4-(isoprenyloxy)-3-methoxy-3,4-deoxymethylenedioxyfagaramide - Compound Card

4-(isoprenyloxy)-3-methoxy-3,4-deoxymethylenedioxyfagaramide

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4-(isoprenyloxy)-3-methoxy-3,4-deoxymethylenedioxyfagaramide

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Cinnamamide
Canonical Smiles COc1cc(/C=C/C(=O)NCC(C)C)ccc1OCC=C(C)C
InChI InChI=1S/C19H27NO3/c1-14(2)10-11-23-17-8-6-16(12-18(17)22-5)7-9-19(21)20-13-15(3)4/h6-10,12,15H,11,13H2,1-5H3,(H,20,21)/b9-7+
InChIKey AQHWIIKLPSSVHK-VQHVLOKHSA-N
Formula C19H27NO3
HBA 3
HBD 1
MW 317.43
Rotatable Bonds 8
TPSA 47.56
LogP 3.83
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.42
Exact Mass 317.2
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Zanthoxylum chalybeum Rutaceae Plantae 1671342

Showing of synonyms

  • Omosa LK, Mbogo GM, et al. (2021). Cytotoxicity of fagaramide derivative and canthin-6-one from Zanthoxylum (Rutaceae) species against multidrug resistant leukemia cells. Natural product research,2021, 35(4), 579-586. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 317.43 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.59
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.220
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.55

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.580
Plasma Protein Binding
45.28
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.450
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.190
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.650
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.040
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
3.100
Rat (Acute)
2.080
Rat (Chronic Oral)
1.970
Fathead Minnow
4.770
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
356.730
Hydration Free Energy
-9.900
Log(D) at pH=7.4
3.340
Log(P)
4.45
Log S
-4.56
Log(Vapor Pressure)
-5.59
Melting Point
116.72
pKa Acid
11.27
pKa Basic
6.52
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9169
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8890
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 4 0.8398
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.8397
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8362
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8355
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8342
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.8309
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8193
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8102
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8050
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7962
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7941
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7905
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7780
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7764
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7745
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 2 0.7685
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7649
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7647
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7635
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7592
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7549
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7510
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7500
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7500
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7488
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7488
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7476
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7473
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7470
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7461
Beta-elicitin cinnamomin P15569 ELIB_PHYCI Phytophthora cinnamomi 3 0.7454
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 2 0.7433
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7424
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7422
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7402
Methyl-branched lipid omega-hydroxylase P9WPP3 CP124_MYCTU Mycobacterium tuberculosis 3 0.7384
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7360
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7348
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7337
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7337
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7321
Lanosterol 14-alpha demethylase CYP51 P10614 CP51_YEAST Saccharomyces cerevisiae 3 0.7317
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7300
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7297
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7273
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7264
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7242
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7241
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7238
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7215
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7196
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7191
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7188
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7180
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7165
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7160
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7150
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7147
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7120
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7111
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7107
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7095
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7092
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7092
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7088
L-seryl-tRNA(Sec) kinase Q58933 PSTK_METJA Methanocaldococcus jannaschii 2 0.7084
Fumarate reductase subunit D P0A8Q3 FRDD_ECOLI Escherichia coli 2 0.7082
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7078
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7077
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7075
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7073
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7072
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7069
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7067
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7064
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7063
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7056
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7045
Odorant binding protein ASP1 Q8WRW5 Q8WRW5_APIME Apis mellifera 2 0.7044
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7023
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7022
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7013

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