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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-22 18:38:25 UTC
Update Date2021-09-16 15:27:36 UTC
HMDB IDHMDB0006230
Secondary Accession Numbers
  • HMDB0060271
  • HMDB06230
  • HMDB60271
Metabolite Identification
Common NameBisdiphosphoinositol tetrakisphosphate
DescriptionDiphosphoinositol tetrakisphosphate (InsP(8)) contains energetic pyrophosphate groups and occurs throughout animal and plant kingdoms. These molecules are synthesized by a recently cloned family of inositol hexakisphosphate kinases (InsP(6)Ks). It is one of the most highly phosphorylated members of the inositol-based cell signaling family (PMID: 9822604 ). Bisdiphosphoinositol tetrakisphosphate regulates many cellular processes including endocytosis, vesicle trafficking, apoptosis, and DNA repair (PMID: 15316027 ).
Structure
Data?1582752376
Synonyms
ValueSource
Bis-diphosphoinositol tetrakisphosphateChEBI
Bis-diphosphoinositol tetrakisphosphoric acidGenerator
Bisdiphosphoinositol tetrakisphosphoric acidGenerator
Bis (diphospho)inositol tetrakisphosphateHMDB
Diphosphoinositol tetrakisphosphateHMDB
Chemical FormulaC6H20O30P8
Average Molecular Weight819.9951
Monoisotopic Molecular Weight819.794031396
IUPAC Name{[hydroxy({[(1S,2S,3R,4S,5R,6R)-2-{[hydroxy(phosphonooxy)phosphoryl]oxy}-3,4,5,6-tetrakis(phosphonooxy)cyclohexyl]oxy})phosphoryl]oxy}phosphonic acid
Traditional Name[hydroxy([(1S,2S,3R,4S,5R,6R)-2-{[hydroxy(phosphonooxy)phosphoryl]oxy}-3,4,5,6-tetrakis(phosphonooxy)cyclohexyl]oxy)phosphoryl]oxyphosphonic acid
CAS Registry Number208107-61-3
SMILES
OP(O)(=O)O[C@H]1[C@@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(=O)OP(O)(O)=O)[C@@H](OP(O)(=O)OP(O)(O)=O)[C@@H]1OP(O)(O)=O
InChI Identifier
InChI=1S/C6H20O30P8/c7-37(8,9)29-1-2(30-38(10,11)12)4(32-40(16,17)18)6(34-44(27,28)36-42(22,23)24)5(3(1)31-39(13,14)15)33-43(25,26)35-41(19,20)21/h1-6H,(H,25,26)(H,27,28)(H2,7,8,9)(H2,10,11,12)(H2,13,14,15)(H2,16,17,18)(H2,19,20,21)(H2,22,23,24)/t1-,2+,3-,4-,5+,6+/m1/s1
InChI KeyGXPFHIDIIMSLOF-YORTWTKJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as inositol phosphates. Inositol phosphates are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentInositol phosphates
Alternative Parents
Substituents
  • Inositol phosphate
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
  • 1D-myo-inositol bis(diphosphate) tetrakisphosphate (CHEBI:52965 )
Ontology
Not AvailableNot 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
PropertyValueSource
Water Solubility12.9 g/LALOGPS
logP0.55ALOGPS
logP-5.4ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)0.14ChemAxon
Physiological Charge-13ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area493.62 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity122.76 m³·mol⁻¹ChemAxon
Polarizability52.01 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+199.85930932474
DeepCCS[M-H]-197.74730932474
DeepCCS[M-2H]-231.55530932474
DeepCCS[M+Na]+205.92430932474
AllCCS[M+H]+230.532859911
AllCCS[M+H-H2O]+230.332859911
AllCCS[M+NH4]+230.632859911
AllCCS[M+Na]+230.632859911
AllCCS[M-H]-227.832859911
AllCCS[M+Na-2H]-229.832859911
AllCCS[M+HCOO]-232.032859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #1C[Si](C)(C)OP(=O)(O)O[C@H]1[C@@H](OP(=O)(O)O)[C@@H](OP(=O)(O)O)[C@H](OP(=O)(O)OP(=O)(O)O)[C@@H](OP(=O)(O)OP(=O)(O)O)[C@@H]1OP(=O)(O)O4970.2Semi standard non polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #1C[Si](C)(C)OP(=O)(O)O[C@H]1[C@@H](OP(=O)(O)O)[C@@H](OP(=O)(O)O)[C@H](OP(=O)(O)OP(=O)(O)O)[C@@H](OP(=O)(O)OP(=O)(O)O)[C@@H]1OP(=O)(O)O5215.1Standard non polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #1C[Si](C)(C)OP(=O)(O)O[C@H]1[C@@H](OP(=O)(O)O)[C@@H](OP(=O)(O)O)[C@H](OP(=O)(O)OP(=O)(O)O)[C@@H](OP(=O)(O)OP(=O)(O)O)[C@@H]1OP(=O)(O)O9049.4Standard polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #2C[Si](C)(C)OP(=O)(O)O[C@H]1[C@@H](OP(=O)(O)O)[C@H](OP(=O)(O)OP(=O)(O)O)[C@@H](OP(=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H]1OP(=O)(O)O4970.2Semi standard non polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #2C[Si](C)(C)OP(=O)(O)O[C@H]1[C@@H](OP(=O)(O)O)[C@H](OP(=O)(O)OP(=O)(O)O)[C@@H](OP(=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H]1OP(=O)(O)O5215.1Standard non polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #2C[Si](C)(C)OP(=O)(O)O[C@H]1[C@@H](OP(=O)(O)O)[C@H](OP(=O)(O)OP(=O)(O)O)[C@@H](OP(=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H]1OP(=O)(O)O9049.4Standard polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #3C[Si](C)(C)OP(=O)(O)O[C@H]1[C@H](OP(=O)(O)OP(=O)(O)O)[C@@H](OP(=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@@H](OP(=O)(O)O)[C@H]1OP(=O)(O)O4969.6Semi standard non polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #3C[Si](C)(C)OP(=O)(O)O[C@H]1[C@H](OP(=O)(O)OP(=O)(O)O)[C@@H](OP(=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@@H](OP(=O)(O)O)[C@H]1OP(=O)(O)O5215.0Standard non polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #3C[Si](C)(C)OP(=O)(O)O[C@H]1[C@H](OP(=O)(O)OP(=O)(O)O)[C@@H](OP(=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@@H](OP(=O)(O)O)[C@H]1OP(=O)(O)O9049.5Standard polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #4C[Si](C)(C)OP(=O)(O[C@@H]1[C@@H](OP(=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@@H](OP(=O)(O)O)[C@@H](OP(=O)(O)O)[C@H]1OP(=O)(O)O)OP(=O)(O)O4901.2Semi standard non polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #4C[Si](C)(C)OP(=O)(O[C@@H]1[C@@H](OP(=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@@H](OP(=O)(O)O)[C@@H](OP(=O)(O)O)[C@H]1OP(=O)(O)O)OP(=O)(O)O5203.3Standard non polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #4C[Si](C)(C)OP(=O)(O[C@@H]1[C@@H](OP(=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@@H](OP(=O)(O)O)[C@@H](OP(=O)(O)O)[C@H]1OP(=O)(O)O)OP(=O)(O)O9025.9Standard polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #5C[Si](C)(C)OP(=O)(O)OP(=O)(O)O[C@@H]1[C@@H](OP(=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@@H](OP(=O)(O)O)[C@@H](OP(=O)(O)O)[C@H]1OP(=O)(O)O4917.8Semi standard non polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #5C[Si](C)(C)OP(=O)(O)OP(=O)(O)O[C@@H]1[C@@H](OP(=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@@H](OP(=O)(O)O)[C@@H](OP(=O)(O)O)[C@H]1OP(=O)(O)O5214.6Standard non polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #5C[Si](C)(C)OP(=O)(O)OP(=O)(O)O[C@@H]1[C@@H](OP(=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@@H](OP(=O)(O)O)[C@@H](OP(=O)(O)O)[C@H]1OP(=O)(O)O9027.8Standard polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #6C[Si](C)(C)OP(=O)(O[C@@H]1[C@@H](OP(=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H]1OP(=O)(O)O)OP(=O)(O)O4901.2Semi standard non polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #6C[Si](C)(C)OP(=O)(O[C@@H]1[C@@H](OP(=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H]1OP(=O)(O)O)OP(=O)(O)O5203.3Standard non polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #6C[Si](C)(C)OP(=O)(O[C@@H]1[C@@H](OP(=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H]1OP(=O)(O)O)OP(=O)(O)O9025.9Standard polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #7C[Si](C)(C)OP(=O)(O)OP(=O)(O)O[C@@H]1[C@@H](OP(=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H]1OP(=O)(O)O4917.8Semi standard non polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #7C[Si](C)(C)OP(=O)(O)OP(=O)(O)O[C@@H]1[C@@H](OP(=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H]1OP(=O)(O)O5214.6Standard non polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #7C[Si](C)(C)OP(=O)(O)OP(=O)(O)O[C@@H]1[C@@H](OP(=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H]1OP(=O)(O)O9027.8Standard polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #8C[Si](C)(C)OP(=O)(O)O[C@H]1[C@H](OP(=O)(O)OP(=O)(O)O)[C@@H](OP(=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@@H]1OP(=O)(O)O4969.6Semi standard non polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #8C[Si](C)(C)OP(=O)(O)O[C@H]1[C@H](OP(=O)(O)OP(=O)(O)O)[C@@H](OP(=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@@H]1OP(=O)(O)O5215.0Standard non polar33892256
Bisdiphosphoinositol tetrakisphosphate,1TMS,isomer #8C[Si](C)(C)OP(=O)(O)O[C@H]1[C@H](OP(=O)(O)OP(=O)(O)O)[C@@H](OP(=O)(O)OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@@H]1OP(=O)(O)O9049.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bisdiphosphoinositol tetrakisphosphate GC-MS (TMS_1_7) - 70eV, PositiveNot Available2022-08-08Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)Not Available2022-08-06Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisdiphosphoinositol tetrakisphosphate 10V, Positive-QTOFsplash10-00dl-2300004970-ced83d24ee7ebf6728fd2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisdiphosphoinositol tetrakisphosphate 20V, Positive-QTOFsplash10-00di-1100004910-a8a5b3d9099ec59f7ec62016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisdiphosphoinositol tetrakisphosphate 40V, Positive-QTOFsplash10-006x-4300198200-9af96e295e6f5fcd37802016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisdiphosphoinositol tetrakisphosphate 10V, Negative-QTOFsplash10-016r-4100000190-96155ec2cb529fa77cc82016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisdiphosphoinositol tetrakisphosphate 20V, Negative-QTOFsplash10-004i-9300001230-2a05f3cc062754a067b02016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisdiphosphoinositol tetrakisphosphate 40V, Negative-QTOFsplash10-004i-9000000010-144b88c8bfd557b7df362016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisdiphosphoinositol tetrakisphosphate 10V, Negative-QTOFsplash10-014i-0000000090-2b76ef58a075df30e2ed2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisdiphosphoinositol tetrakisphosphate 20V, Negative-QTOFsplash10-004i-9000000130-103a492e9ed6f2d7f19b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisdiphosphoinositol tetrakisphosphate 40V, Negative-QTOFsplash10-004i-9100000100-2e78b3210a61e11b4ff82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisdiphosphoinositol tetrakisphosphate 10V, Positive-QTOFsplash10-00di-0000000090-ab7423d32c92321863d82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisdiphosphoinositol tetrakisphosphate 20V, Positive-QTOFsplash10-006x-0000003920-4b7239e8676753bec0142021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bisdiphosphoinositol tetrakisphosphate 40V, Positive-QTOFsplash10-03ec-0100079000-131ab0caa911490079362021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Nucleus
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023850
KNApSAcK IDNot Available
Chemspider ID26333173
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2265082
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25245165
PDB IDNot Available
ChEBI ID52965
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Safrany ST, Caffrey JJ, Yang X, Bembenek ME, Moyer MB, Burkhart WA, Shears SB: A novel context for the 'MutT' module, a guardian of cell integrity, in a diphosphoinositol polyphosphate phosphohydrolase. EMBO J. 1998 Nov 16;17(22):6599-607. [PubMed:9822604 ]
  2. Pesesse X, Choi K, Zhang T, Shears SB: Signaling by higher inositol polyphosphates. Synthesis of bisdiphosphoinositol tetrakisphosphate ("InsP8") is selectively activated by hyperosmotic stress. J Biol Chem. 2004 Oct 15;279(42):43378-81. Epub 2004 Aug 16. [PubMed:15316027 ]
  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 ]