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([C@@]1(O)C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CCN3[C@H]2[C@H](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/t10-,11?,13-,14-,17-,18+/m1/s1
InChIKey CKPJPJSVQMEGBC-SQEGYQCZSA-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 Solanecio angulatus Asteraceae Plantae 1670880
2 Solanecio mannii Asteraceae Plantae —
3 Solanecio tuberosus var. tuberosus Asteraceae Plantae 189251

Showing of synonyms

  • Asres K, Sporer F, et al. (2008). Occurrence of pyrrolizidine alkaloids in three Ethiopian Solanecio species. Biochemical Systematics and Ecology,2008,36(5-6),399-407. [View] [PubMed]
Pubchem: 72614

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)
-5.04
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.95
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.97

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.45
Plasma Protein Binding
22.02
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
5.82
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.54
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.02
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
10.24
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
-6.7
Rat (Acute)
3.44
Rat (Chronic Oral)
1.85
Fathead Minnow
3.94
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
385.86
Hydration Free Energy
-11.02
Log(D) at pH=7.4
1.07
Log(P)
0.88
Log S
-2.33
Log(Vapor Pressure)
-8.29
Melting Point
173.49
pKa Acid
6.09
pKa Basic
6.33
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7859
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7859
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7228
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7228

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