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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
Molecular Formula C20H30O
Molecular Weight 286.4516
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

CNS Active
3913
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

Esterfield, T.H.|McDowell, J.C.
1
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

2015
471
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Inhibitor
8297
 11.69 µM [IC50]
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
 11.0 µM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Basic research
Unknown

Approved Use

Unknown
Curative
Basic research
Unknown

Approved Use

Unknown
Curative
Basic research
Unknown

Approved Use

Unknown
Curative
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A cyclic peroxide of clerodenoic acid from the Taiwanese liverwort Schistochila acuminata.
2001
Effects of (+)-totarol, a diterpenoid antibacterial agent, on phospholipid model membranes.
2001 Apr 2
Anti-tumor promoting diterpenes from the stem bark of Thuja standishii (Cupressaceae).
2001 Jul
(+)-Totarol from Chamaecyparis nootkatensis and activity against Mycobacterium tuberculosis.
2001 Jun
Aromatase inhibitory activities of standishinal and the diterpenoids from the bark of Thuja standishii.
2002 Aug
A MAS-NMR study of the location of (+)-totarol, a diterpenoid bioactive molecule, in phospholipid model membranes.
2002 Oct
Development of a method to quantify in vitro the synergistic activity of "natural" antimicrobials.
2003 Aug 25
Synthesis of totarol amino alcohol derivatives and their antiplasmodial activity and cytotoxicity.
2003 Oct 1
Novel domino reactions for diterpene synthesis.
2004 Dec 10
Antimycobacterial constituents from Juniperus procera, Ferula communis and Plumbago zeylanica and their in vitro synergistic activity with isonicotinic acid hydrazide.
2004 Nov
Antineoplastic agents. 529. Isolation and structure of nootkastatins 1 and 2 from the Alaskan yellow cedar Chamaecyparis nootkatensis.
2004 Sep
Gastroprotective and cytotoxic effect of semisynthetic ferruginol derivatives.
2007 Feb
Antiparasitic, nematicidal and antifouling constituents from Juniperus berries.
2008 Dec
Antibacterial novel phenolic diterpenes from Podocarpus macrophyllus D. Don.
2008 Dec
Engineering and Applications of fungal laccases for organic synthesis.
2008 Nov 20
Harnessing gene expression to identify the genetic basis of drug resistance.
2009
Antimycobacterial terpenoids from Juniperus communis L. (Cuppressaceae).
2009 Dec 10
Molecular basis of the anti-inflammatory property exhibited by cyclo-pentano phenanthrenol isolated from Lippia nodiflora.
2010
Synthesis of antimicrobial natural products targeting FtsZ: (+)-totarol and related totarane diterpenes.
2010 Aug 6
Patents

Patents

20060017769
1
20090041691
1
JPH01311019A
1

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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:28:44 GMT 2023
Edited
by admin
on Sat Dec 16 01:28:44 GMT 2023
Record UNII
67NH2854WW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TOTAROL
INCI  
INCI  
Official Name English
(4BS-TRANS)-4B,5,6,7,8,8A,9,10-OCTAHYDRO-4B,8,8-TRIMETHYL-1-(1-ISOPROPYL)-2-PHENANTHRENOL
Common Name English
(4AS,10AS)-7-HYDROXY-8-ISOPROPYL-1,1,4A-TRIMETHYL-1,2,3,4,4A,9,10,10A-OCTAHYDROPHENANTHRENE
Common Name English
2-PHENANTHRENOL, 4B,5,6,7,8,8A,9,10-OCTAHYDRO-4B,8,8-TRIMETHYL-1-(1-METHYLETHYL)-, (4BS-TRANS)-
Common Name English
2-PHENANTHRENOL, 4B,5,6,7,8,8A,9,10-OCTAHYDRO-4B,8,8-TRIMETHYL-1-(1-METHYLETHYL)-, (4BS,8AS)-
Common Name English
NSC-299936
Code English
(+)-TOTAROL
Common Name English
TOTAROL [INCI]
Common Name English
TRANS-TOTAROL
Common Name English
PODOCARPA-8,11,13-TRIEN-13-OL, 14-ISOPROPY
Common Name English
Code System Code Type Description
DAILYMED
67NH2854WW
Created by admin on Sat Dec 16 01:28:44 GMT 2023 , Edited by admin on Sat Dec 16 01:28:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID9047752
Created by admin on Sat Dec 16 01:28:44 GMT 2023 , Edited by admin on Sat Dec 16 01:28:44 GMT 2023
PRIMARY
FDA UNII
67NH2854WW
Created by admin on Sat Dec 16 01:28:44 GMT 2023 , Edited by admin on Sat Dec 16 01:28:44 GMT 2023
PRIMARY
RXCUI
1600439
Created by admin on Sat Dec 16 01:28:44 GMT 2023 , Edited by admin on Sat Dec 16 01:28:44 GMT 2023
PRIMARY RxNorm
CAS
511-15-9
Created by admin on Sat Dec 16 01:28:44 GMT 2023 , Edited by admin on Sat Dec 16 01:28:44 GMT 2023
PRIMARY
WIKIPEDIA
TOTAROL
Created by admin on Sat Dec 16 01:28:44 GMT 2023 , Edited by admin on Sat Dec 16 01:28:44 GMT 2023
PRIMARY
MESH
C078548
Created by admin on Sat Dec 16 01:28:44 GMT 2023 , Edited by admin on Sat Dec 16 01:28:44 GMT 2023
PRIMARY
PUBCHEM
92783
Created by admin on Sat Dec 16 01:28:44 GMT 2023 , Edited by admin on Sat Dec 16 01:28:44 GMT 2023
PRIMARY
NSC
299936
Created by admin on Sat Dec 16 01:28:44 GMT 2023 , Edited by admin on Sat Dec 16 01:28:44 GMT 2023
PRIMARY
NIH
NCATS
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