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Record Information
Version1.0
Created at2022-09-12 16:07:07 UTC
Updated at2022-09-12 16:07:07 UTC
NP-MRD IDNP0330607
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-[(1r,3as,5ar,7r,9r,9as,11ar)-3a,7,9-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one
DescriptionAcovenosigenin belongs to the class of organic compounds known as cardenolides and derivatives. These are steroid lactones containing a furan-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. 4-[(1r,3as,5ar,7r,9r,9as,11ar)-3a,7,9-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one is found in Streptocaulon juventas. It was first documented in 2003 (PMID: 14640513). Based on a literature review a small amount of articles have been published on Acovenosigenin (PMID: 31250411) (PMID: 25555472) (PMID: 23286880) (PMID: 17510995).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC23H34O5
Average Mass390.5200 Da
Monoisotopic Mass390.24062 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
C[C@]12CCC3C(CC[C@@H]4C[C@@H](O)C[C@@H](O)[C@]34C)[C@@]1(O)CC[C@@H]2C1=CC(=O)OC1
InChI Identifier
InChI=1S/C23H34O5/c1-21-7-5-17-18(4-3-14-10-15(24)11-19(25)22(14,17)2)23(21,27)8-6-16(21)13-9-20(26)28-12-13/h9,14-19,24-25,27H,3-8,10-12H2,1-2H3/t14-,15-,16-,17?,18?,19-,21-,22+,23+/m1/s1
InChI KeyCSKIDXJFNAYMTR-YTAKEYINSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptocaulon juventasLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cardenolides and derivatives. These are steroid lactones containing a furan-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentCardenolides and derivatives
Alternative Parents
Substituents
  • Cardanolide-skeleton
  • 3-hydroxysteroid
  • 1-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 14-hydroxysteroid
  • Hydroxysteroid
  • 2-furanone
  • Cyclic alcohol
  • Dihydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Lactone
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen 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
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID12022
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12539
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Pecio L, Hassan EM, Omer EA, Gajek G, Kontek R, Sobieraj A, Stochmal A, Oleszek W: Cytotoxic Cardenolides from the Leaves of Acokanthera oblongifolia. Planta Med. 2019 Aug;85(11-12):965-972. doi: 10.1055/a-0958-2566. Epub 2019 Jun 27. [PubMed:31250411 ]
  2. Xue R, Han N, Xia M, Ye C, Hao Z, Wang L, Wang Y, Yang J, Saiki I, Yin J: TXA9, a cardiac glycoside from Streptocaulon juventas, exerts a potent anti-tumor activity against human non-small cell lung cancer cells in vitro and in vivo. Steroids. 2015 Feb;94:51-9. doi: 10.1016/j.steroids.2014.12.015. Epub 2014 Dec 30. [PubMed:25555472 ]
  3. Xue R, Han N, Ye C, Wang HB, Yin J: Cardenolide glycosides from root of Streptocaulon juventas. Phytochemistry. 2013 Apr;88:105-11. doi: 10.1016/j.phytochem.2012.12.004. Epub 2012 Dec 31. [PubMed:23286880 ]
  4. Zhang XH, Zhu HL, Yu Q, Xuan LJ: Cytotoxic cardenolides from Streptocaulon griffithii. Chem Biodivers. 2007 May;4(5):998-1002. doi: 10.1002/cbdv.200790091. [PubMed:17510995 ]
  5. Ueda JY, Tezuka Y, Banskota AH, Tran QL, Tran QK, Saiki I, Kadota S: Constituents of the Vietnamese medicinal plant Streptocaulon juventas and their antiproliferative activity against the human HT-1080 fibrosarcoma cell line. J Nat Prod. 2003 Nov;66(11):1427-33. doi: 10.1021/np030177h. [PubMed:14640513 ]
  6. LOTUS database [Link]