2-hydroxy-3-methylanthraquinone - Compound Card

2-hydroxy-3-methylanthraquinone

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2-hydroxy-3-methylanthraquinone

Structure
Zoomed Structure
  • Family: Plantae - Verbenaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles O=C1c2cc(O)c(cc2C(=O)c2c1cccc2)C
InChI InChI=1S/C15H10O3/c1-8-6-11-12(7-13(8)16)15(18)10-5-3-2-4-9(10)14(11)17/h2-7,16H,1H3
InChIKey RNJHIYAJJKOFIO-UHFFFAOYSA-N
Formula C15H10O3
HBA 3
HBD 1
MW 238.24
Rotatable Bonds 0
TPSA 54.37
LogP 2.48
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 238.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Morinda lucida Rubiaceae Plantae 339305
2 Tectona grandis Verbenaceae Plantae 41396

Showing of synonyms

  • Kopa T, Tchinda A, et al. (2014). Antiplasmodial anthraquinones and hemisynthetic derivatives from the leaves of Tectona grandis (Verbenaceae). Phytochemistry Letters, 2014, 8, 41-45. [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: 10889963
Nmrshiftdb2: 60020211
CPRiL: 221023
Structure

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

Level: 0

Mol. Weight: 238.24 g/mol

Antimalarial

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.350
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.99

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.910
Plasma Protein Binding
57.76
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
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.330
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.680
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.120
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.920
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
4.680
Rat (Acute)
2.240
Rat (Chronic Oral)
2.370
Fathead Minnow
4.500
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
389.720
Hydration Free Energy
-7.000
Log(D) at pH=7.4
2.300
Log(P)
3.25
Log S
-5.55
Log(Vapor Pressure)
-7.82
Melting Point
254.16
pKa Acid
6.78
pKa Basic
5.34
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9696
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9363
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9188
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9094
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8995
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8925
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8890
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8887
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.8786
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.8754
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8710
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8576
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.8556
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8475
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8410
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8381
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8371
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8364
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8313
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8283
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8196
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.8151
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.8131
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.8107
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8082
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8017
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8016
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8012
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7997
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7996
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.7979
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7900
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7878
Enoyl-[acyl-carrier-protein] reductase [NADH] Q5NGQ3 Q5NGQ3_FRATT Francisella tularensis subsp. tularensis 3 0.7869
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7840
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7817
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7791
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7737
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7733
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7710
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7682
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7639
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7610
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7605
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7604
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7591
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7560
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7559
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 4 0.7556
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7548
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7535
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7534
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7531
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7529
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7528
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7498
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7491
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.7472
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7456
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7445
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7441
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7432
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7424
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7405
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7405
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7384
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7370
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7366
2-Hydroxyacid oxidase 1 Q9UJM8 HAOX1_HUMAN Homo sapiens 3 0.7362
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7354
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7337
Ketimine reductase mu-crystallin O54983 CRYM_MOUSE Mus musculus 2 0.7329
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7315
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7315
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7314
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7311
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7297
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7296
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7288
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7260
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7230
A disintegrin and metalloproteinase with thrombospondin motifs 5 Q9UNA0 ATS5_HUMAN Homo sapiens 3 0.7225
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7212
Bifunctional dihydrofolate reductase-thymidylate synthase Q27793 DRTS_TRYCR Trypanosoma cruzi 3 0.7205
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7203
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7200
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7160
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7147
Tubulin alpha chain A0A0R4I993 A0A0R4I993_SUSBA Sus barbatus 3 0.7139
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7133
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 2 0.7125
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7114
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7110
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7091
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7087
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 2 0.7076
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7052
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7039
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7035
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7030
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7029
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7023
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7014
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7008
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7005

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