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Pellitorine
- 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
Pellitorine
Pellitorin
Trans-Pellitorin
(2E,4E)-N-(2-methylpropyl)deca-2,4-dienamide
(E,E)-N-Isobutyl-2,4-decadienamide
(2E,4E)-N-(2-Methylpropyl)-2,4-decadienamide
N-Isobutyldeca-trans-2,trans-4-dienamide
Optaflow A
Trans-Pellitorine
2,4-Decadienamide, N-(2-methylpropyl)-, (2E,4E)-
BRN 1725967
2,4-DECADIENAMIDE, N-ISOBUTYL-, (E,E)-
2,4-Decadienamide, N-(2-methylpropyl)-, (E,E)-
AI3-19560
PELLITORINE [MI]
8IS5231171
FEMA NO. 4148
4-04-00-00636 (Beilstein Handbook Reference)
Pellitorine (6CI)
N-ISOBUTYL (E,E)-2,4-DECADIENAMIDE
N-ISOBUTYL-2,4-DECADIENAMIDE, TRANS,TRANS-
METHYLPROPYL)-2,4-DECADIENAMIDE, (E,E)-N-(2-
639-620-7
18836-52-7
(E,E)-N-(2-Methylpropyl)-2,4-decadienamide
(2E,4E)-N-isobutyldeca-2,4-dienamide
CHEBI:69686
UNII-8IS5231171
Pellitorine (Standard)
53608-76-7
SCHEMBL258097
SCHEMBL258098
CHEMBL271242
MEGxp0_000048
HY-N3097R
DTXSID301019978
HY-N3097
BDBM50479137
HB4019
AKOS028109310
2E,4E-decadienoic acid-N-isobutylamide
DA-76697
FP146495
MS-23255
DB-234821
CS-0023218
NS00123373
F82123
A1-06834
Q27138027
(2E,4E)-N-(2-methyl-propyl)-deca-2,4-dienoic acid amide
NCGC00385817-01!(2E,4E)-N-(2-methylpropyl)deca-2,4-dienamide
- 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]
Pubchem:
5318516
Cas:
18836-52-7
Gnps:
CCMSLIB00000848299
Zinc:
ZINC000013838505
Chebi:
69686
Nmrshiftdb2:
60021233
Metabolights:
MTBLC69686
Chembl:
CHEMBL271242
Bindingdb:
50479137
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 |