Lecanoric acid - Compound Card

Lecanoric acid

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Lecanoric acid

Structure
Zoomed Structure
  • Family: Fungi - Chaetomiaceae
  • Kingdom: Fungi
  • Class: Phenolic
Canonical Smiles Oc1cc(C)c(c(c1)O)C(=O)Oc1cc(C)c(c(c1)O)C(=O)O
InChI InChI=1S/C16H14O7/c1-7-3-9(17)5-11(18)14(7)16(22)23-10-4-8(2)13(15(20)21)12(19)6-10/h3-6,17-19H,1-2H3,(H,20,21)
InChIKey HEMSJKZDHNSSEW-UHFFFAOYSA-N
Formula C16H14O7
HBA 6
HBD 4
MW 318.28
Rotatable Bonds 3
TPSA 124.29
LogP 2.34
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 318.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Chaetomium sp. Chaetomiaceae Fungi 1769349

Showing of synonyms

  • Talontsi FM, Douanla-Meli C, et al. (2013). Depsidones from an Endophytic Fungus Chaetomium sp. Associated with Zanthoxylum leprieurii. Z. Naturforsch, 2013, 68b, 1259 – 1264. [View]
CPRiL: 37327
Structure

SMILES: c1ccccc1C(=O)Oc2ccccc2

Level: 1

Mol. Weight: 318.28 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 318.28 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.04
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.970
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.85

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.310
Plasma Protein Binding
58.16
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.790
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.460
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.360
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.730
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
Toxic
T. Pyriformis
7.250
Rat (Acute)
2.120
Rat (Chronic Oral)
3.360
Fathead Minnow
3.790
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
460.280
Hydration Free Energy
-6.350
Log(D) at pH=7.4
1.320
Log(P)
3.91
Log S
-3.59
Log(Vapor Pressure)
-9.59
Melting Point
240.89
pKa Acid
6.58
pKa Basic
5.0
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9535
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9497
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.9119
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9087
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.9073
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8971
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8958
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8943
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8922
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8863
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8832
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8788
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.8757
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8629
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.8593
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8587
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8560
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8499
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8497
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 3 0.8481
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8473
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8443
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.8414
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8386
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8350
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 5 0.8329
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8304
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8261
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8259
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8250
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8213
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.8190
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8142
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8141
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8129
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8107
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 3 0.8103
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8099
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.8072
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8065
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8061
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8052
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8032
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8032
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8030
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8021
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8016
Ornithine transcarbamylase, mitochondrial P00480 OTC_HUMAN Homo sapiens 3 0.8015
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7996
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7994
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7975
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7961
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7930
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 4 0.7895
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.7894
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7840
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.7828
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7820
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7808
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7750
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7745
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7731
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7721
Cyclin homolog Q01043 CGH2_SHV21 Saimiriine herpesvirus 2 4 0.7704
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7686
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7672
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7661
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7649
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7631
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7627
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7593
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7591
Transthyretin P02766 TTHY_HUMAN Homo sapiens 4 0.7583
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7534
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 4 0.7531
Aspartate carbamoyltransferase catalytic subunit P0A786 PYRB_ECOLI Escherichia coli 3 0.7521
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 4 0.7498
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.7472
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7450
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7445
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7439
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7439
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7432
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7429
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7426
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.7418
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7386
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 3 0.7367
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7366
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7337
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7319
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 4 0.7290
NTPase P4 Q94M05 Q94M05_9VIRU Pseudomonas phage phi12 3 0.7279
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7248
Ribosomal protein S6 kinase alpha-1 Q15418 KS6A1_HUMAN Homo sapiens 3 0.7245
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 4 0.7233
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.7211
Reticuline oxidase P30986 RETO_ESCCA Eschscholzia californica 4 0.7203
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7178
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7172
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7166
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7156
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7148
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7127
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7127
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7126
orotidine-5'-phosphate decarboxylase Q8T6J6 Q8T6J6_PLAFA Plasmodium falciparum 4 0.7110
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7105
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7102
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7098
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7080
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7079
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7077
Catechol 2,3-dioxygenase Q6REQ5 Q6REQ5_9NOCA Rhodococcus sp. DK17 3 0.7060
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7060
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7058
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7056
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 2 0.7052
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7027
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7025
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7013
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7009

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