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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:43 UTC
Update Date2022-03-07 02:49:14 UTC
HMDB IDHMDB0002231
Secondary Accession Numbers
  • HMDB02231
Metabolite Identification
Common Name11Z-Eicosenoic acid
Description11Z-Eicosenoic acid, also known as gondoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. 11Z-Eicosenoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). More specifically, 11Z-Eicosenoic acid is a monounsaturated omega-9 fatty acid found in a variety of nuts and plant oils. It is not produced by humans and comes from the diet. It has been found in the red blood cell membrane with increased concentrations in children with regressive autism (PMID: 16581239 ).
Structure
Data?1582752237
Synonyms
ValueSource
(11Z)-Eicosenoic acidChEBI
(11Z)-Icosenoic acidChEBI
(Z)-Eicos-11-enoic acidChEBI
(Z)-Icos-11-enoic acidChEBI
(Z)-Icosa-11-enoic acidChEBI
11-Eicosenoic acidChEBI
11-Icosenoic acidChEBI
20:1ChEBI
cis-11-Eicosenoic acidChEBI
cis-Delta(11)-Eicosenoic acidChEBI
cis-Gondoic acidChEBI
Eicosenoic acidChEBI
Gondoic acidChEBI
Z-Delta(11)-EicosensaeureChEBI
(11Z)-EicosenoateGenerator
(11Z)-IcosenoateGenerator
(Z)-Eicos-11-enoateGenerator
(Z)-Icos-11-enoateGenerator
(Z)-Icosa-11-enoateGenerator
11-EicosenoateGenerator
11-IcosenoateGenerator
cis-11-EicosenoateGenerator
cis-delta(11)-EicosenoateGenerator
cis-Δ(11)-eicosenoateGenerator
cis-Δ(11)-eicosenoic acidGenerator
cis-GondoateGenerator
EicosenoateGenerator
GondoateGenerator
Z-Δ(11)-eicosensaeureGenerator
11Z-EicosenoateGenerator
(11Z)-Icos-11-enoateHMDB
(11Z)-Icos-11-enoic acidHMDB
11(Z)-EicosenoateHMDB
11(Z)-Eicosenoic acidHMDB
11-cis-EicosenoateHMDB
11-cis-Eicosenoic acidHMDB
11Z-Eicosenoic acidHMDB
20:1(N-9)HMDB
20:1n9HMDB
cis-11-IcosenoateHMDB
cis-11-Icosenoic acidHMDB
FA(20:1(11Z))HMDB
FA(20:1n9)HMDB
(11Z)-11-Eicosenoic acidPhytoBank
(Z)-11-Eicosenoic acidPhytoBank
cis-delta11-Eicosenoic acidPhytoBank
cis-Δ11-Eicosenoic acidPhytoBank
Chemical FormulaC20H38O2
Average Molecular Weight310.5145
Monoisotopic Molecular Weight310.28718046
IUPAC Name(11Z)-icos-11-enoic acid
Traditional Namecis-11-eicosenoic acid
CAS Registry Number5561-99-9
SMILES
CCCCCCCC\C=C/CCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h9-10H,2-8,11-19H2,1H3,(H,21,22)/b10-9-
InChI KeyBITHHVVYSMSWAG-KTKRTIGZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point426.30 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.00096 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP8.760 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available183.95http://allccs.zhulab.cn/database/detail?ID=AllCCS00001851
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.0e-05 g/LALOGPS
logP8.4ALOGPS
logP7.67ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity96.6 m³·mol⁻¹ChemAxon
Polarizability41.32 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+185.16531661259
DarkChem[M-H]-184.22331661259
DeepCCS[M+H]+185.80530932474
DeepCCS[M-H]-181.78530932474
DeepCCS[M-2H]-218.47330932474
DeepCCS[M+Na]+194.6230932474
AllCCS[M+H]+189.132859911
AllCCS[M+H-H2O]+186.332859911
AllCCS[M+NH4]+191.632859911
AllCCS[M+Na]+192.432859911
AllCCS[M-H]-186.932859911
AllCCS[M+Na-2H]-188.732859911
AllCCS[M+HCOO]-191.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
11Z-Eicosenoic acidCCCCCCCC\C=C/CCCCCCCCCC(O)=O3360.2Standard polar33892256
11Z-Eicosenoic acidCCCCCCCC\C=C/CCCCCCCCCC(O)=O2285.2Standard non polar33892256
11Z-Eicosenoic acidCCCCCCCC\C=C/CCCCCCCCCC(O)=O2346.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
11Z-Eicosenoic acid,1TMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCC(=O)O[Si](C)(C)C2416.6Semi standard non polar33892256
11Z-Eicosenoic acid,1TMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCC(=O)O[Si](C)(C)C2416.6Semi standard non polar33892256
11Z-Eicosenoic acid,1TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2687.6Semi standard non polar33892256
11Z-Eicosenoic acid,1TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2687.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 11Z-Eicosenoic acid GC-EI-TOF (Non-derivatized)splash10-00mk-3900000000-c719ddc966597d00d2c52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 11Z-Eicosenoic acid GC-EI-TOF (Non-derivatized)splash10-00mk-3900000000-c719ddc966597d00d2c52018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11Z-Eicosenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9450000000-350fb3d4ba5a967ba8b52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11Z-Eicosenoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0g70-9551000000-c82b71c168fb5563f7d42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11Z-Eicosenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11Z-Eicosenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11Z-Eicosenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11Z-Eicosenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 11Z-Eicosenoic acid n/a 21V, negative-QTOFsplash10-0006-0090000000-1756232c26bf8fc138c52020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 11Z-Eicosenoic acid n/a 21V, positive-QTOFsplash10-0006-0290000000-fa5d9f6e60781ae83e2e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 11Z-Eicosenoic acid Orbitrap 10V, positive-QTOFsplash10-0006-5490000000-0cbb37e5b7ecad5adaaa2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 11Z-Eicosenoic acid Orbitrap 12V, positive-QTOFsplash10-000y-9650000000-ba5e2b939e8a556b6d1f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 11Z-Eicosenoic acid Orbitrap 14V, positive-QTOFsplash10-00l2-9410000000-9496a07390108fe35cab2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 11Z-Eicosenoic acid Orbitrap 16V, positive-QTOFsplash10-05nb-9300000000-b3b200aebba967262b9b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 11Z-Eicosenoic acid Orbitrap 17V, positive-QTOFsplash10-067j-9200000000-91f2ccafad22a2bb80692020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 11Z-Eicosenoic acid Orbitrap 21V, positive-QTOFsplash10-067j-9100000000-dbb0d513ad4f77e24d3c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 11Z-Eicosenoic acid Orbitrap 26V, positive-QTOFsplash10-067i-9000000000-1b21d5d4d80742618d4c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 11Z-Eicosenoic acid Orbitrap 32V, positive-QTOFsplash10-067i-9000000000-d00f7dd8a36d506bf1b52020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 11Z-Eicosenoic acid Orbitrap 39V, positive-QTOFsplash10-0aor-9000000000-de7f5670d39d685918e02020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 11Z-Eicosenoic acid Orbitrap 47V, positive-QTOFsplash10-0ar0-9000000000-509d8fad571b855680992020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 11Z-Eicosenoic acid n/a 21V, positive-QTOFsplash10-004i-2890000000-dcdc3d85495da91cc6db2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 11Z-Eicosenoic acid n/a 21V, positive-QTOFsplash10-070e-1920000000-1c2aeaf08cc4ea4f05402020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z-Eicosenoic acid 10V, Positive-QTOFsplash10-03dl-0197000000-fa25affc2bb6f0cd695b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z-Eicosenoic acid 20V, Positive-QTOFsplash10-0i03-4691000000-b79f41c0508982a461112016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z-Eicosenoic acid 40V, Positive-QTOFsplash10-0007-9850000000-3d2cfec12ab1aec5686b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z-Eicosenoic acid 10V, Negative-QTOFsplash10-0a4i-0029000000-c49b53bb3e3caf9cb0422016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z-Eicosenoic acid 20V, Negative-QTOFsplash10-0a4i-1079000000-9504027ae4d5b071c4a02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z-Eicosenoic acid 40V, Negative-QTOFsplash10-0a4l-9240000000-7e3a558d23fc622e0aa22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z-Eicosenoic acid 10V, Negative-QTOFsplash10-0a4i-0019000000-0d96115f81e42756fc2f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z-Eicosenoic acid 20V, Negative-QTOFsplash10-0a4i-1059000000-4c31464e6f8ead1139f32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z-Eicosenoic acid 40V, Negative-QTOFsplash10-0006-9020000000-90362612fe130589b56d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z-Eicosenoic acid 10V, Positive-QTOFsplash10-03dl-5397000000-d942974f980afe9a14c52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z-Eicosenoic acid 20V, Positive-QTOFsplash10-0btc-9561000000-bf355ad19adfba5af8df2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
Tissue Locations
  • Erythrocyte
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.663 +/- 0.59 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.498 +/- 1.213 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified11.722 +/- 5.378 uMAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [PubMed:22024767 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012569
KNApSAcK IDC00035628
Chemspider ID4445895
KEGG Compound IDC16526
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEicosenoic acid
METLIN ID6563
PubChem Compound5282768
PDB IDNot Available
ChEBI ID32425
Food Biomarker OntologyNot Available
VMH IDCE2510
MarkerDB IDNot Available
Good Scents IDrw1230181
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bu B, Ashwood P, Harvey D, King IB, Water JV, Jin LW: Fatty acid compositions of red blood cell phospholipids in children with autism. Prostaglandins Leukot Essent Fatty Acids. 2006 Apr;74(4):215-21. [PubMed:16581239 ]
  2. Deshimaru R, Ishitani K, Makita K, Horiguchi F, Nozawa S: Analysis of fatty acid composition in human bone marrow aspirates. Keio J Med. 2005 Sep;54(3):150-5. [PubMed:16237277 ]
  3. 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 ]