NAV

N-[(6S)-6-Carboxy-6-(glycylamino)hexanoyl]-D-alanyl-D-alanine

Identification

Generic Name
N-[(6S)-6-Carboxy-6-(glycylamino)hexanoyl]-D-alanyl-D-alanine
DrugBank Accession Number
DB02578
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 374.3895
Monoisotopic: 374.180149206
Chemical Formula
C15H26N4O7
Synonyms
  • Glycyl-L-alpha-amino-epsilon-pimelyl-D-alanyl-D-alanine
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UD-alanyl-D-alanine carboxypeptidaseNot AvailableStreptomyces sp. (strain R61)
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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
N-acyl-L-alpha-amino acids / Alpha amino acid amides / Alanine and derivatives / Medium-chain fatty acids / Amino fatty acids / N-acyl amines / Dicarboxylic acids and derivatives / Secondary carboxylic acid amides / Amino acids / Carboxylic acids
show 5 more
Substituents
Alanine or derivatives / Aliphatic acyclic compound / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-dipeptide / Amine / Amino acid / Amino acid or derivatives / Amino fatty acid / Carbonyl group
show 22 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
RALBRZJHHGWNNU-BBBLOLIVSA-N
InChI
InChI=1S/C15H26N4O7/c1-8(13(22)18-9(2)14(23)24)17-11(20)6-4-3-5-10(15(25)26)19-12(21)7-16/h8-10H,3-7,16H2,1-2H3,(H,17,20)(H,18,22)(H,19,21)(H,23,24)(H,25,26)/t8-,9-,10+/m1/s1
IUPAC Name
(2S)-2-(2-aminoacetamido)-6-{[(1R)-1-{[(1R)-1-carboxyethyl]carbamoyl}ethyl]carbamoyl}hexanoic acid
SMILES
[H]N([H])CC(=O)N([H])[C@@H](CCCCC(=O)N([H])[C@H](C)C(=O)N([H])[C@H](C)C(O)=O)C(O)=O

References

General References
Not Available
PubChem Compound
446306
PubChem Substance
46508348
ChemSpider
393699
ZINC
ZINC000015599994
PDBe Ligand
REX
PDB Entries
1ikg

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 Solubility1.07 mg/mLALOGPS
logP-2.9ALOGPS
logP-4.9Chemaxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.2Chemaxon
pKa (Strongest Basic)8.14Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area187.92 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity87.89 m3·mol-1Chemaxon
Polarizability37.69 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9644
Blood Brain Barrier+0.7695
Caco-2 permeable-0.8081
P-glycoprotein substrateSubstrate0.5616
P-glycoprotein inhibitor INon-inhibitor0.9387
P-glycoprotein inhibitor IINon-inhibitor0.9503
Renal organic cation transporterNon-inhibitor0.9528
CYP450 2C9 substrateNon-substrate0.8476
CYP450 2D6 substrateNon-substrate0.8333
CYP450 3A4 substrateNon-substrate0.6255
CYP450 1A2 substrateNon-inhibitor0.9732
CYP450 2C9 inhibitorNon-inhibitor0.9446
CYP450 2D6 inhibitorNon-inhibitor0.9609
CYP450 2C19 inhibitorNon-inhibitor0.9554
CYP450 3A4 inhibitorNon-inhibitor0.9571
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9916
Ames testNon AMES toxic0.8567
CarcinogenicityNon-carcinogens0.8982
BiodegradationReady biodegradable0.788
Rat acute toxicity1.8059 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9784
hERG inhibition (predictor II)Non-inhibitor0.9602
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-MSsplash10-053u-9133000000-6e248e75e4e603e0c8ef
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ar0-1159000000-c6ddd1d6daa353bc30dc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-052r-4149000000-44af853f93eef757490d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f97-2391000000-14abd1455776c27dbf31
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-005l-4292000000-ca956229307b6211d936
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dl-9851000000-973857f2492a231cd9b9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000f-7590000000-e3c9567447efd9195fe0
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]-180.5768
predicted
DeepCCS 1.0 (2019)
[M+H]+182.97237
predicted
DeepCCS 1.0 (2019)
[M+Na]+188.8849
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. D-alanyl-D-alanine carboxypeptidase
Kind
Protein
Organism
Streptomyces sp. (strain R61)
Pharmacological action
Unknown
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Catalyzes distinct carboxypeptidation and transpeptidation reactions during the last stages of wall peptidoglycan synthesis. Mistaking a beta-lactam antibiotic molecule for a normal substrate (i.e....
Gene Name
Not Available
Uniprot ID
P15555
Uniprot Name
D-alanyl-D-alanine carboxypeptidase
Molecular Weight
42916.725 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 01, 2020 13:43