Pellitorine - Compound Card

Pellitorine

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Pellitorine

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Amide
Canonical Smiles CCCCC/C=C/C=C/C(=O)NCC(C)C
InChI InChI=1S/C14H25NO/c1-4-5-6-7-8-9-10-11-14(16)15-12-13(2)3/h8-11,13H,4-7,12H2,1-3H3,(H,15,16)/b9-8+,11-10+
InChIKey MAGQQZHFHJDIRE-BNFZFUHLSA-N
Formula C14H25NO
HBA 1
HBD 1
MW 223.36
Rotatable Bonds 8
TPSA 29.1
LogP 3.45
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 16
Formal Charge 0
Fraction CSP3 0.64
Exact Mass 223.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia dracunculus Asteraceae Plantae 72341
2 Matricaria pubescens Asteraceae Plantae 99022
3 Zanthoxylum usambarense Rutaceae Plantae 2562172
4 Zanthoxylum usambarense Rutaceae Plantae 2562172
5 Zanthoxylum gilletii Rutaceae Plantae 1291627

Showing of synonyms

  • Saadali B, Boriky D, et al. (2001). Alkamides from Artemisia dracunculus.. Phytochemistry,2001,58,1083-1086. [View] [PubMed]
  • Weenen H, Nkunya MH, et al. (1990). Antimalarial compounds containing an alpha,beta-unsaturated carbonyl moiety from Tanzanian medicinal plants.. Planta medica,1990,56(4),371-373. [View] [PubMed]
  • He W, Van Puyvelde L, et al. (2002). Chemical constituents and biological activities of Zanthoxylum usambarense. Phytotherapy Research,2002,16(1),66-70. [View] [PubMed]
  • Greger H, Hofer O (1984). On the pungent principle of Matricaria pubescens. Phytochemistry,1984,23(5),1173-1174. [View]
  • He W, De Kimpe N. (2000). Study of biological active principles from Kenyan medicinal plants. PhD Thesis, University of Ghent, Belgium, 2000-2001. [View]
CPRiL: 160899

No scaffolds available.

Antifungal
Antimalarial
Fungicidal
Insecticidal

Absorption

Caco-2 (logPapp)
-4.4
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.9
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.02

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.51
Plasma Protein Binding
42.0
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
Inhibitor
CYP 2C9 Substrate
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
8.35
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.31
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.73
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.68
Micronucleos
Safe
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
5.06
Rat (Acute)
1.88
Rat (Chronic Oral)
1.93
Fathead Minnow
4.37
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
290.99
Hydration Free Energy
-6.9
Log(D) at pH=7.4
3.35
Log(P)
4.55
Log S
-3.76
Log(Vapor Pressure)
-4.24
Melting Point
54.98
pKa Acid
10.83
pKa Basic
5.51
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8617
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8617
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8094
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8094
SKP1-like protein 1A Q39255 SKP1A_ARATH Arabidopsis thaliana 3 0.7884
SKP1-like protein 1A Q39255 SKP1A_ARATH Arabidopsis thaliana 3 0.7884
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7869
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7869
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7776
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7776
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7761
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7761
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7757
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7757
Peridinin-chlorophyll a protein, high-salt form O76183 O76183_AMPCA Amphidinium carterae 2 0.7731
Peridinin-chlorophyll a protein, high-salt form O76183 O76183_AMPCA Amphidinium carterae 2 0.7731
Avd protein A7YYL1 A7YYL1_XENTR Xenopus tropicalis 3 0.7728
Avd protein A7YYL1 A7YYL1_XENTR Xenopus tropicalis 3 0.7728
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7727
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7727
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7644
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7644
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7564
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7564
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.7555
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.7555
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7541
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7541
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7532
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7532
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7531
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7531
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7494
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7494
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7494
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7494
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7492
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7492
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7451
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7451
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7436
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7436
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7412
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7412
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7399
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7399
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7362
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7362
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7352
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7352
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7348
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7348
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7335
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7335
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7332
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7332
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7314
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7314
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7309
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7309
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 2 0.7278
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 2 0.7278
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7263
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7263
N-acyl-aromatic-L-amino acid amidohydrolase (carboxylate-forming) Q91XE4 ACY3_MOUSE Mus musculus 2 0.7257
N-acyl-aromatic-L-amino acid amidohydrolase (carboxylate-forming) Q91XE4 ACY3_MOUSE Mus musculus 2 0.7257
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7244
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7244
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 2 0.7203
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 2 0.7203
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 2 0.7201
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7201
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 2 0.7201
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7201
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7174
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7174
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7125
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7125
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7120
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7120
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7117
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7117
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7102
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7102
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7101
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7101
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7100
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7100
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7058
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7058
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7042
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7042
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7038
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7038
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7029
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7029

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