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Record Information
Version2.0
Created at2022-04-29 00:32:44 UTC
Updated at2022-04-29 00:32:44 UTC
NP-MRD IDNP0079528
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Kaji-ichigoside F1
DescriptionKaji-ichigoside 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. (+)-Kaji-ichigoside F1 is found in Anchusa strigosa, Photinia serratifolia, Potentilla erecta, Rosa laevigata, Rosa multiflora , Rosa rugosa, Rubus ellipticus, Rubus ellipticus var.obcordatus , Sanguisorba alpina, Sanguisorba officinalis and Vitex altissima. (+)-Kaji-ichigoside F1 was first documented in 2014 (PMID: 24697904). Based on a literature review a small amount of articles have been published on kaji-ichigoside F1 (PMID: 35069981) (PMID: 32318240) (PMID: 32298737) (PMID: 28287271).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC36H58O10
Average Mass650.8500 Da
Monoisotopic Mass650.40300 Da
IUPAC Name(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,2R,4aS,6aS,6bR,8aR,10S,11R,12aR,12bR,14bS)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate
Traditional Name(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,2R,4aS,6aS,6bR,8aR,10S,11R,12aR,12bR,14bS)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate
CAS Registry NumberNot Available
SMILES
C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2[C@]1(C)O)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C36H58O10/c1-18-10-13-36(30(43)46-29-26(41)25(40)24(39)21(17-37)45-29)15-14-33(5)19(27(36)35(18,7)44)8-9-23-32(4)16-20(38)28(42)31(2,3)22(32)11-12-34(23,33)6/h8,18,20-29,37-42,44H,9-17H2,1-7H3/t18-,20-,21-,22+,23-,24-,25+,26-,27-,28-,29+,32+,33-,34-,35-,36+/m1/s1
InChI KeyMLKQAGPAYHTNQQ-FUZXVMJXSA-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
Anchusa strigosaLOTUS Database
Photinia serratifoliaLOTUS Database
Potentilla erectaLOTUS Database
Rosa laevigataLOTUS Database
Rosa multifloraPlant
Rosa rugosaLOTUS Database
Rubus ellipticusLOTUS Database
Rubus ellipticus var.obcordatusPlant
Sanguisorba alpinaLOTUS Database
Sanguisorba officinalisLOTUS Database
Vitex altissimaLOTUS Database
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
  • Hexose monosaccharide
  • Monosaccharide
  • Oxane
  • Cyclic alcohol
  • Tertiary alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Acetal
  • Polyol
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Primary 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
logP3.07ALOGPS
logP2ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)12.18ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area177.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity169.1 m³·mol⁻¹ChemAxon
Polarizability71.71 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
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 IDC00044210
Chemspider ID62879798
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14019178
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Zeng Q, Du S, Xu Y, Yang F, Wu L, Wang N, Zhang S, Wei S, Wang G, Zhang S, Lu H, Luo P: Assessing the Potential Value and Mechanism of Kaji-Ichigoside F1 on Arsenite-Induced Skin Cell Senescence. Oxid Med Cell Longev. 2022 Jan 11;2022:9574473. doi: 10.1155/2022/9574473. eCollection 2022. [PubMed:35069981 ]
  2. Shi C, Zhan L, Wu Y, Li Z, Li J, Li Y, Wei J, Zhang Y, Li L: Kaji-Ichigoside F1 and Rosamultin Protect Vascular Endothelial Cells against Hypoxia-Induced Apoptosis via the PI3K/AKT or ERK1/2 Signaling Pathway. Oxid Med Cell Longev. 2020 Apr 12;2020:6837982. doi: 10.1155/2020/6837982. eCollection 2020. [PubMed:32318240 ]
  3. Shi C, Li Z, Wu Y, Li X, Li Y, Wei J, Li J, Zhang Y, Li L: Euscaphic acid and Tormentic acid protect vascular endothelial cells against hypoxia-induced apoptosis via PI3K/AKT or ERK 1/2 signaling pathway. Life Sci. 2020 Jul 1;252:117666. doi: 10.1016/j.lfs.2020.117666. Epub 2020 Apr 13. [PubMed:32298737 ]
  4. Luo XL, Dan HL, Li N, Li YH, Zhang YJ, Zhao P: A new catechin derivative from the fruits of Rosa sterilis S. D. Shi. Nat Prod Res. 2017 Oct;31(19):2239-2244. doi: 10.1080/14786419.2017.1299728. Epub 2017 Mar 13. [PubMed:28287271 ]
  5. Morikawa T, Ninomiya K, Imura K, Yamaguchi T, Akagi Y, Yoshikawa M, Hayakawa T, Muraoka O: Hepatoprotective triterpenes from traditional Tibetan medicine Potentilla anserina. Phytochemistry. 2014 Jun;102:169-81. doi: 10.1016/j.phytochem.2014.03.002. Epub 2014 Mar 31. [PubMed:24697904 ]