Altenusin - Compound Card

Altenusin

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Altenusin

Structure
Zoomed Structure
  • Family: Fungi - Pleosporaceae
  • Kingdom: Fungi
  • Class: Phenolic
Canonical Smiles COc1cc(O)c(c(c1)c1cc(O)c(cc1C)O)C(=O)O
InChI InChI=1S/C15H14O6/c1-7-3-11(16)12(17)6-9(7)10-4-8(21-2)5-13(18)14(10)15(19)20/h3-6,16-18H,1-2H3,(H,19,20)
InChIKey ADPBTBPPIIKLEH-UHFFFAOYSA-N
Formula C15H14O6
HBA 5
HBD 4
MW 290.27
Rotatable Bonds 3
TPSA 107.22
LogP 2.49
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.13
Exact Mass 290.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Alternaria species Pleosporaceae Fungi 5598
2 Alternaria species Pleosporaceae Fungi 5598
3 Alternaria species Pleosporineae Fungi 5598

Showing of synonyms

  • Aly AH, Edrada-Ebel R, et al. (2008). Cytotoxic metabolites from the fungal endophyte Alternaria sp. and their subsequent detection in its host plant Polygonum senegalense. Journal of Natural Products,2008,71(6),972-980. [View] [PubMed]
  • Aly AH, Ebel R, et al. (2009). Protein kinase inhibitors from the endophytic fungus Alternaria sp. isolated from Polygonum senegalense Growing in Egypt. Planta Medica,2009,75-PE55. [View]
CPRiL: 122707
Structure

SMILES: c1ccccc1-c2ccccc2

Level: 1

Mol. Weight: 290.27 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 290.27 g/mol

Cytotoxic
Kinase inhibitory

Absorption

Caco-2 (logPapp)
-5.74
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.730
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.42

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.320
Plasma Protein Binding
59.83
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
Non-Inhibitor
CYP 2C9 Substrate
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
10.610
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.400
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.850
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.030
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
4.800
Rat (Acute)
2.010
Rat (Chronic Oral)
3.610
Fathead Minnow
3.700
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
413.100
Hydration Free Energy
-6.690
Log(D) at pH=7.4
1.110
Log(P)
3.3
Log S
-3.34
Log(Vapor Pressure)
-8.06
Melting Point
237.78
pKa Acid
8.04
pKa Basic
4.96
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9195
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9195
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8835
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8835
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8831
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8831
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8827
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8827
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.8798
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.8798
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8780
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8780
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8758
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8758
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8705
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8705
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8678
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8678
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8652
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8652
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8574
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8574
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8547
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8547
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 3 0.8459
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 3 0.8459
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8411
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8411
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8322
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8322
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8267
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8267
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8263
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8263
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8254
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8254
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8204
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8204
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8133
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8133
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.8103
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.8103
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8095
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8095
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 3 0.8081
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 3 0.8081
Three-prime repair exonuclease 1 Q91XB0 TREX1_MOUSE Mus musculus 3 0.8055
Three-prime repair exonuclease 1 Q91XB0 TREX1_MOUSE Mus musculus 3 0.8055
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8036
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8036
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7972
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7972
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7969
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7969
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7955
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7955
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7810
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7810
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7807
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7807
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7773
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7773
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7663
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7663
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 3 0.7656
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 3 0.7656
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7626
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7626
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7557
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7557
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7507
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7507
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7492
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7492
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7442
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7442
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7385
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7385
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7339
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7339
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7333
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7333
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7292
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7292
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7290
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7290
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7259
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7259
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7249
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7249
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7247
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7247
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7246
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7246
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7236
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7236
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7205
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7205
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7198
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7198
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7198
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7198
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7188
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7188
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7166
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7166
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 3 0.7157
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 3 0.7157
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7142
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7142
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 3 0.7119
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 3 0.7119
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7107
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7107
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.7075
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.7075
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7069
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7069
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7054
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7054
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7047
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7047
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7040
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7040
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7030
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7030
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7024
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7024
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7022
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7022
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7016
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7016
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7014
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7014
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7014
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7014
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7012
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7012
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7012
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7012
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7004
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7004

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