R-bgugaine - Compound Card

R-bgugaine

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R-bgugaine

Structure
Zoomed Structure
  • Family: Plantae - Araceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolidine Alkaloid
Canonical Smiles CCCCCCCCCCCCCC[C@H]1CCCN1C
InChI InChI=1S/C19H39N/c1-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(19)2/h19H,3-18H2,1-2H3/t19-/m0/s1
InChIKey NCSCAOYXUUEXIP-IBGZPJMESA-N
Formula C19H39N
HBA 1
HBD 0
MW 281.53
Rotatable Bonds 13
TPSA 3.24
LogP 6.17
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 1.0
Exact Mass 281.31
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Arisarum vulgare Araceae Plantae 267624

Showing of synonyms

  • Lamkadern M, Melhaoui A, et al. (2000). Cytotoxic effect and electrophysiological activity of (S)-bgugaine, an alkylpyrrolidine alkaloid against MRC-5 fibroblasts. Phytomedicine,2000,7(2),145-149. [View] [PubMed]
Pubchem: 11196781
Nmrshiftdb2: 80001916
CPRiL: 275064
Structure

SMILES: C1CCNC1

Level: 0

Mol. Weight: 281.53 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.92
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.08
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-3.39

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.63
Plasma Protein Binding
44.19
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.88
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.4
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Toxic
Eye Irritation
Toxic
Maximum Tolerated Dose
1.12
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
7.8
Micronucleos
Safe
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
5.03
Rat (Acute)
2.52
Rat (Chronic Oral)
2.02
Fathead Minnow
3.89
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
342.26
Hydration Free Energy
-0.22
Log(D) at pH=7.4
4.93
Log(P)
7.18
Log S
-5.08
Log(Vapor Pressure)
-4.11
Melting Point
14.51
pKa Acid
10.34
pKa Basic
8.63
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7246
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7246
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7115
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7115
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 2 0.7085
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 2 0.7085

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