NAV

(S)-2-Amino-4-[(2s,3r)-2,3,5-Trihydroxy-4-Oxo-Pentyl]Mercapto-Butyric Acid

Identification

Generic Name
(S)-2-Amino-4-[(2s,3r)-2,3,5-Trihydroxy-4-Oxo-Pentyl]Mercapto-Butyric Acid
DrugBank Accession Number
DB04182
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 267.299
Monoisotopic: 267.077657971
Chemical Formula
C9H17NO6S
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
US-ribosylhomocysteine lyaseNot AvailableBacillus subtilis (strain 168)
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 l-alpha-amino acids. These are alpha amino acids which have the L-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
L-alpha-amino acids
Alternative Parents
Thia fatty acids / Hydroxy fatty acids / Acyloins / Beta-hydroxy ketones / Monosaccharides / Alpha-hydroxy ketones / Secondary alcohols / Amino acids / Sulfenyl compounds / Polyols
show 7 more
Substituents
Acyloin / Alcohol / Aliphatic acyclic compound / Alpha-hydroxy ketone / Amine / Amino acid / Beta-hydroxy ketone / Carbonyl group / Carboxylic acid / Dialkylthioether
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
QFXXRJSDEMCBPH-ARDNSNSESA-N
InChI
InChI=1S/C9H17NO6S/c10-5(9(15)16)1-2-17-4-7(13)8(14)6(12)3-11/h5,7-8,11,13-14H,1-4,10H2,(H,15,16)/t5-,7+,8-/m0/s1
IUPAC Name
(2S)-2-amino-4-{[(2S,3R)-2,3,5-trihydroxy-4-oxopentyl]sulfanyl}butanoic acid
SMILES
[H][C@](N)(CCSC[C@@]([H])(O)[C@@]([H])(O)C(=O)CO)C(O)=O

References

General References
Not Available
PubChem Compound
5288675
PubChem Substance
46508110
ChemSpider
4450788
ZINC
ZINC000012504198
PDBe Ligand
KRI
PDB Entries
1ycl

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 Solubility21.3 mg/mLALOGPS
logP-2.6ALOGPS
logP-4.6Chemaxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.87Chemaxon
pKa (Strongest Basic)9.48Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area141.08 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity61.13 m3·mol-1Chemaxon
Polarizability26.08 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6708
Blood Brain Barrier-0.7197
Caco-2 permeable-0.7831
P-glycoprotein substrateNon-substrate0.5589
P-glycoprotein inhibitor INon-inhibitor0.9302
P-glycoprotein inhibitor IINon-inhibitor0.9553
Renal organic cation transporterNon-inhibitor0.9061
CYP450 2C9 substrateNon-substrate0.8856
CYP450 2D6 substrateNon-substrate0.8316
CYP450 3A4 substrateNon-substrate0.7407
CYP450 1A2 substrateNon-inhibitor0.6291
CYP450 2C9 inhibitorNon-inhibitor0.8978
CYP450 2D6 inhibitorNon-inhibitor0.8862
CYP450 2C19 inhibitorNon-inhibitor0.8678
CYP450 3A4 inhibitorNon-inhibitor0.9042
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9898
Ames testNon AMES toxic0.7294
CarcinogenicityNon-carcinogens0.9418
BiodegradationReady biodegradable0.7785
Rat acute toxicity1.7225 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9493
hERG inhibition (predictor II)Non-inhibitor0.8905
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-MSsplash10-0a4i-9440000000-69959ae294616b0552de
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fsr-4980000000-b0efefc124cb1c460176
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00yi-5900000000-41ac411ce512da98f364
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w29-4900000000-3812a60ece0aa28f27a4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-05gi-9500000000-73a42f8d40a10842ad3d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9000000000-d6bbdee6dce714452320
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-9000000000-d183acef6da116f0a024
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]-153.08237
predicted
DeepCCS 1.0 (2019)
[M+H]+155.4405
predicted
DeepCCS 1.0 (2019)
[M+Na]+161.66806
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. S-ribosylhomocysteine lyase
Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
S-ribosylhomocysteine lyase activity
Specific Function
Involved in the synthesis of autoinducer 2 (AI-2) which is secreted by bacteria and is used to communicate both the cell density and the metabolic potential of the environment. The regulation of ge...
Gene Name
luxS
Uniprot ID
O34667
Uniprot Name
S-ribosylhomocysteine lyase
Molecular Weight
17714.11 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 June 12, 2020 16:52