Jacoline - Compound Card

Jacoline

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Jacoline

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles C[C@H]([C@@]1(O)C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3)O
InChI InChI=1S/C18H27NO7/c1-10-8-18(24,11(2)20)16(22)26-13-5-7-19-6-4-12(14(13)19)9-25-15(21)17(10,3)23/h4,10-11,13-14,20,23-24H,5-9H2,1-3H3/t10-,11-,13-,14-,17-,18+/m1/s1
InChIKey FMWJEBGSMAOQNN-YLFNNMARSA-N
Formula C18H27NO7
HBA 8
HBD 3
MW 369.41
Rotatable Bonds 1
TPSA 116.53
LogP -0.64
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.78
Exact Mass 369.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Senecio incanus Asteraceae Plantae 189239
2 Senecio minutus Asteraceae Plantae 189241
3 Senecio ambiguus Asteraceae Plantae 189228
4 Senecio cineraria Asteraceae Plantae 252537
5 Senecio gnaphalodes Asteraceae Plantae 2868836
6 Senecio jacobaea Asteraceae Plantae 98722
7 Crotalaria fascicularis Leguminosae/Fabaceae Plantae 1132202

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]
  • Asres K, Sporer F, et al. (2004). Patterns of pyrrolizidine alkaloids in 12 Ethiopian Crotalaria species.. Biochemical systematics and ecology,2004,32(10),915-930. [View] [PubMed]
Pubchem: 78358487
Chebi: 136452
Metabolights: MTBLC136452
CPRiL: 410214
Structure

SMILES: C1CN2CCC(C2C=13)OC(=O)CCCCC(=O)OC3

Level: 0

Mol. Weight: 369.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.04
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.96
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.78

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.44
Plasma Protein Binding
21.44
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.51
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.34
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.47
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
9.02
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
-5.88
Rat (Acute)
3.81
Rat (Chronic Oral)
2.19
Fathead Minnow
3.83
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
404.84
Hydration Free Energy
-12.98
Log(D) at pH=7.4
0.34
Log(P)
-0.58
Log S
-1.63
Log(Vapor Pressure)
-9.29
Melting Point
187.33
pKa Acid
5.62
pKa Basic
6.59
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 0.8375
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8375
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7682
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7682
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7620
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7620
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7466
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7466
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7354
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7354

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