N-methyl-2(2'-hydroxybutyl),6(2''-hydroxybutyl)-Delta3-piperidine - Compound Card

N-methyl-2(2'-hydroxybutyl),6(2''-hydroxybutyl)-Delta3-piperidine

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N-methyl-2(2'-hydroxybutyl),6(2''-hydroxybutyl)-Delta3-piperidine

Structure
Zoomed Structure
  • Family: Plantae - Campanulaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Piperidine Alkaloid
Canonical Smiles CCC(CC1CC=CC(N1C)CC(CC)O)O
InChI InChI=1S/C14H27NO2/c1-4-13(16)9-11-7-6-8-12(15(11)3)10-14(17)5-2/h6-7,11-14,16-17H,4-5,8-10H2,1-3H3
InChIKey JYEDTYMWZCKFSV-UHFFFAOYSA-N
Formula C14H27NO2
HBA 3
HBD 2
MW 241.37
Rotatable Bonds 6
TPSA 43.7
LogP 1.94
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 241.2
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Lobelia laxiflora Campanulaceae Plantae 252775

Showing of synonyms

  • Rahman EHA, Monem ARA (2014). Cholinesterase inhibiting activity and a new piperidine alkaloid from Lobelia laxiflora L. roots (Campanulaceae).. Records of Natural Products,2014,8(2),199-202. [View]
Pubchem: 566033

No compound-protein relationship available.

Structure

SMILES: C1=CCNCC1

Level: 0

Mol. Weight: 241.37 g/mol

Cholinesterase inhibiting

Absorption

Caco-2 (logPapp)
-4.9
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.09
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.56

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.18
Plasma Protein Binding
3.45
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.49
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.33
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.61
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.77
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
2.38
Rat (Acute)
2.1
Rat (Chronic Oral)
1.65
Fathead Minnow
3.44
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
289.1
Hydration Free Energy
-9.07
Log(D) at pH=7.4
0.42
Log(P)
1.81
Log S
-0.91
Log(Vapor Pressure)
-5.09
Melting Point
42.78
pKa Acid
10.19
pKa Basic
9.18
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8803
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8803
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.8795
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.8795
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8742
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8742
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8606
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8606
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8463
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8463
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8418
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8418
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8389
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8389
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8363
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8363
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8311
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8311
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8125
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8125
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.8108
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.8108
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8012
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8012
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7995
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7995
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7977
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7977
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7966
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7966
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7939
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7939
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7827
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7827
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7815
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7815
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7775
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7775
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7746
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7746
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7681
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7681
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7664
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7664
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7610
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7610
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7602
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7602
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7563
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7563
Cartilage oligomeric matrix protein Q9R0G6 COMP_MOUSE Mus musculus 3 0.7562
Cartilage oligomeric matrix protein Q9R0G6 COMP_MOUSE Mus musculus 3 0.7562
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 4 0.7560
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 4 0.7560
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7510
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7510
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7433
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7433
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7385
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7385
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7354
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7354
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7353
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7353
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7346
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7346
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7332
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7332
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7324
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7324
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7323
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7323
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7318
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7318
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7302
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7302
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7299
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7299
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7292
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7292
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7277
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7277
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7276
Androgen receptor P19091 ANDR_MOUSE Mus musculus 3 0.7276
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7276
Androgen receptor P19091 ANDR_MOUSE Mus musculus 3 0.7276
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7266
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7266
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7264
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7264
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7262
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7262
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7251
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7251
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7236
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7236
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 4 0.7234
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 4 0.7234
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7220
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7220
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7180
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7180
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7160
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7160
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7157
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7157
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7118
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7118
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7110
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7110
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7102
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7102
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7098
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7098
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7085
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7085
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7066
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7066
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7059
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7059
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7051
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7051
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7037
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7037
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7034
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7034
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7028
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7028
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7010
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7010
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7008
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7008
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7003
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7003

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