Alternariol 5-O-sulphate - Compound Card

Alternariol 5-O-sulphate

Select a section from the left sidebar

Alternariol 5-O-sulphate

Structure
Zoomed Structure
  • Family: Pleosporaceae, Pleosporineae
  • Kingdom: Fungi
  • Class: Coumarin
    • Subclass: Coumestan
Canonical Smiles Oc1cc(C)c2c(c1)oc(=O)c1c2cc(cc1O)OS(=O)(=O)O
InChI InChI=1S/C14H10O8S/c1-6-2-7(15)3-11-12(6)9-4-8(22-23(18,19)20)5-10(16)13(9)14(17)21-11/h2-5,15-16H,1H3,(H,18,19,20)
InChIKey IOBDCMVQCAWFQQ-UHFFFAOYSA-N
Formula C14H10O8S
HBA 7
HBD 3
MW 338.29
Rotatable Bonds 2
TPSA 134.27
LogP 1.85
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 338.01
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Alternaria species Pleosporaceae Fungi 5598
2 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]
Pubchem: 24899915
Nmrshiftdb2: 80005808
Bindingdb: 50479264

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1c23)oc(=O)c2cccc3

Level: 0

Mol. Weight: 196.21 g/mol

Cytotoxic
Kinase inhibitory

Absorption

Caco-2 (logPapp)
-5.6
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.330
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-4.57

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.190
Plasma Protein Binding
69.32
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
8.780
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.950
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.400
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.300
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
9.110
Rat (Acute)
2.060
Rat (Chronic Oral)
2.640
Fathead Minnow
3.970
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
521.510
Hydration Free Energy
-5.860
Log(D) at pH=7.4
1.130
Log(P)
0.57
Log S
-2.1
Log(Vapor Pressure)
-10.26
Melting Point
252.01
pKa Acid
8.33
pKa Basic
3.51
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 0.8975
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8975
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8955
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8955
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8829
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8829
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8711
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8711
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8613
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8613
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8589
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8589
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8517
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8517
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8490
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8490
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8427
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8427
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8401
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8401
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 4 0.8346
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 4 0.8346
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8319
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8319
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8207
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8207
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8184
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8184
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8179
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8179
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8144
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8144
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8136
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8136
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.8101
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.8101
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.8079
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.8079
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8035
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8035
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8029
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8029
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8029
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8029
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7987
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7987
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7957
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7957
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7947
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7947
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7881
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7881
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 4 0.7868
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 4 0.7868
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7679
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7679
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7657
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7657
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.7639
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.7639
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.7635
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.7635
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7606
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7606
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7590
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7590
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7576
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7576
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7558
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7558
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7538
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7538
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7521
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7521
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7512
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7512
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7504
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7504
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7496
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7496
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7486
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7486
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7453
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7453
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7445
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7445
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7428
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7428
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7427
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7427
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7416
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7416
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7409
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7409
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 3 0.7384
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 3 0.7384
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7324
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7324
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7323
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7323
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7302
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7302
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7283
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7283
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7272
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7272
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7268
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7268
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7259
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7259
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7258
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7258
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7242
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7242
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7238
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7238
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7215
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7215
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7184
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7184
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7159
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7159
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7150
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7150
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7124
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7124
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7077
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7077
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7072
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7072
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7049
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7049
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7048
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7048
Orotidine 5'-phosphate decarboxylase O58462 PYRF_PYRHO Pyrococcus horikoshii 3 0.7041
Orotidine 5'-phosphate decarboxylase O58462 PYRF_PYRHO Pyrococcus horikoshii 3 0.7041
Ribosomal protein L11 methyltransferase, putative C3MWA1 C3MWA1_SULIM Sulfolobus islandicus 4 0.7030
Ribosomal protein L11 methyltransferase, putative C3MWA1 C3MWA1_SULIM Sulfolobus islandicus 4 0.7030
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7026
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7026
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7019
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7019
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 4 0.7009
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 4 0.7009

Download SDF