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Showing metabocard for 3-Sulfinoalanine (HMDB0000996)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:22 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000996 (3-Sulfinoalanine)

  Mrv1652303192023122D          

  9  8  0  0  0  0            999 V2000
10003.636210003.4937    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.920910003.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.207310003.4937    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10002.207310004.3177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.491610003.0802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.351110003.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.063910003.4937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.351110002.2579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.636210004.3177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  9  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
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3D MOL for HMDB0000996 (3-Sulfinoalanine)

HMDB0000996
     RDKit          3D
3-Sulfinoalanine
 16 15  0  0  0  0  0  0  0  0999 V2000
   -1.0555    1.8671    0.2225 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5994    0.5203    0.0073 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8802    0.4453    0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5106   -1.2234    0.0336 S   0  0  0  0  0  4  0  0  0  0  0  0
    3.0039   -1.2015    0.3684 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2577   -1.7275   -1.5712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3928   -0.3839    0.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3067    0.0096    1.6025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1234   -1.7394    0.7952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2516    2.5294    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7560    2.1850   -0.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7264    0.2167   -1.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1632    0.8308    1.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3839    1.0910   -0.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6141   -1.0442   -2.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6019   -2.3752    0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  2  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  6
  3 13  1  0
  3 14  1  0
  6 15  1  0
  9 16  1  0
M  END
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3D SDF for HMDB0000996 (3-Sulfinoalanine)

  Mrv1652303192023122D          

  9  8  0  0  0  0            999 V2000
10003.636210003.4937    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.920910003.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.207310003.4937    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10002.207310004.3177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.491610003.0802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.351110003.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.063910003.4937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.351110002.2579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.636210004.3177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  9  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000996

> <DATABASE_NAME>
hmdb

> <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_KEY>
ADVPTQAUNPRNPO-REOHCLBHSA-N

> <FORMULA>
C3H7NO4S

> <MOLECULAR_WEIGHT>
153.157

> <EXACT_MASS>
153.009578407

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
12.949980949636586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-amino-3-[(R)-sulfino]propanoic acid

> <ALOGPS_LOGP>
-2.06

> <JCHEM_LOGP>
-3.82971344535222

> <ALOGPS_LOGS>
-0.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
1.994188668600013

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1165371093144163

> <JCHEM_PKA_STRONGEST_BASIC>
9.086747204482425

> <JCHEM_POLAR_SURFACE_AREA>
100.62

> <JCHEM_REFRACTIVITY>
28.9921

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.02e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-sulfinoalanine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000996 (3-Sulfinoalanine)

HMDB0000996
     RDKit          3D
3-Sulfinoalanine
 16 15  0  0  0  0  0  0  0  0999 V2000
   -1.0555    1.8671    0.2225 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5994    0.5203    0.0073 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8802    0.4453    0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5106   -1.2234    0.0336 S   0  0  0  0  0  4  0  0  0  0  0  0
    3.0039   -1.2015    0.3684 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2577   -1.7275   -1.5712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3928   -0.3839    0.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3067    0.0096    1.6025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1234   -1.7394    0.7952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2516    2.5294    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7560    2.1850   -0.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7264    0.2167   -1.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1632    0.8308    1.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3839    1.0910   -0.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6141   -1.0442   -2.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6019   -2.3752    0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  2  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  6
  3 13  1  0
  3 14  1  0
  6 15  1  0
  9 16  1  0
M  END
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PDB for HMDB0000996 (3-Sulfinoalanine)

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0    8673.4548673.188   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8672.1198672.420   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0    8670.7878673.188   0.000  0.00  0.00           S+0
HETATM    4  O   UNK     0    8670.7878674.726   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8669.4518672.416   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8674.7898672.420   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8676.1198673.188   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8674.7898670.881   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0    8673.4548674.726   0.000  0.00  0.00           N+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    1    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    1                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0000996 (3-Sulfinoalanine)

COMPND    HMDB0000996
HETATM    1  N1  UNL     1      -1.055   1.867   0.223  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.599   0.520   0.007  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.880   0.445   0.287  1.00  0.00           C  
HETATM    4  S1  UNL     1       1.511  -1.223   0.034  1.00  0.00           S  
HETATM    5  O1  UNL     1       3.004  -1.201   0.368  1.00  0.00           O  
HETATM    6  O2  UNL     1       1.258  -1.728  -1.571  1.00  0.00           O  
HETATM    7  C3  UNL     1      -1.393  -0.384   0.843  1.00  0.00           C  
HETATM    8  O3  UNL     1      -2.307   0.010   1.602  1.00  0.00           O  
HETATM    9  O4  UNL     1      -1.123  -1.739   0.795  1.00  0.00           O  
HETATM   10  H1  UNL     1      -0.252   2.529   0.188  1.00  0.00           H  
HETATM   11  H2  UNL     1      -1.756   2.185  -0.495  1.00  0.00           H  
HETATM   12  H3  UNL     1      -0.726   0.217  -1.070  1.00  0.00           H  
HETATM   13  H4  UNL     1       1.163   0.831   1.275  1.00  0.00           H  
HETATM   14  H5  UNL     1       1.384   1.091  -0.467  1.00  0.00           H  
HETATM   15  H6  UNL     1       1.614  -1.044  -2.195  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.602  -2.375   0.175  1.00  0.00           H  
CONECT    1    2   10   11
CONECT    2    3    7   12
CONECT    3    4   13   14
CONECT    4    5    5    6
CONECT    6   15
CONECT    7    8    8    9
CONECT    9   16
END
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SMILES for HMDB0000996 (3-Sulfinoalanine)

N[C@@H](CS(O)=O)C(O)=O
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INCHI for HMDB0000996 (3-Sulfinoalanine)

InChI=1S/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2H,1,4H2,(H,5,6)(H,7,8)/t2-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
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
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
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 ID3SALA
MarkerDB IDNot Available
Good Scents 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)Not Available
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

Enzyme Details
1. Aspartate aminotransferase, cytoplasmic
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 + Glutamic aciddetails
Enzyme Details
2. Aspartate aminotransferase, mitochondrial
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 + Glutamic aciddetails
Enzyme Details
3. Glutamate decarboxylase 2
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
Enzyme Details
4. Glutamate decarboxylase 1
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
Enzyme Details
5. Cysteine sulfinic acid decarboxylase
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
Enzyme Details
6. Cysteine dioxygenase type 1
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
Enzyme Details
7. Cysteine dioxygenase
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