1-hydroxy-3-methoxy-6-methylanthraquinone - Compound Card

1-hydroxy-3-methoxy-6-methylanthraquinone

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1-hydroxy-3-methoxy-6-methylanthraquinone

Structure
Zoomed Structure
  • Family: Fungi - Pleosporaceae
  • Kingdom: Fungi
  • Class: Anthraquinone
Canonical Smiles COc1cc(O)c2c(c1)C(=O)c1c(C2=O)ccc(c1)C
InChI InChI=1S/C16H12O4/c1-8-3-4-10-11(5-8)15(18)12-6-9(20-2)7-13(17)14(12)16(10)19/h3-7,17H,1-2H3
InChIKey IBTIVMOKTOHUFA-UHFFFAOYSA-N
Formula C16H12O4
HBA 4
HBD 1
MW 268.27
Rotatable Bonds 1
TPSA 63.6
LogP 2.48
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 268.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Stemphylium globuliferum Pleosporaceae Fungi 245170

Showing of synonyms

  • Moussa M, Ebrahim W, et al. (2016). Tetrahydroanthraquinone derivatives from the mangrove-derived endophytic fungus Stemphylium globuliferum.. Tetrahedron Letters, 2016, 57(36), 4074–4078.. [View]
Pubchem: 179389
Nmrshiftdb2: 60076360

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 268.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.64
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.350
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.43

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.920
Plasma Protein Binding
56.79
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
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
6.030
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.640
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.050
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.400
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
4.610
Rat (Acute)
2.370
Rat (Chronic Oral)
2.450
Fathead Minnow
4.550
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
403.400
Hydration Free Energy
-7.390
Log(D) at pH=7.4
2.730
Log(P)
3.83
Log S
-6.18
Log(Vapor Pressure)
-6.77
Melting Point
191.28
pKa Acid
7.0
pKa Basic
3.87
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9694
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9396
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9345
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9179
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.9152
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9145
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9138
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.9132
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9113
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9106
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9075
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.9021
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8856
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8819
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8763
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8740
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8710
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8707
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8682
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8595
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8579
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8552
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8551
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8538
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.8504
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8499
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8461
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8444
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8430
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8385
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8354
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8339
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8334
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8334
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.8270
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8267
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.8223
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.8213
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8206
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.8145
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8100
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Q9R1E6 ENPP2_MOUSE Mus musculus 4 0.8093
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8078
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 4 0.8074
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.8067
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.8052
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8028
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8017
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8010
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7992
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7991
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7932
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7928
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7846
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7839
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7834
Enoyl-[acyl-carrier-protein] reductase [NADH] Q5NGQ3 Q5NGQ3_FRATT Francisella tularensis subsp. tularensis 3 0.7816
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7790
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7780
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7760
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7681
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7679
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7649
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7642
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 2 0.7616
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7614
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7601
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7580
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7572
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7572
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7541
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7529
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7519
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7519
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7509
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7508
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7490
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7482
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7482
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7434
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7431
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7390
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7387
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7382
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 3 0.7364
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7363
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7361
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7349
Serine/threonine-protein kinase TBK1 Q9UHD2 TBK1_HUMAN Homo sapiens 3 0.7346
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7329
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.7329
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7327
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7320
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7320
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7295
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7289
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7286
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7283
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7282
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7280
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 4 0.7274
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7273
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7273
Bifunctional F420 biosynthesis protein FbiB P9WP79 FBIB_MYCTU Mycobacterium tuberculosis 5 0.7271
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7271
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7268
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7267
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7247
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.7231
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.7230
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7230
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7226
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7224
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7209
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7208
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7196
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7192
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7190
Tyrosine-protein kinase Lyn P25911 LYN_MOUSE Mus musculus 3 0.7182
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7172
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7163
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7152
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7146
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 3 0.7091
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7090
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7079
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7078
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7078
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7077
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7064
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7064
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 4 0.7057
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 3 0.7046
Enoyl-acyl carrier protein reductase Q6TEI5 Q6TEI5_PLABE Plasmodium berghei 3 0.7039
Repressor Q8KLP4 Q8KLP4_STEMA Stenotrophomonas maltophilia 4 0.7030
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7020
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7020
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7009
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7000

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