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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:49 UTC
HMDB IDHMDB0000996
Secondary Accession Numbers
  • HMDB0060179
  • HMDB00996
  • HMDB60179
Metabolite Identification
Common Name3-Sulfinoalanine
Description3-Sulfinoalanine or cysteinesulfinic acid is an N-methyl-D-aspartate agonist. It is a product of cysteine dioxygenase or CDO (EC 1.13.11.20). In humans, cysteine catabolism is tightly regulated via regulation of cysteine dioxygenase (CDO) levels in the liver, with the turnover of CDO protein being dramatically decreased when intracellular cysteine levels increase. This occurs in response to changes in the intracellular cysteine concentration via changes in the rate of CDO ubiquitination and degradation. Expressed at high levels in the liver with lower levels in the kidney, brain, and lung, cysteine dioxygenase catalyzes the addition of molecular oxygen to the sulfhydryl group of cysteine, yielding cysteinesulfinic acid. The oxidative catabolism of cysteine to cysteinesulfinate by CDO represents an irreversible loss of cysteine from the free amino acid pool. Once generated, cysteinesulfinate is shuttled into several pathways including hypotaurine/taurine synthesis, sulfite/sulfate production, and the generation of pyruvate.
Structure
Data?1582752169
Synonyms
ValueSource
(2R)-2-Amino-3-sulfinopropanoic acidChEBI
3-SulfinoalanineChEBI
3-Sulphino-L-alanineChEBI
L-Cysteinesulfinic acidChEBI
(2R)-2-Amino-3-sulfinopropanoateGenerator
(2R)-2-Amino-3-sulphinopropanoateGenerator
(2R)-2-Amino-3-sulphinopropanoic acidGenerator
3-SulphinoalanineGenerator
3-Sulfino-L-alanineGenerator
L-CysteinesulfinateGenerator
L-CysteinesulphinateGenerator
L-Cysteinesulphinic acidGenerator
3-Sulfinato-L-alaninic acidGenerator
3-Sulphinato-L-alaninateGenerator
3-Sulphinato-L-alaninic acidGenerator
Cysteine hydrogen sulfite esterMeSH
Alanine 3-sulfinic acidMeSH
Cysteine sulfinateMeSH
Cysteine sulfinic acidMeSH
3-Sulfinato-L-alaninateHMDB
Alanine-3-sulfinic acidHMDB
Alaninesulfinic acidHMDB
CysteinesulfinateHMDB
Cysteinesulfinic acidHMDB
L-2-Amino-3-sulfinopropionic acidHMDB
Chemical FormulaC3H7NO4S
Average Molecular Weight153.157
Monoisotopic Molecular Weight153.009578407
IUPAC Name(2R)-2-amino-3-[(R)-sulfino]propanoic acid
Traditional Name3-sulfinoalanine
CAS Registry Number1115-65-7
SMILES
N[C@@H](CS(O)=O)C(O)=O
InChI Identifier
InChI=1S/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2H,1,4H2,(H,5,6)(H,7,8)/t2-/m0/s1
InChI KeyADVPTQAUNPRNPO-REOHCLBHSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
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
  • Organic nitrogen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility54.6 g/LALOGPS
logP-2.1ALOGPS
logP-3.8ChemAxon
logS-0.7ALOGPS
pKa (Strongest Acidic)1.12ChemAxon
pKa (Strongest Basic)9.09ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.99 m³·mol⁻¹ChemAxon
Polarizability12.95 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0gbi-1940000000-6f5b1dbc8f18bf19a1baSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0uxr-0960000000-763d242d0ca2b186b658Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uy0-0930000000-702fcc20f2a851fa2e6dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-1c518aa1229684a41ad6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-7900000000-c7e561e94593d4ba17dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-2900000000-9b7727f6206fcc55e671Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-1d1369a5e4254a8a3d13Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-2d3ebcfaec61e7e36777Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03dr-9000000000-7b240ef61fb159b7bfafSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-9000000000-c2f11bb7938942651955Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-9000000000-000940516fee7eeb5521Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-9000000000-178c25e031c7d6908256Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-9000000000-245b34836035470b4abeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udr-4900000000-260a6f39fe371359dc23Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9400000000-25d12760dd813f0fa087Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9300000000-97e345cd50da1d6cff01Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0096-9100000000-b40b8be15e2a1f73f828Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a6r-9000000000-74510742c38b33776349Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-5bea4c5d79e7334083a8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-242d94ad2d408f9da90cSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0fki-8900000000-c2c0cb790e021c7e4e88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pbi-1900000000-37118160b153b5d34bf8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5l-9800000000-81881a595728a3c4f9e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-b6696507c06f0123a942Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3900000000-ac1441828c0aa5b22204Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ik9-9500000000-c214c5e872f8b7db390cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-9000000000-c766714b455939044f05Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.38 +/- 0.28 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected but not Quantified Children (1-13 years old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.0732 +/- 0.284 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.163 +/- 0.345 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.316 +/- 0.424 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.546 +/- 0.508 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.546 +/- 0.508 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.627 +/- 0.484 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified28.4 +/- 7.7 uMChildren (1-13 years old)Not SpecifiedMethotrexate treatment details
Associated Disorders and Diseases
Disease References
Methotrexate treatment
  1. Quinn CT, Griener JC, Bottiglieri T, Hyland K, Farrow A, Kamen BA: Elevation of homocysteine and excitatory amino acid neurotransmitters in the CSF of children who receive methotrexate for the treatment of cancer. J Clin Oncol. 1997 Aug;15(8):2800-6. [PubMed:9256122 ]
Associated OMIM IDsNone
DrugBank IDDB02153
Phenol Explorer Compound IDNot Available
FooDB IDFDB022358
KNApSAcK IDNot Available
Chemspider ID1266065
KEGG Compound IDC00606
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCysteine_sulfinic_acid
METLIN IDNot Available
PubChem Compound1549098
PDB IDCSD
ChEBI ID16345
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceKissman, Henry M.; Baker, B. R. Preparation of various amides of p-methoxy-L-phenylalanine. Journal of Medicinal & Pharmaceutical Chemistry (1960), 2 415-23.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lin SY, Nui DM, Tu CP, Cheng YD, Lin HL: Evidence of L-cysteinesulfinic acid in PKU neonatal hair roots, with disappearance after dietary control. Ultrastruct Pathol. 2000 Sep-Oct;24(5):351-2. [PubMed:11071575 ]
  2. Hoeltzli SD, Kelley LK, Moe AJ, Smith CH: Anionic amino acid transport systems in isolated basal plasma membrane of human placenta. Am J Physiol. 1990 Jul;259(1 Pt 1):C47-55. [PubMed:1973601 ]
  3. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  4. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Plays a key role in amino acid metabolism (By similarity).
Gene Name:
GOT1
Uniprot ID:
P17174
Molecular weight:
46247.14
Reactions
3-Sulfinoalanine + Oxoglutaric acid → 3-Sulfinylpyruvic acid + L-Glutamic aciddetails
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:
GOT2
Uniprot ID:
P00505
Molecular weight:
47517.285
Reactions
3-Sulfinoalanine + Oxoglutaric acid → 3-Sulfinylpyruvic acid + L-Glutamic aciddetails
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the production of GABA.
Gene Name:
GAD2
Uniprot ID:
Q05329
Molecular weight:
65410.77
Reactions
3-Sulfinoalanine → Hypotaurine + Carbon dioxidedetails
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the production of GABA.
Gene Name:
GAD1
Uniprot ID:
Q99259
Molecular weight:
66896.065
Reactions
3-Sulfinoalanine → Hypotaurine + Carbon dioxidedetails
General function:
Involved in carboxy-lyase activity
Specific function:
Not Available
Gene Name:
CSAD
Uniprot ID:
Q9Y600
Molecular weight:
55022.79
Reactions
3-Sulfinoalanine → Hypotaurine + CO(2)details
3-Sulfinoalanine → Hypotaurine + Carbon dioxidedetails
General function:
Involved in iron ion binding
Specific function:
Initiates several important metabolic pathways related to pyruvate and several sulfurate compounds including sulfate, hypotaurine and taurine. Critical regulator of cellular cysteine concentrations. Has an important role in maintaining the hepatic concentation of intracellular free cysteine within a proper narrow range.
Gene Name:
CDO1
Uniprot ID:
Q16878
Molecular weight:
22971.745
Reactions
L-Cysteine + Oxygen → 3-Sulfinoalaninedetails
General function:
Involved in iron ion binding
Specific function:
L-CYSTEINE + O(2) = 3-SULFINOALANINE
Gene Name:
CDO-1
Uniprot ID:
Q16857
Molecular weight:
6589.4