Adonifoline - Compound Card

Adonifoline

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Adonifoline

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles CC1OCC23CC1(O)C(=O)O[C@H]1CCN4[C@H]1C(=CC4)COC(=O)C3(O2)C
InChI InChI=1S/C18H23NO7/c1-10-18(22)8-17(9-24-10)16(2,26-17)14(20)23-7-11-3-5-19-6-4-12(13(11)19)25-15(18)21/h3,10,12-13,22H,4-9H2,1-2H3/t10?,12-,13-,16?,17?,18?/m0/s1
InChIKey MYOFCWPLRKBPJD-CDZGDAMASA-N
Formula C18H23NO7
HBA 8
HBD 1
MW 365.38
Rotatable Bonds 0
TPSA 97.83
LogP -0.46
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.78
Exact Mass 365.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Senecio abrotanifolius Asteraceae Plantae 189225
2 Senecio adonidifolius Asteraceae Plantae 189226

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: 91746988
Nmrshiftdb2: 60069745

No compound-protein relationship available.

Structure

SMILES: C123C(O3)C(=O)OCC=4C5C(CCN5CC4)OC(=O)C(C1)COC2

Level: 0

Mol. Weight: 365.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.31
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.93
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.23

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.26
Plasma Protein Binding
6.89
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
10.22
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.37
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.26
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
10.13
Micronucleos
Toxic
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
-6.35
Rat (Acute)
4.3
Rat (Chronic Oral)
1.76
Fathead Minnow
3.96
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
377.13
Hydration Free Energy
-7.12
Log(D) at pH=7.4
-0.17
Log(P)
-0.9
Log S
-1.84
Log(Vapor Pressure)
-7.83
Melting Point
154.36
pKa Acid
4.48
pKa Basic
5.38
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7720
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7720
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7573
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7573

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