3-Sulfinoalanine

Identification

Name
3-Sulfinoalanine
Accession Number
DB02153  (EXPT01040, EXPT01032, DB01769)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • S-Cysteinesulfinic acid
  • S-Sulfinocysteine
International/Other Brands
3-Sulfino-L-alanine / 3-sulphino-L-alanine / L-Cysteinesulfinic acid
Categories
Not Available
UNII
56X032NVQL
CAS number
1115-65-7
Weight
Average: 153.157
Monoisotopic: 153.009578407
Chemical Formula
C3H7NO4S
InChI Key
ADVPTQAUNPRNPO-REOHCLBHSA-N
InChI
InChI=1S/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2H,1,4H2,(H,5,6)(H,7,8)/t2-/m0/s1
IUPAC Name
(2R)-2-amino-3-[(R)-sulfino]propanoic acid
SMILES

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPyridoxamine kinaseNot AvailableEscherichia coli (strain K12)
UBeta-lactamase 2Not AvailableBacillus cereus
UPoly(A) polymerase alphaNot AvailableHuman
UChorismate mutase AroHNot AvailableBacillus subtilis (strain 168)
UGlutathione reductase, mitochondrialNot AvailableHuman
US-ribosylhomocysteine lyaseNot AvailableDeinococcus radiodurans (strain ATCC 13939 / DSM 20539 / JCM 16871 / LMG 4051 / NBRC 15346 / NCIMB 9279 / R1 / VKM B-1422)
UCarboxymethylenebutenolidaseNot AvailablePseudomonas sp. (strain B13)
UDimethyl sulfoxide/trimethylamine N-oxide reductaseNot AvailableRhodobacter sphaeroides
UPeroxiredoxin-2Not AvailableHuman
UPeptide deformylaseNot AvailableStaphylococcus aureus (strain MW2)
UMalonamidase E2Not AvailableBradyrhizobium japonicum
UHMG-CoA synthaseNot AvailableStaphylococcus aureus
UOsmotically inducible protein CNot AvailableThermus thermophilus
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
Human Metabolome Database
HMDB60179
KEGG Compound
C00606
PubChem Compound
1549098
PubChem Substance
46505410
ChemSpider
1266065
ChEBI
16345
ChEMBL
CHEMBL1160508
HET
CSD
PDB Entries
1acd / 1bi5 / 1bq6 / 1c0t / 1c0u / 1c1b / 1c1c / 1d6h / 1d6i / 1din
show 379 more

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 Solubility30.2 mg/mLALOGPS
logP-2.1ALOGPS
logP-3ChemAxon
logS-0.7ALOGPS
pKa (Strongest Acidic)-0.78ChemAxon
pKa (Strongest Basic)9.09ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.99 m3·mol-1ChemAxon
Polarizability12.95 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.554
Blood Brain Barrier+0.57
Caco-2 permeable-0.6654
P-glycoprotein substrateNon-substrate0.8665
P-glycoprotein inhibitor INon-inhibitor0.959
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.9629
CYP450 2C9 substrateNon-substrate0.8186
CYP450 2D6 substrateNon-substrate0.8215
CYP450 3A4 substrateNon-substrate0.7013
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9072
CYP450 2D6 inhibitorNon-inhibitor0.9311
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9547
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9967
Ames testNon AMES toxic0.6768
CarcinogenicityNon-carcinogens0.6854
BiodegradationReady biodegradable0.8865
Rat acute toxicity1.8571 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9622
hERG inhibition (predictor II)Non-inhibitor0.9317
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
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0gbi-1940000000-6f5b1dbc8f18bf19a1ba
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0uxr-0960000000-763d242d0ca2b186b658
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0uy0-0930000000-702fcc20f2a851fa2e6d
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
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0udi-2900000000-9b7727f6206fcc55e671
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-9000000000-1d1369a5e4254a8a3d13
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-9000000000-2d3ebcfaec61e7e36777
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03dr-9000000000-7b240ef61fb159b7bfaf
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03di-9000000000-c2f11bb7938942651955
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-9000000000-000940516fee7eeb5521
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-9000000000-178c25e031c7d6908256
MS/MS Spectrum - , negativeLC-MS/MSsplash10-000i-9000000000-245b34836035470b4abe
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udr-4900000000-260a6f39fe371359dc23
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-9400000000-25d12760dd813f0fa087
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-9300000000-97e345cd50da1d6cff01
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0096-9100000000-b40b8be15e2a1f73f828
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a6r-9000000000-74510742c38b33776349
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-5bea4c5d79e7334083a8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-242d94ad2d408f9da90c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0fki-8900000000-c2c0cb790e021c7e4e88

Taxonomy

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
Sulfinic acids / Amino acids / Alkanesulfinic acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organosulfur compounds / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
show 1 more
Substituents
L-alpha-amino acid / Sulfinic acid / Sulfinic acid derivative / Alkanesulfinic acid or derivatives / Alkanesulfinic acid / Amino acid / Carboxylic acid / Monocarboxylic acid or derivatives / Organopnictogen compound / Organic oxygen compound
show 11 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
S-substituted L-cysteine, organosulfinic acid (CHEBI:16345) / Other amino acids (C00606)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Phosphorylates B6 vitamers; functions in a salvage pathway. Uses pyridoxamine, but has negligible activity toward pyridoxal and pyridoxine as substrates.
Gene Name
pdxY
Uniprot ID
P77150
Uniprot Name
Pyridoxamine kinase
Molecular Weight
31322.01 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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Bacillus cereus
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Can hydrolyze carbapenem compounds.
Gene Name
blm
Uniprot ID
P04190
Uniprot Name
Beta-lactamase 2
Molecular Weight
28092.24 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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Rna binding
Specific Function
Polymerase that creates the 3'-poly(A) tail of mRNA's. Also required for the endoribonucleolytic cleavage reaction at some polyadenylation sites. May acquire specificity through interaction with a ...
Gene Name
PAPOLA
Uniprot ID
P51003
Uniprot Name
Poly(A) polymerase alpha
Molecular Weight
82841.78 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. [PubMed:17139284]
  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. [PubMed:17016423]
  3. 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. [PubMed:10592235]
Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Chorismate mutase activity
Specific Function
Catalyzes the Claisen rearrangement of chorismate to prephenate. Probably involved in the aromatic amino acid biosynthesis.
Gene Name
aroH
Uniprot ID
P19080
Uniprot Name
Chorismate mutase AroH
Molecular Weight
14516.91 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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Nadp binding
Specific Function
Maintains high levels of reduced glutathione in the cytosol.
Gene Name
GSR
Uniprot ID
P00390
Uniprot Name
Glutathione reductase, mitochondrial
Molecular Weight
56256.565 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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Deinococcus radiodurans (strain ATCC 13939 / DSM 20539 / JCM 16871 / LMG 4051 / NBRC 15346 / NCIMB 9279 / R1 / VKM B-1422)
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
Q9RRU8
Uniprot Name
S-ribosylhomocysteine lyase
Molecular Weight
17394.625 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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Pseudomonas sp. (strain B13)
Pharmacological action
Unknown
General Function
Carboxymethylenebutenolidase activity
Specific Function
Ring cleavage of cyclic ester dienelactone to produce maleylacetate.
Gene Name
clcD
Uniprot ID
P0A115
Uniprot Name
Carboxymethylenebutenolidase
Molecular Weight
25554.855 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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Rhodobacter sphaeroides
Pharmacological action
Unknown
General Function
Trimethylamine-n-oxide reductase (cytochrome c) activity
Specific Function
Catalyzes the reduction of dimethyl sulfoxide (DMSO) and trimethylamine N-oxide (TMAO) to dimethyl sulfide (DMS) and trimethylamine, respectively. The terminal DMSO reductase can also use various s...
Gene Name
dmsA
Uniprot ID
Q57366
Uniprot Name
Dimethyl sulfoxide/trimethylamine N-oxide reductase
Molecular Weight
89206.805 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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Thioredoxin peroxidase activity
Specific Function
Involved in redox regulation of the cell. Reduces peroxides with reducing equivalents provided through the thioredoxin system. It is not able to receive electrons from glutaredoxin. May play an imp...
Gene Name
PRDX2
Uniprot ID
P32119
Uniprot Name
Peroxiredoxin-2
Molecular Weight
21891.725 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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Staphylococcus aureus (strain MW2)
Pharmacological action
Unknown
General Function
Peptide deformylase activity
Specific Function
Removes the formyl group from the N-terminal Met of newly synthesized proteins. Requires at least a dipeptide for an efficient rate of reaction. N-terminal L-methionine is a prerequisite for activi...
Gene Name
def
Uniprot ID
Q8NX78
Uniprot Name
Peptide deformylase
Molecular Weight
20559.37 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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Bradyrhizobium japonicum
Pharmacological action
Unknown
General Function
Carbon-nitrogen ligase activity, with glutamine as amido-n-donor
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q9ZIV5
Uniprot Name
Malonamidase E2
Molecular Weight
43681.365 Da
Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
Unknown
General Function
Hydroxymethylglutaryl-coa synthase activity
Specific Function
Not Available
Gene Name
mvaS
Uniprot ID
Q9FD87
Uniprot Name
HMG-CoA synthase
Molecular Weight
43217.195 Da
Kind
Protein
Organism
Thermus thermophilus
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Peroxidase activity
Gene Name
tthHB8IM
Uniprot ID
P84124
Uniprot Name
Osmotically inducible protein C
Molecular Weight
Not Available

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
Lipid transport protein in adipocytes. Binds both long chain fatty acids and retinoic acid. Delivers long-chain fatty acids and retinoic acid to their cognate receptors in the nucleus (By similarity).
Gene Name
FABP4
Uniprot ID
P15090
Uniprot Name
Fatty acid-binding protein, adipocyte
Molecular Weight
14718.815 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. [PubMed:17139284]
  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. [PubMed:17016423]
  3. 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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:10