3-O-methylalaternin - Compound Card

3-O-methylalaternin

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3-O-methylalaternin

Structure
Zoomed Structure
  • Family: Fungi - Phaeosphaeriaceae
  • Kingdom: Fungi
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)c(c(c1)C)O
InChI InChI=1S/C16H12O6/c1-6-3-8-12(16(21)13(6)18)15(20)11-9(14(8)19)4-7(22-2)5-10(11)17/h3-5,17-18,21H,1-2H3
InChIKey IOPGGNYCFGEWPF-UHFFFAOYSA-N
Formula C16H12O6
HBA 6
HBD 3
MW 300.27
Rotatable Bonds 1
TPSA 104.06
LogP 1.9
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 300.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ampelomyces species Phaeosphaeriaceae Fungi 50729

Showing of synonyms

  • Aly AH, Edrada-Ebel R, et al. (2008). Bioactive metabolites from the endophytic fungus Ampelomyces sp. isolated from the medicinal plant Urospermum picroides. Phytochemistry,2008,69(8),1716-1725. [View] [PubMed]
Pubchem: 177458
Nmrshiftdb2: 70000562
Bindingdb: 50480483
CPRiL: 458033
Structure

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 300.27 g/mol

Antimicrobial
Cytotoxic

Absorption

Caco-2 (logPapp)
-5.03
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.890
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.6

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.960
Plasma Protein Binding
69.71
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
10.400
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.760
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.110
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.150
Micronucleos
Toxic
NR-AhR
Toxic
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
4.900
Rat (Acute)
2.490
Rat (Chronic Oral)
3.200
Fathead Minnow
4.260
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
451.420
Hydration Free Energy
-9.990
Log(D) at pH=7.4
2.190
Log(P)
3.23
Log S
-6.27
Log(Vapor Pressure)
-7.19
Melting Point
228.59
pKa Acid
5.81
pKa Basic
4.3
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9655
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9655
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9347
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9347
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9306
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9306
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9233
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9233
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9180
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9180
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9140
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9140
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9103
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9103
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9096
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9096
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9074
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9074
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8753
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8753
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8673
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8673
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8655
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8655
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8615
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8615
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8592
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8592
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8540
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8540
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8532
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8532
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8492
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8492
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8488
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8488
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8407
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8407
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8387
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8387
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8329
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8329
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8309
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8309
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8246
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8246
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8200
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8200
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8157
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8157
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8130
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8130
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8130
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8130
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8023
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8023
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7963
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7963
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7929
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7929
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7881
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7881
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7872
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7872
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7851
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7851
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7848
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7848
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7802
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7802
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7789
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7789
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.7787
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.7787
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7685
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7685
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7678
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7678
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7660
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7660
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7655
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7655
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7655
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7655
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7628
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7628
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7627
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7627
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7626
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7626
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.7611
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.7611
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7520
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7520
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7514
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7514
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7454
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7454
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7438
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7438
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7400
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7400
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7374
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7374
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7366
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7366
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7364
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7364
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7356
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7356
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7311
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7311
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7304
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7304
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7295
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7295
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7291
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7291
Reaction center protein L chain P0C0Y8 RCEL_RHOSH Rhodobacter sphaeroides 3 0.7287
Reaction center protein L chain P0C0Y8 RCEL_RHOSH Rhodobacter sphaeroides 3 0.7287
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7237
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7237
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7213
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7213
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7188
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7188
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7176
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7176
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7165
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7165
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7160
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7160
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7158
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7158
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7156
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7156
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7131
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7131
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7131
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7131
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7129
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7129
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7125
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7125
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7114
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7114
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7086
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7086
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7085
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7085
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7076
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7076
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7052
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7052
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7036
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7036
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7034
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7034
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7031
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7031
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7023
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7023
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7023
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7023
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7022
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7022
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7013
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7013
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7009
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7009
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7005
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7005

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