5-chloro-6,8,10-trihydroxy-1-methoxy-3-methyl-9(10H)-anthracenone - Compound Card

5-chloro-6,8,10-trihydroxy-1-methoxy-3-methyl-9(10H)-anthracenone

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5-chloro-6,8,10-trihydroxy-1-methoxy-3-methyl-9(10H)-anthracenone

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Quinone
    • Subclass: Anthrone
Canonical Smiles COc1cc(C)cc2c1C(=O)c1c([C@@H]2O)c(Cl)c(cc1O)O
InChI InChI=1S/C16H13ClO5/c1-6-3-7-11(10(4-6)22-2)16(21)12-8(18)5-9(19)14(17)13(12)15(7)20/h3-5,15,18-20H,1-2H3/t15-/m1/s1
InChIKey XLQCTJILGLSGOE-OAHLLOKOSA-N
Formula C16H13ClO5
HBA 5
HBD 3
MW 320.73
Rotatable Bonds 1
TPSA 86.99
LogP 2.69
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.19
Exact Mass 320.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Penicillium species Trichocomaceae Fungi 5073

Showing of synonyms

  • Aly AH, Debbab A, et al. (2011). NF kappa B inhibitors and antitrypanosomal metabolites from endophytic fungus Penicillium sp. isolated from Limonium tubiflorum. Bioorganic and Medicinal Chemistry,2011,19(1),414-421. [View] [PubMed]
Pubchem: 162953819
Nmrshiftdb2: 80008158

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)Cc3c(C2=O)cccc3

Level: 0

Mol. Weight: 320.73 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.850
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.14

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.290
Plasma Protein Binding
87.71
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.070
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.510
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.180
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.760
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
2.620
Rat (Acute)
2.270
Rat (Chronic Oral)
3.030
Fathead Minnow
4.330
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
420.750
Hydration Free Energy
-11.340
Log(D) at pH=7.4
2.480
Log(P)
3.11
Log S
-5.23
Log(Vapor Pressure)
-7.22
Melting Point
195.21
pKa Acid
5.93
pKa Basic
3.11
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.9453
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.9453
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9375
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9375
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.9220
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.9220
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9158
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9158
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8802
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8802
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8728
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8728
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.8548
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.8548
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8545
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8545
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8328
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8328
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8317
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8317
Alpha/beta hydrolase fold A5VAT9 A5VAT9_SPHWW Sphingomonas wittichii 3 0.8236
Alpha/beta hydrolase fold A5VAT9 A5VAT9_SPHWW Sphingomonas wittichii 3 0.8236
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8114
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8114
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8106
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8106
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.8038
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.8038
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8017
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8017
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8001
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8001
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7998
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7998
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.7994
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.7994
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 4 0.7939
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 4 0.7939
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7922
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7922
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7896
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7896
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 3 0.7890
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 3 0.7890
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7871
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7871
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.7811
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.7811
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7806
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7806
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Q9R1E6 ENPP2_MOUSE Mus musculus 4 0.7781
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Q9R1E6 ENPP2_MOUSE Mus musculus 4 0.7781
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7746
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7746
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7690
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7690
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7675
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7675
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7658
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7658
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7632
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7632
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7630
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7630
Enoyl-[acyl-carrier-protein] reductase [NADH] Q5NGQ3 Q5NGQ3_FRATT Francisella tularensis subsp. tularensis 3 0.7610
Enoyl-[acyl-carrier-protein] reductase [NADH] Q5NGQ3 Q5NGQ3_FRATT Francisella tularensis subsp. tularensis 3 0.7610
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7573
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7573
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.7563
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.7563
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7549
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7549
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7528
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7528
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7523
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7523
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7520
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7520
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7489
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7489
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7486
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7486
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7473
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7473
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7468
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7468
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7457
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7457
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7441
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7441
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7441
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7441
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7433
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7433
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7408
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7408
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7378
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7378
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7364
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7364
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7349
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7349
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7333
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7333
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7307
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7307
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7304
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7304
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7285
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7285
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7261
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7261
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7260
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7260
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7253
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7253
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7244
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7244
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7239
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7239
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7221
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7221
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7214
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7214
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 4 0.7214
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 4 0.7214
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7185
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7185
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial P08559 ODPA_HUMAN Homo sapiens 3 0.7171
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial P08559 ODPA_HUMAN Homo sapiens 3 0.7171
Thymidylate synthase Q9Y052 Q9Y052_CAEEL Caenorhabditis elegans 4 0.7170
Thymidylate synthase Q9Y052 Q9Y052_CAEEL Caenorhabditis elegans 4 0.7170
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7161
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7161
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7155
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7155
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7146
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7146
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7145
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7145
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7115
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7115
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7102
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7102
D-mycarose 3-C-methyltransferase Q194Q4 Q194Q4_STRAA Streptomyces argillaceus 4 0.7090
D-mycarose 3-C-methyltransferase Q194Q4 Q194Q4_STRAA Streptomyces argillaceus 4 0.7090
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.7083
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.7083
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7049
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7049
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7030
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7030
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7021
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7021

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