gamma-carboxy-L-glutamic acid
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Identification
- Generic Name
- gamma-carboxy-L-glutamic acid
- DrugBank Accession Number
- DB03847
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 191.1388
Monoisotopic: 191.042987025 - Chemical Formula
- C6H9NO6
- Synonyms
- (3S)-3-amino-1,1,3-propanetricarboxylic acid
- gamma-carboxy-glutamic acid
- gamma-Carboxyglutamic acid
- γ-carboxy-L-glutamic acid
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AProthrombin inhibitorHumans ACoagulation factor IX inhibitorHumans ACoagulation factor X inhibitorHumans UOsteocalcin Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- L-alpha-amino acids
- Alternative Parents
- Tricarboxylic acids and derivatives / Amino fatty acids / 1,3-dicarbonyl compounds / Amino acids / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
- Substituents
- 1,3-dicarbonyl compound / Aliphatic acyclic compound / Amine / Amino acid / Amino fatty acid / Carbonyl group / Carboxylic acid / Fatty acyl / Hydrocarbon derivative / L-alpha-amino acid
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- non-proteinogenic L-alpha-amino acid, tricarboxylic acid (CHEBI:41450)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 16FQV4RZKL
- CAS number
- 53861-57-7
- InChI Key
- UHBYWPGGCSDKFX-VKHMYHEASA-N
- InChI
- InChI=1S/C6H9NO6/c7-3(6(12)13)1-2(4(8)9)5(10)11/h2-3H,1,7H2,(H,8,9)(H,10,11)(H,12,13)/t3-/m0/s1
- IUPAC Name
- (1S)-1-aminopropane-1,3,3-tricarboxylic acid
- SMILES
- N[C@@H](CC(C(O)=O)C(O)=O)C(O)=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 104625
- PubChem Substance
- 46505246
- ChemSpider
- 94455
- BindingDB
- 50076390
- ChEBI
- 61936
- ChEMBL
- CHEMBL38397
- ZINC
- ZINC000002004603
- PDBe Ligand
- CGU
- PDB Entries
- 1ad7 / 1ag7 / 1awy / 1cfi / 1dan / 1iod / 1j34 / 1j35 / 1lqv / 1mgx … show 61 more
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 22.5 mg/mL ALOGPS logP -3 ALOGPS logP -3.6 Chemaxon logS -0.93 ALOGPS pKa (Strongest Acidic) 1.48 Chemaxon pKa (Strongest Basic) 9.54 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 137.92 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 37.58 m3·mol-1 Chemaxon Polarizability 16.24 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.5674 Blood Brain Barrier + 0.5 Caco-2 permeable - 0.8533 P-glycoprotein substrate Non-substrate 0.7338 P-glycoprotein inhibitor I Non-inhibitor 0.9853 P-glycoprotein inhibitor II Non-inhibitor 0.9843 Renal organic cation transporter Non-inhibitor 0.9646 CYP450 2C9 substrate Non-substrate 0.871 CYP450 2D6 substrate Non-substrate 0.869 CYP450 3A4 substrate Non-substrate 0.8146 CYP450 1A2 substrate Non-inhibitor 0.9401 CYP450 2C9 inhibitor Non-inhibitor 0.9644 CYP450 2D6 inhibitor Non-inhibitor 0.9366 CYP450 2C19 inhibitor Non-inhibitor 0.9553 CYP450 3A4 inhibitor Non-inhibitor 0.8797 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9973 Ames test Non AMES toxic 0.922 Carcinogenicity Non-carcinogens 0.8488 Biodegradation Ready biodegradable 0.8961 Rat acute toxicity 1.2544 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9901 hERG inhibition (predictor II) Non-inhibitor 0.9889
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0fdp-8900000000-84628f987e0eddc857f8 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-008c-0900000000-fb0a22423ec59627882b Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0fkc-0900000000-c46c11c60c21a5b53e8b Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-1900000000-d2e4a99755ec3d3a24f1 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0900000000-c5ffcb1d71acb8b05a1c Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0ukc-9400000000-72f9bc4b4f7d87d43f44 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00dl-9100000000-7e7e889a2247d7b4b30f Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 144.4034034 predictedDarkChem Lite v0.1.0 [M-H]- 132.0525 predictedDeepCCS 1.0 (2019) [M+H]+ 144.6625034 predictedDarkChem Lite v0.1.0 [M+H]+ 134.44807 predictedDeepCCS 1.0 (2019) [M+Na]+ 144.4169034 predictedDarkChem Lite v0.1.0 [M+Na]+ 142.17758 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsProthrombin
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Thrombin, which cleaves bonds after Arg and Lys, converts fibrinogen to fibrin and activates factors V, VII, VIII, XIII, and, in complex with thrombomodulin, protein C. Functions in blood homeostasis, inflammation and wound healing. Thrombin triggers the production of pro-inflammatory cytokines, such as MCP-1/CCL2 and IL8/CXCL8, in endothelial cells (PubMed:30568593, PubMed:9780208)
- Specific Function
- calcium ion binding
- Gene Name
- F2
- Uniprot ID
- P00734
- Uniprot Name
- Prothrombin
- Molecular Weight
- 70036.295 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
2. DetailsCoagulation factor IX
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Factor IX is a vitamin K-dependent plasma protein that participates in the intrinsic pathway of blood coagulation by converting factor X to its active form in the presence of Ca(2+) ions, phospholipids, and factor VIIIa
- Specific Function
- calcium ion binding
- Gene Name
- F9
- Uniprot ID
- P00740
- Uniprot Name
- Coagulation factor IX
- Molecular Weight
- 51778.11 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
3. DetailsCoagulation factor X
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Factor Xa is a vitamin K-dependent glycoprotein that converts prothrombin to thrombin in the presence of factor Va, calcium and phospholipid during blood clotting. Factor Xa activates pro-inflammatory signaling pathways in a protease-activated receptor (PAR)-dependent manner (PubMed:24041930, PubMed:30568593, PubMed:34831181). Up-regulates expression of protease-activated receptors (PARs) F2R, F2RL1 and F2RL2 in dermal microvascular endothelial cells (PubMed:35738824). Triggers the production of pro-inflammatory cytokines, such as MCP-1/CCL2 and IL6, in cardiac fibroblasts and umbilical vein endothelial cells in PAR-1 (F2R)-dependent manner (PubMed:30568593, PubMed:34831181). Triggers the production of pro-inflammatory cytokines, such as MCP-1/CCL2, IL6, TNF-alpha/TNF, IL-1beta/IL1B, IL8/CXCL8 and IL18, in endothelial cells and atrial tissues (PubMed:24041930, PubMed:35738824, PubMed:9780208). Induces expression of adhesion molecules, such as ICAM1, VCAM1 and SELE, in endothelial cells and atrial tissues (PubMed:24041930, PubMed:35738824, PubMed:9780208). Increases expression of phosphorylated ERK1/2 in dermal microvascular endothelial cells and atrial tissues (PubMed:24041930, PubMed:35738824). Triggers activation of the transcription factor NF-kappa-B in dermal microvascular endothelial cells and atrial tissues (PubMed:24041930, PubMed:35738824). Up-regulates expression of plasminogen activator inhibitor 1 (SERPINE1) in atrial tissues (PubMed:24041930)
- Specific Function
- calcium ion binding
- Gene Name
- F10
- Uniprot ID
- P00742
- Uniprot Name
- Coagulation factor X
- Molecular Weight
- 54731.255 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
4. DetailsOsteocalcin
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Bone protein that constitutes 1-2% of the total bone protein, and which acts as a negative regulator of bone formation (PubMed:3019668, PubMed:6967872). Functions to limit bone formation without impairing bone resorption or mineralization (By similarity). It binds strongly to apatite and calcium (PubMed:6967872)
- Specific Function
- calcium ion binding
- Gene Name
- BGLAP
- Uniprot ID
- P02818
- Uniprot Name
- Osteocalcin
- Molecular Weight
- 10962.445 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:22