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Record Information
Version2.0
Created at2022-09-09 06:59:45 UTC
Updated at2022-09-09 06:59:45 UTC
NP-MRD IDNP0280936
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1as,4s,4as,7s,7ar,7br)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-ol
DescriptionGlobulol belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. Thus, globulol is considered to be an isoprenoid. (1as,4s,4as,7s,7ar,7br)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-ol is found in Angelica sylvestris, Calypogeia muelleriana, Frullania tamarisci, Jackiella javanica, Mylia taylorii and Tritomaria quinquedentata. (1as,4s,4as,7s,7ar,7br)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-ol was first documented in 2022 (PMID: 36037596). Based on a literature review a small amount of articles have been published on Globulol (PMID: 35946642) (PMID: 35735854) (PMID: 35344272) (PMID: 36085404).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC15H26O
Average Mass222.3720 Da
Monoisotopic Mass222.19837 Da
IUPAC Name(1aR,1bR,2S,4aS,5S,7aS)-1,1,2,5-tetramethyl-decahydro-1H-cyclopropa[e]azulen-5-ol
Traditional Name(1aR,1bR,2S,4aS,5S,7aS)-1,1,2,5-tetramethyl-octahydro-1aH-cyclopropa[e]azulen-5-ol
CAS Registry NumberNot Available
SMILES
C[C@H]1CC[C@H]2[C@H]1[C@@H]1[C@H](CC[C@]2(C)O)C1(C)C
InChI Identifier
InChI=1S/C15H26O/c1-9-5-6-10-12(9)13-11(14(13,2)3)7-8-15(10,4)16/h9-13,16H,5-8H2,1-4H3/t9-,10-,11-,12-,13-,15-/m0/s1
InChI KeyAYXPYQRXGNDJFU-RQWGMIHLSA-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
Angelica sylvestrisLOTUS Database
Calypogeia muellerianaLOTUS Database
Frullania tamarisciLOTUS Database
Jackiella javanicaLOTUS Database
Mylia tayloriLOTUS Database
Trilophozia quinquedentataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct Parent5,10-cycloaromadendrane sesquiterpenoids
Alternative Parents
Substituents
  • 5,10-cycloaromadendrane sesquiterpenoid
  • Guaiane sesquiterpenoid
  • Tertiary alcohol
  • Cyclic alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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
logP3.18ChemAxon
pKa (Strongest Basic)-0.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity66.6 m³·mol⁻¹ChemAxon
Polarizability27.32 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00021213
Chemspider ID113385699
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12304982
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Arya A, Mittal V, Kaushik D, Kumar M, Alotaibi SS, Albogami SM, El-Saber Batiha G, Jeandet P: Mutivariate optimization strategy for the sonication-based extraction of Nardostachys jatamansi roots and analysis for chemical composition, anti-oxidant and acetylcholinesterase inhibitory potential. Ultrason Sonochem. 2022 Sep;89:106133. doi: 10.1016/j.ultsonch.2022.106133. Epub 2022 Aug 24. [PubMed:36037596 ]
  2. Santana MLG, Melo JPR, Camara CAGD, Moraes MM, Araujo CA, Vasconcelos GJN, Pereira MRS, Zartman CE: Lethal and sublethal effects of essential oils fromPiper capitarianumYunck andPiper krukoffiiYunck onPlutella xylostellaL. An Acad Bras Cienc. 2022 Aug 8;94(2):e20200072. doi: 10.1590/0001-3765202220200072. eCollection 2022. [PubMed:35946642 ]
  3. Ebadollahi A, Naseri B, Abedi Z, Setzer WN, Changbunjong T: Promising Insecticidal Efficiency of Essential Oils Isolated from Four Cultivated Eucalyptus Species in Iran against the Lesser Grain Borer, Rhyzopertha dominica (F.). Insects. 2022 May 31;13(6):517. doi: 10.3390/insects13060517. [PubMed:35735854 ]
  4. Zhang X, Wang J, Zhu H, Wang J, Zhang H: Chemical Composition, Antibacterial, Antioxidant and Enzyme Inhibitory Activities of the Essential Oil from Leaves of Psidium guajava L. Chem Biodivers. 2022 May;19(5):e202100951. doi: 10.1002/cbdv.202100951. Epub 2022 Apr 12. [PubMed:35344272 ]
  5. Karacelik AA, Turkucar SA, Karakose M: Phytochemical Composition and Biological Activities of Angelica sylvestris L. var. stenoptera Ave-Lall ex Boiss.: An Endangered Medicinal Plant of Northeast Turkey. Chem Biodivers. 2022 Oct;19(10):e202200552. doi: 10.1002/cbdv.202200552. Epub 2022 Sep 29. [PubMed:36085404 ]
  6. LOTUS database [Link]