1,5-dihydroxy-3,4-dimethoxy-2-methylanthraquinone - Compound Card

1,5-dihydroxy-3,4-dimethoxy-2-methylanthraquinone

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1,5-dihydroxy-3,4-dimethoxy-2-methylanthraquinone

Structure
Zoomed Structure
  • Family: Monera - Streptomycetaceae
  • Kingdom: Monera
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1c(OC)c(C)c(c2c1C(=O)c1c(O)cccc1C2=O)O
InChI InChI=1S/C17H14O6/c1-7-13(19)11-12(17(23-3)16(7)22-2)15(21)10-8(14(11)20)5-4-6-9(10)18/h4-6,18-19H,1-3H3
InChIKey WDACTVCJHNVGNV-UHFFFAOYSA-N
Formula C17H14O6
HBA 6
HBD 2
MW 314.29
Rotatable Bonds 2
TPSA 93.06
LogP 2.2
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.18
Exact Mass 314.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Streptomyces species Eg8. Streptomycetaceae Monera 1883

Showing of synonyms

  • Abdelfattah MS (2014). Isolation and crystal structure of a new anthraquinone derivative from Actinomycete.. Chemistry of Natural Compounds,2014,50(4),613-616. [View]
Pubchem: 129882362
Nmrshiftdb2: 80014407

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 314.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.51
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.710
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.2

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.860
Plasma Protein Binding
64.0
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
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
9.570
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.290
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.960
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.170
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
4.410
Rat (Acute)
2.430
Rat (Chronic Oral)
3.060
Fathead Minnow
4.570
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
430.160
Hydration Free Energy
-7.790
Log(D) at pH=7.4
2.990
Log(P)
4.08
Log S
-6.6
Log(Vapor Pressure)
-7.05
Melting Point
183.11
pKa Acid
7.27
pKa Basic
2.48
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9392
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9392
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9248
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9248
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9064
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9064
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9030
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9030
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8974
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8974
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8968
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8968
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8958
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8958
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8947
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8947
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8722
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8722
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8721
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8721
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8468
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8468
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8336
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8336
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8335
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8335
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8317
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8317
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8274
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8274
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8265
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8265
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8228
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8228
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8221
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8221
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8190
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8190
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8065
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8065
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8058
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8058
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8055
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8055
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.8053
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.8053
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8049
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8049
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7987
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7987
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7893
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7893
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7892
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7892
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7835
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7835
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7752
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7752
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7717
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7717
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7660
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7660
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7637
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7637
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7631
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7631
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7601
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7601
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7598
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7598
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7582
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7582
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7574
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7574
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7573
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7573
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7568
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7568
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7550
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7550
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7544
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7544
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7527
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7527
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7523
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7523
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7521
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7521
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7519
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7519
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7515
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7515
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7484
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7484
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7457
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7457
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7435
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7435
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7429
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7429
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7407
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7407
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7387
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7387
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7387
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7387
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7382
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7382
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7378
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7378
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7362
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7362
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7358
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7358
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7347
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7347
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7327
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7327
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7291
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7291
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7289
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7289
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7276
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7276
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7252
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7252
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7237
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7237
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7225
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7225
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7221
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7221
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 2 0.7217
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 2 0.7217
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 3 0.7213
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 3 0.7213
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7213
Enoyl-[acyl-carrier-protein] reductase [NADH], chloroplastic P80030 FABI_BRANA Brassica napus 4 0.7213
Enoyl-[acyl-carrier-protein] reductase [NADH], chloroplastic P80030 FABI_BRANA Brassica napus 4 0.7213
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7213
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7184
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7184
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7183
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7183
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7179
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7179
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7137
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7137
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7126
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7126
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7118
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7118
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7114
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7114
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7107
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7107
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7101
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7101
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7074
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7074
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7073
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7073
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7058
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7058
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7049
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7049
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7038
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7038
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7004
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7004
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7002
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7002

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