Np mrd loader

Record Information
Version1.0
Created at2021-06-21 00:42:22 UTC
Updated at2021-06-30 00:18:49 UTC
NP-MRD IDNP0043240
Secondary Accession NumbersNone
Natural Product Identification
Common Nametenuifolin D
Provided ByJEOL DatabaseJEOL Logo
DescriptionTenuifolin D belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. tenuifolin D is found in Isodon tenuifolius. It was first documented in 2002 (PMID: 33651529). Based on a literature review a small amount of articles have been published on Tenuifolin D (PMID: 33079503) (PMID: 26389513) (PMID: 26389498) (PMID: 26389454) (PMID: 33851450) (PMID: 24702811).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC24H36O7
Average Mass436.5450 Da
Monoisotopic Mass436.24610 Da
IUPAC Name(1R,2S,4R,6S,8S,9R,10S,11S,13S,15R)-8-(acetyloxy)-2,6,15-trihydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-11-yl acetate
Traditional Name(1R,2S,4R,6S,8S,9R,10S,11S,13S,15R)-8-(acetyloxy)-2,6,15-trihydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-11-yl acetate
CAS Registry NumberNot Available
SMILES
[H]O[C@]1([H])C(=C([H])[H])[C@@]2([H])C([H])([H])[C@@]11[C@@]([H])(O[H])C([H])([H])[C@]3([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]3(C([H])([H])[H])[C@]1([H])[C@@]([H])(OC(=O)C([H])([H])[H])C2([H])[H]
InChI Identifier
InChI=1S/C24H36O7/c1-11-14-7-15(30-12(2)25)20-23(6)16(8-18(28)24(20,10-14)21(11)29)22(4,5)17(27)9-19(23)31-13(3)26/h14-21,27-29H,1,7-10H2,2-6H3/t14-,15+,16-,17+,18+,19+,20+,21-,23+,24+/m1/s1
InChI KeyOTPQVCJGZXJUEW-KNGCFTRFSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 600 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Isodon tenuifoliusJEOL database
    • Yang, J. -H., et al, J. Nat. Prod. 76, 256 (2013)
Chemical Taxonomy
Description Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentKaurane diterpenoids
Alternative Parents
Substituents
  • Kaurane diterpenoid
  • Dicarboxylic acid or derivatives
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP1.39ALOGPS
logP0.35ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)13.86ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity111.41 m³·mol⁻¹ChemAxon
Polarizability46.08 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID29420429
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71579051
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Authors unspecified: Curcumin (Curcuma, Turmeric) and Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:33651529 ]
  2. Authors unspecified: Cancer Therapy Interactions With Foods and Dietary Supplements (PDQ(R)): Health Professional Version. 2002. [PubMed:33079503 ]
  3. Authors unspecified: Planning the Transition to End-of-Life Care in Advanced Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:26389513 ]
  4. Authors unspecified: Childhood Central Nervous System Germ Cell Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389498 ]
  5. Authors unspecified: Childhood Acute Myeloid Leukemia/Other Myeloid Malignancies Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389454 ]
  6. Koganezawa N, Sekino Y, Kawakami H, Fuchino H, Kawahara N, Shirao T: NMDA receptor-dependent and -independent effects of natural compounds and crude drugs on synaptic states as revealed by drebrin imaging analysis. Eur J Neurosci. 2021 Jun;53(11):3548-3560. doi: 10.1111/ejn.15231. Epub 2021 Apr 27. [PubMed:33851450 ]
  7. Zhou YH, Zhang SY, Guo Q, Chai XY, Jiang Y, Tu PF: Chemical investigation of the roots of Polygala sibirica L. Chin J Nat Med. 2014 Mar;12(3):225-8. doi: 10.1016/S1875-5364(14)60038-8. [PubMed:24702811 ]
  8. Ma B, Li X, Li J, Zhang Q, Liu Y, Yang X, Sun J, Yao D, Liu L, Liu X, Ying H: Quantitative analysis of tenuifolin concentrations in rat plasma and tissue using LCMS/MS: application to pharmacokinetic and tissue distribution study. J Pharm Biomed Anal. 2014 Jan;88:191-200. doi: 10.1016/j.jpba.2013.07.012. Epub 2013 Jul 23. [PubMed:24055855 ]
  9. Zhang H, Han T, Zhang L, Yu CH, Wan DG, Rahman K, Qin LP, Peng C: Effects of tenuifolin extracted from radix polygalae on learning and memory: a behavioral and biochemical study on aged and amnesic mice. Phytomedicine. 2008 Aug;15(8):587-94. doi: 10.1016/j.phymed.2007.12.004. Epub 2008 Mar 4. [PubMed:18289838 ]
  10. Diome C, Mitaine-Offer AC, Miyamoto T, Delaude C, Mirjolet JF, Duchamp O, Lacaille-Dubois MA: Saponins from the roots of Nylandtia spinosa. J Nat Prod. 2007 Oct;70(10):1680-2. doi: 10.1021/np0703186. Epub 2007 Oct 11. [PubMed:17927264 ]
  11. Yang, J. -H., et al. (2013). Yang, J. -H., et al, J. Nat. Prod. 76, 256 (2013). J. Nat. Prod..