Np mrd loader

Record Information
Version1.0
Created at2021-06-20 19:24:55 UTC
Updated at2021-06-30 00:07:41 UTC
NP-MRD IDNP0036171
Secondary Accession NumbersNone
Natural Product Identification
Common Name4beta,10alpha-dihydroxy-5alphaH-guai-1(2),11(13)-dien-12,8alpha-olide
Provided ByJEOL DatabaseJEOL Logo
Description4Beta,10alpha-dihydroxy-5alphaH-guai-1(2),11(13)-dien-12,8alpha-olide is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 4beta,10alpha-dihydroxy-5alphaH-guai-1(2),11(13)-dien-12,8alpha-olide is found in Carpesium faberi and Inula hupehensis. It was first documented in 2011 (PMID: 21894898). Based on a literature review very few articles have been published on 4beta,10alpha-dihydroxy-5alphaH-guai-1(2),11(13)-dien-12,8alpha-olide (PMID: 25993354).
Structure
Thumb
Synonyms
ValueSource
4b,10a-Dihydroxy-5alphah-guai-1(2),11(13)-dien-12,8a-olideGenerator
4Β,10α-dihydroxy-5alphah-guai-1(2),11(13)-dien-12,8α-olideGenerator
4,10-DGO CPDMeSH
Chemical FormulaC15H20O4
Average Mass264.3210 Da
Monoisotopic Mass264.13616 Da
IUPAC Name(3aR,4aR,5S,8R,9aS)-5,8-dihydroxy-5,8-dimethyl-3-methylidene-2H,3H,3aH,4H,4aH,5H,6H,8H,9H,9aH-azuleno[6,5-b]furan-2-one
Traditional Name(3aR,4aR,5S,8R,9aS)-5,8-dihydroxy-5,8-dimethyl-3-methylidene-3aH,4H,4aH,6H,9H,9aH-azuleno[6,5-b]furan-2-one
CAS Registry NumberNot Available
SMILES
[H]O[C@@]1(C([H])([H])[H])C([H])([H])C([H])=C2[C@@]1([H])C([H])([H])[C@]1([H])C(=C([H])[H])C(=O)O[C@@]1([H])C([H])([H])[C@]2(O[H])C([H])([H])[H]
InChI Identifier
InChI=1S/C15H20O4/c1-8-9-6-11-10(4-5-14(11,2)17)15(3,18)7-12(9)19-13(8)16/h4,9,11-12,17-18H,1,5-7H2,2-3H3/t9-,11-,12+,14+,15-/m1/s1
InChI KeySKXYOUKPVUIPFP-HTZLXXLYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Carpesium faberiLOTUS Database
Inula hupehensisJEOL database
    • Qin, J. -J., et al, J. Nat. Prod. 74, 1881 (2011)
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
logP1.49ALOGPS
logP0.66ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)14.18ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity70.59 m³·mol⁻¹ChemAxon
Polarizability28.22 ųChemAxon
Number of Rings3ChemAxon
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 ID26379204
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID69333
Good Scents IDNot Available
References
General References
  1. Qin JJ, Zhu JX, Zeng Q, Cheng XR, Zhu Y, Zhang SD, Shan L, Jin HZ, Zhang WD: Pseudoguaianolides and guaianolides from Inula hupehensis as potential anti-inflammatory agents. J Nat Prod. 2011 Sep 23;74(9):1881-7. doi: 10.1021/np200319x. Epub 2011 Sep 6. [PubMed:21894898 ]
  2. Gohari AR, Mosaddegh M, Naghibi F, Eslami-Tehrani B, Pirani A, Hamzeloo-Moghadam M, Read RW: Cytotoxic sesquiterpene lactones from the aerial parts of Inula aucheriana. An Acad Bras Cienc. 2015 Apr-Jun;87(2):777-85. doi: 10.1590/0001-3765201520140063. Epub 2015 May 8. [PubMed:25993354 ]
  3. Qin, J. -J., et al. (2011). Qin, J. -J., et al, J. Nat. Prod. 74, 1881 (2011). J. Nat. Prod..