Isoline - Compound Card

Isoline

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Isoline

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)(OC(=O)C)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3
InChI InChI=1S/C20H29NO7/c1-5-20(25)10-12(2)19(4,28-13(3)22)17(23)26-11-14-6-8-21-9-7-15(16(14)21)27-18(20)24/h6,12,15-16,25H,5,7-11H2,1-4H3/t12-,15-,16-,19+,20-/m1/s1
InChIKey IYLGZMTXKJYONK-ACLXAEORSA-N
Formula C20H29NO7
HBA 8
HBD 1
MW 395.45
Rotatable Bonds 2
TPSA 102.37
LogP 0.96
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 395.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Senecio ruwenzoriensis Asteraceae Plantae 1896791

Showing of synonyms

  • Benn M, Were O. (1992). Ruwenine and ruzorine: pyrrolizidine alkaloids of Senecio ruwenzoriensis. Phytochemistry,1992,31(9),3295-3296. [View] [PubMed]
Pubchem: 185716
Nmrshiftdb2: 70106306
CPRiL: 231676
Structure

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

Level: 0

Mol. Weight: 395.45 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Non-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
-3.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.46
Plasma Protein Binding
31.23
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.65
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.57
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
10.3
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
-12.96
Rat (Acute)
3.64
Rat (Chronic Oral)
1.94
Fathead Minnow
3.98
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
387.6
Hydration Free Energy
-6.77
Log(D) at pH=7.4
0.84
Log(P)
1.11
Log S
-2.37
Log(Vapor Pressure)
-7.94
Melting Point
156.25
pKa Acid
5.96
pKa Basic
6.07
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8533
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8533
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7781
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7781
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7080
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7080

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