Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C42H62O16.H3N |
Molecular Weight | 839.9626 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 19 / 19 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
N.[H][C@@]12C[C@](C)(CC[C@]1(C)CC[C@]3(C)C2=CC(=O)[C@]4([H])[C@@]5(C)CC[C@H](O[C@H]6O[C@@H]([C@@H](O)[C@H](O)[C@H]6O[C@@H]7O[C@@H]([C@@H](O)[C@H](O)[C@H]7O)C(O)=O)C(O)=O)C(C)(C)[C@]5([H])CC[C@@]34C)C(O)=O
InChI
InChIKey=ILRKKHJEINIICQ-OOFFSTKBSA-N
InChI=1S/C42H62O16.H3N/c1-37(2)21-8-11-42(7)31(20(43)16-18-19-17-39(4,36(53)54)13-12-38(19,3)14-15-41(18,42)6)40(21,5)10-9-22(37)55-35-30(26(47)25(46)29(57-35)33(51)52)58-34-27(48)23(44)24(45)28(56-34)32(49)50;/h16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54);1H3/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+;/m0./s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/9570253 | https://www.ncbi.nlm.nih.gov/pubmed/8783808https://www.ncbi.nlm.nih.gov/pubmed/24493924 | https://www.ncbi.nlm.nih.gov/pubmed/19144869 | https://www.ncbi.nlm.nih.gov/pubmed/17613133 | https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/cfrsearch.cfm?fr=184.1408http://www.etatpur.co.uk/index.php/enoxolone-sheethttps://www.ncbi.nlm.nih.gov/pubmed/27376261https://www.ncbi.nlm.nih.gov/pubmed/17613133https://www.ncbi.nlm.nih.gov/pubmed/17613133 | http://onlinelibrary.wiley.com/doi/10.2903/j.efsa.2015.3971/pdf | http://www.cosmeticsinfo.org/ingredient/disodium-glycyrrhizate | http://www.google.com.pg/patents/WO2009115455A1https://www.ncbi.nlm.nih.gov/pubmed/17613133 | http://www.cosmeticsinfo.org/ingredient/potassium-glycyrrhetinateCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19429429 | https://www.ncbi.nlm.nih.gov/pubmed/27520483
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9570253 | https://www.ncbi.nlm.nih.gov/pubmed/8783808https://www.ncbi.nlm.nih.gov/pubmed/24493924 | https://www.ncbi.nlm.nih.gov/pubmed/19144869 | https://www.ncbi.nlm.nih.gov/pubmed/17613133 | https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/cfrsearch.cfm?fr=184.1408http://www.etatpur.co.uk/index.php/enoxolone-sheethttps://www.ncbi.nlm.nih.gov/pubmed/27376261https://www.ncbi.nlm.nih.gov/pubmed/17613133https://www.ncbi.nlm.nih.gov/pubmed/17613133 | http://onlinelibrary.wiley.com/doi/10.2903/j.efsa.2015.3971/pdf | http://www.cosmeticsinfo.org/ingredient/disodium-glycyrrhizate | http://www.google.com.pg/patents/WO2009115455A1https://www.ncbi.nlm.nih.gov/pubmed/17613133 | http://www.cosmeticsinfo.org/ingredient/potassium-glycyrrhetinate
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19429429 | https://www.ncbi.nlm.nih.gov/pubmed/27520483
Potassium Glycyrrhetinate (CAS no. 85985-61-1) is the
potassium salt of Glycyrrhetinic Acid. Potassium Glycyrrhetinate
is also known as Olean-12-En-29-Oic Acid, 3-Hydroxy-1,
1-Oxo-, Monopotassium Salt. Potassium Glycyrrhetinate functions as a flavoring agent and skin-conditioning agent—miscellaneous in cosmetic products.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0072593 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19144869 |
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Target ID: Q9UBK2|||Q3LIG1 Gene ID: 10891.0 Gene Symbol: PPARGC1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24675225 |
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Target ID: P24298 Gene ID: 2875.0 Gene Symbol: GPT Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10574137 |
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Target ID: CHEMBL2391 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19429429 |
779.0 nM [IC50] | ||
Target ID: CHEMBL2908 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19429429 |
257.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Palliative | Stronger Neo-Minophagen C Approved UseChronic Hepatitis C Launch Date1948 |
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Preventing | MASO65D (Xclair®) Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
103.89 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18452416 |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENOXOLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1396.97 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18452416 |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENOXOLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.46 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18452416 |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENOXOLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely | ||||
likely | ||||
yes [IC50 6.12 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
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Sources: https://pubmed.ncbi.nlm.nih.gov/18204840/ Page: 6.0 |
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Sources: https://pubmed.ncbi.nlm.nih.gov/18204840/ Page: 6.0 |
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PubMed
Title | Date | PubMed |
---|---|---|
Therapeutic basis of glycyrrhizin on chronic hepatitis B. | 1996 May |
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Review article: glycyrrhizin as a potential treatment for chronic hepatitis C. | 1998 Mar |
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[The assessment of safety of enoxaparin administration during percutaneous transluminal coronary angioplasty after ticlopidine pretreatment. Application of low molecular weigh heparins in prevention of coronary micro-embolization]. | 2001 |
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Spreading depolarization waves triggered by vagal stimulation in the embryonic chick brain: optical evidence for intercellular communication in the developing central nervous system. | 2001 |
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Gap-junctional communication is required for the maturation process of osteoblastic cells in culture. | 2001 Apr |
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Endothelium-dependent vasorelaxation independent of nitric oxide and K(+) release in isolated renal arteries of rats. | 2001 Apr |
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The effect of absorption enhancers on the initial degradation kinetics of insulin by alpha-chymotrypsin. | 2001 Apr 17 |
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Inhibition of gap-junctional communication induces the trans-differentiation of osteoblasts to an adipocytic phenotype in vitro. | 2001 Apr 27 |
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Do gap junctions couple interstitial cells of Cajal pacing and neurotransmission to gastrointestinal smooth muscle? | 2001 Aug |
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In vivo 11beta-HSD-2 activity: variability, salt-sensitivity, and effect of licorice. | 2001 Dec 1 |
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Effects of glycyrrhetinic acid on collagen metabolism of hepatic stellate cells at different stages of liver fibrosis in rats. | 2001 Feb |
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A gap-junction-mediated signal, rather than an external paracrine factor, predominates during meiotic induction in isolated mouse oocytes. | 2001 Feb |
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Blockade of chloride channels reveals relaxations of rat small mesenteric arteries to raised potassium. | 2001 Jan |
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A population physiologically based pharmacokinetic/pharmacodynamic model for the inhibition of 11-beta-hydroxysteroid dehydrogenase activity by glycyrrhetic acid. | 2001 Jan 1 |
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Origin and propagation of spontaneous excitation in smooth muscle of the guinea-pig urinary bladder. | 2001 Jan 15 |
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Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5. | 2001 Jan 22 |
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Expression of the 11beta-hydroxysteroid dehydrogenase type II enzyme in breast tumors and modulation of activity and cell growth in PMC42 cells. | 2001 Jan-Mar |
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Toward prevention of hepatocellular carcinoma developing in chronic hepatitis C. | 2001 Jul |
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Antibacterial compounds of licorice against upper airway respiratory tract pathogens. | 2001 Jun |
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Immunoglobulin and cytokine expression in mixed lymphocyte cultures is reduced by disruption of gap junction intercellular communication. | 2001 Mar |
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The pharmacokinetics of glycyrrhizic acid evaluated by physiologically based pharmacokinetic modeling. | 2001 May |
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Characterization of bovine angiogenin-1 and lactogenin-like protein as glycyrrhizin-binding proteins and their in vitro phosphorylation by C-kinase. | 2001 May |
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Potentiation of L-type calcium channels reveals nonsynaptic mechanisms that correlate spontaneous activity in the developing mammalian retina. | 2001 Nov 1 |
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Mechanisms of anandamide-induced vasorelaxation in rat isolated coronary arteries. | 2001 Oct |
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Bimodal inhibition of connexin 43 gap junctions decreases ACTH-induced steroidogenesis and increases bovine adrenal cell population growth. | 2001 Oct |
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LAF1, a MYB transcription activator for phytochrome A signaling. | 2001 Oct 1 |
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[Licorice-induced pseudoaldosteronism in a patient with a non-functioning adrenal tumor]. | 2001 Sep |
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Characterization of secretory type IIA phospholipase A2 (sPLA2-IIA) as a glycyrrhizin (GL)-binding protein and the GL-induced inhibition of the CK-II-mediated stimulation of sPLA2-IIA activity in vitro. | 2001 Sep |
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Stimulation of melanogenesis by glycyrrhizin in B16 melanoma cells. | 2001 Sep 30 |
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[Immunoenzyme test-system for detection of glycyrrhizic acid]. | 2001 Sep-Oct |
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An unexpected case of primary pulmonary hypertension of the neonate (PPHN). Potential role of topical administration of enoxolone. | 2002 |
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Molecular pharmacophore determination of lipid lowering drugs with the receptor mapping method. | 2002 Apr |
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Glycyrrhizic acid suppresses type 2 11 beta-hydroxysteroid dehydrogenase expression in vivo. | 2002 Apr |
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Short-term cortisol infusion in the brachial artery, with and without inhibiting 11 beta-hydroxysteroid dehydrogenase, does not alter forearm vascular resistance in normotensive and hypertensive subjects. | 2002 Dec |
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Effect of glycyrrhetinic acid on 11 beta-hydroxysteroid dehydrogenase activity in normotensive and hypertensive subjects. | 2002 Feb |
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[Quantitative determinations of glycyrrhizic acid, glycyrrhetinic acid, morphine and sodium benzoate in compound liquorice tablets by capillary zone electrophoresis]. | 2002 Jan |
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Influence of honey on the gastrointestinal metabolism and disposition of glycyrrhizin and glycyrrhetic acid in rabbits. | 2002 Jan |
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Stimulation of the BK(Ca) channel in cultured smooth muscle cells of human trachea by magnolol. | 2002 Jan |
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Glycyrrhetinic derivatives inhibit hyperpolarization in endothelial cells of guinea pig and rat arteries. | 2002 Jan |
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Hydrogen peroxide is an endothelium-derived hyperpolarizing factor in human mesenteric arteries. | 2002 Jan 25 |
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IL-1beta-induced production of metalloproteinases by synovial cells depends on gap junction conductance. | 2002 Jun |
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[Licorice--not just candy]. | 2002 Mar 20 |
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Metabolism of constituents in Huangqin-Tang, a prescription in traditional Chinese medicine, by human intestinal flora. | 2002 May |
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Bone morphogenetic protein-2 modulation of chondrogenic differentiation in vitro involves gap junction-mediated intercellular communication. | 2002 Nov |
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Foetal lung maturation in 11beta-hydroxysteroid dehydrogenase type 1 knockout mice. | 2002 Oct |
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11beta-hydroxysteroid dehydrogenase type 1: a new regulator of fetal lung maturation. | 2002 Oct |
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[Rhabdomyolysis due to licorice ingestion]. | 2002 Sep |
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Inhibition of 3 alpha/beta,20 beta-hydroxysteroid dehydrogenase by dexamethasone, glycyrrhetinic acid and spironolactone is attenuated by deletion of 12 carboxyl-terminal residues. | 2002 Sep |
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Subjects with essential hypertension are more sensitive to the inhibition of 11 beta-HSD by liquorice. | 2003 Feb |
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Ammonium glycyrrhizinate-loaded niosomes as a potential nanotherapeutic system for anti-inflammatory activity in murine models. | 2014 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21681505
Curator's Comment: Disodium Glycyrrhizate was not carcinogenic in mice in a drinking water study at exposure levels up to 12.2 mg/kg day(-1) for 96 weeks.
100 ml/day of intravenous glycyrrhizin
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7721345
Curator's Comment: The suppressor cell activity of T6S cells was clearly counteracted by glycyrrhizin mononuclear cells (GR-MNC) in vitro in a mixed lymphocyte-tumor cell reaction. The type of cells responsible for anti-suppressor cells in GR-MNC was shown to be a CD4+ CD28+ TCR alpha/beta + Vicia villosa lectin-adherent T cell. These results suggest that GR may reverse the increased susceptibility of thermally injured mice to herpes simplex virus type 1 (HSV) infection through the induction of CD4+ contrasuppressor T cells.
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Classification Tree | Code System | Code | ||
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DSLD |
3785 (Number of products:2)
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35348
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3VRD35U26C
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53956-04-0
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SUB11707MIG
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SUB50039
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3VRD35U26C
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1311505
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53956-04-0
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1029929
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C45678
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CONCEPT | Industrial Aid | ||
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2800
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100000091521
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C77525
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SUB11707MIG
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53956-04-0
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62074
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53956-04-0
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258-887-7
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD