Dehydrosenkirkine - Compound Card

Dehydrosenkirkine

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Dehydrosenkirkine

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles C/C=C\1/CC(=C)[C@@](C)(O)C(=O)OCC2=CCN(CC[C@@H](OC1=O)C2=O)C
InChI InChI=1S/C19H25NO6/c1-5-13-10-12(2)19(3,24)18(23)25-11-14-6-8-20(4)9-7-15(16(14)21)26-17(13)22/h5-6,15,24H,2,7-11H2,1,3-4H3/b13-5-,14-6?/t15-,19-/m1/s1
InChIKey GRQOJAAONJAOJH-HFTZCKCTSA-N
Formula C19H25NO6
HBA 7
HBD 1
MW 363.41
Rotatable Bonds 0
TPSA 93.14
LogP 0.93
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 363.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Senecio carniolicus Asteraceae Plantae 189240
2 Senecio halleri Asteraceae Plantae 214899
3 Senecio leucophyllus Asteraceae Plantae 214900
4 Senecio persoonii Asteraceae Plantae 214902
5 Senecio delphinifolius Asteraceae Plantae 214896

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: 163078082

No compound-protein relationship available.

Structure

SMILES: C1OC(=O)CC(=C)CC(=C)C(=O)OC(C2=O)CCNCC=C12

Level: 0

Mol. Weight: 363.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.82
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.85

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.45
Plasma Protein Binding
32.58
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
7.24
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.79
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.81
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.83
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
-4.94
Rat (Acute)
3.34
Rat (Chronic Oral)
1.69
Fathead Minnow
4.06
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
380.51
Hydration Free Energy
-9.7
Log(D) at pH=7.4
1.24
Log(P)
0.33
Log S
-1.35
Log(Vapor Pressure)
-8.28
Melting Point
181.1
pKa Acid
5.0
pKa Basic
6.55
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8476
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8476
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7934
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7934
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7804
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7804
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7738
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7738
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7508
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7508
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7506
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7506
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7216
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7216
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 3 0.7155
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 3 0.7155
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7093
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7093

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