Senecivernine - Compound Card

Senecivernine

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Senecivernine

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles C=C1C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@@H]([C@H]1C)C)(C)O
InChI InChI=1S/C18H25NO5/c1-10-11(2)16(20)24-14-6-8-19-7-5-13(15(14)19)9-23-17(21)18(4,22)12(10)3/h5,10,12,14-15,22H,2,6-9H2,1,3-4H3/t10-,12+,14+,15+,18+/m0/s1
InChIKey FLUOSFVUPTUYEX-QHOAOGIMSA-N
Formula C18H25NO5
HBA 6
HBD 1
MW 335.4
Rotatable Bonds 0
TPSA 76.07
LogP 1.05
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 335.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Senecio abrotanifolius Asteraceae Plantae 189225
2 Senecio alpinus Asteraceae Plantae 189227
3 Senecio cineraria Asteraceae Plantae 252537
4 Senecio gnaphalodes Asteraceae Plantae 2868836
5 Senecio jacobaea Asteraceae Plantae 98722
6 Senecio subalpinus Asteraceae Plantae 189250

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: 442764
Kegg Ligand: C10393
Chebi: 9109
Nmrshiftdb2: 60069572

No compound-protein relationship available.

Structure

SMILES: C1OC(=O)CCCC(=C)C(=O)OC(C2C1=3)CCN2CC3

Level: 0

Mol. Weight: 335.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
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
-2.91

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.54
Plasma Protein Binding
30.01
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
7.21
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.83
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.13
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.37
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-3.21
Rat (Acute)
3.55
Rat (Chronic Oral)
1.85
Fathead Minnow
3.96
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
363.73
Hydration Free Energy
-7.87
Log(D) at pH=7.4
0.87
Log(P)
1.19
Log S
-2.27
Log(Vapor Pressure)
-7.4
Melting Point
192.7
pKa Acid
6.22
pKa Basic
6.78
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 0.9263
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9263
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7847
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7847
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7604
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7604
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7539
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7539
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7468
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7468
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7465
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7465
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7432
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7432
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7369
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7369
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7171
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7171
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7139
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7139
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7080
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7080

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