1,8-dihydroxy-3-(hydroxyl methyl)-5-methoxy anthracene-9,10-dione - Compound Card

1,8-dihydroxy-3-(hydroxyl methyl)-5-methoxy anthracene-9,10-dione

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1,8-dihydroxy-3-(hydroxyl methyl)-5-methoxy anthracene-9,10-dione

Structure
Zoomed Structure
  • Family: Euphorbiaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1ccc(c2c1C(=O)c1cc(CO)cc(c1C2=O)O)O
InChI InChI=1S/C16H12O6/c1-22-11-3-2-9(18)13-14(11)15(20)8-4-7(6-17)5-10(19)12(8)16(13)21/h2-5,17-19H,6H2,1H3
InChIKey KMNJTAQXPSBWQA-UHFFFAOYSA-N
Formula C16H12O6
HBA 6
HBD 3
MW 300.27
Rotatable Bonds 2
TPSA 104.06
LogP 1.37
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 300.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia polyacantha Euphorbiaceae Plantae 260993

Showing of synonyms

  • ELhassan GOM, Adhikari A, et al. (2015). Chemical constituents of Euphorbia Polyacantha Boiss. and their immunomodulatory properties. Records of Natural Products,2015,9(1),146-152. [View]
Pubchem: 162817263

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 208.22 g/mol

Oxidative burst inhibitory

Absorption

Caco-2 (logPapp)
-5.02
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.820
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.8

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.810
Plasma Protein Binding
57.53
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
8.720
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.090
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.040
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.870
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
3.820
Rat (Acute)
2.430
Rat (Chronic Oral)
3.390
Fathead Minnow
4.130
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
446.890
Hydration Free Energy
-10.510
Log(D) at pH=7.4
1.760
Log(P)
2.51
Log S
-5.47
Log(Vapor Pressure)
-7.39
Melting Point
186.66
pKa Acid
6.49
pKa Basic
3.83
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 0.9065
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9065
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.8800
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.8800
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8765
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8765
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8696
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8696
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8686
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8686
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8543
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8543
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8267
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8267
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8118
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8118
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8075
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8075
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8067
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8067
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8059
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8059
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8021
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8021
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8008
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8008
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7970
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7970
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.7962
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.7962
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7914
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7914
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7877
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7877
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7859
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7859
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7833
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7833
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7830
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7830
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7826
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7826
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7762
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7762
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7738
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7738
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7718
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7718
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7686
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7686
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7650
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7650
Dimethylsulfonioproprionate demethylase DmdA Q4FP21 DMDA_PELUB Pelagibacter ubique 4 0.7603
Dimethylsulfonioproprionate demethylase DmdA Q4FP21 DMDA_PELUB Pelagibacter ubique 4 0.7603
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7594
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7594
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7593
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7593
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7564
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7564
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7538
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7538
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 5 0.7505
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 5 0.7505
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7498
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7498
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 4 0.7486
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 4 0.7486
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7424
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7424
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7408
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7408
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7398
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7398
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7397
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7397
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7379
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7379
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7313
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7313
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7311
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7311
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.7264
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.7264
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7260
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7260
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7208
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7208
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7164
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7164
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7130
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7130
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7127
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7127
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7117
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7117
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7105
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7105
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7104
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7104
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7097
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7097
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7092
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7092
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7072
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7072
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7060
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7060
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7028
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7028
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7009
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7009
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7007
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7007

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