Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H30O |
Molecular Weight | 286.4516 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CCC3=C(C=CC(O)=C3C(C)C)[C@@]1(C)CCCC2(C)C
InChI
InChIKey=ZRVDANDJSTYELM-FXAWDEMLSA-N
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
DescriptionCurator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19755141
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19755141
Totarol is a meroterpene, and more precisely a terpenophenolic, a chemical compound that is part terpene and part natural phenol. It is a naturally produced diterpene that is bioactive as (+)-totarol. It was first isolated by McDowell and Esterfield from the heartwood of Podocarpus totara, a yew tree found in New Zealand. Totarol showed good activity against Mycobacterium tuberculosis H(37)Rv (MIC of 73.7 uM). It was also most active against the isoniazid-, streptomycin-, and moxifloxacin-resistant variants (MIC of 38.4, 83.4 and 60 uM, respectively). Totarol demonstrated nematicidal and antifouling activities against Caenorhabditis elegans and Artemia salina, it inhibited Leishmania donovani promastigotes, showed good antimicrobial activity against effluxing strains of Staphylococcus aureus. Totarol inhibits bacterial proliferation by targeting FtsZ and it may be useful as a lead compound to develop an effective antitubercular drug.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26440581
Curator's Comment: Totarol prevented glutamate- and oxygen and glucose deprivation-induced neuronal death in primary rat cerebellar granule neuronal cells and cerebral cortical neurons.
Originator
Sources: http://www.bifcpresidency.tn.gov.in/Totarol.html
Curator's Comment: Totarol was first isolated by McDowell and Esterfield from the heartwood of Podocarpus totara, a yew tree found in New Zealand.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL352 |
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Target ID: CHEMBL612856 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22196513 |
11.69 µM [IC50] | ||
Target ID: CHEMBL2111188 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19755141 |
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Target ID: CHEMBL367 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19067375 |
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Target ID: CHEMBL4213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17348691 |
11.0 µM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Unknown Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Aromatase inhibitory activities of standishinal and the diterpenoids from the bark of Thuja standishii. | 2002 Aug |
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Novel domino reactions for diterpene synthesis. | 2004 Dec 10 |
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The antifungal compound totarol of Thujopsis dolabrata var. hondai seeds selects for fungi on seedling root surfaces. | 2007 Dec |
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Antimycobacterial terpenoids from Juniperus communis L. (Cuppressaceae). | 2009 Dec 10 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26440581
Rats were intravenously treated with totarol at
2 h, 4 h and 6 h after ischemia onset. Animals were randomly divided into six groups (n = 8–12 per group): Sham, Vehicle, totarol (0.1 ug/kg), totarol (1 ug/kg), totarol (10 ug/kg)
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19067375
Totarol demonstrated nematicidal and antifouling activities against Caenorhabditis elegans and Artemia salina at a concentration of 80 ug/mL and 1 ug/mL, respectively.
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DTXSID9047752
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TOTAROL
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SUBSTANCE RECORD