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EMODIC ACID
ID: ALA290914
Max Phase: Preclinical
Molecular Formula: C15H8O7
Molecular Weight: 300.22
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (1): Emodic Acid
Synonyms from Alternative Forms(1):
Canonical SMILES: O=C(O)c1cc(O)c2c(c1)C(=O)c1cc(O)cc(O)c1C2=O
Standard InChI: InChI=1S/C15H8O7/c16-6-3-8-12(10(18)4-6)14(20)11-7(13(8)19)1-5(15(21)22)2-9(11)17/h1-4,16-18H,(H,21,22)
Standard InChI Key: ZJXVNNSMRGTDBI-UHFFFAOYSA-N
Associated Targets(Human)
Leukocyte elastase 8173 Activities
Cathepsin G 2304 Activities
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NCI/ADR-RES 33767 Activities
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PANC-1 6144 Activities
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DLD-1 17511 Activities
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Histone deacetylase 1 10854 Activities
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Induced myeloid leukemia cell differentiation protein Mcl-1 3820 Activities
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ATP-dependent DNA helicase Q1 5575 Activities
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DNA-(apurinic or apyrimidinic site) lyase 38016 Activities
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Tyrosyl-DNA phosphodiesterase 1 345557 Activities
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Microtubule-associated protein tau 95507 Activities
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Pyruvate kinase isozymes M1/M2 14841 Activities
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Aldehyde dehydrogenase 1A1 77053 Activities
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MAP kinase ERK2 25055 Activities
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Menin/Histone-lysine N-methyltransferase MLL 48157 Activities
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Lethal(3)malignant brain tumor-like protein 1 14536 Activities
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15-hydroxyprostaglandin dehydrogenase [NAD+] 24926 Activities
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DNA polymerase beta 23632 Activities
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Cytochrome P450 3A4 53859 Activities
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Lysine-specific demethylase 4A 52245 Activities
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Nuclear factor erythroid 2-related factor 2 95332 Activities
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Bromodomain adjacent to zinc finger domain protein 2B 56204 Activities
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Runt-related transcription factor 1/Core-binding factor subunit beta 7867 Activities
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DNA polymerase iota 116820 Activities
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Flap endonuclease 1 12055 Activities
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DNA polymerase eta 21678 Activities
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DNA polymerase kappa 8653 Activities
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Ubiquitin carboxyl-terminal hydrolase 1 22556 Activities
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Glutaminase kidney isoform, mitochondrial 16997 Activities
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Ataxin-2 54410 Activities
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Werner syndrome ATP-dependent helicase 8824 Activities
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Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 36611 Activities
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Solute carrier organic anion transporter family member 1B1 2672 Activities
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Solute carrier organic anion transporter family member 1B3 2517 Activities
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Rap guanine nucleotide exchange factor 4 11476 Activities
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Muscleblind-like protein 1 34431 Activities
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Serine/threonine-protein kinase PLK1 28605 Activities
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Rap guanine nucleotide exchange factor 3 15528 Activities
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Jurkat 10389 Activities
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K562 73714 Activities
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HeLa 62764 Activities
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Associated Targets(non-human)
Elastase 2A 403 Activities
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Alpha-chymotrypsin 819 Activities
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Staphylococcus aureus 210822 Activities
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Pseudomonas aeruginosa 123386 Activities
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Candida albicans 78123 Activities
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Pyruvate kinase 6726 Activities
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Luciferase 1637 Activities
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Nuclear receptor ROR-gamma 89407 Activities
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Thioredoxin glutathione reductase 28579 Activities
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4'-phosphopantetheinyl transferase ffp 24982 Activities
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Putative fructose-1,6-bisphosphate aldolase 15559 Activities
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Plasmodium falciparum 966862 Activities
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Luciferin 4-monooxygenase 66902 Activities
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Phosphoglycerate kinase, glycosomal 2184 Activities
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Accessory gene regulator protein A 29 Activities
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Molecule Features
| Natural Product: Yes | Oral: No | Chemical Probe: No | Parenteral: No |
| Molecule Type: Small molecule | Topical: No | First In Class: No | Black Box: No |
| Chirality: No | Availability: No | Prodrug: No |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
|---|
Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
|---|
Properties
| Molecular Weight: 300.22 | Molecular Weight (Monoisotopic): 300.0270 | AlogP: 1.28 | #Rotatable Bonds: 1 |
| Polar Surface Area: 132.13 | Molecular Species: ACID | HBA: 6 | HBD: 4 |
| #RO5 Violations: 0 | HBA (Lipinski): 7 | HBD (Lipinski): 4 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 3.40 | CX Basic pKa: | CX LogP: 2.97 | CX LogD: -0.84 |
| Aromatic Rings: 2 | Heavy Atoms: 22 | QED Weighted: 0.53 | Np Likeness Score: 1.20 |
References
| 1. Zembower DE, Kam CM, Powers JC, Zalkow LH.. (1992) Novel anthraquinone inhibitors of human leukocyte elastase and cathepsin G., 35 (9): [PMID:1578486] [10.1021/jm00087a014] |
| 2. Kemami Wangun HV, Wood A, Fiorilla C, Reed JK, McCarthy PJ, Wright AE.. (2010) Gymnochromes E and F, cytotoxic phenanthroperylenequinones from a deep-water crinoid, Holopus rangii., 73 (4): [PMID:20158243] [10.1021/np900526y] |
| 3. PubChem BioAssay data set, |
| 4. PubChem BioAssay data set, |
| 5. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP.. (2013) Structure-based identification of OATP1B1/3 inhibitors., 83 (6): [PMID:23571415] [10.1124/mol.112.084152] |
| 6. Figueroa M, Jarmusch AK, Raja HA, El-Elimat T, Kavanaugh JS, Horswill AR, Cooks RG, Cech NB, Oberlies NH.. (2014) Polyhydroxyanthraquinones as quorum sensing inhibitors from the guttates of Penicillium restrictum and their analysis by desorption electrospray ionization mass spectrometry., 77 (6): [PMID:24911880] [10.1021/np5000704] |
| 7. Luo M, Cui Z, Huang H, Song X, Sun A, Dang Y, Lu L, Ju J.. (2017) Amino Acid Conjugated Anthraquinones from the Marine-Derived Fungus Penicillium sp. SCSIO sof101., 80 (5): [PMID:28509552] [10.1021/acs.jnatprod.7b00269] |
Source
Source(2):