NAV

(2s,5s)-5-Carboxymethylproline

Identification

Generic Name
(2s,5s)-5-Carboxymethylproline
DrugBank Accession Number
DB03215
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 173.1665
Monoisotopic: 173.068807845
Chemical Formula
C7H11NO4
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCarbapenam-3-carboxylate synthaseNot AvailableErwinia carotovora
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 proline and derivatives. These are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Proline and derivatives
Alternative Parents
L-alpha-amino acids / Pyrrolidine carboxylic acids / Dicarboxylic acids and derivatives / Amino acids / Dialkylamines / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Aliphatic heteromonocyclic compound / Alpha-amino acid / Amine / Amino acid / Azacycle / Carbonyl group / Carboxylic acid / Dicarboxylic acid or derivatives / Hydrocarbon derivative / L-alpha-amino acid
show 13 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
dicarboxylic acid, L-proline derivative (CHEBI:45757)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
LIZWYFXJOOUDNV-WHFBIAKZSA-N
InChI
InChI=1S/C7H11NO4/c9-6(10)3-4-1-2-5(8-4)7(11)12/h4-5,8H,1-3H2,(H,9,10)(H,11,12)/t4-,5-/m0/s1
IUPAC Name
(2S,5S)-5-(carboxymethyl)pyrrolidine-2-carboxylic acid
SMILES
[H][C@@]1(CC(O)=O)CC[C@]([H])(N1)C(O)=O

References

General References
Not Available
KEGG Compound
C17366
PubChem Compound
447989
PubChem Substance
46507557
ChemSpider
394928
ChEBI
45757
PDBe Ligand
SSC
PDB Entries
1q19

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility43.9 mg/mLALOGPS
logP-2.6ALOGPS
logP-2.9Chemaxon
logS-0.6ALOGPS
pKa (Strongest Acidic)1.51Chemaxon
pKa (Strongest Basic)11.93Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area86.63 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity38.52 m3·mol-1Chemaxon
Polarizability16.45 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.652
Blood Brain Barrier+0.5435
Caco-2 permeable-0.7493
P-glycoprotein substrateNon-substrate0.608
P-glycoprotein inhibitor INon-inhibitor0.9775
P-glycoprotein inhibitor IINon-inhibitor0.9665
Renal organic cation transporterNon-inhibitor0.897
CYP450 2C9 substrateNon-substrate0.8291
CYP450 2D6 substrateNon-substrate0.8182
CYP450 3A4 substrateNon-substrate0.7234
CYP450 1A2 substrateNon-inhibitor0.8935
CYP450 2C9 inhibitorNon-inhibitor0.9413
CYP450 2D6 inhibitorNon-inhibitor0.9509
CYP450 2C19 inhibitorNon-inhibitor0.966
CYP450 3A4 inhibitorNon-inhibitor0.9845
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9939
Ames testNon AMES toxic0.9274
CarcinogenicityNon-carcinogens0.974
BiodegradationReady biodegradable0.7919
Rat acute toxicity1.8813 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.908
hERG inhibition (predictor II)Non-inhibitor0.96
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
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-004l-9700000000-a95d1797eafe6fed0add
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ai-5900000000-ce5a43a7cfc2e4235e04
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0900000000-f23af12f55f8f287e19d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-9800000000-7249d5eb3afb91175414
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-2900000000-72dc95b304c1782b5b65
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001l-9100000000-e59a87fadfc89bef6fb9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-9100000000-8c7a6b0648c19609aff5
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]-135.43333
predicted
DeepCCS 1.0 (2019)
[M+H]+137.48518
predicted
DeepCCS 1.0 (2019)
[M+Na]+143.39772
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Carbapenam-3-carboxylate synthase
Kind
Protein
Organism
Erwinia carotovora
Pharmacological action
Unknown
General Function
Atp binding
Specific Function
Involved in the biosynthesis of carbapenam-3-carboxylate, a beta-lactam antibiotic of the carbapenem class. Catalyzes the ATP-dependent formation of (3S,5S)-carbapenam-3-carboxylate from (2S,5S)-5-...
Gene Name
carA
Uniprot ID
Q9XB61
Uniprot Name
Carbapenam-3-carboxylate synthase
Molecular Weight
55997.77 Da

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52