Matairesinol dimethyl ether - Compound Card

Matairesinol dimethyl ether

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Matairesinol dimethyl ether

Structure
Zoomed Structure
  • Family: Plantae - Piperaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles COc1ccc(cc1OC)C[C@H]1C(=O)OC[C@@H]1Cc1ccc(c(c1)OC)OC
InChI InChI=1S/C22H26O6/c1-24-18-7-5-14(11-20(18)26-3)9-16-13-28-22(23)17(16)10-15-6-8-19(25-2)21(12-15)27-4/h5-8,11-12,16-17H,9-10,13H2,1-4H3/t16-,17+/m0/s1
InChIKey SNAOLIMFHAAIER-DLBZAZTESA-N
Formula C22H26O6
HBA 6
HBD 0
MW 386.44
Rotatable Bonds 8
TPSA 63.22
LogP 3.3
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.41
Exact Mass 386.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Peperomia vulcanica Piperaceae Plantae 1719589

Showing of synonyms

  • Ngemenya M, Metuge H, et al. (2015). Isolation of Natural Product Hits from Peperomia species with Synergistic Activity against Resistant Plasmodium falciparum Strains. European Journal of Medicinal Plants, 2015, 5(1). [View]
CPRiL: 451961
Structure

SMILES: c1ccccc1CC(C2=O)C(CO2)Cc3ccccc3

Level: 2

Mol. Weight: 386.44 g/mol

Structure

SMILES: O=C1CC(CO1)Cc2ccccc2

Level: 1

Mol. Weight: 386.44 g/mol

Structure

SMILES: O1CCC(C1=O)Cc2ccccc2

Level: 1

Mol. Weight: 386.44 g/mol

Structure

SMILES: O=C1CCCO1

Level: 0

Mol. Weight: 386.44 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 386.44 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.820
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.870
Plasma Protein Binding
78.44
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.630
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.620
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.510
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.170
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
-11.790
Rat (Acute)
2.660
Rat (Chronic Oral)
1.910
Fathead Minnow
5.020
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
458.620
Hydration Free Energy
-5.930
Log(D) at pH=7.4
2.910
Log(P)
2.57
Log S
-3.92
Log(Vapor Pressure)
-7.02
Melting Point
126.45
pKa Acid
9.91
pKa Basic
3.47
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9562
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9549
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.9358
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9200
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8843
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8841
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8782
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8745
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8701
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8683
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8647
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8622
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8596
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8592
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.8568
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8555
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8511
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8476
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8457
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8400
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.8391
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8346
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8095
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.8082
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8039
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.8006
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7947
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7933
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7912
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7905
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7899
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7873
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7851
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7804
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7762
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7755
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7750
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7742
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7727
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7724
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7720
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7684
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7678
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7675
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7660
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7657
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7653
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7646
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7642
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.7621
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7611
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7591
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7587
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7587
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7555
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7546
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7536
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7535
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7524
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7524
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7514
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7508
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7504
Thymidylate synthase Q4JQW2 TYSY_VZVO Varicella-zoster virus 3 0.7482
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7481
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7472
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7467
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7464
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7462
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7456
Macrophage colony-stimulating factor 1 receptor P07333 CSF1R_HUMAN Homo sapiens 3 0.7455
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7452
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7451
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7450
clade A/E 93TH057 HIV-1 gp120 core A0A0M3KKW9 A0A0M3KKW9_9HIV1 Human immunodeficiency virus 1 2 0.7446
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7444
LL-diaminopimelate aminotransferase, chloroplastic Q93ZN9 DAPAT_ARATH Arabidopsis thaliana 2 0.7431
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7428
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7422
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7411
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7395
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7394
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7383
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7383
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7374
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7372
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7371
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7371
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7365
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7349
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7349
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7346
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7341
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7339
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7336
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7321
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7302
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 2 0.7286
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7285
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7281
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7279
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7273
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7272
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7271
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7261
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7256
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7248
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7241
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 3 0.7237
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7237
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7237
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7235
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 2 0.7233
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7229
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7221
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7221
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7220
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7219
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7219
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7216
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7216
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7215
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 2 0.7207
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7192
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7190
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7189
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7183
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7180
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7179
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 2 0.7177
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 2 0.7176
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7172
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7171
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7162
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7159
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7158
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7155
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7149
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7144
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7141
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7137
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7117
Serine hydroxymethyltransferase Q7SIB6 Q7SIB6_GEOSE Geobacillus stearothermophilus 3 0.7114
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7113
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7091
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7083
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7080
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7073
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 2 0.7072
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7064
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7054
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7053
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 2 0.7053
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7049
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 3 0.7038
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7037
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7030
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7027
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7025
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7020
High affinity nerve growth factor receptor P04629 NTRK1_HUMAN Homo sapiens 3 0.7017
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7015
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7008
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7007
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7006
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7005

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