BOC-GAMMA-D-GLU-L-LYS(CBZ)-D-BOROALA

Identification

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Name
BOC-GAMMA-D-GLU-L-LYS(CBZ)-D-BOROALA
Accession Number
DB04647
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 580.436
Monoisotopic: 580.291574018
Chemical Formula
C26H41BN4O10
InChI Key
OTTYWVUOPWENAJ-HOJAQTOUSA-N
InChI
InChI=1S/C26H41BN4O10/c1-17(27(38)39)29-22(33)19(12-8-9-15-28-24(36)40-16-18-10-6-5-7-11-18)30-21(32)14-13-20(23(34)35)31-25(37)41-26(2,3)4/h5-7,10-11,17,19-20,38-39H,8-9,12-16H2,1-4H3,(H,28,36)(H,29,33)(H,30,32)(H,31,37)(H,34,35)/t17-,19+,20+/m1/s1
IUPAC Name
(2S)-4-{[(1S)-5-{[(benzyloxy)carbonyl]amino}-1-{[(1S)-1-(dihydroxyboranyl)ethyl]carbamoyl}pentyl]carbamoyl}-2-{[(tert-butoxy)carbonyl]amino}butanoic acid
SMILES
C[C@@H](NC(=O)[C@H](CCCCNC(=O)OCC1=CC=CC=C1)NC(=O)CC[C@H](NC(=O)OC(C)(C)C)C(O)=O)B(O)O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UD-alanyl-D-alanine carboxypeptidase DacANot AvailableEscherichia coli O6:H1 (strain CFT073 / ATCC 700928 / UPEC)
UD-alanyl-D-alanine carboxypeptidase DacANot AvailableEscherichia coli (strain K12)
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
5287824
PubChem Substance
46508422
ChemSpider
4450121
HET
BO9
PDB Entries
1z6f

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.0237 mg/mLALOGPS
logP1.17ALOGPS
logP1.69ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)3.72ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area212.62 Å2ChemAxon
Rotatable Bond Count19ChemAxon
Refractivity141.61 m3·mol-1ChemAxon
Polarizability60.95 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7462
Blood Brain Barrier-0.5554
Caco-2 permeable-0.6757
P-glycoprotein substrateSubstrate0.7526
P-glycoprotein inhibitor INon-inhibitor0.5802
P-glycoprotein inhibitor IINon-inhibitor0.9587
Renal organic cation transporterNon-inhibitor0.9343
CYP450 2C9 substrateNon-substrate0.7301
CYP450 2D6 substrateNon-substrate0.7981
CYP450 3A4 substrateNon-substrate0.5251
CYP450 1A2 substrateNon-inhibitor0.8529
CYP450 2C9 inhibitorNon-inhibitor0.8449
CYP450 2D6 inhibitorNon-inhibitor0.8841
CYP450 2C19 inhibitorNon-inhibitor0.6797
CYP450 3A4 inhibitorNon-inhibitor0.6947
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8158
Ames testNon AMES toxic0.6993
CarcinogenicityNon-carcinogens0.8029
BiodegradationNot ready biodegradable0.9808
Rat acute toxicity2.4749 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9407
hERG inhibition (predictor II)Non-inhibitor0.75
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Glutamine and derivatives / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Benzyloxycarbonyls / N-acyl amines / Carbamate esters / Secondary carboxylic acid amides / Boronic acids / Organic carbonic acids and derivatives / Organic metalloid salts
show 8 more
Substituents
Alpha-dipeptide / Glutamine or derivatives / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives / Benzyloxycarbonyl / N-acyl-amine / Monocyclic benzene moiety / Fatty amide
show 24 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Escherichia coli O6:H1 (strain CFT073 / ATCC 700928 / UPEC)
Pharmacological action
Unknown
General Function
Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
Specific Function
Serine-type d-ala-d-ala carboxypeptidase activity
Gene Name
dacA
Uniprot ID
P0AEB3
Uniprot Name
D-alanyl-D-alanine carboxypeptidase DacA
Molecular Weight
44443.62 Da
References
  1. Nicola G, Peddi S, Stefanova M, Nicholas RA, Gutheil WG, Davies C: Crystal structure of Escherichia coli penicillin-binding protein 5 bound to a tripeptide boronic acid inhibitor: a role for Ser-110 in deacylation. Biochemistry. 2005 Jun 14;44(23):8207-17. [PubMed:15938610]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
Gene Name
dacA
Uniprot ID
P0AEB2
Uniprot Name
D-alanyl-D-alanine carboxypeptidase DacA
Molecular Weight
44443.62 Da

Drug created on September 11, 2007 11:49 / Updated on August 02, 2019 07:37