Jacobine - Compound Card

Jacobine

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Jacobine

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles O=C1OCC2=CCN3[C@H]2[C@@H](CC3)OC(=O)[C@@]2(C[C@H]([C@@]1(C)O)C)O[C@H]2C
InChI InChI=1S/C18H25NO6/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/h4,10-11,13-14,22H,5-9H2,1-3H3/t10-,11+,13-,14-,17-,18+/m1/s1
InChIKey IAPHXJRHXBQDQJ-WKMWQDDRSA-N
Formula C18H25NO6
HBA 7
HBD 1
MW 351.4
Rotatable Bonds 0
TPSA 88.6
LogP 0.4
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.78
Exact Mass 351.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Senecio incanus Asteraceae Plantae 189239
2 Senecio cannabifolius Asteraceae Plantae 189232
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 Solanecio angulatus Asteraceae Plantae 1670880
8 Solanecio mannii Asteraceae Plantae —
9 Solanecio tuberosus var. tuberosus Asteraceae Plantae 189251

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. (2008). Occurrence of pyrrolizidine alkaloids in three Ethiopian Solanecio species. Biochemical Systematics and Ecology,2008,36(5-6),399-407. [View] [PubMed]
Pubchem: 442741
Kegg Ligand: C10339
Chebi: 6080
Nmrshiftdb2: 60026166
Metabolights: MTBLC6080
CPRiL: 42818
Structure

SMILES: O1CC12C(=O)OC3C4C(=CCN4CC3)COC(=O)CCC2

Level: 0

Mol. Weight: 351.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.26
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
-3.3

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.26
Plasma Protein Binding
9.14
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
11.12
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.44
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.18
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
9.15
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-4.06
Rat (Acute)
4.22
Rat (Chronic Oral)
1.85
Fathead Minnow
3.81
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
384.16
Hydration Free Energy
-7.56
Log(D) at pH=7.4
0.3
Log(P)
0.46
Log S
-2.04
Log(Vapor Pressure)
-7.5
Melting Point
157.6
pKa Acid
4.73
pKa Basic
6.04
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8052
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8052
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7990
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7990
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7955
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7955
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7904
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7904
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7842
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7842
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7731
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7731
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7729
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7729
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7517
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7517
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7375
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7375
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7267
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7267
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7124
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7124
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7096
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7096
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7011
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7011

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