1,6-dihydroxy-2-hydroxymethyl-5-methoxy-9,10-anthracenedione - Compound Card

1,6-dihydroxy-2-hydroxymethyl-5-methoxy-9,10-anthracenedione

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1,6-dihydroxy-2-hydroxymethyl-5-methoxy-9,10-anthracenedione

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1c(O)ccc2c1C(=O)c1ccc(c(c1C2=O)O)CO
InChI InChI=1S/C16H12O6/c1-22-16-10(18)5-4-9-12(16)15(21)8-3-2-7(6-17)13(19)11(8)14(9)20/h2-5,17-19H,6H2,1H3
InChIKey BEQICHUYUVZVRQ-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 Morinda lucida Rubiaceae Plantae 339305
2 Morinda lucida Rubiaceae Plantae 339305

Showing of synonyms

  • Mfonku NA, Tadjong AT, et al. (2021). Isolation and characterization of antisalmonellal anthraquinones and coumarins from Morinda lucida Benth. (Rubiaceae). Chem. Pap. 2021, 75, 2067-2073. [View]
  • Longue Ekon J, Zra T, et al. (2020). New anthraquinone derivatives from the stem barks of Morinda lucida Benth. Phytochemistry Letters, 2020, 39, 94-98. [View]
Pubchem: 155292923

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 300.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.78
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.750
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.49

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.870
Plasma Protein Binding
64.08
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-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
9.290
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.110
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.010
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.370
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
3.780
Rat (Acute)
2.380
Rat (Chronic Oral)
3.270
Fathead Minnow
4.150
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
444.180
Hydration Free Energy
-10.520
Log(D) at pH=7.4
1.120
Log(P)
2.18
Log S
-5.03
Log(Vapor Pressure)
-7.39
Melting Point
211.38
pKa Acid
6.48
pKa Basic
3.83
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8829
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8787
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8755
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8704
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8679
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8623
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8593
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8590
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8580
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8567
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8453
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8431
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8428
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8387
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8383
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8379
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8345
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8295
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8294
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8225
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.8189
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8174
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8162
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8143
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8054
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8001
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7950
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.7944
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7925
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7919
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7905
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 4 0.7879
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7836
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7822
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.7812
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7807
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7806
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7785
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7768
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7765
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7762
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7739
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7731
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7731
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7688
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7685
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7662
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7657
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7614
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7609
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7598
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7594
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7574
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 3 0.7571
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7562
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7558
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7546
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7534
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7510
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7479
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7471
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7464
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7444
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7440
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7417
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7404
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7396
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7396
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7375
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7315
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7310
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 4 0.7285
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7282
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7277
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7274
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7262
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7255
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7224
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7215
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7184
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7181
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7174
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7166
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7165
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7143
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7141
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7110
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7107
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7104
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7100
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7093
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7091
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7084
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7074
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7069
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7056
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7051
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7049
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7047
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7033
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7030
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7028
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7006
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7003

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