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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:39:44 UTC
NP-MRD IDNP0000120
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Cysteine
DescriptionCysteine (Cys), also known as L-cysteine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-alanine is one of 20 proteinogenic amino acids, i.E., The amino acids used in the biosynthesis of proteins. Cysteine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, non-polar, sulfur-containing amino acid. Cysteine is an important source of sulfur in human metabolism, and although it is classified as a non-essential amino acid, cysteine may be essential for infants, the elderly, and individuals with certain metabolic disease or who suffer from malabsorption syndromes. Cysteine can occasionally be considered as an essential or conditionally essential amino acid. Cysteine is unique amongst the twenty natural amino acids as it contains a thiol group. Thiol groups can undergo oxidation/reduction (redox) reactions; when cysteine is oxidized it can form cystine, which is two cysteine residues joined by a disulfide bond. This reaction is reversible since the reduction of this disulphide bond regenerates two cysteine molecules. The disulphide bonds of cystine are crucial to defining the structures of many proteins. Cysteine is often involved in electron-transfer reactions, and help the enzyme catalyze its reaction. Cysteine is also part of the antioxidant glutathione. N-Acetyl-L-cysteine (NAC) is a form of cysteine where an acetyl group is attached to cysteine's nitrogen atom and is sold as a dietary supplement. Cysteine is named after cystine, which comes from the Greek word kustis meaning bladder (cystine was first isolated from kidney stones). Oxidation of cysteine can produce a disulfide bond with another thiol and further oxidation can produce sulphfinic or sulfonic acids. The cysteine thiol group is also a nucleophile and can undergo addition and substitution reactions. Thiol groups become much more reactive when they are ionized, and cysteine residues in proteins have pKa values close to neutrality, so they are often in their reactive thiolate form in the cell. The thiol group also has a high affinity for heavy metals and proteins containing cysteine will bind metals such as mercury, lead, and cadmium tightly. Due to this ability to undergo redox reactions, cysteine has antioxidant properties. Cysteine is important in energy metabolism. As cystine, it is a structural component of many tissues and hormones. Cysteine has clinical uses ranging from treating baldness to psoriasis to preventing smoker's hack. In some cases, oral cysteine therapy has proved excellent for treatment of asthmatics, enabling them to stop theophylline and other medications. Cysteine also enhances the effect of topically applied silver, tin, and zinc salts in preventing dental cavities. In the future, cysteine may play a role in the treatment of cobalt toxicity, diabetes, psychosis, cancer, and seizures (http://Www.Dcnutrition.Com/AminoAcids/). Cysteine has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ).
Structure
Thumb
Synonyms
ValueSource
(2R)-2-Amino-3-mercaptopropanoic acidChEBI
(2R)-2-Amino-3-sulfanylpropanoic acidChEBI
(R)-2-Amino-3-mercaptopropanoic acidChEBI
CChEBI
CysChEBI
CYSTEINEChEBI
e 920ChEBI
e-920ChEBI
e920ChEBI
FREE cysteineChEBI
L-2-Amino-3-mercaptopropionic acidChEBI
L-CysteinChEBI
L-ZysteinChEBI
EcolanKegg
(2R)-2-Amino-3-mercaptopropanoateGenerator
(2R)-2-Amino-3-sulfanylpropanoateGenerator
(2R)-2-Amino-3-sulphanylpropanoateGenerator
(2R)-2-Amino-3-sulphanylpropanoic acidGenerator
(R)-2-Amino-3-mercaptopropanoateGenerator
L-2-Amino-3-mercaptopropionateGenerator
(+)-2-Amino-3-mercaptopropionic acidHMDB
(R)-(+)-CysteineHMDB
(R)-2-Amino-3-mercapto-propanoateHMDB
(R)-2-Amino-3-mercapto-propanoic acidHMDB
(R)-CysteineHMDB
2-Amino-3-mercaptopropanoateHMDB
2-Amino-3-mercaptopropanoic acidHMDB
2-Amino-3-mercaptopropionateHMDB
2-Amino-3-mercaptopropionic acidHMDB
3-Mercapto-L-alanineHMDB
AcetylcysteineHMDB
alpha-Amino-beta-thiolpropionic acidHMDB
b-MercaptoalanineHMDB
beta-MercaptoalanineHMDB
CarbocysteineHMDB
CisteinaHMDB
CisteinumHMDB
CysteinHMDB
CysteinumHMDB
Half-cystineHMDB
L CysteineHMDB
L-(+)-CysteineHMDB
L-2-Amino-3-mercaptopropanoateHMDB
L-2-Amino-3-mercaptopropanoic acidHMDB
PolycysteineHMDB
ThioserineHMDB
Cysteine hydrochlorideHMDB
Zinc cysteinateHMDB
Half cystineHMDB
Chemical FormulaC3H7NO2S
Average Mass121.1580 Da
Monoisotopic Mass121.01975 Da
IUPAC Name(2R)-2-amino-3-sulfanylpropanoic acid
Traditional NameL-cysteine
CAS Registry Number52-90-4
SMILES
N[C@@H](CS)C(O)=O
InChI Identifier
InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1
InChI KeyXUJNEKJLAYXESH-REOHCLBHSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)V.dorna832021-07-25View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentus
Actinidia chinensis
Agaricus bisporus
Agave
Allium ampeloprasum
Allium ascalonicum
Allium cepaFooDB
Allium cepa L.
Allium fistulosum
Allium sativumFooDB
Allium schoenoprasum
Allium tuberosum
Aloysia triphylla
Amaranthus
Amelanchier alnifolia
Anacardium occidentale
Ananas comosus
Anas platyrhynchos
Anatidae
Anethum graveolens
Angelica keiskei
Annona cherimola
Annona muricata
Annona reticulata
Annona squamosa
Anser anser
Anthriscus cerefolium
Apium graveolens
Apium graveolens var. dulce
Apium graveolens var. rapaceum
Apium graveolens var. secalinum
Arachis hypogaea
Arctium lappa
Armoracia rusticana
Artemisia dracunculus
Artemisia vulgaris
Artocarpus altilis
Artocarpus heterophyllus
Asparagus officinalis
Attalea speciosa
Auricularia auricula-judae
Auricularia polytricha
Avena sativa L.
Averrhoa carambola
Basella alba
Benincasa hispida
Bertholletia excelsa
Beta vulgaris
Beta vulgaris ssp. cicla
Bison bison
Borago officinalis
Bos taurus
Bos taurus X Bison bison
Brassica alboglabra
Brassica juncea
Brassica napus
Brassica napus var. napus
Brassica oleracea
Brassica oleracea var. botrytis
Brassica oleracea var. capitata
Brassica oleracea var. gemmifera
Brassica oleracea var. gongylodes
Brassica oleracea var. italica
Brassica oleracea var. sabauda
Brassica oleracea var. viridis
Brassica rapa
Brassica rapa ssp. chinensis
Brassica rapa var. pekinensis
Brassica rapa var. rapa
Brassica ruvo
Brosimum alicastrum
Bubalus bubalis
Byrsonima crassifolia
Cajanus cajan
Canarium ovatum
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibarius
Capparis spinosa
Capra aegagrus hircus
Capsicum annuum
Capsicum annuum L.
Capsicum annuum var. annuum
Capsicum chinense
Capsicum pubescens
Carica papaya L.
Carissa macrocarpa
Carthamus tinctorius
Carum carvi
Carya
Carya illinoinensis
Castanea
Castanea crenata
Castanea mollissima
Castanea sativa
Ceratonia siliqua
Cervidae
Cervus canadensis
Chamaemelum nobile
Chamerion angustifolium
Chenopodium album
Chenopodium quinoa
Chrysanthemum coronarium
Cicer arietinum
Cichorium endivia
Cichorium intybus
Cinnamomum
Cinnamomum aromaticum
Cinnamomum verum
Cirsium
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)
Citrus aurantiifolia
Citrus latifolia
Citrus limon
Citrus maxima
Citrus paradisi
Citrus reticulata
Citrus X sinensis (L.) Osbeck (pro. sp.)
Cocos nucifera
Coffea arabica L.FooDB
Coffea canephora
Colocasia esculenta
Columba
Columbidae
Corchorus olitorius
Coriandrum sativum L.
Corylus
Corylus avellana
Crateva religiosa
Crocus sativus
Cucumis melo
Cucumis metuliferus
Cucumis sativus L.
Cucurbita
Cucurbita maxima
Cucurbita moschata
Cuminum cyminum
Curcuma longa
Cydonia oblonga
Cymbopogon citratus
Cynara cardunculus
Cynara scolymus
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dimocarpus longan
Dioscorea
Dioscorea pentaphylla
Diospyros
Diospyros kaki
Diospyros virginiana
Dromaius novaehollandiae
Durio zibethinus
Dysphania ambrosioides
Elaeis
Eleocharis dulcis
Elettaria cardamomum
Empetrum nigrum
Equus caballus
Eragrostis tef
Eriobotrya japonica
Eruca vesicaria subsp. Sativa
Eugenia javanica
Eugenia uniflora
Eutrema japonicum
Fagopyrum esculentum
Fagopyrum tataricum
Fagus
Feijoa sellowiana
Ficus carica
Flammulina velutipes
Foeniculum vulgare
Fragaria x ananassa
Gallus gallus
Garcinia mangostana
Gaylussacia baccata
Ginkgo bilobaFooDB
Glycine maxFooDB
Gossypium
Grifola frondosa
Hedysarum alpinum
Helianthus annuus L.FooDB
Helianthus tuberosus
Hibiscus sabbariffa
Hippophae rhamnoides
Hordeum vulgare
Hyssopus officinalis L.
Illicium verum
Ipomoea aquatica
Ipomoea batatas
Juglans
Juglans ailanthifolia
Juglans cinerea
Juglans nigra L.
Juglans regia
Lablab purpureus
Lactuca sativa
Lagenaria siceraria
Lagopus muta
Lathyrus sativus
Laurus nobilis L.
Lens culinaris
Lentinus edodes
Lepidium sativum
Leporidae
Lepus timidus
Levisticum officinale
Linum usitatissimumFooDB
Litchi chinensis
Luffa aegyptiaca
Lupinus
Lupinus albus
Macadamia
Macadamia tetraphylla
Malpighia emarginata
Malus
Malus pumila
Mammea americana
Mangifera indica
Manihot esculenta
Manilkara zapota
Maranta arundinacea
Matricaria recutita
Matteuccia struthiopteris
Medicago sativa
Melanitta fusca
Meleagris gallopavo
Melissa officinalis L.
Mentha
Mentha aquatica
Mentha arvensis
Mentha spicata
Mentha x piperita
Mespilus germanica
Metroxylon sagu
Momordica charantia
Morchellaceae
Morella rubra
Moringa oleifera
Morus
Morus nigra
Musa acuminata
Musa x paradisiaca
Myrica
Myristica fragrans
Nelumbo
Nelumbo nucifera
Nephelium lappaceum
Numida meleagris
Nuphar lutea
Ocimum basilicum
Odocoileus
Oenothera biennis
Olea europaea
Opuntia
Opuntia cochenillifera
Opuntia macrorhiza
Origanum majorana
Origanum onites
Origanum vulgare
Origanum X majoricum
Oryctolagus
Oryza rufipogon
Oryza sativaFooDB
Ovis aries
Pachyrhizus erosus
Panax ginseng
Pangium edule
Panicum miliaceum
Passiflora edulis
Pastinaca sativa
Pediomelum esculentum
Perideridia oregana
Persea americana
Petasites japonicus
Petroselinum crispum
Phaseolus coccineus
Phaseolus lunatus
Phaseolus vulgaris
Phasianidae
Phasianus colchicus
Phoenix dactyliferaFooDB
Photinia melanocarpa
Phyllostachys edulis
Physalis
Physalis philadelphica var. immaculata
Phytolacca americana
Pimenta dioica
Pimpinella anisum
Pinus
Pinus edulis
Piper nigrum L.
Pistacia vera
Pisum sativum
Pleurotus ostreatus
Polygonum alpinum
Portulaca oleracea
Pouteria sapota
Prunus armeniaca
Prunus avium
Prunus avium L.
Prunus cerasus
Prunus domestica
Prunus dulcis
Prunus persica
Prunus persica var. nucipersica
Prunus persica var. persica
Prunus tomentosa
Prunus virginiana
Psidium cattleianum
Psidium guajava
Psophocarpus tetragonolobus
Punica granatum
Pyrus communis
Pyrus pyrifolia
Quercus
Raphanus sativus
Raphanus sativus var. longipinnatus
Raphanus sativus var. sativus
Rheum rhabarbarum
Ribes aureum
Ribes glandulosum
Ribes nigrum
Ribes rubrum
Ribes uva-crispa
Rosa
Rubus arcticus
Rubus chamaemorus
Rubus idaeus
Rubus occidentalis
Rubus spectabilis
Rumex
Rumex acetosa
Rumex articus
Sagittaria latifolia
Salix pulchra
Salvia elegans
Salvia hispanica
Salvia officinalis
Salvia rosmarinus
Sambucus nigra
Sambucus nigra L.
Satureja hortensis L.
Satureja montana
Scorzonera hispanica
Secale cereale
Sechium edule
Sesamum indicum
Sesbania bispinosa
Sinapis alba
Sisymbrium
Solanum lycopersicum
Solanum lycopersicum var. cerasiforme
Solanum lycopersicum var. lycopersicum
Solanum melongena
Solanum quitoense
Solanum tuberosum
Sorbus aucuparia
Sorghum bicolor
Spinacia oleracea
Struthio camelus
Sus scrofa
Sus scrofa domestica
Syzygium aromaticum
Syzygium cumini
Syzygium jambos
Tamarindus indica
Taraxacum officinale
Tetragonia tetragonioides
Thelesperma
Thymus pulegioides
Thymus vulgaris
Tilia cordata
Tilia L.FooDB
Tragopogon porrifolius
Trigonella foenum-graecum
Triticum
Triticum aestivumFooDB
Triticum durum
Triticum spelta
Triticum turanicum
Typha angustifolia
Vaccinium
Vaccinium angustifolium
Vaccinium angustifolium X Vaccinium corymbosum
Vaccinium arboreum
Vaccinium corymbosum
Vaccinium deliciosum
Vaccinium elliottii
Vaccinium macrocarpon
Vaccinium myrtilloides
Vaccinium myrtillus
Vaccinium ovalifolium
Vaccinium ovatum
Vaccinium oxycoccos
Vaccinium parvifolium
Vaccinium reticulatum
Vaccinium stamineum
Vaccinium uliginosum
Vaccinium vitis-idaea
Valerianella locusta
Vanilla
Verbena officinalis
Viburnum edule
Vicia faba
Vigna aconitifolia
Vigna angularis
Vigna mungo
Vigna radiata
Vigna umbellata
Vigna unguiculata
Vigna unguiculata ssp. cylindrica
Vigna unguiculata ssp. unguiculata
Vigna unguiculata var. sesquipedalis
Vitis
Vitis aestivalis
Vitis labrusca
Vitis rotundifolia
Vitis vinifera L.
Xanthosoma sagittifolium
Zea mays L.
Zingiber officinaleFooDB
Zizania
Zizania aquatica
Ziziphus zizyphus
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCysteine and derivatives
Alternative Parents
Substituents
  • Cysteine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Amino acid
  • Alkylthiol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point220 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility277 mg/mL at 25 °CBeilstein Handbook of Organic Chemistry (Handbuch der Organischen Chemie), 4th Edition
LogP-2.49Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility23.1 g/LALOGPS
logP-2.6ALOGPS
logP-2.8ChemAxon
logS-0.72ALOGPS
pKa (Strongest Acidic)2.35ChemAxon
pKa (Strongest Basic)9.05ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.22 m³·mol⁻¹ChemAxon
Polarizability11.41 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000574
DrugBank IDDB00151
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012678
KNApSAcK IDC00001351
Chemspider ID5653
KEGG Compound IDC00097
BioCyc IDCYS
BiGG ID33843
Wikipedia LinkCysteine
METLIN ID5556
PubChem Compound5862
PDB IDNot Available
ChEBI ID17561
Good Scents IDrw1018061
References
General References
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  7. Paivalainen S, Suokas M, Lahti O, Heape AM: Degraded myelin-associated glycoprotein (dMAG) formation from pure human brain myelin-associated glycoprotein (MAG) is not mediated by calpain or cathepsin L-like activities. J Neurochem. 2003 Feb;84(3):533-45. [PubMed:12558973 ]
  8. Iyer S, Leonidas DD, Swaminathan GJ, Maglione D, Battisti M, Tucci M, Persico MG, Acharya KR: The crystal structure of human placenta growth factor-1 (PlGF-1), an angiogenic protein, at 2.0 A resolution. J Biol Chem. 2001 Apr 13;276(15):12153-61. Epub 2000 Nov 7. [PubMed:11069911 ]
  9. Nishiya Y, Yoshida Y, Yoshimura M, Fukamachi H, Nakano Y: Homogeneous enzymatic assay for L-cysteine with betaC-S lyase. Biosci Biotechnol Biochem. 2005 Nov;69(11):2244-6. [PubMed:16306712 ]
  10. Santamaria I, Velasco G, Cazorla M, Fueyo A, Campo E, Lopez-Otin C: Cathepsin L2, a novel human cysteine proteinase produced by breast and colorectal carcinomas. Cancer Res. 1998 Apr 15;58(8):1624-30. [PubMed:9563472 ]
  11. Eriksson A, Tohonen V, Wedell A, Nordqvist K: Isolation of the human testatin gene and analysis in patients with abnormal gonadal development. Mol Hum Reprod. 2002 Jan;8(1):8-15. [PubMed:11756564 ]
  12. Kaminska J, Wisniewska A, Koscielak J: Chemical modifications of alpha1,6-fucosyltransferase define amino acid residues of catalytic importance. Biochimie. 2003 Mar-Apr;85(3-4):303-10. [PubMed:12770769 ]
  13. Li Y, Gamper N, Shapiro MS: Single-channel analysis of KCNQ K+ channels reveals the mechanism of augmentation by a cysteine-modifying reagent. J Neurosci. 2004 Jun 2;24(22):5079-90. [PubMed:15175377 ]
  14. Lindzen M, Gottschalk KE, Fuzesi M, Garty H, Karlish SJ: Structural interactions between FXYD proteins and Na+,K+-ATPase: alpha/beta/FXYD subunit stoichiometry and cross-linking. J Biol Chem. 2006 Mar 3;281(9):5947-55. Epub 2005 Dec 21. [PubMed:16373350 ]
  15. Norris FA, Wilson MP, Wallis TS, Galyov EE, Majerus PW: SopB, a protein required for virulence of Salmonella dublin, is an inositol phosphate phosphatase. Proc Natl Acad Sci U S A. 1998 Nov 24;95(24):14057-9. [PubMed:9826652 ]
  16. Foss CA, Mease RC, Fan H, Wang Y, Ravert HT, Dannals RF, Olszewski RT, Heston WD, Kozikowski AP, Pomper MG: Radiolabeled small-molecule ligands for prostate-specific membrane antigen: in vivo imaging in experimental models of prostate cancer. Clin Cancer Res. 2005 Jun 1;11(11):4022-8. [PubMed:15930336 ]
  17. Kozaki K, Miyaishi O, Asai N, Iida K, Sakata K, Hayashi M, Nishida T, Matsuyama M, Shimizu S, Kaneda T, et al.: Tissue distribution of ERp61 and association of its increased expression with IgG production in hybridoma cells. Exp Cell Res. 1994 Aug;213(2):348-58. [PubMed:8050492 ]
  18. Amberger VR, Hensel T, Ogata N, Schwab ME: Spreading and migration of human glioma and rat C6 cells on central nervous system myelin in vitro is correlated with tumor malignancy and involves a metalloproteolytic activity. Cancer Res. 1998 Jan 1;58(1):149-58. [PubMed:9426071 ]
  19. Zhang JT, Li QX, Wang D, Zhu ZL, Yang YH, Cui DS, Wang MW, Sun XF: Up-regulation of PINCH in the stroma of oral squamous cell carcinoma predicts nodal metastasis. Oncol Rep. 2005 Dec;14(6):1519-22. [PubMed:16273248 ]
  20. Taveau M, Bourg N, Sillon G, Roudaut C, Bartoli M, Richard I: Calpain 3 is activated through autolysis within the active site and lyses sarcomeric and sarcolemmal components. Mol Cell Biol. 2003 Dec;23(24):9127-35. [PubMed:14645524 ]
  21. Naisbitt DJ, Vilar FJ, Stalford AC, Wilkins EG, Pirmohamed M, Park BK: Plasma cysteine deficiency and decreased reduction of nitrososulfamethoxazole with HIV infection. AIDS Res Hum Retroviruses. 2000 Dec 10;16(18):1929-38. [PubMed:11153075 ]
  22. Baker DH, Czarnecki-Maulden GL: Pharmacologic role of cysteine in ameliorating or exacerbating mineral toxicities. J Nutr. 1987 Jun;117(6):1003-10. [PubMed:3298579 ]
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  24. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]