Jaconine - Compound Card

Jaconine

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Jaconine

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles CC(C1(O)CC(C)C(C)(O)C(=O)OCC2=CCN3C2C(OC1=O)CC3)Cl
InChI InChI=1S/C18H26ClNO6/c1-10-8-18(24,11(2)19)16(22)26-13-5-7-20-6-4-12(14(13)20)9-25-15(21)17(10,3)23/h4,10-11,13-14,23-24H,5-9H2,1-3H3
InChIKey CKPJPJSVQMEGBC-UHFFFAOYSA-N
Formula C18H26ClNO6
HBA 7
HBD 2
MW 387.86
Rotatable Bonds 1
TPSA 96.3
LogP 0.6
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.78
Exact Mass 387.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Senecio incanus Asteraceae Plantae 189239
2 Senecio ambiguus Asteraceae Plantae 189228
3 Senecio cineraria Asteraceae Plantae 252537
4 Senecio gnaphalodes Asteraceae Plantae 2868836
5 Senecio jacobaea Asteraceae Plantae 98722

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: 119200
Nmrshiftdb2: 60069747

No compound-protein relationship available.

Structure

SMILES: C1CN2CCC(C2C=13)OC(=O)CCCCC(=O)OC3

Level: 0

Mol. Weight: 387.86 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.05
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.93
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.73

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.42
Plasma Protein Binding
-1.52
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
5.5
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.48
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.0
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.46
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
-1.26
Rat (Acute)
3.51
Rat (Chronic Oral)
1.84
Fathead Minnow
4.01
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
379.6
Hydration Free Energy
-10.34
Log(D) at pH=7.4
0.94
Log(P)
0.87
Log S
-2.15
Log(Vapor Pressure)
-7.74
Melting Point
168.0
pKa Acid
6.18
pKa Basic
6.75
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9254
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9254
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8179
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8179
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8052
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8052
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7646
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7646
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7462
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7462
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7305
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7305

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