Sennecicannabine - Compound Card

Sennecicannabine

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Sennecicannabine

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles O=C1O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@@]2(CC31O[C@H]3C)OC2)(C)O
InChI InChI=1S/C18H23NO7/c1-10-18(26-10)8-17(9-24-17)16(2,22)14(20)23-7-11-3-5-19-6-4-12(13(11)19)25-15(18)21/h3,10,12-13,22H,4-9H2,1-2H3/t10-,12+,13+,16-,17-,18?/m0/s1
InChIKey LTFQUYMOUGXPEW-SAUXSIBXSA-N
Formula C18H23NO7
HBA 8
HBD 1
MW 365.38
Rotatable Bonds 0
TPSA 101.13
LogP -0.46
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.78
Exact Mass 365.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Senecio cannabifolius Asteraceae Plantae 189232
2 Senecio ambiguus Asteraceae Plantae 189228

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: 158192
Nmrshiftdb2: 60069746

No compound-protein relationship available.

Structure

SMILES: O1CC12C(=O)OC3C4C(=CCN4CC3)COC(=O)CC5(CO5)C2

Level: 0

Mol. Weight: 365.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.19
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.91
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.66

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.18
Plasma Protein Binding
4.64
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
9.8
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.41
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.0
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
11.26
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
-11.58
Rat (Acute)
4.32
Rat (Chronic Oral)
1.54
Fathead Minnow
3.91
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
397.12
Hydration Free Energy
-6.76
Log(D) at pH=7.4
-0.67
Log(P)
-0.86
Log S
-1.86
Log(Vapor Pressure)
-7.84
Melting Point
151.11
pKa Acid
3.59
pKa Basic
5.15
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8702
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8702
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8307
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8307
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8237
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8237
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7762
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7762
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7646
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7646
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7234
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7234
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7159
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7159

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