Deacetyldoronine - Compound Card

Deacetyldoronine

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Deacetyldoronine

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles CN1CC[C@@H]2OC(=O)C(O)(C[C@@H]([C@](C(=O)OCC(=CC1)C2=O)(C)O)C)C(Cl)C
InChI InChI=1S/C19H28ClNO7/c1-11-9-19(26,12(2)20)17(24)28-14-6-8-21(4)7-5-13(15(14)22)10-27-16(23)18(11,3)25/h5,11-12,14,25-26H,6-10H2,1-4H3/t11-,12?,14-,18-,19?/m0/s1
InChIKey OMHSMPLRLNEBIB-YHFLNUOISA-N
Formula C19H28ClNO7
HBA 8
HBD 2
MW 417.89
Rotatable Bonds 1
TPSA 113.37
LogP 0.42
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.74
Exact Mass 417.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Senecio abrotanifolius Asteraceae Plantae 189225
2 Senecio adonidifolius Asteraceae Plantae 189226
3 Senecio othonnae Asteraceae Plantae 214901
4 Senecio ambiguus Asteraceae Plantae 189228
5 Senecio cineraria Asteraceae Plantae 252537
6 Senecio gnaphalodes Asteraceae Plantae 2868836

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: 91746997
Nmrshiftdb2: 60069749

No compound-protein relationship available.

Structure

SMILES: C12=CCNCCC(C1=O)OC(=O)CCCCC(=O)OC2

Level: 0

Mol. Weight: 417.89 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.98
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.86
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.11

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.36
Plasma Protein Binding
20.01
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
8.13
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.36
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.57
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
10.12
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
-6.42
Rat (Acute)
3.15
Rat (Chronic Oral)
1.78
Fathead Minnow
3.98
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
391.32
Hydration Free Energy
-12.3
Log(D) at pH=7.4
1.06
Log(P)
0.36
Log S
-1.7
Log(Vapor Pressure)
-8.79
Melting Point
179.2
pKa Acid
4.95
pKa Basic
6.08
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 3 0.8098
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8098
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7914
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7914
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7672
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7672
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7605
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7605
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7568
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7568
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7096
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7096
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7091
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7091
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7038
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7038

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