Erucifoline - Compound Card

Erucifoline

Select a section from the left sidebar

Erucifoline

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles C/C=C\1/C[C@@]2(CO)O[C@@]2(C)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3
InChI InChI=1S/C18H23NO6/c1-3-11-8-18(10-20)17(2,25-18)16(22)23-9-12-4-6-19-7-5-13(14(12)19)24-15(11)21/h3-4,13-14,20H,5-10H2,1-2H3/b11-3-/t13-,14-,17+,18+/m1/s1
InChIKey NOQVBHHOUTTZGE-LUZNJDLOSA-N
Formula C18H23NO6
HBA 7
HBD 1
MW 349.38
Rotatable Bonds 1
TPSA 88.6
LogP 0.33
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 349.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Senecio boissieri Asteraceae Plantae 214893
2 Senecio minutus Asteraceae Plantae 189241
3 Senecio persoonii Asteraceae Plantae 214902
4 Senecio ambiguus Asteraceae Plantae 189228
5 Senecio aquaticus Asteraceae Plantae 189230
6 Senecio chrysanthemoides Asteraceae Plantae 189235
7 Senecio erucifolius Asteraceae Plantae 189238
8 Senecio gnaphalodes Asteraceae Plantae 2868836
9 Senecio jacobaea Asteraceae Plantae 98722

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: 76308652
Chebi: 136462
Nmrshiftdb2: 70036005
Metabolights: MTBLC136462
CPRiL: 141607
Structure

SMILES: C12C(O2)CC(=C)C(=O)OC3C4C(COC1=O)=CCN4CC3

Level: 0

Mol. Weight: 349.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.32
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.91
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.18

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.31
Plasma Protein Binding
8.02
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
11.24
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.37
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.38
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
10.87
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
-6.53
Rat (Acute)
4.09
Rat (Chronic Oral)
1.7
Fathead Minnow
3.98
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
411.18
Hydration Free Energy
-8.57
Log(D) at pH=7.4
0.04
Log(P)
-0.29
Log S
-1.88
Log(Vapor Pressure)
-7.72
Melting Point
146.82
pKa Acid
5.16
pKa Basic
5.99
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 0.8568
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8568
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8113
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8113
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8062
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8062
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7747
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7747
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7491
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7491
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7152
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7152
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7063
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7063
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7063
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7063
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7032
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7032
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7005
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7005

Download SDF