Spartioidine - Compound Card

Spartioidine

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Spartioidine

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles C/C=C/1\CC(=C)[C@@](C)(O)C(=O)OCC2=CCN3C2[C@@H](OC1=O)CC3
InChI InChI=1S/C18H23NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,14-15,22H,2,6-10H2,1,3H3/b12-4+/t14-,15?,18+/m0/s1
InChIKey FCEVNJIUIMLVML-MIULREJOSA-N
Formula C18H23NO5
HBA 6
HBD 1
MW 333.38
Rotatable Bonds 0
TPSA 76.07
LogP 1.11
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.56
Exact Mass 333.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Senecio halleri Asteraceae-Compositae Plantae 214899
2 Senecio incanus Asteraceae-Compositae Plantae 189239
3 Senecio leucophyllus Asteraceae-Compositae Plantae 214900
4 Senecio persoonii Asteraceae-Compositae Plantae 214902
5 Senecio othonnae Asteraceae-Compositae Plantae 214901
6 Senecio paludosus Asteraceae-Compositae Plantae 189244
7 Senecio alpinus Asteraceae-Compositae Plantae 189227
8 Senecio chrysanthemoides Asteraceae-Compositae Plantae 189235
9 Senecio jacobaea Asteraceae-Compositae 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: 91746605

No compound-protein relationship available.

Structure

SMILES: C1OC(=O)CC(=C)CC(=C)C(=O)OC(C2C1=3)CCN2CC3

Level: 0

Mol. Weight: 289.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.81
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.9
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.84

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.58
Plasma Protein Binding
36.36
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
5.13
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.94
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.04
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.2
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
-2.76
Rat (Acute)
3.69
Rat (Chronic Oral)
1.79
Fathead Minnow
4.24
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
370.62
Hydration Free Energy
-8.23
Log(D) at pH=7.4
1.08
Log(P)
0.8
Log S
-2.02
Log(Vapor Pressure)
-7.35
Melting Point
183.24
pKa Acid
5.85
pKa Basic
6.93
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 0.8428
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8428
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7921
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7921
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7638
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7638
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7625
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7625
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7519
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7519
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7369
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7369
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7307
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7307
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7266
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7266
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7209
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7209
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7188
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7188
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7143
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7143
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7119
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7119
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7117
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7117
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7076
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7076
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7011
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7011

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