Totarolenone - Compound Card

Totarolenone

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Totarolenone

Structure
Zoomed Structure
  • Family: Plantae - Cupressaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles O=C1C=CC2([C@H](C1(C)C)CCc1c2ccc(c1C(C)C)O)C
InChI InChI=1S/C20H26O2/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/h7-8,10-12,16,21H,6,9H2,1-5H3/t16-,20?/m0/s1
InChIKey FJOFVCSAFYIQEB-DJZRFWRSSA-N
Formula C20H26O2
HBA 2
HBD 1
MW 298.43
Rotatable Bonds 1
TPSA 37.3
LogP 4.5
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.55
Exact Mass 298.19
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: 162978563
Nmrshiftdb2: 60071048

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)CCC3C2C=CC(=O)C3

Level: 0

Mol. Weight: 298.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.490
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.610
Plasma Protein Binding
68.49
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
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.200
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.350
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.160
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.590
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
3.360
Rat (Acute)
2.420
Rat (Chronic Oral)
1.950
Fathead Minnow
4.320
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
362.790
Hydration Free Energy
-6.100
Log(D) at pH=7.4
4.240
Log(P)
4.24
Log S
-4.88
Log(Vapor Pressure)
-5.88
Melting Point
132.8
pKa Acid
10.24
pKa Basic
5.66
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 0.8887
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8887
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8761
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8761
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8471
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8471
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8373
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8373
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8205
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8205
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8125
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8125
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7828
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7828
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7820
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7820
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7818
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7818
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7626
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7626
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7621
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7621
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7602
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7602
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7553
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7553
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7541
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7541
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7515
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7515
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7471
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7471
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7408
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7408
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7340
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7340
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7240
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7240
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7186
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7186
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.7171
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.7171
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7165
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7165
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7067
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7067

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