2,7-dihydroxy-3-hydroxymethylanthraquinone - Compound Card

2,7-dihydroxy-3-hydroxymethylanthraquinone

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2,7-dihydroxy-3-hydroxymethylanthraquinone

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles OCc1cc2C(=O)c3ccc(cc3C(=O)c2cc1O)O
InChI InChI=1S/C15H10O5/c16-6-7-3-10-12(5-13(7)18)15(20)11-4-8(17)1-2-9(11)14(10)19/h1-5,16-18H,6H2
InChIKey VFILSEYHXFPERI-UHFFFAOYSA-N
Formula C15H10O5
HBA 5
HBD 3
MW 270.24
Rotatable Bonds 1
TPSA 94.83
LogP 1.37
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 270.05
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: 10869333
Nmrshiftdb2: 70058203

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 270.24 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.63
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.42

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.78
Plasma Protein Binding
56.87
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-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
8.06
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.91
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.91
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.54
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Toxic
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
3.96
Rat (Acute)
2.24
Rat (Chronic Oral)
3.16
Fathead Minnow
4.08
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
447.97
Hydration Free Energy
-11.79
Log(D) at pH=7.4
0.91
Log(P)
1.5
Log S
-4.73
Log(Vapor Pressure)
-8.57
Melting Point
296.22
pKa Acid
6.59
pKa Basic
5.2
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9120
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8906
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8861
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8838
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8714
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8714
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8698
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8522
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8520
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8461
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8456
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8406
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8395
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8315
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8312
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8269
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8213
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8204
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8115
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8104
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8082
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8080
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8029
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7996
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7992
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7991
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7968
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7961
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 5 0.7959
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7933
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7904
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7883
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7870
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7822
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7797
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7777
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7774
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7747
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7733
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7704
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7673
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7646
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7644
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7610
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7606
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7589
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7573
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7500
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7473
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7451
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7439
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 3 0.7418
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7395
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7393
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7378
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7374
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7356
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7348
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7344
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7323
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7289
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7280
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 4 0.7273
Glutamate receptor 2 P42262 GRIA2_HUMAN Homo sapiens 3 0.7259
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7242
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7233
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7231
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7228
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7225
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7211
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7200
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7198
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7189
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7188
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7184
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7181
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7144
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7144
Matrix metalloproteinase-9 P14780 MMP9_HUMAN Homo sapiens 3 0.7139
Nicotinamide phosphoribosyltransferase P43490 NAMPT_HUMAN Homo sapiens 3 0.7134
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7112
Bifunctional dihydrofolate reductase-thymidylate synthase D9N170 D9N170_PLAFA Plasmodium falciparum 3 0.7089
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7088
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7087
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7065
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7056
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7055
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7042
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.7040
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7039
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7037
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7026

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