(+)-(S,R)-epoxyartemidin - Compound Card

(+)-(S,R)-epoxyartemidin

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(+)-(S,R)-epoxyartemidin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Coumarin
Canonical Smiles CC[C@@H]1O[C@H]1c1cc2ccccc2c(=O)o1
InChI InChI=1S/C13H12O3/c1-2-10-12(15-10)11-7-8-5-3-4-6-9(8)13(14)16-11/h3-7,10,12H,2H2,1H3/t10-,12+/m0/s1
InChIKey VNEONZFLGNRQJT-CMPLNLGQSA-N
Formula C13H12O3
HBA 3
HBD 0
MW 216.24
Rotatable Bonds 2
TPSA 42.74
LogP 2.64
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 16
Formal Charge 0
Fraction CSP3 0.31
Exact Mass 216.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia campestris Asteraceae Plantae 72337

Showing of synonyms

  • Ferchichi L, Merza J, et al. (2006). Occurrence of isocoumarinic and phenolic derivatives in Artemisia campestris L. subsp. campestris.. Biochemical Systematics and Ecology,2006,34,829-832. [View]

No compound-protein relationship available.

Structure

SMILES: O=c1oc(C2CO2)cc(c13)cccc3

Level: 1

Mol. Weight: 216.24 g/mol

Structure

SMILES: c1cccc(c12)ccoc2=O

Level: 0

Mol. Weight: 216.24 g/mol

Structure

SMILES: C1CO1

Level: 0

Mol. Weight: 216.24 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.1
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.52

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.49
Plasma Protein Binding
47.69
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
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.73
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.49
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.52
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.51
Micronucleos
Toxic
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
2.73
Rat (Acute)
1.99
Rat (Chronic Oral)
1.59
Fathead Minnow
4.12
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
352.08
Hydration Free Energy
-7.55
Log(D) at pH=7.4
2.2
Log(P)
2.2
Log S
-3.46
Log(Vapor Pressure)
-4.8
Melting Point
52.14
pKa Acid
5.3
pKa Basic
0.62
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9492
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9492
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9142
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9142
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8750
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8750
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8644
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8644
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8335
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8335
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8327
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8327
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8292
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8292
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.8108
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.8108
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.8030
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.8030
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7964
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7964
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7958
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7958
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7943
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7943
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 3 0.7920
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 3 0.7920
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7816
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7816
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7815
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7815
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7801
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7801
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7766
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7766
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7685
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7685
Thymidine phosphorylase P07650 TYPH_ECOLI Escherichia coli 4 0.7659
Thymidine phosphorylase P07650 TYPH_ECOLI Escherichia coli 4 0.7659
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7642
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7642
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7634
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7634
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7631
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7631
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7617
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7617
Dihydroorotate dehydrogenase (quinone), mitochondrial Q02127 PYRD_HUMAN Homo sapiens 3 0.7611
Dihydroorotate dehydrogenase (quinone), mitochondrial Q02127 PYRD_HUMAN Homo sapiens 3 0.7611
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7607
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7607
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7571
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7571
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7563
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7563
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7554
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7554
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7549
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7549
Fumarate reductase subunit D P0A8Q3 FRDD_ECOLI Escherichia coli 2 0.7548
Fumarate reductase subunit D P0A8Q3 FRDD_ECOLI Escherichia coli 2 0.7548
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7534
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7534
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7510
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7510
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7499
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7499
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7462
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7462
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 2 0.7447
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 2 0.7447
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7421
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7421
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7421
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7421
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7374
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7374
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7371
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7371
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7362
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7362
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7343
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7343
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7340
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7340
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7327
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7327
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7319
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7319
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7298
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7298
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7298
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7298
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7293
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7293
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7289
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7289
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7280
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7280
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7275
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7275
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 2 0.7260
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 2 0.7260
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7225
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7225
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7203
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7203
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7186
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7186
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7173
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7173
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7164
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7164
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7160
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7160
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7154
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7154
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7147
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7147
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7125
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7125
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7107
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7107
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7103
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7103
Cytochrome b-c1 complex subunit 1, mitochondrial P31800 QCR1_BOVIN Bos taurus 3 0.7097
Cytochrome b-c1 complex subunit 1, mitochondrial P31800 QCR1_BOVIN Bos taurus 3 0.7097
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7094
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7094
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7087
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7087
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7086
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7086
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7081
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7081
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7073
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7073
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7072
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7072
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 2 0.7065
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 2 0.7065
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7064
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7064
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7062
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7062
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7041
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7041
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 2 0.7038
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 2 0.7038
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7033
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7033
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 2 0.7002
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 2 0.7002

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