NAV

(3R)-4-{[(3,4-dihydroxyphenyl)acetyl]oxy}-N-(2-formylindolizin-3-yl)-3-sulfino-D-valine

Identification

Generic Name
(3R)-4-{[(3,4-dihydroxyphenyl)acetyl]oxy}-N-(2-formylindolizin-3-yl)-3-sulfino-D-valine
DrugBank Accession Number
DB08116
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 490.483
Monoisotopic: 490.104601002
Chemical Formula
C22H22N2O9S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBeta-lactamase SHV-1Not AvailableKlebsiella pneumoniae
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 d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-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
D-alpha-amino acids
Alternative Parents
Indolizines / Catechols / 1-hydroxy-2-unsubstituted benzenoids / Thia fatty acids / 1-hydroxy-4-unsubstituted benzenoids / Aryl-aldehydes / Secondary alkylarylamines / Hydroxy fatty acids / Substituted pyrroles / Benzene and substituted derivatives
show 14 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aldehyde / Alkanesulfinic acid / Alkanesulfinic acid or derivatives / Amine / Amino acid / Aromatic heteropolycyclic compound / Aryl-aldehyde / Azacycle
show 32 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
DEOZLEGRVHDNKC-UGKGYDQZSA-N
InChI
InChI=1S/C22H22N2O9S/c1-22(34(31)32,12-33-18(28)9-13-5-6-16(26)17(27)8-13)19(21(29)30)23-20-14(11-25)10-15-4-2-3-7-24(15)20/h2-8,10-11,19,23,26-27H,9,12H2,1H3,(H,29,30)(H,31,32)/t19-,22-/m0/s1
IUPAC Name
(2S,3R)-4-{[2-(3,4-dihydroxyphenyl)acetyl]oxy}-2-[(2-formylindolizin-3-yl)amino]-3-methyl-3-[(S)-sulfino]butanoic acid
SMILES
[H][C@](NC1=C(C=O)C=C2C=CC=CN12)(C(O)=O)[C@](C)(COC(=O)CC1=CC(O)=C(O)C=C1)[S@](O)=O

References

General References
Not Available
PubChem Compound
46937126
PubChem Substance
99444587
ChemSpider
25058472
ZINC
ZINC000058639150
PDBe Ligand
LN1
PDB Entries
3d4f

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 Solubility1.71 mg/mLALOGPS
logP2.77ALOGPS
logP2.08Chemaxon
logS-2.5ALOGPS
pKa (Strongest Acidic)1.98Chemaxon
pKa (Strongest Basic)-6Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area174.87 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity121.93 m3·mol-1Chemaxon
Polarizability46.6 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.5811
Blood Brain Barrier-0.7265
Caco-2 permeable-0.6355
P-glycoprotein substrateSubstrate0.5414
P-glycoprotein inhibitor INon-inhibitor0.755
P-glycoprotein inhibitor IINon-inhibitor0.9733
Renal organic cation transporterNon-inhibitor0.9174
CYP450 2C9 substrateNon-substrate0.5695
CYP450 2D6 substrateNon-substrate0.8095
CYP450 3A4 substrateNon-substrate0.5108
CYP450 1A2 substrateNon-inhibitor0.6879
CYP450 2C9 inhibitorNon-inhibitor0.6925
CYP450 2D6 inhibitorNon-inhibitor0.8386
CYP450 2C19 inhibitorNon-inhibitor0.7125
CYP450 3A4 inhibitorNon-inhibitor0.7416
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6033
Ames testNon AMES toxic0.586
CarcinogenicityNon-carcinogens0.6904
BiodegradationNot ready biodegradable0.986
Rat acute toxicity2.4949 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9521
hERG inhibition (predictor II)Inhibitor0.5616
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/MSsplash10-006x-0226900000-47cd1ee3d50883d05e46
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ab9-0291000000-0e8acaa0790545425ccb
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-05fr-2960000000-e3375158fdbe349536fe
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fk9-0901600000-991a369f2ad1654082e2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03k9-6942200000-81a56a8729ab00bfd909
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dm-0920100000-7e9d94accaa306e6ef38
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]-193.77213
predicted
DeepCCS 1.0 (2019)
[M+H]+196.1677
predicted
DeepCCS 1.0 (2019)
[M+Na]+202.08022
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Beta-lactamase SHV-1
Kind
Protein
Organism
Klebsiella pneumoniae
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Beta-lactamase activity
Gene Name
bla
Uniprot ID
P0AD64
Uniprot Name
Beta-lactamase SHV-1
Molecular Weight
31223.635 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 21:28 / Updated at June 12, 2020 16:52