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Record Information
Version2.0
Created at2021-06-20 22:45:16 UTC
Updated at2021-06-30 00:14:40 UTC
NP-MRD IDNP0040648
Secondary Accession NumbersNone
Natural Product Identification
Common Nametotarol
Provided ByJEOL DatabaseJEOL Logo
Description totarol is found in Afrocarpus gracilior, Apis mellifera, Biota orientalis, Callitropsis nootkatensis, Chamaecyparis formosensis, Chamaecyparis pisifera, Cryptomeria japonica, Cupressus sempervirens, Dacrycarpus vieillardii, Juniperus chinensis, Juniperus communis, Juniperus formosana, Juniperus phoenicea, Juniperus rigida, Nageia nagi, Platycladus orientalis, Podocarpus gnidioides, Podocarpus macrophyllus , Podocarpus sylvestris, Podocarpus totara, Podocarpus totara L. , Retrophyllum comptonii, Retrophyllum minus, Schistochila acuminata, Tetraclinis articulata, Thuja occidentalis, Thuja plicata, Thuja standishii and Thujopsis dolabrata. totarol was first documented in 2021 (PMID: 34227213). Based on a literature review a small amount of articles have been published on (+)-totarol (PMID: 33568294) (PMID: 34299601) (PMID: 34298240) (PMID: 34077024).
Structure
Thumb
Synonyms
ValueSource
4b,5,6,7,8,8a,9,10-Octahydro-4b,8,8-trimethyl-1-(1-methylethyl)-2-phenanthrenolMeSH
14-Isopropylpodocarpa-8,11,13-trien-13-olMeSH
Chemical FormulaC20H30O
Average Mass286.4590 Da
Monoisotopic Mass286.22967 Da
IUPAC Name(4bS,8aS)-4b,8,8-trimethyl-1-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-ol
Traditional Nametotarol
CAS Registry NumberNot Available
SMILES
[H]OC1=C([H])C([H])=C2C(=C1C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@]1([H])[C@]2(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H]
InChI Identifier
InChI=1S/C20H30O/c1-13(2)18-14-7-10-17-19(3,4)11-6-12-20(17,5)15(14)8-9-16(18)21/h8-9,13,17,21H,6-7,10-12H2,1-5H3/t17-,20+/m0/s1
InChI KeyZRVDANDJSTYELM-FXAWDEMLSA-N
Experimental Spectra
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
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
logP6.62ALOGPS
logP6.25ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)10.77ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity89.71 m³·mol⁻¹ChemAxon
Polarizability35.45 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID83757
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Ribeiro VP, Arruda C, Aldana-Mejia JA, Bastos JK, Tripathi SK, Khan SI, Khan IA, Ali Z: Phytochemical, Antiplasmodial, Cytotoxic and Antimicrobial Evaluation of a Southeast Brazilian Brown Propolis Produced by Apis mellifera Bees. Chem Biodivers. 2021 Jul 5. doi: 10.1002/cbdv.202100288. [PubMed:34227213 ]
  2. Ma LT, Wang CH, Hon CY, Lee YR, Chu FH: Discovery and characterization of diterpene synthases in Chamaecyparis formosensis Matsum. which participated in an unprecedented diterpenoid biosynthesis route in conifer. Plant Sci. 2021 Mar;304:110790. doi: 10.1016/j.plantsci.2020.110790. Epub 2020 Dec 9. [PubMed:33568294 ]
  3. Kim C, Le D, Lee M: Diterpenoids Isolated from Podocarpus macrophyllus Inhibited the Inflammatory Mediators in LPS-Induced HT-29 and RAW 264.7 Cells. Molecules. 2021 Jul 17;26(14). pii: molecules26144326. doi: 10.3390/molecules26144326. [PubMed:34299601 ]
  4. Laamari Y, Oubella A, Bimoussa A, El Mansouri AE, Ketatni EM, Mentre O, Ait Itto MY, Morjani H, Khouili M, Auhmani A: Design, Hemiysnthesis, crystal structure and anticancer activity of 1, 2, 3-triazoles derivatives of totarol. Bioorg Chem. 2021 Oct;115:105165. doi: 10.1016/j.bioorg.2021.105165. Epub 2021 Jul 14. [PubMed:34298240 ]
  5. Xu T, Huang L, Liu Z, Ma D, Zhang G, Ning X, Lu X, Liu H, Jiang B: Totarol, a natural diterpenoid, induces selective antitumor activity in SGC-7901 human gastric carcinoma cells by triggering apoptosis, cell cycle disruption and suppression of cancer cell migration. J BUON. 2021 Mar-Apr;26(2):640. [PubMed:34077024 ]
  6. Zaugg, J., et al. (2011). Zaugg, J., et al, J. Nat. Prod. 74, 1764 (2011). J. Nat. Prod..