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Record Information
Version2.0
Created at2022-04-28 16:40:09 UTC
Updated at2022-04-28 16:40:09 UTC
NP-MRD IDNP0071280
Secondary Accession NumbersNone
Natural Product Identification
Common NameGinsenoside F1
DescriptionGinsenoside F1 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. Ginsenoside F1 is found in Gynostemma yixingense, Panax ginseng , Panax notoginseng , Panax quinquefolium and Panax spp.. Ginsenoside F1 was first documented in 2021 (PMID: 34764724). Based on a literature review a small amount of articles have been published on ginsenoside F1 (PMID: 35058728) (PMID: 35054451) (PMID: 34535878) (PMID: 34301288).
Structure
Thumb
Synonyms
ValueSource
(20S)-Ginsenoside F1ChEBI
Ginsenoside g-F1MeSH
Chemical FormulaC36H62O9
Average Mass638.8830 Da
Monoisotopic Mass638.43938 Da
IUPAC Name(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(2S)-6-methyl-2-[(1R,2R,5S,7R,8S,10R,11R,14S,15R,16R)-5,8,16-trihydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]hept-5-en-2-yl]oxy}oxane-3,4,5-triol
Traditional Name(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(2S)-6-methyl-2-[(1R,2R,5S,7R,8S,10R,11R,14S,15R,16R)-5,8,16-trihydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]hept-5-en-2-yl]oxy}oxane-3,4,5-triol
CAS Registry NumberNot Available
SMILES
CC(C)=CCC[C@](C)(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H]1CC[C@]2(C)[C@@H]1[C@H](O)C[C@@H]1[C@@]3(C)CC[C@H](O)C(C)(C)[C@@H]3[C@@H](O)C[C@@]21C
InChI Identifier
InChI=1S/C36H62O9/c1-19(2)10-9-13-36(8,45-31-29(43)28(42)27(41)23(18-37)44-31)20-11-15-34(6)26(20)21(38)16-24-33(5)14-12-25(40)32(3,4)30(33)22(39)17-35(24,34)7/h10,20-31,37-43H,9,11-18H2,1-8H3/t20-,21+,22-,23+,24+,25-,26-,27+,28-,29+,30-,31-,33+,34+,35+,36-/m0/s1
InChI KeyXNGXWSFSJIQMNC-FIYORUNESA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Gynostemma yixingenseLOTUS Database
Panax ginsengPlant
Panax notoginsengPlant
Panax quinquefoliusPlant
Panax spp.Plant
Chemical Taxonomy
Description 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
  • Triterpenoid
  • 3-hydroxysteroid
  • 14-alpha-methylsteroid
  • 12-hydroxysteroid
  • 6-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxysteroid
  • Steroid
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Monosaccharide
  • Fatty acyl
  • Oxane
  • Cyclic alcohol
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Polyol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Primary alcohol
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
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
logP2.68ALOGPS
logP2.45ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area160.07 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity171.24 m³·mol⁻¹ChemAxon
Polarizability71.68 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00030388
Chemspider ID7985298
KEGG Compound IDNot Available
BioCyc IDCPD-15448
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9809542
PDB IDNot Available
ChEBI ID77150
Good Scents IDrw1878371
References
General References
  1. Hou J, Jeon B, Baek J, Yun Y, Kim D, Chang B, Kim S, Kim S: High fat diet-induced brain damaging effects through autophagy-mediated senescence, inflammation and apoptosis mitigated by ginsenoside F1-enhanced mixture. J Ginseng Res. 2022 Jan;46(1):79-90. doi: 10.1016/j.jgr.2021.04.002. Epub 2021 Apr 16. [PubMed:35058728 ]
  2. Yun YJ, Park BH, Hou J, Oh JP, Han JH, Kim SC: Ginsenoside F1 Protects the Brain against Amyloid Beta-Induced Toxicity by Regulating IDE and NEP. Life (Basel). 2022 Jan 1;12(1). pii: life12010058. doi: 10.3390/life12010058. [PubMed:35054451 ]
  3. Kim SJ, Lee J, Choi WS, Kim HJ, Kim MY, Kim SC, Kim HS: Ginsenoside F1 Attenuates Eosinophilic Inflammation in Chronic Rhinosinusitis by Promoting NK Cell Function. J Ginseng Res. 2021 Nov;45(6):695-705. doi: 10.1016/j.jgr.2021.03.007. Epub 2021 Mar 29. [PubMed:34764724 ]
  4. Chun YL, Lee S, Park KH, Park C, Huh Y, Jeong NY, Jung J: Protective and therapeutic effect of (S)-ginsenoside F1 on peripheral nerve degeneration targeting Schwann cells: a pharmaco-neuroanatomical approach. Anat Sci Int. 2022 Jan;97(1):79-89. doi: 10.1007/s12565-021-00630-x. Epub 2021 Sep 17. [PubMed:34535878 ]
  5. Wang L, Chen MY, Shao L, Zhang W, Li XP, Huang WH: Personalized bioconversion of Panax notoginseng saponins mediated by gut microbiota between two different diet-pattern healthy subjects. Chin Med. 2021 Jul 23;16(1):60. doi: 10.1186/s13020-021-00476-5. [PubMed:34301288 ]