NAV

N-(carboxycarbonyl)-D-phenylalanine

Identification

Generic Name
N-(carboxycarbonyl)-D-phenylalanine
DrugBank Accession Number
DB08263
Background

N-(carboxycarbonyl)-D-phenylalanine is a solid. This compound belongs to the n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. It targets the protein hypoxia-inducible factor 1-alpha inhibitor.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 237.2087
Monoisotopic: 237.063722467
Chemical Formula
C11H11NO5
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UHypoxia-inducible factor 1-alpha inhibitorNot 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 phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine 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
Phenylalanine and derivatives
Alternative Parents
N-acyl-alpha amino acids / Phenylpropanoic acids / Amphetamines and derivatives / Dicarboxylic acids and derivatives / Secondary carboxylic acid amides / Carboxylic acids / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
3-phenylpropanoic-acid / Amphetamine or derivatives / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid / Dicarboxylic acid or derivatives / Hydrocarbon derivative / Monocyclic benzene moiety
show 10 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
856680-67-6
InChI Key
ULQWGBCNOHBNDB-MRVPVSSYSA-N
InChI
InChI=1S/C11H11NO5/c13-9(11(16)17)12-8(10(14)15)6-7-4-2-1-3-5-7/h1-5,8H,6H2,(H,12,13)(H,14,15)(H,16,17)/t8-/m1/s1
IUPAC Name
(2R)-2-(carboxyformamido)-3-phenylpropanoic acid
SMILES
[H][C@](CC1=CC=CC=C1)(NC(=O)C(O)=O)C(O)=O

References

General References
Not Available
PubChem Compound
5288998
PubChem Substance
99444734
ChemSpider
4451055
BindingDB
26107
ChEMBL
CHEMBL486146
ZINC
ZINC000026637924
PDBe Ligand
NDF
PDB Entries
1yci / 7yxl

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 Solubility1.16 mg/mLALOGPS
logP0.61ALOGPS
logP0.86Chemaxon
logS-2.3ALOGPS
pKa (Strongest Acidic)2.79Chemaxon
pKa (Strongest Basic)-6.3Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area103.7 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity56.36 m3·mol-1Chemaxon
Polarizability22.28 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7757
Blood Brain Barrier+0.8545
Caco-2 permeable-0.7439
P-glycoprotein substrateNon-substrate0.6988
P-glycoprotein inhibitor INon-inhibitor0.9812
P-glycoprotein inhibitor IINon-inhibitor0.976
Renal organic cation transporterNon-inhibitor0.962
CYP450 2C9 substrateNon-substrate0.8256
CYP450 2D6 substrateNon-substrate0.8723
CYP450 3A4 substrateNon-substrate0.7271
CYP450 1A2 substrateNon-inhibitor0.9599
CYP450 2C9 inhibitorNon-inhibitor0.9729
CYP450 2D6 inhibitorNon-inhibitor0.9469
CYP450 2C19 inhibitorNon-inhibitor0.9723
CYP450 3A4 inhibitorNon-inhibitor0.9771
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9933
Ames testNon AMES toxic0.8871
CarcinogenicityNon-carcinogens0.9257
BiodegradationReady biodegradable0.8217
Rat acute toxicity1.4022 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9968
hERG inhibition (predictor II)Non-inhibitor0.9844
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-MSsplash10-0006-9810000000-ea0b62d790f89a303a67
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dr-0950000000-daf043e69307573eceba
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000f-2940000000-1888ac18241233937441
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0900000000-197895805d3cc219221c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-7910000000-cee3a2cc60e26721033c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-3900000000-0cd9a8140779da8aa50a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9800000000-cd66bb209ac0fd98d167
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]-149.00493
predicted
DeepCCS 1.0 (2019)
[M+H]+151.4005
predicted
DeepCCS 1.0 (2019)
[M+Na]+157.36064
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Hypoxia-inducible factor 1-alpha inhibitor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Hydroxylates HIF-1 alpha at 'Asp-803' in the C-terminal transactivation domain (CAD). Functions as an oxygen sensor and, under normoxic conditions, the hydroxylation prevents interaction of HIF-1 w...
Gene Name
HIF1AN
Uniprot ID
Q9NWT6
Uniprot Name
Hypoxia-inducible factor 1-alpha inhibitor
Molecular Weight
40285.25 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 21:30 / Updated at June 12, 2020 16:52