2-hydroxy-3-hydroxymethylanthraquinone - Compound Card

2-hydroxy-3-hydroxymethylanthraquinone

Select a section from the left sidebar

2-hydroxy-3-hydroxymethylanthraquinone

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles OCc1cc2c(cc1O)C(=O)c1c(C2=O)cccc1
InChI InChI=1S/C15H10O4/c16-7-8-5-11-12(6-13(8)17)15(19)10-4-2-1-3-9(10)14(11)18/h1-6,16-17H,7H2
InChIKey LMXDYBJTJGPZPD-UHFFFAOYSA-N
Formula C15H10O4
HBA 4
HBD 2
MW 254.24
Rotatable Bonds 1
TPSA 74.6
LogP 1.66
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

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]
Pubchem: 44445519
Chebi: 69520
Nmrshiftdb2: 60063726
Metabolights: MTBLC69520

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)
-4.65
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.26
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.45

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.85
Plasma Protein Binding
57.86
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
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.29
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.26
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.96
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.31
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
3.91
Rat (Acute)
2.16
Rat (Chronic Oral)
2.9
Fathead Minnow
4.22
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
426.94
Hydration Free Energy
-11.3
Log(D) at pH=7.4
1.16
Log(P)
1.92
Log S
-4.49
Log(Vapor Pressure)
-8.63
Melting Point
253.87
pKa Acid
5.98
pKa Basic
5.32
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9423
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.9262
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8772
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8768
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8659
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8654
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8610
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8582
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8491
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8337
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.8289
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8261
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.8234
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8174
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8143
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8141
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8096
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.8064
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7911
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7892
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7876
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7810
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7784
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7780
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7761
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 3 0.7754
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7743
Gag-Pol polyprotein O12158 POL_HV192 Human immunodeficiency virus type 1 group M subtype C 3 0.7697
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7593
O-GlcNAcase NagJ Q0TR53 OGA_CLOP1 Clostridium perfringens 4 0.7584
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7560
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7539
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7510
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7509
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 3 0.7498
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7460
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7457
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7452
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7440
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7440
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 4 0.7412
Nicotinamide phosphoribosyltransferase P43490 NAMPT_HUMAN Homo sapiens 3 0.7402
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7390
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7384
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7364
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7341
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7320
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7311
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7307
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7302
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7298
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7297
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7295
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7276
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7262
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7258
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7243
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7238
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 3 0.7232
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7225
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7219
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7207
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7207
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7201
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7198
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7173
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7167
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7161
Aklanonic acid methyl ester cyclase AcmA O52646 DNRD_STRGJ Streptomyces galilaeus 3 0.7157
Thymidylate kinase Q9HZN8 KTHY_PSEAE Pseudomonas aeruginosa 4 0.7150
Pentalenic acid synthase Q825I8 CYP28_STRAW Streptomyces avermitilis 2 0.7136
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7135
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7131
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7129
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7125
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7123
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7114
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7091
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7089
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7085
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7082
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7081
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 4 0.7077
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7074
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7065
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7062
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7058
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 2 0.7050
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7046
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 2 0.7015

Download SDF