Aschantin - Compound Card

Aschantin

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Aschantin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Lignan
    • Subclass: Diepoxylignan
Canonical Smiles COc1cc(cc(c1OC)OC)C1OCC2C1COC2c1ccc2c(c1)OCO2
InChI InChI=1S/C22H24O7/c1-23-18-7-13(8-19(24-2)22(18)25-3)21-15-10-26-20(14(15)9-27-21)12-4-5-16-17(6-12)29-11-28-16/h4-8,14-15,20-21H,9-11H2,1-3H3
InChIKey ONDWGDNAFRAXCN-UHFFFAOYSA-N
Formula C22H24O7
HBA 7
HBD 0
MW 400.43
Rotatable Bonds 5
TPSA 64.61
LogP 3.52
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.45
Exact Mass 400.15
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: 3836321
CPRiL: 176951
Structure

SMILES: O1COc(c12)ccc(c2)C3OCC(C34)C(OC4)c5ccccc5

Level: 2

Mol. Weight: 400.43 g/mol

Structure

SMILES: O1COc(c12)ccc(c2)C3OCC(C34)COC4

Level: 1

Mol. Weight: 400.43 g/mol

Structure

SMILES: C1OCC(C12)COC2c3ccccc3

Level: 1

Mol. Weight: 400.43 g/mol

Structure

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 400.43 g/mol

Structure

SMILES: C1OCC(C12)COC2

Level: 0

Mol. Weight: 400.43 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 400.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.99
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.640
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.23

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.220
Plasma Protein Binding
38.84
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
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.580
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.180
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.600
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.980
Micronucleos
Safe
NR-AhR
Toxic
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
Toxic
T. Pyriformis
-50.190
Rat (Acute)
2.350
Rat (Chronic Oral)
1.420
Fathead Minnow
5.230
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
457.930
Hydration Free Energy
-3.440
Log(D) at pH=7.4
2.540
Log(P)
3.17
Log S
-4.16
Log(Vapor Pressure)
-7.45
Melting Point
100.2
pKa Acid
9.79
pKa Basic
2.37
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 0.9521
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9521
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9369
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9369
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9327
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9327
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9250
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9250
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9223
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9223
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9125
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9125
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8838
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8838
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8829
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8829
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8791
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8791
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8662
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8662
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8603
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8603
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8554
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8554
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8509
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8509
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8391
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8391
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8376
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8376
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.8131
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.8131
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7934
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7934
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7919
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7919
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7911
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7911
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7876
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7876
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7742
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7742
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7712
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7712
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7685
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7685
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7656
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7656
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7605
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7605
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7522
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7522
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7521
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7521
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.7474
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.7474
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7461
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7461
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7460
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7460
Cell division protein FtsZ P0A029 FTSZ_STAAM Staphylococcus aureus 3 0.7443
Cell division protein FtsZ P0A029 FTSZ_STAAM Staphylococcus aureus 3 0.7443
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7437
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7437
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7430
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7430
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7425
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7425
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7409
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7409
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7388
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7388
Decaprenylphosphoryl-beta-D-ribose oxidase I6X8C4 I6X8C4_MYCTU Mycobacterium tuberculosis 3 0.7386
Decaprenylphosphoryl-beta-D-ribose oxidase I6X8C4 I6X8C4_MYCTU Mycobacterium tuberculosis 3 0.7386
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7356
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7356
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7350
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7350
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7319
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7319
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7295
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7295
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7282
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7282
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7280
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7280
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7278
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7278
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7257
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7257
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7240
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7240
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7240
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7240
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7239
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7239
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7237
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7237
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7226
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7226
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7225
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7225
Acetolactate synthase catalytic subunit, mitochondrial P07342 ILVB_YEAST Saccharomyces cerevisiae 3 0.7218
Acetolactate synthase catalytic subunit, mitochondrial P07342 ILVB_YEAST Saccharomyces cerevisiae 3 0.7218
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7173
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7173
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.7156
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.7156
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7154
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7154
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7143
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7143
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7139
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7139
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7115
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7115
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7092
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7092
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7092
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7092
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7080
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7080
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7078
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7078
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7060
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7060
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7059
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7059
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7050
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7050
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7041
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7041
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7035
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7035
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7026
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7026
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7019
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7019
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7014
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7014

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