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

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

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N-methyl-2(2'-methoxybutyl),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(OC)CC)O
InChI InChI=1S/C15H29NO2/c1-5-14(17)10-12-8-7-9-13(16(12)3)11-15(6-2)18-4/h7,9,12-15,17H,5-6,8,10-11H2,1-4H3
InChIKey KHRQOARMKNDSNW-UHFFFAOYSA-N
Formula C15H29NO2
HBA 3
HBD 1
MW 255.4
Rotatable Bonds 7
TPSA 32.7
LogP 2.59
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.87
Exact Mass 255.22
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: 163087434

No compound-protein relationship available.

Structure

SMILES: C1=CCNCC1

Level: 0

Mol. Weight: 255.4 g/mol

Cholinesterase inhibiting

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.24
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.87

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.11
Plasma Protein Binding
6.7
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
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.31
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.91
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.36
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.46
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
1.75
Rat (Acute)
2.38
Rat (Chronic Oral)
1.31
Fathead Minnow
3.56
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
278.87
Hydration Free Energy
-7.91
Log(D) at pH=7.4
1.42
Log(P)
2.43
Log S
-0.89
Log(Vapor Pressure)
-3.97
Melting Point
14.05
pKa Acid
11.06
pKa Basic
8.87
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.9509
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.9509
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.9082
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.9082
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9024
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9024
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8992
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8992
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8873
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8873
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8640
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8640
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8621
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8621
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8463
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8463
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8107
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8107
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7911
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7911
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7886
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7886
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7849
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7849
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7752
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7752
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7690
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7690
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7581
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7581
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7553
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7553
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7491
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7491
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7450
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7450
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7438
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7438
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7397
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7397
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7386
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7386
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 4 0.7341
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 4 0.7341
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7320
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7320
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7300
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7300
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7290
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7290
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7287
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7287
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7279
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7279
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7266
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7266
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7260
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7260
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7260
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7260
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7251
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7251
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7209
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7209
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7194
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7194
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7189
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7189
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7177
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7177
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7172
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7172
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7119
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7119
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7105
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7105
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7102
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7102
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7083
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7083
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7060
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7060
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7049
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7049
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7039
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7039
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7023
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7023

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