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2-Aminopropanedioic Acid

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Identification

Generic Name
2-Aminopropanedioic Acid
DrugBank Accession Number
DB02289
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 119.0761
Monoisotopic: 119.021857653
Chemical Formula
C3H5NO4
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
ASerine-protein kinase ATM
inhibitor
Humans
UArylsulfataseNot AvailablePseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
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
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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
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acids
Alternative Parents
Dicarboxylic acids and derivatives / 1,3-dicarbonyl compounds / Amino acids / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
Substituents
1,3-dicarbonyl compound / Aliphatic acyclic compound / Alpha-amino acid / Amine / Amino acid / Carbonyl group / Carboxylic acid / Dicarboxylic acid or derivatives / Hydrocarbon derivative / Organic nitrogen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
amino dicarboxylic acid (CHEBI:17475)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
1068-84-4
InChI Key
JINBYESILADKFW-UHFFFAOYSA-N
InChI
InChI=1S/C3H5NO4/c4-1(2(5)6)3(7)8/h1H,4H2,(H,5,6)(H,7,8)
IUPAC Name
2-aminopropanedioic acid
SMILES
NC(C(O)=O)C(O)=O

References

General References
Not Available
Human Metabolome Database
HMDB0001147
KEGG Compound
C00872
PubChem Compound
100714
PubChem Substance
46505306
ChemSpider
90998
ChEBI
17475
ChEMBL
CHEMBL1232731
ZINC
ZINC000000895421
PDBe Ligand
FGL
PDB Entries
1auk / 2vh3 / 2w8s / 4mq9 / 4oin / 4oip / 4oiq / 4oir

Clinical Trials

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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
PropertyValueSource
Water Solubility126.0 mg/mLALOGPS
logP-3.5ALOGPS
logP-3.4Chemaxon
logS0.03ALOGPS
pKa (Strongest Acidic)0.45Chemaxon
pKa (Strongest Basic)8.5Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area100.62 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity21.98 m3·mol-1Chemaxon
Polarizability9.48 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.5056
Blood Brain Barrier+0.5359
Caco-2 permeable-0.8814
P-glycoprotein substrateNon-substrate0.8233
P-glycoprotein inhibitor INon-inhibitor0.9898
P-glycoprotein inhibitor IINon-inhibitor0.9922
Renal organic cation transporterNon-inhibitor0.973
CYP450 2C9 substrateNon-substrate0.8665
CYP450 2D6 substrateNon-substrate0.8948
CYP450 3A4 substrateNon-substrate0.8275
CYP450 1A2 substrateNon-inhibitor0.8898
CYP450 2C9 inhibitorNon-inhibitor0.9437
CYP450 2D6 inhibitorNon-inhibitor0.9001
CYP450 2C19 inhibitorNon-inhibitor0.9267
CYP450 3A4 inhibitorNon-inhibitor0.8207
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9967
Ames testNon AMES toxic0.9596
CarcinogenicityNon-carcinogens0.7457
BiodegradationReady biodegradable0.8718
Rat acute toxicity1.0741 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.993
hERG inhibition (predictor II)Non-inhibitor0.9893
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-001i-2910000000-56ddccdbe51afd85dd6c
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0gb9-1790000000-1a2cf2f982d08de4d2c9
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00xu-9200000000-a92a1873b06d13a3cb1b
GC-MS Spectrum - GC-MSGC-MSsplash10-001i-2910000000-56ddccdbe51afd85dd6c
GC-MS Spectrum - GC-MSGC-MSsplash10-0gb9-1790000000-1a2cf2f982d08de4d2c9
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0012-1920000000-706a1afd4a87657ef924
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-0bdec0fee8a2b08dead3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00xr-9700000000-247ee3963421aeff847a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-5ef7b536f329b506a5c3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-6ad8138c81d65b7ff9b0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-9000000000-b91d6d5a16055738781f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-006x-9000000000-09f59da4ca0a883a456b
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-118.6204359
predicted
DarkChem Lite v0.1.0
[M-H]-118.5077359
predicted
DarkChem Lite v0.1.0
[M-H]-116.44139
predicted
DeepCCS 1.0 (2019)
[M+H]+119.7488359
predicted
DarkChem Lite v0.1.0
[M+H]+119.5813359
predicted
DarkChem Lite v0.1.0
[M+H]+119.24184
predicted
DeepCCS 1.0 (2019)
[M+Na]+118.5286359
predicted
DarkChem Lite v0.1.0
[M+Na]+118.6630359
predicted
DarkChem Lite v0.1.0
[M+Na]+127.547295
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Serine-protein kinase ATM
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serine/threonine protein kinase which activates checkpoint signaling upon double strand breaks (DSBs), apoptosis and genotoxic stresses such as ionizing ultraviolet A light (UVA), thereby acting as a DNA damage sensor (PubMed:10550055, PubMed:10839545, PubMed:10910365, PubMed:12556884, PubMed:14871926, PubMed:15064416, PubMed:15448695, PubMed:15456891, PubMed:15790808, PubMed:15916964, PubMed:17923702, PubMed:21757780, PubMed:24534091, PubMed:35076389, PubMed:9733514). Recognizes the substrate consensus sequence [ST]-Q (PubMed:10550055, PubMed:10839545, PubMed:10910365, PubMed:12556884, PubMed:14871926, PubMed:15448695, PubMed:15456891, PubMed:15916964, PubMed:17923702, PubMed:24534091, PubMed:9733514). Phosphorylates 'Ser-139' of histone variant H2AX at double strand breaks (DSBs), thereby regulating DNA damage response mechanism (By similarity). Also plays a role in pre-B cell allelic exclusion, a process leading to expression of a single immunoglobulin heavy chain allele to enforce clonality and monospecific recognition by the B-cell antigen receptor (BCR) expressed on individual B-lymphocytes. After the introduction of DNA breaks by the RAG complex on one immunoglobulin allele, acts by mediating a repositioning of the second allele to pericentromeric heterochromatin, preventing accessibility to the RAG complex and recombination of the second allele. Also involved in signal transduction and cell cycle control. May function as a tumor suppressor. Necessary for activation of ABL1 and SAPK. Phosphorylates DYRK2, CHEK2, p53/TP53, FBXW7, FANCD2, NFKBIA, BRCA1, CREBBP/CBP, RBBP8/CTIP, MRE11, nibrin (NBN), RAD50, RAD17, PELI1, TERF1, UFL1, RAD9, UBQLN4 and DCLRE1C (PubMed:10550055, PubMed:10766245, PubMed:10802669, PubMed:10839545, PubMed:10910365, PubMed:10973490, PubMed:11375976, PubMed:12086603, PubMed:15456891, PubMed:19965871, PubMed:21757780, PubMed:24534091, PubMed:26240375, PubMed:26774286, PubMed:30612738, PubMed:30886146, PubMed:30952868, PubMed:38128537, PubMed:9733515, PubMed:9843217). May play a role in vesicle and/or protein transport. Could play a role in T-cell development, gonad and neurological function. Plays a role in replication-dependent histone mRNA degradation. Binds DNA ends. Phosphorylation of DYRK2 in nucleus in response to genotoxic stress prevents its MDM2-mediated ubiquitination and subsequent proteasome degradation (PubMed:19965871). Phosphorylates ATF2 which stimulates its function in DNA damage response (PubMed:15916964). Phosphorylates ERCC6 which is essential for its chromatin remodeling activity at DNA double-strand breaks (PubMed:29203878). Phosphorylates TTC5/STRAP at 'Ser-203' in the cytoplasm in response to DNA damage, which promotes TTC5/STRAP nuclear localization (PubMed:15448695). Also involved in pexophagy by mediating phosphorylation of PEX5: translocated to peroxisomes in response to reactive oxygen species (ROS), and catalyzes phosphorylation of PEX5, promoting PEX5 ubiquitination and induction of pexophagy (PubMed:26344566)
Specific Function
1-phosphatidylinositol-3-kinase activity
Gene Name
ATM
Uniprot ID
Q13315
Uniprot Name
Serine-protein kinase ATM
Molecular Weight
350684.105 Da
References
  1. 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]
Details2. Arylsulfatase
Kind
Protein
Organism
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action
Unknown
General Function
Hydrolyzes the bond between sulfate and the aromatic ring in a compound such as 4-nitrocatechol sulfate.
Specific Function
arylsulfatase activity
Gene Name
atsA
Uniprot ID
P51691
Uniprot Name
Arylsulfatase
Molecular Weight
59945.155 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]

Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:22