Otosenine - Compound Card

Otosenine

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Otosenine

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles CN1CC[C@H]2OC(=O)C3(O[C@@H]3C)C[C@H](C(C(=O)OCC(=CC1)C2=O)(C)O)C
InChI InChI=1S/C19H27NO7/c1-11-9-19(12(2)27-19)17(23)26-14-6-8-20(4)7-5-13(15(14)21)10-25-16(22)18(11,3)24/h5,11-12,14,24H,6-10H2,1-4H3/t11-,12-,14-,18?,19?/m1/s1
InChIKey CZQLULNMKQAIQL-BYTHXJOKSA-N
Formula C19H27NO7
HBA 8
HBD 1
MW 381.43
Rotatable Bonds 0
TPSA 105.67
LogP 0.22
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.74
Exact Mass 381.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Senecio abrotanifolius Asteraceae Plantae 189225
2 Senecio adonidifolius Asteraceae Plantae 189226
3 Senecio ambiguus Asteraceae Plantae 189228
4 Senecio cineraria Asteraceae Plantae 252537
5 Senecio gnaphalodes Asteraceae Plantae 2868836

Showing of synonyms

  • Pelser PB, De Vos H, et al. (2005). Frequent gain and loss of pyrrolizidine alkaloids in the evolution of Senecio section Jacobaea (Asteraceae). Phytochemistry,2005,66,1285-1295. [View] [PubMed]
Pubchem: 91746991
Nmrshiftdb2: 60069748

No compound-protein relationship available.

Structure

SMILES: O1CC12C(=O)OC3C(=O)C(=CCNCC3)COC(=O)CCC2

Level: 0

Mol. Weight: 381.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.18
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.84
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.34

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.25
Plasma Protein Binding
8.96
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-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
11.78
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.11
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.75
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.55
Micronucleos
Toxic
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
-6.38
Rat (Acute)
3.84
Rat (Chronic Oral)
1.58
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
384.09
Hydration Free Energy
-7.68
Log(D) at pH=7.4
0.2
Log(P)
0.09
Log S
-1.53
Log(Vapor Pressure)
-7.73
Melting Point
167.02
pKa Acid
4.36
pKa Basic
5.47
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8402
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8402
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8341
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8341
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8319
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8319
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8118
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8118
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8024
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8024
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7488
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7488
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7450
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7450
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7435
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7435
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7270
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7270
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7264
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7264
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7253
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7253
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7186
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7186
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7157
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7157
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7129
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7129
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7111
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7111
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7105
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7105
Androgen receptor P19091 ANDR_MOUSE Mus musculus 3 0.7100
Androgen receptor P19091 ANDR_MOUSE Mus musculus 3 0.7100
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7077
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7077
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7068
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7068
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7063
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7063
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7060
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7060
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7051
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7051
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7035
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7035
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7017
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7017

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