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Totarol
- Family: Plantae - Cupressaceae
- Kingdom: Plantae, Animalia
-
Class: Terpenoid
- Subclass: Diterpenoid
| Canonical Smiles | CC(c1c(O)ccc2c1CC[C@@H]1[C@]2(C)CCCC1(C)C)C |
|---|---|
| InChI | 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 |
| InChIKey | ZRVDANDJSTYELM-FXAWDEMLSA-N |
| Formula | C20H30O |
| HBA | 1 |
| HBD | 1 |
| MW | 286.46 |
| Rotatable Bonds | 1 |
| TPSA | 20.23 |
| LogP | 5.55 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.7 |
| Exact Mass | 286.23 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Apis mellifica | Apidae | Animalia | 7460 |
| 2 | Juniperus phoenicea | Cupressaceae | Plantae | 61308 |
| 3 | Tetraclinis articulata | Cupressaceae | Plantae | 13717 |
Showing of synonyms
Totarol
511-15-9
(+)-Totarol
14-Isopropylpodocarpa-8,11,13-trien-13-ol
UNII-67NH2854WW
67NH2854WW
(+)-8,11,13-totara-trien-13-ol
Trans-Totarol
(4bS,8aS)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-2-ol
DTXSID9047752
NSC 299936
NSC-299936
2-Phenanthrenol, 4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-1-(1-methylethyl)-, (4bS,8aS)-
2-Phenanthrenol, 4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-1-(1-methylethyl)-, (4bS-trans)-
PODOCARPA-8,11,13-TRIEN-13-OL, 14-ISOPROPY
(4BS-TRANS)-4B,5,6,7,8,8A,9,10-OCTAHYDRO-4B,8,8-TRIMETHYL-1-(1-ISOPROPYL)-2-PHENANTHRENOL
TOTAROL [INCI]
DTXCID4027735
Zrvdandjstyelm-uhfffaoysa-n
CHEBI:69241
(4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol (>90%)
(4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol, 60%
(4bS-trans)-4b,5,6,7,8,8a,9,10-Octahydro-4b,8,8-trimethyl-1-(1-methylethyl)-2-phenanthrenol
Totarol - 98%
(4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol
MLS002695958
SCHEMBL285501
CHEMBL487602
BCBcMAP01_000081
ZRVDANDJSTYELM-FXAWDEMLSA-N
HY-N1136
BDBM50392993
AKOS025296157
FS-9301
FT65191
LMPR0104070001
4b,5,6,7,8,8a,9,10-Octahydro-4b,8,8-trimethyl-1-(1-methylethyl)-2-phenanthrenol
SMP1_000215
NCGC00385162-01
FT159642
SMR001562118
CS-0016424
G78505
Q7828277
(4AS,10AS)-7-HYDROXY-8-ISOPROPYL-1,1,4A-TRIMETHYL-1,2,3,4,4A,9,10,10A-OCTAHYDROPHENANTHRENE
(4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol, 98%
(4bS,8aS)-4b,8,8-trimethyl-1-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-ol
- Boufadi YM, Soubhye J, et al. (2014). Characterization and antioxidant properties of six Algerian propolis extracts: ethyl acetate extracts inhibit myeloperoxidase activity. International Journal of Molecular Sciences,2014,15(2),2327-2345. [View] [PubMed]
- Nasri N, Tlili N, et al. (2011). Chemical compounds from Phoenician juniper berries (Juniperus phoenicea). Natural Product Research,2011,25(18),1733-1742. [View]
- Barrero AF, Quılez del Moral JF, et al. (2003). Diterpenoids from Tetraclinis articulata that inhibit various human leukocyte functions. Journal of Natural Products,2003,66(6),844-850. [View] [PubMed]
Pubchem:
92783
Cas:
511-15-9
Gnps:
CCMSLIB00004689564
Zinc:
ZINC000001872131
Chebi:
69241
Nmrshiftdb2:
60031896
Metabolights:
MTBLC69241
Chembl:
CHEMBL487602
Comptox:
DTXSID9047752
Bindingdb:
50392993
CPRiL:
184279
SMILES: c1cccc(c12)CCC3C2CCCC3
Level: 0
Mol. Weight: 286.46 g/mol
Antibacterial
Absorption
- Caco-2 (logPapp)
- -4.8
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.6
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.8
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.6
- Plasma Protein Binding
- 86.52
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 9.3
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 2.98
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.04
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.4
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 3.57
- Rat (Acute)
- 2.1
- Rat (Chronic Oral)
- 1.97
- Fathead Minnow
- 4.11
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 332.3
- Hydration Free Energy
- -3.0
- Log(D) at pH=7.4
- 5.4
- Log(P)
- 5.86
- Log S
- -5.49
- Log(Vapor Pressure)
- -5.51
- Melting Point
- 121.99
- pKa Acid
- 11.86
- pKa Basic
- 7.43
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 3 | 0.8356 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 3 | 0.8356 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7511 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7511 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7499 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7499 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7432 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7432 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7261 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7261 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7256 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7256 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7089 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7089 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7039 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7039 |