Emodic acid - Compound Card

Emodic acid

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Emodic acid

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Alkaloid
    • Subclass: Cyclic Peptide
Canonical Smiles Oc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)cc(c1)C(=O)O
InChI InChI=1S/C15H8O7/c16-6-3-8-12(10(18)4-6)14(20)11-7(13(8)19)1-5(15(21)22)2-9(11)17/h1-4,16-18H,(H,21,22)
InChIKey ZJXVNNSMRGTDBI-UHFFFAOYSA-N
Formula C15H8O7
HBA 6
HBD 4
MW 300.22
Rotatable Bonds 1
TPSA 132.13
LogP 1.28
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 300.03
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Talaromyces wortmannii Trichocomaceae Fungi 28567

Showing of synonyms

  • Bara R (2012). Natural Products from Endophytic Fungus Talaromyces wortmannii: Their Structure and mechanism of Actions. PhD Thesis, Institute for Pharmaceutical Biology and Biotechnology, University of Dusseldorf,2012, pp. 1-142.. [View]
CPRiL: 410963
Structure

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

Level: 0

Mol. Weight: 300.22 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.02
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.05
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.93

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.92
Plasma Protein Binding
65.74
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.27
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.0
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.95
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.41
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
2.83
Rat (Acute)
2.32
Rat (Chronic Oral)
3.9
Fathead Minnow
4.13
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
484.32
Hydration Free Energy
-9.85
Log(D) at pH=7.4
-0.58
Log(P)
3.09
Log S
-4.27
Log(Vapor Pressure)
-8.11
Melting Point
322.81
pKa Acid
7.88
pKa Basic
2.77
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9052
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9052
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9032
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9032
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8993
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8993
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.8967
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.8967
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8960
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8960
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8844
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8844
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8839
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8839
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8801
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8801
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8793
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8793
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8616
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8616
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.8603
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.8603
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8517
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8517
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8507
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8507
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8462
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8462
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8455
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8455
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8376
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8376
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.8366
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.8366
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8330
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8330
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 4 0.8299
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 4 0.8299
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8286
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8286
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8241
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8241
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8197
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8197
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 3 0.8138
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 3 0.8138
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8135
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8135
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.8117
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.8117
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 4 0.8103
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 4 0.8103
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8101
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8101
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8040
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8040
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7952
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7952
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7945
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7945
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7908
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7908
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7898
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7898
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7890
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7890
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7881
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7881
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7880
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7880
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7838
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7838
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7821
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7821
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7806
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7806
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7804
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7804
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.7792
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.7792
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7759
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7759
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7757
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7757
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7729
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7729
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7708
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7708
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7693
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7693
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7691
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7691
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7660
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7660
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7659
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7659
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7615
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7615
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.7611
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.7611
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7576
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7576
GMP reductase 2 Q9P2T1 GMPR2_HUMAN Homo sapiens 4 0.7543
GMP reductase 2 Q9P2T1 GMPR2_HUMAN Homo sapiens 4 0.7543
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7542
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7542
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7515
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7515
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7462
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7462
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7424
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7424
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7331
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7331
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7317
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7317
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7306
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7306
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7300
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7300
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7260
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7260
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7207
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7207
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7198
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7198
Aklanonic acid methyl ester cyclase AcmA O52646 DNRD_STRGJ Streptomyces galilaeus 3 0.7189
Aklanonic acid methyl ester cyclase AcmA O52646 DNRD_STRGJ Streptomyces galilaeus 3 0.7189
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7169
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7169
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7158
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7158
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7150
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7150
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7116
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7116
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7116
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7116
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7095
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7095
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7089
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7089
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7080
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7080
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7075
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7075
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7060
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7060
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.7051
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.7051
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7019
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7019
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7014
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7014

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