2,4-dihydro-3,9-dihydroxy-6,8-dimethoxy-3-methylanthracen-1-one - Compound Card

2,4-dihydro-3,9-dihydroxy-6,8-dimethoxy-3-methylanthracen-1-one

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2,4-dihydro-3,9-dihydroxy-6,8-dimethoxy-3-methylanthracen-1-one

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Anthracene
    • Subclass: Anthracenone
Canonical Smiles COc1cc2cc3CC(C)(O)CC(=O)c3c(c2c(c1)OC)O
InChI InChI=1S/C17H18O5/c1-17(20)7-10-4-9-5-11(21-2)6-13(22-3)15(9)16(19)14(10)12(18)8-17/h4-6,19-20H,7-8H2,1-3H3
InChIKey SNXBVENZIZULGD-UHFFFAOYSA-N
Formula C17H18O5
HBA 5
HBD 2
MW 302.33
Rotatable Bonds 2
TPSA 75.99
LogP 2.44
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 302.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus wentii Trichocomaceae Fungi 5066

Showing of synonyms

  • Form I.C, Bonus M, et al. (2019). Xanthone, benzophenone and bianthrone derivatives from the hypersaline lake-derived fungus Aspergillus wentii. Bioorg Med Chem,2019,27(20),115005. [View] [PubMed]
Pubchem: 21681429

No compound-protein relationship available.

Structure

SMILES: O=C1CCCc(c12)cc3c(c2)cccc3

Level: 0

Mol. Weight: 302.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.51
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.650
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.08

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.910
Plasma Protein Binding
50.35
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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.670
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.450
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.570
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.850
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
3.810
Rat (Acute)
2.310
Rat (Chronic Oral)
2.430
Fathead Minnow
4.410
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
406.610
Hydration Free Energy
-10.530
Log(D) at pH=7.4
2.460
Log(P)
3.24
Log S
-3.99
Log(Vapor Pressure)
-6.58
Melting Point
154.63
pKa Acid
7.48
pKa Basic
4.18
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9712
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9496
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9402
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9312
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9284
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.9038
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.9028
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8974
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8894
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8882
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8823
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8815
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.8793
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8664
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8661
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.8647
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8632
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8595
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8517
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8467
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8397
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8208
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8186
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8172
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8129
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8092
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.8089
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7968
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7942
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7903
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7900
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7832
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7830
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7769
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7763
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7761
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7759
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7745
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7675
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7671
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7657
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7650
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7561
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7526
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7465
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7459
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7449
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7434
Protein mono-ADP-ribosyltransferase PARP14 Q460N5 PAR14_HUMAN Homo sapiens 3 0.7433
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7401
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7363
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7352
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7350
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7294
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7277
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7277
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 3 0.7272
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7263
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7261
D-mycarose 3-C-methyltransferase Q194Q4 Q194Q4_STRAA Streptomyces argillaceus 4 0.7260
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7251
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7249
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7243
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7241
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 3 0.7233
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7233
SRSF protein kinase 1 Q96SB4 SRPK1_HUMAN Homo sapiens 3 0.7228
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7222
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7208
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7193
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7193
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7193
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7189
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7180
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7161
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7158
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7141
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7104
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7102
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7101
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7083
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7080
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7060
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7059
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7045
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7036
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7018

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