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Record Information
Version2.0
Created at2024-06-24 23:45:09 UTC
Updated at2025-07-31 01:09:29 UTC
NP-MRD IDNP0333492
Natural Product DOIhttps://doi.org/10.57994/2946
Secondary Accession NumbersNone
Natural Product Identification
Common NameCyclocephagenol
DescriptionCyclocephagenol belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. Cyclocephagenol was first documented in 2022 (PMID: 36323752). Based on a literature review very few articles have been published on Cyclocephagenol (PMID: 37024895).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC30H50O5
Average Mass490.7250 Da
Monoisotopic Mass490.36582 Da
IUPAC Name(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-15-[(2R,5R)-5-hydroxy-2,6,6-trimethyloxan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecane-6,9,14-triol
Traditional Name(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-15-[(2R,5R)-5-hydroxy-2,6,6-trimethyloxan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecane-6,9,14-triol
CAS Registry NumberNot Available
SMILES
[H][C@@]1([C@@H](O)C[C@@]2(C)[C@]3([H])C[C@H](O)[C@]4([H])[C@]5(C[C@@]35CC[C@]12C)CC[C@H](O)C4(C)C)[C@@]1(C)CC[C@@H](O)C(C)(C)O1
InChI Identifier
InChI=1S/C30H50O5/c1-24(2)20(33)9-11-30-16-29(30)13-12-26(5)23(28(7)10-8-21(34)25(3,4)35-28)18(32)15-27(26,6)19(29)14-17(31)22(24)30/h17-23,31-34H,8-16H2,1-7H3/t17-,18-,19-,20-,21+,22-,23-,26+,27-,28+,29-,30+/m0/s1
InChI KeyVIOYSPVPEAYUTR-LTTAEMHKSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, C5D5N, experimental)faydogan@olemiss.eduUniversity of MississippiSophie Fadime Aydogan2024-06-24View Spectrum
NOESY NMR[1H, 1H] NMR Spectrum (2D, 500 MHz, C5D5N, experimental)faydogan@olemiss.eduUniversity of MississippiSophie Fadime Aydogan2024-06-24View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, C5D5N, experimental)faydogan@olemiss.eduUniversity of MississippiSophie Fadime Aydogan2024-06-24View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 500 MHz, C5D5N, experimental)faydogan@olemiss.eduUniversity of MississippiSophie Fadime Aydogan2024-06-24View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, C5D5N, experimental)faydogan@olemiss.eduUniversity of MississippiSophie Fadime Aydogan2024-06-24View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, C5D5N, experimental)faydogan@olemiss.eduUniversity of MississippiSophie Fadime Aydogan2024-06-24View Spectrum
1D NMR1H NMR Spectrum (1D, 499.782337089 MHz, C5D5N, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 499.782337089, C5D5N, simulated)faydogan@olemiss.eduUniversity of MississippiSophie Fadime Aydogan2024-06-24View Spectrum
Species
Species of Origin
Species NameSourceReference
Astragalus condensatus
      Not Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentTriterpene saponins
Alternative Parents
Substituents
  • Triterpene saponin
  • Cycloartanol-skeleton
  • Triterpenoid
  • Cycloartane-skeleton
  • 9b,19-cyclo-lanostane-skeleton
  • Tetrahydroxy bile acid, alcohol, or derivatives
  • 24-hydroxysteroid
  • Hydroxy bile acid, alcohol, or derivatives
  • Bile acid, alcohol, or derivatives
  • Polyprenol skeleton
  • 3-beta-hydroxysteroid
  • 16-hydroxysteroid
  • 16-beta-hydroxysteroid
  • Hydroxysteroid
  • 6-hydroxysteroid
  • 3-hydroxysteroid
  • Steroid
  • Oxane
  • Cyclic alcohol
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • 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
logP2.6ChemAxon
pKa (Strongest Acidic)13.84ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity135.72 m³·mol⁻¹ChemAxon
Polarizability57.02 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
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 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. Kucuksolak M, Yilmaz S, Ballar-Kirmizibayrak P, Bedir E: Potent telomerase activators from a novel sapogenin via biotransformation utilizing Camarosporium laburnicola, an endophytic fungus. Microb Cell Fact. 2023 Apr 6;22(1):66. doi: 10.1186/s12934-023-02069-3. [PubMed:37024895 ]
  2. Kucuksolak M, Uner G, Ballar Kirmizibayrak P, Bedir E: Neuroprotective metabolites via fungal biotransformation of a novel sapogenin, cyclocephagenol. Sci Rep. 2022 Nov 2;12(1):18481. doi: 10.1038/s41598-022-22799-5. [PubMed:36323752 ]