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Record Information
Version2.0
Created at2022-04-28 15:06:34 UTC
Updated at2022-04-28 15:06:34 UTC
NP-MRD IDNP0069765
Secondary Accession NumbersNone
Natural Product Identification
Common NameCycloposine
DescriptionCYCLOPOSINE belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative. Cycloposine is found in Fritillaria pallidiflora and Veratrum californicum. Cycloposine was first documented in 2013 (PMID: 24079166). Based on a literature review very few articles have been published on CYCLOPOSINE (PMID: 34641477).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC33H51NO7
Average Mass573.7710 Da
Monoisotopic Mass573.36655 Da
IUPAC Name(2R,3R,4S,5S,6R)-2-[(3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3',6',10,11b-tetramethyl-1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-octadecahydro-3'H-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridine]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Name(2R,3R,4S,5S,6R)-2-[(3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3',6',10,11b-tetramethyl-2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a-hexadecahydro-1H,3'H-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridine]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
CAS Registry NumberNot Available
SMILES
C[C@@H]1[C@@H]2NC[C@@H](C)C[C@H]2O[C@]11CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC2=C1C)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C33H51NO7/c1-16-11-25-27(34-14-16)18(3)33(41-25)10-8-21-22-6-5-19-12-20(7-9-32(19,4)24(22)13-23(21)17(33)2)39-31-30(38)29(37)28(36)26(15-35)40-31/h5,16,18,20-22,24-31,34-38H,6-15H2,1-4H3/t16-,18+,20-,21-,22-,24-,25+,26+,27-,28+,29-,30+,31+,32-,33-/m0/s1
InChI KeyOSOOWXRUSUHLOX-PBFVMIKGSA-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
Fritillaria pallidifloraPlant
Veratrum californicumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroidal saponins
Alternative Parents
Substituents
  • Steroidal saponin
  • Diterpene glycoside
  • Jerveratrum-type alkaloid
  • Diterpenoid
  • Steroidal alkaloid
  • Terpene glycoside
  • Azasteroid
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Alkaloid or derivatives
  • Monosaccharide
  • Oxane
  • Piperidine
  • Oxolane
  • Secondary alcohol
  • Polyol
  • Dialkyl ether
  • Secondary aliphatic amine
  • Acetal
  • Secondary amine
  • Organoheterocyclic compound
  • Ether
  • Azacycle
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Organopnictogen compound
  • Amine
  • 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
logP2.35ALOGPS
logP2.03ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)10.03ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area120.64 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity154.58 m³·mol⁻¹ChemAxon
Polarizability67 ųChemAxon
Number of Rings7ChemAxon
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 IDC00028119
Chemspider ID19958909
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25078000
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Dirks ML, Seale JT, Collins JM, McDougal OM: Review: Veratrum californicum Alkaloids. Molecules. 2021 Sep 30;26(19). pii: molecules26195934. doi: 10.3390/molecules26195934. [PubMed:34641477 ]
  2. Chandler CM, Habig JW, Fisher AA, Ambrose KV, Jimenez ST, McDougal OM: Improved extraction and complete mass spectral characterization of steroidal alkaloids from Veratrum californicum. Nat Prod Commun. 2013 Aug;8(8):1059-64. [PubMed:24079166 ]