Epiyangambin - Compound Card

Epiyangambin

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Epiyangambin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Lignan
    • Subclass: Diepoxylignan
Canonical Smiles COc1cc(cc(c1OC)OC)C1OCC2C1COC2c1cc(OC)c(c(c1)OC)OC
InChI InChI=1S/C24H30O8/c1-25-17-7-13(8-18(26-2)23(17)29-5)21-15-11-32-22(16(15)12-31-21)14-9-19(27-3)24(30-6)20(10-14)28-4/h7-10,15-16,21-22H,11-12H2,1-6H3
InChIKey HRLFUIXSXUASEX-UHFFFAOYSA-N
Formula C24H30O8
HBA 8
HBD 0
MW 446.5
Rotatable Bonds 8
TPSA 73.84
LogP 3.81
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 446.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia arborescens Asteraceae Plantae 72386

Showing of synonyms

  • Marco JA, Sanz-Cervera JF, et al. (1997). Sesquiterpene lactones and lignans from Artemisia arborescens.. Phytochemistry,1997,44(6),1133-1137. [View]
Pubchem: 99091
Chebi: 182352
Nmrshiftdb2: 70127795
Bindingdb: 69394
CPRiL: 71267
Structure

SMILES: c1ccccc1C(OC2)C(C23)COC3c4ccccc4

Level: 2

Mol. Weight: 446.5 g/mol

Structure

SMILES: C1OCC(C12)COC2c3ccccc3

Level: 1

Mol. Weight: 446.5 g/mol

Structure

SMILES: C1OCC(C12)COC2

Level: 0

Mol. Weight: 446.5 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 446.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.810
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.13

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.940
Plasma Protein Binding
16.94
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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.800
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.410
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.380
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.550
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
-144.250
Rat (Acute)
2.790
Rat (Chronic Oral)
2.000
Fathead Minnow
5.660
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
458.630
Hydration Free Energy
-3.030
Log(D) at pH=7.4
2.800
Log(P)
2.75
Log S
-3.36
Log(Vapor Pressure)
-7.18
Melting Point
115.21
pKa Acid
9.52
pKa Basic
2.05
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9525
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9525
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9461
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9461
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9236
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9236
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9136
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9136
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9125
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9125
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.9083
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.9083
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8992
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8992
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8896
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8896
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8505
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8505
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8450
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8450
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8249
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8249
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8111
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8111
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8110
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8110
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8090
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8090
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7796
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7796
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7774
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7774
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7769
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7769
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7769
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7769
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7766
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7766
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7752
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7752
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7688
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7688
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7601
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7601
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B Q13370 PDE3B_HUMAN Homo sapiens 3 0.7557
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B Q13370 PDE3B_HUMAN Homo sapiens 3 0.7557
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7555
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7555
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7552
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7552
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7550
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7550
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7550
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7550
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7541
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7541
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7539
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7539
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7512
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7512
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7411
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7411
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7409
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7409
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7407
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7407
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7370
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7370
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7370
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7370
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7368
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7368
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7359
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7359
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7357
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7357
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7343
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7343
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7307
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7307
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7302
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7302
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7289
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7289
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 3 0.7274
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 3 0.7274
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7262
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7262
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7261
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7261
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7260
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7260
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7245
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7245
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7242
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7242
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7239
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7239
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7218
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7218
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7209
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7209
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7198
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7198
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7172
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7172
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7171
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7171
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7161
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7161
Unconventional myosin-Va Q02440 MYO5A_CHICK Gallus gallus 2 0.7160
Unconventional myosin-Va Q02440 MYO5A_CHICK Gallus gallus 2 0.7160
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7150
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7150
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7140
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7140
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7123
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7123
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7107
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7107
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7102
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7102
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7101
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7101
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7092
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7092
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7065
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7065
Interleukin-1 receptor-associated kinase 4 Q9NWZ3 IRAK4_HUMAN Homo sapiens 3 0.7057
Interleukin-1 receptor-associated kinase 4 Q9NWZ3 IRAK4_HUMAN Homo sapiens 3 0.7057
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7054
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7054
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7043
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7043
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7034
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7034
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7028
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7028
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7025
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7025
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7015
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7015
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7015
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7015
Bifunctional protein GlmU P43889 GLMU_HAEIN Haemophilus influenzae 4 0.7005
Bifunctional protein GlmU P43889 GLMU_HAEIN Haemophilus influenzae 4 0.7005

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