Doronine - Compound Card

Doronine

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Doronine

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles CN1CC[C@H]2OC(=O)[C@](O)(C[C@H]([C@@](C(=O)OCC(=CC1)C2=O)(C)OC(=O)C)C)[C@H](Cl)C
InChI InChI=1S/C21H30ClNO8/c1-12-10-21(28,13(2)22)19(27)30-16-7-9-23(5)8-6-15(17(16)25)11-29-18(26)20(12,4)31-14(3)24/h6,12-13,16,28H,7-11H2,1-5H3/t12-,13-,16-,20-,21+/m1/s1
InChIKey VGRSISYREBBIAL-YLRKQKNVSA-N
Formula C21H30ClNO8
HBA 9
HBD 1
MW 459.92
Rotatable Bonds 2
TPSA 119.44
LogP 0.99
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.71
Exact Mass 459.17
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 othonnae Asteraceae Plantae 214901
4 Senecio ambiguus Asteraceae Plantae 189228
5 Senecio cineraria Asteraceae Plantae 252537

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: 5281726
Kegg Ligand: C10286
Chebi: 4701
Nmrshiftdb2: 60069751
CPRiL: 414421
Structure

SMILES: C12=CCNCCC(C1=O)OC(=O)CCCCC(=O)OC2

Level: 0

Mol. Weight: 459.92 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.99
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.86
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.99

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.28
Plasma Protein Binding
37.92
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.31
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.42
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.83
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.66
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
-18.86
Rat (Acute)
3.06
Rat (Chronic Oral)
1.9
Fathead Minnow
4.02
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
411.71
Hydration Free Energy
-6.72
Log(D) at pH=7.4
1.13
Log(P)
0.78
Log S
-2.11
Log(Vapor Pressure)
-8.79
Melting Point
173.56
pKa Acid
5.22
pKa Basic
5.88
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8076
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8076
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7829
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7829
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7484
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7484
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7283
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7283
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7245
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7245
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7085
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7085
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7081
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7081
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7021
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7021

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