Acetylerucifoline - Compound Card

Acetylerucifoline

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Acetylerucifoline

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles C/C=C\1/C[C@]2(COC(=O)C)O[C@@]2(C)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3
InChI InChI=1S/C20H25NO7/c1-4-13-9-20(11-26-12(2)22)19(3,28-20)18(24)25-10-14-5-7-21-8-6-15(16(14)21)27-17(13)23/h4-5,15-16H,6-11H2,1-3H3/b13-4-/t15-,16-,19+,20-/m1/s1
InChIKey PSLAXCVGXXVNFJ-ALWXOEHVSA-N
Formula C20H25NO7
HBA 8
HBD 0
MW 391.42
Rotatable Bonds 2
TPSA 94.67
LogP 0.9
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 391.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Senecio aquaticus Asteraceae Plantae 189230
2 Senecio chrysanthemoides Asteraceae Plantae 189235

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: 101621380
Nmrshiftdb2: 60069752

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 391.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.23
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.92
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.28

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.35
Plasma Protein Binding
15.91
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
11.09
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.08
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.17
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
10.5
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
-14.26
Rat (Acute)
4.11
Rat (Chronic Oral)
1.73
Fathead Minnow
4.05
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Toxic
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
414.17
Hydration Free Energy
-5.92
Log(D) at pH=7.4
0.79
Log(P)
0.16
Log S
-2.48
Log(Vapor Pressure)
-7.52
Melting Point
139.67
pKa Acid
5.54
pKa Basic
5.63
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8779
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8779
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8274
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8274
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7617
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7617
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7558
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7558
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7548
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7548
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7123
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7123
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7039
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7039

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