Totarolone - Compound Card

Totarolone

Select a section from the left sidebar

Totarolone

Structure
Zoomed Structure
  • Family: Plantae - Cupressaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles O=C1CCC2(C(C1(C)C)CCc1c2ccc(c1C(C)C)O)C
InChI InChI=1S/C20H28O2/c1-12(2)18-13-6-9-16-19(3,4)17(22)10-11-20(16,5)14(13)7-8-15(18)21/h7-8,12,16,21H,6,9-11H2,1-5H3
InChIKey AOHUEFCBXPOOLQ-UHFFFAOYSA-N
Formula C20H28O2
HBA 2
HBD 1
MW 300.44
Rotatable Bonds 1
TPSA 37.3
LogP 4.72
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 300.21
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tetraclinis articulata Cupressaceae Plantae 13717

Showing of synonyms

  • 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: 625254
Nmrshiftdb2: 70017860

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)CCC3C2CCC(=O)C3

Level: 0

Mol. Weight: 300.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.590
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.59

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.750
Plasma Protein Binding
44.34
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.670
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.340
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.030
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.840
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
Toxic
T. Pyriformis
3.700
Rat (Acute)
2.290
Rat (Chronic Oral)
1.830
Fathead Minnow
4.330
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
356.670
Hydration Free Energy
-5.250
Log(D) at pH=7.4
4.050
Log(P)
4.2
Log S
-4.86
Log(Vapor Pressure)
-5.73
Melting Point
121.76
pKa Acid
10.22
pKa Basic
6.48
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9269
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9269
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.9071
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.9071
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8865
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8865
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8796
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8796
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8550
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8550
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8499
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8499
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8429
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8429
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8161
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8161
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8032
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8032
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8024
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8024
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7749
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7749
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7667
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7667
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.7657
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.7657
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7627
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7627
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7625
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7625
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7559
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7559
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7546
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7546
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7527
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7527
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7490
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7490
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7442
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7442
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7403
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7403
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7355
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7355
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7346
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7346
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7329
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7329
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7280
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7280
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7228
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7228
Caspase-7 P55210 CASP7_HUMAN Homo sapiens 3 0.7182
Caspase-7 P55210 CASP7_HUMAN Homo sapiens 3 0.7182
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7178
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7178
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7173
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7173
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7100
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7100
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7077
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7077
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7074
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7074
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7065
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7065
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7046
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7046
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7045
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7045

Download SDF