Structure Database (LMSD)
Common Name
(+)-Totarol
Systematic Name
(+)-8,11,13-totara-trien-13-ol
Synonyms
3D model of (+)-Totarol
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Level 4 Class
Biological Context
Totarol is a diterpene originally isolated from P. totara that has diverse biological activities, including antibacterial, antioxidant, and neuroprotective properties.1 It is active against Gram-positive bacteria, including P. acnes, S. mutans, B. subtilis, and B. ammoniagenes (MICs = 0.39, 0.78, 1.56, and 0.78 µg/ml, respectively), as well as penicillin-resistant and -susceptible strains of S. aureus (MICs = 0.78 and 1.56 µg/ml, respectively).2 It inhibits mitochondrial respiration in P. aeruginosa, inhibiting NADH-cytochrome c, NADH-DPIP, and NADH-coenzyme Q reductases but not cytochrome c oxidase.3 Totarol inhibits Fe(III)-ADP/NADPH-induced lipid oxidation in rat liver microsomes and mitochondria (IC50s = 4.79 and 0.47 µM, respectively) and autooxidation of linoleic acid with an IC50 value of 9.8 µM.4 In rat primary cerebellar granule cells, totarol increases Akt and GSK-3β phosphorylation when used at a concentration of 5 µM and prevents neuronal death induced by glutamate or oxygen and glucose deprivation.5 It also reduces infarct volume in a rat model of acute cerebral ischemic injury when administered at doses of 1 and 10 microgram/kg.
This information has been provided by Cayman Chemical
References
1. Short, W.F., and Stromberg, H. Totarol. Part I. J. Chem. Soc. 516-520 (1937).
2. Kubo, I., Muroi, H., and Himehima, M. Antibacterial activity of totarol and its potentiation. J. Nat. Prod. 55(10), 1436-1440 (1992).
4. Haraguchi, H., Ishikawa, H., and Kubo, I. Antioxidative action of diterpenoids from Podocarpus nagi. Planta Med. 63(3), 213-215 (1997).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Podocarpus totara
(#56901)
Pinopsida
(#58019)
Totarol. Part II,
J Chem Soc, 1951
J Chem Soc, 1951
DOI:
10.1039/JR9510002979
String Representations
InChiKey (Click to copy)
ZRVDANDJSTYELM-FXAWDEMLSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
C1CC[C@]2(C)C3C=CC(O)=C(C(C)C)C=3CC[C@@]2([H])C1(C)C
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
21
Rings
3
Aromatic Rings
1
Rotatable Bonds
1
Van der Waals Molecular Volume
307.45
Topological Polar Surface Area
20.23
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
1
logP
5.55
Molar Refractivity
88.99
Admin
Created at
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Updated at
6th Feb 2024