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Record Information
Version2.0
Created at2024-09-11 06:27:19 UTC
Updated at2024-09-11 06:27:20 UTC
NP-MRD IDNP0336483
Secondary Accession NumbersNone
Natural Product Identification
Common NameChakasaponin I
DescriptionChakasaponin I 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. Chakasaponin I was first documented in 2020 (PMID: 32560563). Based on a literature review very few articles have been published on Chakasaponin I.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC59H92O26
Average Mass1217.3590 Da
Monoisotopic Mass1216.58768 Da
IUPAC Name(2S,3S,4S,5R)-6-{[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-9-(acetyloxy)-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-10-{[(2E)-2-methylbut-2-enoyl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-4-{[(2S,3R,4S,5S)-4,5-dihydroxy-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R)-6-{[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-9-(acetyloxy)-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-10-{[(2E)-2-methylbut-2-enoyl]oxy}-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-4-{[(2S,3R,4S,5S)-4,5-dihydroxy-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
[H][C@@]12CC(C)(C)[C@@H](OC(=O)C(\C)=C\C)[C@H](OC(C)=O)[C@]1(CO)[C@H](O)C[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](OC4O[C@@H]([C@@H](O)[C@H](O[C@@H]5OC[C@H](O)[C@H](O)[C@H]5O[C@@H]5OC[C@@H](O)[C@H](O)[C@H]5O)[C@H]4O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)C(O)=O)C(C)(C)[C@]3([H])CC[C@@]12C
InChI Identifier
InChI=1/C59H92O26/c1-11-24(2)49(75)85-46-47(78-25(3)62)59(23-61)27(18-54(46,4)5)26-12-13-32-56(8)16-15-34(55(6,7)31(56)14-17-57(32,9)58(26,10)19-33(59)65)80-53-45(84-51-40(71)38(69)37(68)30(20-60)79-51)42(41(72)43(82-53)48(73)74)81-52-44(36(67)29(64)22-77-52)83-50-39(70)35(66)28(63)21-76-50/h11-12,27-47,50-53,60-61,63-72H,13-23H2,1-10H3,(H,73,74)/b24-11+/t27-,28+,29-,30+,31-,32+,33+,34-,35-,36-,37-,38-,39+,40+,41-,42-,43-,44+,45+,46-,47-,50-,51-,52-,53?,56-,57+,58+,59-/s2
InChI KeyPJXRLTHWHNMGKR-ZAFIUNOJNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot 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
  • Triterpenoid
  • Oligosaccharide
  • Hydroxysteroid
  • 16-oxosteroid
  • Oxosteroid
  • 7-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Steroid
  • Fatty acyl glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Tricarboxylic acid or derivatives
  • Beta-hydroxy acid
  • Fatty acid ester
  • Hydroxy acid
  • Fatty acyl
  • Pyran
  • Oxane
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Cyclic alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Carboxylic acid
  • Oxacycle
  • Acetal
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • 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
logP-0.11ChemAxon
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area406.5 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity288.5 m³·mol⁻¹ChemAxon
Polarizability127.4 ųChemAxon
Number of Rings9ChemAxon
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 IDC00029931
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. Ren N, Chen L, Li B, Rankin GO, Chen YC, Tu Y: Purified Tea (Camellia sinensis (L.) Kuntze) Flower Saponins Induce the p53-Dependent Intrinsic Apoptosis of Cisplatin-Resistant Ovarian Cancer Cells. Int J Mol Sci. 2020 Jun 17;21(12). pii: ijms21124324. doi: 10.3390/ijms21124324. [PubMed:32560563 ]