity133.89 m³·mol⁻¹ChemAxon
Polarizability55.47 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
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 ID78436654
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139584108
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Watanabe K, Mimaki Y, Fukaya H, Matsuo Y: Cycloartane and Oleanane Glycosides from the Tubers of Eranthis cilicica. Molecules. 2018 Dec 25;24(1). pii: molecules24010069. doi: 10.3390/molecules24010069. [PubMed:30585226 ]
  2. Piyasirananda W, Beekman A, Ganesan A, Bidula S, Stokes L: Insights into the Structure-Activity Relationship of Glycosides as Positive Allosteric Modulators Acting on P2X7 Receptors. Mol Pharmacol. 2021 Feb;99(2):163-174. doi: 10.1124/molpharm.120.000129. Epub 2020 Dec 17. [PubMed:33334897 ]
  3. Hamaguchi T, Kawakami K, Shinzawa-Itoh K, Inoue-Kashino N, Itoh S, Ifuku K, Yamashita E, Maeda K, Yonekura K, Kashino Y: Structure of the far-red light utilizing photosystem I of Acaryochloris marina. Nat Commun. 2021 Apr 20;12(1):2333. doi: 10.1038/s41467-021-22502-8. [PubMed:33879791 ]
  4. Riedl B, Schmid W: A concise route to access C-glycosidic tetrazolyl analogues of Kdo as bioisosteres. Carbohydr Res. 2018 Feb 1;456:30-34. doi: 10.1016/j.carres.2017.12.006. Epub 2017 Dec 14. [PubMed:29272779 ]
  5. Tellez J, Gallen A, Ferrer J, Lahoz FJ, Garcia-Orduna P, Riera A, Verdaguer X, Carmona D, Grabulosa A: Half-sandwich complexes of Ir(iii), Rh(iii) and Ru(ii) with the MaxPhos ligand: metal centred chirality and cyclometallation. Dalton Trans. 2017 Nov 21;46(45):15865-15874. doi: 10.1039/c7dt03327c. [PubMed:29114677 ]
  6. LOTUS database [Link]