1,5-dihydroxy-6-methoxy-2-methylanthraquinone - Compound Card

1,5-dihydroxy-6-methoxy-2-methylanthraquinone

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1,5-dihydroxy-6-methoxy-2-methylanthraquinone

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1ccc2c(c1O)C(=O)c1c(C2=O)c(O)c(cc1)C
InChI InChI=1S/C16H12O5/c1-7-3-4-8-11(13(7)17)14(18)9-5-6-10(21-2)16(20)12(9)15(8)19/h3-6,17,20H,1-2H3
InChIKey JJTIQZJKQCQNJK-UHFFFAOYSA-N
Formula C16H12O5
HBA 5
HBD 2
MW 284.27
Rotatable Bonds 1
TPSA 83.83
LogP 2.19
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 284.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Morinda lucida Rubiaceae Plantae 339305

Showing of synonyms

  • 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]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 284.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.47
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.660
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.95

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.980
Plasma Protein Binding
62.2
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
7.080
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.450
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.430
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.440
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)
2.560
Rat (Chronic Oral)
2.980
Fathead Minnow
4.460
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
417.430
Hydration Free Energy
-8.590
Log(D) at pH=7.4
2.690
Log(P)
4.06
Log S
-6.49
Log(Vapor Pressure)
-7.19
Melting Point
199.51
pKa Acid
5.69
pKa Basic
4.24
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9480
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9268
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9194
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9089
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9086
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8980
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8950
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8876
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8843
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8719
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8699
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8676
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8673
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8512
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8469
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8390
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8237
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8205
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.8185
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8067
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8033
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7995
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7958
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7957
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7914
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7874
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7836
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7834
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7818
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7808
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7738
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7712
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7710
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7686
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7666
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7665
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7583
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7573
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7548
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7528
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7513
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7509
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7505
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7488
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7469
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7468
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7467
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7463
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7460
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7447
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7445
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7439
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7429
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7410
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7386
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7380
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7376
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7369
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7366
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7363
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7358
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7334
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7318
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7295
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7293
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7285
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7283
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7281
Enoyl-[acyl-carrier-protein] reductase [NADH], chloroplastic P80030 FABI_BRANA Brassica napus 4 0.7275
Serine/threonine-protein kinase TBK1 Q9UHD2 TBK1_HUMAN Homo sapiens 3 0.7258
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7236
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7235
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7234
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7229
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7228
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7226
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7222
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7213
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7212
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7206
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.7195
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7191
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7181
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7178
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7177
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7175
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7168
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7157
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7154
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7154
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7148
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7136
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Q9R1E6 ENPP2_MOUSE Mus musculus 4 0.7119
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7103
Beta-glucosidase Q8T0W7 Q8T0W7_9NEOP Neotermes koshunensis 3 0.7101
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7075
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7073
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7061
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7057
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7039
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7032
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7032
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7015

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