1,2-dimethoxyanthraquinone - Compound Card

1,2-dimethoxyanthraquinone

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1,2-dimethoxyanthraquinone

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
Canonical Smiles COc1c(OC)ccc2c1C(=O)c1ccccc1C2=O
InChI InChI=1S/C16H12O4/c1-19-12-8-7-11-13(16(12)20-2)15(18)10-6-4-3-5-9(10)14(11)17/h3-8H,1-2H3
InChIKey AMKRBKSZCGCEJK-UHFFFAOYSA-N
Formula C16H12O4
HBA 4
HBD 0
MW 268.27
Rotatable Bonds 2
TPSA 52.6
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 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]
Pubchem: 4217712
Nmrshiftdb2: 60077657

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)
-4.59
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.340
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.51

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.850
Plasma Protein Binding
58.59
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
Non-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
6.590
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.970
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.100
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.550
Micronucleos
Safe
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
4.150
Rat (Acute)
2.390
Rat (Chronic Oral)
2.190
Fathead Minnow
4.790
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
397.650
Hydration Free Energy
-7.310
Log(D) at pH=7.4
2.010
Log(P)
3.14
Log S
-5.01
Log(Vapor Pressure)
-6.04
Melting Point
173.62
pKa Acid
7.61
pKa Basic
2.16
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9707
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9626
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9357
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9329
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9327
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9275
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.9224
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9103
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.9049
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8994
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8802
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8722
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8719
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8709
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8676
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8640
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8619
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8581
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8537
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8463
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.8352
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8343
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.8247
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8209
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8048
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8022
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7989
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7960
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7925
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7904
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7887
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7874
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7859
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7858
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7853
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7805
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7797
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7789
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7740
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7732
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7715
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7672
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7655
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7601
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7579
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7554
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7542
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7536
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7535
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7532
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7518
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7508
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7487
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7480
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7473
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7472
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7471
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7466
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7464
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7462
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7406
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7400
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7393
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7365
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7343
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7338
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7335
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7330
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7327
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7327
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7306
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7304
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7295
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7291
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7284
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7283
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7277
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7268
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7253
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7247
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7237
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7222
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7222
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7220
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7217
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7216
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7211
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7207
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7203
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7201
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7195
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7192
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7180
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7176
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7150
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7148
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7138
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7119
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7117
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 2 0.7113
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 2 0.7090
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7077
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7076
Renin P00797 RENI_HUMAN Homo sapiens 2 0.7056
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 2 0.7056
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7051
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7029
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7021
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7021
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7009

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