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2-hydroxymethylanthraquinone
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
-
Class: Quinone
- Subclass: Anthraquinone
| Canonical Smiles | OCc1ccc2c(c1)C(=O)c1c(C2=O)cccc1 |
|---|---|
| InChI | InChI=1S/C15H10O3/c16-8-9-5-6-12-13(7-9)15(18)11-4-2-1-3-10(11)14(12)17/h1-7,16H,8H2 |
| InChIKey | JYKHAJGLEVKEAA-UHFFFAOYSA-N |
| Formula | C15H10O3 |
| HBA | 3 |
| HBD | 1 |
| MW | 238.24 |
| Rotatable Bonds | 1 |
| TPSA | 54.37 |
| LogP | 1.95 |
| 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 | Pentas schimperi | Rubiaceae | Plantae | 25384 |
| 2 | Pentas schimperi | Rubiaceae | Plantae | 25384 |
Showing of synonyms
2-hydroxymethylanthraquinone
2-(Hydroxymethyl)anthraquinone
17241-59-7
2-(hydroxymethyl)anthracene-9,10-dione
Anthraquinone-2-methanol
9,10-Anthracenedione, 2-(hydroxymethyl)-
MFCD00001236
2-Hydroxymethyl-9,10-anthracenedione
2-(hydroxymethyl)-9,10-dihydroanthracene-9,10-dione
CHEBI:28649
2-(hydroxymethyl)-9,10-anthraquinone
CCRIS 3522
EINECS 241-274-3
BRN 2120452
Anthraquinone, 2-(hydroxymethyl)-
SCHEMBL41511
2-Hydroxymethyl-Anthraquinone
4-08-00-02607 (Beilstein Handbook Reference)
CHEMBL21049
2-(Hydroxymethyl)anthraouinone
DTXSID10169278
BCP24351
HY-N7502
2-hydroxymethyl-9,10-anthraquinone
2-(Hydroxymethyl)anthraquinone, 97%
AKOS015856505
9,10-Anthracenedione,2-(hydroxymethyl)
2-(Hydroxymethyl)anthra-9,10-quinone #
AS-63881
PD167284
DB-043896
CS-0131104
NS00025652
G12036
Q27103810
- Goffin E, Ziemons E, et al. (2002). In vitro antiplasmodial activity of Tithonia diversifolia and identification of its main active constituent: tagitinin C.. Planta medica,2002, 68(6), 543-545. [View] [PubMed]
- Donfack A, Tala M, et al. (2014). Two new anthraquinone dimers from the stem bark of Pentas schimperi (Rubiaceae). Phytochemistry Letters, 2014, 8, 55-58. [View]
Pubchem:
87014
Cas:
17241-59-7
Zinc:
ZINC000003861620
Kegg Ligand:
C10354
Chebi:
28649
Nmrshiftdb2:
60015816
Metabolights:
MTBLC28649
Chembl:
CHEMBL21049
Comptox:
DTXSID10169278
CPRiL:
128481
SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3
Level: 0
Mol. Weight: 238.24 g/mol
Anti-15-lipoxygenase
Absorption
- Caco-2 (logPapp)
- -4.57
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.11
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.56
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.9
- Plasma Protein Binding
- 55.87
- 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
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 4.38
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 1.45
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.51
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.64
- 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
- 3.8
- Rat (Acute)
- 2.11
- Rat (Chronic Oral)
- 2.24
- Fathead Minnow
- 4.34
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 404.55
- Hydration Free Energy
- -8.89
- Log(D) at pH=7.4
- 1.49
- Log(P)
- 2.58
- Log S
- -4.54
- Log(Vapor Pressure)
- -7.87
- Melting Point
- 206.36
- pKa Acid
- 8.14
- pKa Basic
- 4.46
| 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 | 0.9346 |
| Cytohesin-2 | Q99418 | CYH2_HUMAN | Homo sapiens | 3 | 0.9237 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8874 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.8855 |
| EbrA repressor | Q79SH7 | Q79SH7_STRLI | Streptomyces lividans | 3 | 0.8798 |
| Proto-oncogene tyrosine-protein kinase Src | P12931 | SRC_HUMAN | Homo sapiens | 3 | 0.8736 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8654 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8646 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8622 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8585 |
| Fatty acid-binding protein, intestinal | P12104 | FABPI_HUMAN | Homo sapiens | 3 | 0.8539 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.8368 |
| Hematopoietic prostaglandin D synthase | O60760 | HPGDS_HUMAN | Homo sapiens | 3 | 0.8349 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8125 |
| 4,4'-diapophytoene synthase | A9JQL9 | CRTM_STAAU | Staphylococcus aureus | 3 | 0.8107 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8048 |
| Biphenyl-2,3-diol 1,2-dioxygenase | P17297 | BPHC_PSES1 | Pseudomonas sp | 3 | 0.8003 |
| Gastrotropin | P51161 | FABP6_HUMAN | Homo sapiens | 3 | 0.7959 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7909 |
| O-GlcNAcase NagJ | Q0TR53 | OGA_CLOP1 | Clostridium perfringens | 4 | 0.7882 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.7794 |
| Proliferating cell nuclear antigen | P12004 | PCNA_HUMAN | Homo sapiens | 3 | 0.7786 |
| Dihydrofolate reductase type 1 from Tn4003 | P13955 | DYRA_STAAU | Staphylococcus aureus | 3 | 0.7726 |
| Prostaglandin G/H synthase 1 | P05979 | PGH1_SHEEP | Ovis aries | 3 | 0.7719 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7663 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7658 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7656 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 3 | 0.7649 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 3 | 0.7642 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7633 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 3 | 0.7617 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 2 | 0.7595 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7533 |
| Gag-Pol polyprotein | O12158 | POL_HV192 | Human immunodeficiency virus type 1 group M subtype C | 3 | 0.7524 |
| Prostaglandin F2a synthase | Q8I6L9 | Q8I6L9_TRYCR | Trypanosoma cruzi | 2 | 0.7466 |
| Aklanonic acid methyl ester cyclase AcmA | O52646 | DNRD_STRGJ | Streptomyces galilaeus | 3 | 0.7461 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7461 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7459 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7457 |
| Enoyl-ACP reductase | Q9BH77 | Q9BH77_PLAFA | Plasmodium falciparum | 3 | 0.7439 |
| Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 3 | 0.7433 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7429 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7421 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7420 |
| Putative ketoacyl reductase | P16544 | ACT3_STRCO | Streptomyces coelicolor / M145) | 3 | 0.7418 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7411 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.7406 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 2 | 0.7375 |
| Angiotensin-converting enzyme 2 | Q9BYF1 | ACE2_HUMAN | Homo sapiens | 2 | 0.7373 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7367 |
| Protein S100-A13 | Q99584 | S10AD_HUMAN | Homo sapiens | 3 | 0.7362 |
| Dihydrofolate reductase | P0A017 | DYR_STAAU | Staphylococcus aureus | 3 | 0.7337 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 2 | 0.7329 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7325 |
| Acetyl-CoA carboxylase | Q00955 | ACAC_YEAST | Saccharomyces cerevisiae | 3 | 0.7324 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.7313 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7304 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7286 |
| Dihydrofolate reductase | Q81R22 | Q81R22_BACAN | Bacillus anthracis | 3 | 0.7277 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.7277 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7262 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.7249 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 2 | 0.7231 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.7223 |
| Pentalenic acid synthase | Q825I8 | CYP28_STRAW | Streptomyces avermitilis | 2 | 0.7219 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 2 | 0.7205 |
| Cytochrome P450 130 | P9WPN5 | CP130_MYCTU | Mycobacterium tuberculosis | 3 | 0.7200 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7194 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7191 |
| Dihydrofolate reductase | P22906 | DYR_CANAX | Candida albicans | 3 | 0.7172 |
| Hexokinase-4 | P35557 | HXK4_HUMAN | Homo sapiens | 3 | 0.7163 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7150 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7149 |
| Carbonic anhydrase 4 | P22748 | CAH4_HUMAN | Homo sapiens | 3 | 0.7146 |
| Cytochrome P450 2D6 | P10635 | CP2D6_HUMAN | Homo sapiens | 2 | 0.7143 |
| Tannase | B3Y018 | B3Y018_LACPN | Lactiplantibacillus plantarum | 3 | 0.7140 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7130 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.7129 |
| 4,4'-diapophytoene synthase | A9JQL9 | CRTM_STAAU | Staphylococcus aureus | 3 | 0.7126 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7112 |
| Focal adhesion kinase 1 | Q00944 | FAK1_CHICK | Gallus gallus | 3 | 0.7110 |
| Tubulin alpha-1B chain | P81947 | TBA1B_BOVIN | Bos taurus | 3 | 0.7109 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7101 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 2 | 0.7061 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7058 |
| Renin | P00797 | RENI_HUMAN | Homo sapiens | 2 | 0.7054 |
| Cytohesin-2 | Q99418 | CYH2_HUMAN | Homo sapiens | 3 | 0.7049 |
| Formate--tetrahydrofolate ligase | P21164 | FTHS_MOOTH | Moorella thermoacetica | 2 | 0.7034 |
| Transthyretin | P02767 | TTHY_RAT | Rattus norvegicus | 2 | 0.7018 |
| Putative ketoacyl reductase | P16544 | ACT3_STRCO | Streptomyces coelicolor / M145) | 3 | 0.7018 |
| Inosine-5'-monophosphate dehydrogenase | P50097 | IMDH_TRIFO | Tritrichomonas foetus | 2 | 0.7014 |
| Carbonic anhydrase 12 | O43570 | CAH12_HUMAN | Homo sapiens | 2 | 0.7010 |