Np mrd loader

Record Information
Version2.0
Created at2020-12-09 03:29:31 UTC
Updated at2021-07-15 16:54:56 UTC
NP-MRD IDNP0006487
Secondary Accession NumbersNone
Natural Product Identification
Common NameCyrneine A
Provided ByNPAtlasNPAtlas Logo
Description Cyrneine A is found in Sarcodon cyrneus. Cyrneine A was first documented in 2006 (PMID: 16881016). Based on a literature review a significant number of articles have been published on Cyrneine a (PMID: 17320402) (PMID: 30793912) (PMID: 29858575) (PMID: 22431475) (PMID: 17337280).
Structure
Data?1624574732
Synonyms
ValueSource
1,14-Dihydroxycyantha-3,5(10),11-triene-12-carbaldehydeMeSH
Chemical FormulaC20H28O3
Average Mass316.4410 Da
Monoisotopic Mass316.20384 Da
IUPAC Name(3R,3aR,5aR,6S)-3,6-dihydroxy-3a,5a-dimethyl-1-(propan-2-yl)-2H,3H,3aH,4H,5H,5aH,6H,7H-cyclohepta[e]indene-8-carbaldehyde
Traditional Namecyrneine A
CAS Registry NumberNot Available
SMILES
CC(C)C1=C2C3=CC=C(C[C@H](O)[C@]3(C)CC[C@@]2(C)[C@H](O)C1)C=O
InChI Identifier
InChI=1S/C20H28O3/c1-12(2)14-10-17(23)20(4)8-7-19(3)15(18(14)20)6-5-13(11-21)9-16(19)22/h5-6,11-12,16-17,22-23H,7-10H2,1-4H3/t16-,17+,19+,20-/m0/s1
InChI KeyIXBCZHOTZLYJDA-CUDHKJQZSA-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
Sarcodon cyrneusNPAtlas
Chemical Taxonomy
ClassificationNot classified
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
logP3.37ALOGPS
logP1.88ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)14.55ChemAxon
pKa (Strongest Basic)-0.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity93.9 m³·mol⁻¹ChemAxon
Polarizability36.07 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA011935
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10172891
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12000424
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Marcotullio MC, Pagiott R, Maltese F, Obara Y, Hoshino T, Nakahata N, Curini M: Neurite outgrowth activity of cyathane diterpenes from Sarcodon cyrneus, cyrneines A and B. Planta Med. 2006 Jul;72(9):819-23. doi: 10.1055/s-2006-946681. [PubMed:16881016 ]
  2. Marcotullio MC, Pagiotti R, Maltese F, Oball-Mond Mwankie GN, Hoshino T, Obara Y, Nakahata N: Cyathane diterpenes from Sarcodon cyrneus and evaluation of their activities of neuritegenesis and nerve growth factor production. Bioorg Med Chem. 2007 Apr 15;15(8):2878-82. doi: 10.1016/j.bmc.2007.02.019. Epub 2007 Feb 13. [PubMed:17320402 ]
  3. Wu GJ, Zhang YH, Tan DX, He L, Cao BC, He YP, Han FS: Synthetic Studies on Enantioselective Total Synthesis of Cyathane Diterpenoids: Cyrneines A and B, Glaucopine C, and (+)-Allocyathin B2. J Org Chem. 2019 Mar 15;84(6):3223-3238. doi: 10.1021/acs.joc.8b03138. Epub 2019 Mar 4. [PubMed:30793912 ]
  4. Wu GJ, Zhang YH, Tan DX, Han FS: Total synthesis of cyrneines A-B and glaucopine C. Nat Commun. 2018 Jun 1;9(1):2148. doi: 10.1038/s41467-018-04480-6. [PubMed:29858575 ]
  5. Elamparuthi E, Fellay C, Neuburger M, Gademann K: Total synthesis of cyrneine A. Angew Chem Int Ed Engl. 2012 Apr 23;51(17):4071-3. doi: 10.1002/anie.201200515. Epub 2012 Mar 16. [PubMed:22431475 ]
  6. Obara Y, Hoshino T, Marcotullio MC, Pagiotti R, Nakahata N: A novel cyathane diterpene, cyrneine A, induces neurite outgrowth in a Rac1-dependent mechanism in PC12 cells. Life Sci. 2007 Apr 10;80(18):1669-77. doi: 10.1016/j.lfs.2007.01.057. Epub 2007 Feb 12. [PubMed:17337280 ]