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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
Structure of TOTAROL

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

HIDE SMILES / InChI

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
11.69 µM [IC50]
11.0 µM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown
Curative
Unknown
Curative
Unknown
Curative
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
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
Totarol demonstrated nematicidal and antifouling activities against Caenorhabditis elegans and Artemia salina at a concentration of 80 ug/mL and 1 ug/mL, respectively.