Jacozine - Compound Card

Jacozine

Select a section from the left sidebar

Jacozine

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(=C)C[C@]21O[C@H]2C)(C)O
InChI InChI=1S/C18H23NO6/c1-10-8-18(11(2)25-18)16(21)24-13-5-7-19-6-4-12(14(13)19)9-23-15(20)17(10,3)22/h4,11,13-14,22H,1,5-9H2,2-3H3/t11-,13+,14+,17+,18-/m0/s1
InChIKey XCEPKQNOWNOSFH-CGPXFRKCSA-N
Formula C18H23NO6
HBA 7
HBD 1
MW 349.38
Rotatable Bonds 0
TPSA 88.6
LogP 0.32
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 cannabifolius Asteraceae Plantae 189232
2 Senecio ambiguus Asteraceae Plantae 189228
3 Senecio cineraria Asteraceae Plantae 252537
4 Senecio gnaphalodes Asteraceae Plantae 2868836
5 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: 119052
Chebi: 136458
Nmrshiftdb2: 60069743
Metabolights: MTBLC136458

No compound-protein relationship available.

Structure

SMILES: C=C(C1)CC(=O)OCC(=CCN2CC3)C2C3OC(=O)C14CO4

Level: 0

Mol. Weight: 349.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.27
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
-3.25

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.26
Plasma Protein Binding
9.64
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
11.17
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
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.04
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
9.07
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
-4.71
Rat (Acute)
4.19
Rat (Chronic Oral)
1.9
Fathead Minnow
4.01
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
380.27
Hydration Free Energy
-7.48
Log(D) at pH=7.4
0.24
Log(P)
-0.07
Log S
-1.96
Log(Vapor Pressure)
-7.73
Melting Point
171.7
pKa Acid
4.3
pKa Basic
6.06
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8529
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8529
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8487
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8487
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8457
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8457
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8298
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8298
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8236
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8236
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8050
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8050
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7938
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7938
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7908
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7908
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7651
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7651
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7373
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7373
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7193
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7193
Glycogenin-1 P46976 GLYG_HUMAN Homo sapiens 3 0.7089
Glycogenin-1 P46976 GLYG_HUMAN Homo sapiens 3 0.7089
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7085
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7085

Download SDF