2-hydroxy-1-methoxyanthraquinone - Compound Card

2-hydroxy-1-methoxyanthraquinone

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2-hydroxy-1-methoxyanthraquinone

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1c(O)ccc2c1C(=O)c1c(C2=O)cccc1
InChI InChI=1S/C15H10O4/c1-19-15-11(16)7-6-10-12(15)14(18)9-5-3-2-4-8(9)13(10)17/h2-7,16H,1H3
InChIKey VRGZEPNGEFBVIZ-UHFFFAOYSA-N
Formula C15H10O4
HBA 4
HBD 1
MW 254.24
Rotatable Bonds 1
TPSA 63.6
LogP 2.18
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 254.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Morinda lucida Rubiaceae Plantae 339305
2 Galium sinaicum Rubiaceae Plantae 25168

Showing of synonyms

  • Halim A, Abd El-Fattah H, et al. (1992). Anthraquinones from Galium sinaicum. Phytochemistry, 1992, 31(1), 355-356. [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]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 254.24 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.56
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.280
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.44

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.770
Plasma Protein Binding
59.82
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
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
6.660
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.600
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.150
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.370
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
4.270
Rat (Acute)
2.530
Rat (Chronic Oral)
2.560
Fathead Minnow
4.510
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
390.880
Hydration Free Energy
-7.110
Log(D) at pH=7.4
1.520
Log(P)
2.79
Log S
-5.12
Log(Vapor Pressure)
-6.71
Melting Point
211.33
pKa Acid
6.72
pKa Basic
3.23
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 0.9710
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9598
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9277
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9142
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9131
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9131
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8987
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.8977
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8919
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8873
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8844
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8805
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8698
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8687
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8671
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8636
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8523
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8510
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8507
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8498
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8494
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8477
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.8451
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8450
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8438
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.8347
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8307
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.8257
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8228
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8169
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8157
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8100
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.8021
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7979
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7976
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7973
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7894
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7885
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7883
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7843
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7839
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7830
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7815
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7804
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7802
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7793
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7775
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7756
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7725
Cyclin-dependent kinase 6 Q00534 CDK6_HUMAN Homo sapiens 3 0.7721
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7721
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7712
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7708
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7697
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7677
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7675
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7651
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7638
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7629
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7618
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7611
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7569
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7555
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7543
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7542
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7540
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7535
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7513
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7511
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7506
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7505
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7481
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7479
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7449
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7449
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7445
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7437
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7426
Tubulin alpha chain A0A0R4I993 A0A0R4I993_SUSBA Sus barbatus 3 0.7412
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7411
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7410
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7406
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7393
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7389
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7373
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7371
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7369
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7369
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7346
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7335
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7327
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7326
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7325
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7316
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7314
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7307
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7298
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7291
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7290
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7285
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7272
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7260
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7259
Ketimine reductase mu-crystallin O54983 CRYM_MOUSE Mus musculus 2 0.7246
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7233
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7233
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7233
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7230
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7219
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7216
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7216
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7207
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7193
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7193
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7180
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7167
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7163
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7158
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7143
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7129
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7114
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7107
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7101
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7097
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7094
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7087
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7085
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7081
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7079
Histone-lysine N-methyltransferase EHMT2 Q96KQ7 EHMT2_HUMAN Homo sapiens 3 0.7077
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7075
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7073
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7065
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7059
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7056
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7044
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7041
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7036
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7013
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7012
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7004
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7002

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