NAV

4-[4-(2,5-DIOXO-PYRROLIDIN-1-YL)-PHENYLAMINO]-4-HYDROXY-BUTYRIC ACID

Identification

Generic Name
4-[4-(2,5-DIOXO-PYRROLIDIN-1-YL)-PHENYLAMINO]-4-HYDROXY-BUTYRIC ACID
DrugBank Accession Number
DB08378
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 292.2872
Monoisotopic: 292.105921632
Chemical Formula
C14H16N2O5
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UMyosin light chain 6BNot AvailableHumans
UMyosin regulatory light chain 12ANot AvailableHumans
UMyosin-7Not AvailableHumans
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 gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma 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
Gamma amino acids and derivatives
Alternative Parents
Phenylpyrrolidines / Phenylalkylamines / Secondary alkylarylamines / Pyrrolidine-2-ones / Benzene and substituted derivatives / N-substituted carboxylic acid imides / Pyrroles / Dicarboximides / Amino acids / Lactams
show 8 more
Substituents
1-phenylpyrrolidine / 2-pyrrolidone / Alkanolamine / Amine / Amino acid / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid
show 21 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrrolidinone, dicarboximide, monocarboxylic acid (CHEBI:44860)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
SUETUOGYOWOLNJ-NSHDSACASA-N
InChI
InChI=1S/C14H16N2O5/c17-11(5-8-14(20)21)15-9-1-3-10(4-2-9)16-12(18)6-7-13(16)19/h1-4,11,15,17H,5-8H2,(H,20,21)/t11-/m0/s1
IUPAC Name
(4S)-4-{[4-(2,5-dioxopyrrolidin-1-yl)phenyl]amino}-4-hydroxybutanoic acid
SMILES
[H][C@](O)(CCC(O)=O)NC1=CC=C(C=C1)N1C(=O)CCC1=O

References

General References
Not Available
PubChem Compound
46937145
PubChem Substance
99444849
ChemSpider
25058026
ZINC
ZINC000033396944
PDBe Ligand
PDM
PDB Entries
1kwo / 1l2o

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 Solubility2.03 mg/mLALOGPS
logP0.55ALOGPS
logP-0.23Chemaxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.21Chemaxon
pKa (Strongest Basic)0.91Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area106.94 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity73.83 m3·mol-1Chemaxon
Polarizability29.65 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7397
Blood Brain Barrier+0.9377
Caco-2 permeable-0.6531
P-glycoprotein substrateNon-substrate0.6931
P-glycoprotein inhibitor INon-inhibitor0.961
P-glycoprotein inhibitor IINon-inhibitor0.8737
Renal organic cation transporterNon-inhibitor0.9038
CYP450 2C9 substrateNon-substrate0.7561
CYP450 2D6 substrateNon-substrate0.8758
CYP450 3A4 substrateNon-substrate0.6418
CYP450 1A2 substrateNon-inhibitor0.9306
CYP450 2C9 inhibitorNon-inhibitor0.9281
CYP450 2D6 inhibitorNon-inhibitor0.9146
CYP450 2C19 inhibitorNon-inhibitor0.9456
CYP450 3A4 inhibitorNon-inhibitor0.9401
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.983
Ames testNon AMES toxic0.9065
CarcinogenicityNon-carcinogens0.9116
BiodegradationNot ready biodegradable0.7119
Rat acute toxicity2.1932 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9887
hERG inhibition (predictor II)Non-inhibitor0.9591
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-MSsplash10-00ko-3890000000-b3c3aaea2fedf6d9870b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004l-0290000000-369a92d8c9ed5658ebb1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0190000000-2aefba11f01f46f6be89
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-005c-0190000000-8ee40223ecf653a1e0b7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-002n-0090000000-10315f8fe1aa5c55bde9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01w0-2190000000-52c39eefcb2a96964d8d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001v-8970000000-4496ba2a8bf137a96242
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]-161.94151
predicted
DeepCCS 1.0 (2019)
[M+H]+164.29951
predicted
DeepCCS 1.0 (2019)
[M+Na]+170.82185
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Myosin light chain 6B
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Structural constituent of muscle
Specific Function
Regulatory light chain of myosin. Does not bind calcium.
Gene Name
MYL6B
Uniprot ID
P14649
Uniprot Name
Myosin light chain 6B
Molecular Weight
22763.855 Da
References
  1. 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]
Details2. Myosin regulatory light chain 12A
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Calcium ion binding
Specific Function
Myosin regulatory subunit that plays an important role in regulation of both smooth muscle and nonmuscle cell contractile activity via its phosphorylation. Implicated in cytokinesis, receptor cappi...
Gene Name
MYL12A
Uniprot ID
P19105
Uniprot Name
Myosin regulatory light chain 12A
Molecular Weight
19793.96 Da
References
  1. 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]
Details3. Myosin-7
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Microfilament motor activity
Specific Function
Muscle contraction.
Gene Name
MYH7
Uniprot ID
P12883
Uniprot Name
Myosin-7
Molecular Weight
223095.5 Da
References
  1. 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 September 15, 2010 21:31 / Updated at June 12, 2020 16:52