Np mrd loader

Showing NP-Card for L-Homocysteic acid (NP0000639)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2006-05-22 14:17:41 UTC
Updated at2021-06-29 00:47:25 UTC
NP-MRD IDNP0000639
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Homocysteic acid
DescriptionL-homocysteic acid is a homocysteic acid with L-configuration. It has a role as a NMDA receptor agonist. It is an enantiomer of a D-homocysteic acid. L-Homocysteic acid is a sulfur-containing glutamic acid analog and a potent NMDA receptor agonist. It is related to homocysteine, a by-product of methionine metabolism. It 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.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000639 (L-Homocysteic acid)

3-Hydroxycapric acid.mol
  Mrv1652305271900182D          

 11 10  0  0  0  0            999 V2000
   -1.2375   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    1.1270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.3020    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  1  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
  1 10  2  0  0  0  0
  1 11  1  0  0  0  0
M  END
Download

3D MOL for NP0000639 (L-Homocysteic acid)

HMDB0002205
     RDKit          3D
L-Homocysteic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
   -1.1144    0.8092    1.0368 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8038    0.3394   -0.2930 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1973   -1.0353   -0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0778   -1.1066    0.5565 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3573   -0.0822   -0.0653 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.5787   -0.2628    0.7941 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7471   -0.5259   -1.4550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9811    1.5335   -0.0995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0710    0.2370   -1.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0967   -0.1491   -2.2668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2813    0.5726   -0.4855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2884    1.0388    1.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8058    0.1882    1.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1818    1.0778   -0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0568   -1.4039   -1.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9540   -1.7014    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435   -0.9323    1.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4372   -2.1682    0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3338    2.0315    0.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6053    1.5395   -0.4251 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  1  0
  5  6  2  0
  5  7  2  0
  5  8  1  0
  2  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  6
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  8 19  1  0
 11 20  1  0
M  END
Download

3D SDF for NP0000639 (L-Homocysteic acid)

3-Hydroxycapric acid.mol
  Mrv1652305271900182D          

 11 10  0  0  0  0            999 V2000
   -1.2375   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    1.1270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.3020    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  1  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
  1 10  2  0  0  0  0
  1 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000639

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CCS(O)(=O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H9NO5S/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H,8,9,10)/t3-/m0/s1

> <INCHI_KEY>
VBOQYPQEPHKASR-VKHMYHEASA-N

> <FORMULA>
C4H9NO5S

> <MOLECULAR_WEIGHT>
183.183

> <EXACT_MASS>
183.020143093

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.692732434804336

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-sulfobutanoic acid

> <ALOGPS_LOGP>
-2.35

> <JCHEM_LOGP>
-2.90591122812339

> <ALOGPS_LOGS>
-0.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
1.3892367160594725

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.2525954713848684

> <JCHEM_PKA_STRONGEST_BASIC>
9.511223417279629

> <JCHEM_POLAR_SURFACE_AREA>
117.69000000000001

> <JCHEM_REFRACTIVITY>
35.3004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.43e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-homocysteic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000639 (L-Homocysteic acid)

HMDB0002205
     RDKit          3D
L-Homocysteic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
   -1.1144    0.8092    1.0368 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8038    0.3394   -0.2930 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1973   -1.0353   -0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0778   -1.1066    0.5565 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3573   -0.0822   -0.0653 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.5787   -0.2628    0.7941 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7471   -0.5259   -1.4550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9811    1.5335   -0.0995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0710    0.2370   -1.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0967   -0.1491   -2.2668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2813    0.5726   -0.4855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2884    1.0388    1.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8058    0.1882    1.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1818    1.0778   -0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0568   -1.4039   -1.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9540   -1.7014    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435   -0.9323    1.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4372   -2.1682    0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3338    2.0315    0.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6053    1.5395   -0.4251 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  1  0
  5  6  2  0
  5  7  2  0
  5  8  1  0
  2  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  6
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  8 19  1  0
 11 20  1  0
M  END
Download

PDB for NP0000639 (L-Homocysteic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3-Hydroxycapric acid.mol                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -2.310  -0.564   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -2.310   2.104   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.540   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.770  -0.564   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0       2.310  -0.564   0.000  0.00  0.00           S+0
HETATM    7  O   UNK     0       2.310   0.976   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.310  -2.104   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.850  -0.564   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.540  -1.897   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -3.850  -0.564   0.000  0.00  0.00           O+0
CONECT    1    3   10   11                                                  
CONECT    2    3                                                            
CONECT    3    2    1    4                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    1                                                            
CONECT   11    1                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
Download

3D PDB for NP0000639 (L-Homocysteic acid)

COMPND    HMDB0002205
HETATM    1  N1  UNL     1      -1.114   0.809   1.037  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.804   0.339  -0.293  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.197  -1.035  -0.236  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.078  -1.107   0.556  1.00  0.00           C  
HETATM    5  S1  UNL     1       2.357  -0.082  -0.065  1.00  0.00           S  
HETATM    6  O1  UNL     1       3.579  -0.263   0.794  1.00  0.00           O  
HETATM    7  O2  UNL     1       2.747  -0.526  -1.455  1.00  0.00           O  
HETATM    8  O3  UNL     1       1.981   1.533  -0.100  1.00  0.00           O  
HETATM    9  C4  UNL     1      -2.071   0.237  -1.072  1.00  0.00           C  
HETATM   10  O4  UNL     1      -2.097  -0.149  -2.267  1.00  0.00           O  
HETATM   11  O5  UNL     1      -3.281   0.573  -0.485  1.00  0.00           O  
HETATM   12  H1  UNL     1      -0.288   1.039   1.600  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.806   0.188   1.490  1.00  0.00           H  
HETATM   14  H3  UNL     1      -0.182   1.078  -0.835  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.057  -1.404  -1.264  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.954  -1.701   0.230  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.943  -0.932   1.626  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.437  -2.168   0.460  1.00  0.00           H  
HETATM   19  H8  UNL     1       2.334   2.031   0.702  1.00  0.00           H  
HETATM   20  H9  UNL     1      -3.605   1.540  -0.425  1.00  0.00           H  
CONECT    1    2   12   13
CONECT    2    3    9   14
CONECT    3    4   15   16
CONECT    4    5   17   18
CONECT    5    6    6    7    7
CONECT    5    8
CONECT    8   19
CONECT    9   10   10   11
CONECT   11   20
END
Download

SMILES for NP0000639 (L-Homocysteic acid)

N[C@@H](CCS(O)(=O)=O)C(O)=O
Download

INCHI for NP0000639 (L-Homocysteic acid)

InChI=1S/C4H9NO5S/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H,8,9,10)/t3-/m0/s1
Download
View in JSmol
Synonyms
ValueSource
(2S)-2-Amino-4-sulfobutyric acidChEBI
(S)-2-Amino-4-sulfobutanoic acidChEBI
(S)-2-Amino-4-sulfobutyric acidChEBI
Homocysteic acidChEBI
L-2-Amino-4-sulfobutyric acidChEBI
(2S)-2-Amino-4-sulfobutanoic acidKegg
(2S)-2-Amino-4-sulfobutyrateGenerator
(2S)-2-Amino-4-sulphobutyrateGenerator
(2S)-2-Amino-4-sulphobutyric acidGenerator
(S)-2-Amino-4-sulfobutanoateGenerator
(S)-2-Amino-4-sulphobutanoateGenerator
(S)-2-Amino-4-sulphobutanoic acidGenerator
(S)-2-Amino-4-sulfobutyrateGenerator
(S)-2-Amino-4-sulphobutyrateGenerator
(S)-2-Amino-4-sulphobutyric acidGenerator
HomocysteateGenerator
L-2-Amino-4-sulfobutyrateGenerator
L-2-Amino-4-sulphobutyrateGenerator
L-2-Amino-4-sulphobutyric acidGenerator
(2S)-2-Amino-4-sulfobutanoateGenerator
(2S)-2-Amino-4-sulphobutanoateGenerator
(2S)-2-Amino-4-sulphobutanoic acidGenerator
L-HomocysteateGenerator
Chemical FormulaC4H9NO5S
Average Mass183.1830 Da
Monoisotopic Mass183.02014 Da
IUPAC Name(2S)-2-amino-4-sulfobutanoic acid
Traditional NameL-homocysteic acid
CAS Registry Number14857-77-3
SMILES
N[C@@H](CCS(O)(=O)=O)C(O)=O
InChI Identifier
InChI=1S/C4H9NO5S/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H,8,9,10)/t3-/m0/s1
InChI KeyVBOQYPQEPHKASR-VKHMYHEASA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
  • Thia fatty acid
  • Fatty acid
  • Fatty acyl
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Organosulfonic acid
  • Sulfonyl
  • Alkanesulfonic acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point261 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility64.3 g/LALOGPS
logP-2.4ALOGPS
logP-2.9ChemAxon
logS-0.45ALOGPS
pKa (Strongest Acidic)-1.3ChemAxon
pKa (Strongest Basic)9.51ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.3 m³·mol⁻¹ChemAxon
Polarizability15.69 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002205
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022905
KNApSAcK IDNot Available
Chemspider ID154529
KEGG Compound IDC16511
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHomocysteic_acid
METLIN ID6545
PubChem Compound177491
PDB IDNot Available
ChEBI ID132223
Good Scents IDNot Available
References
General References
  1. Boldyrev AA: Homocysteinic acid causes oxidative stress in lymphocytes by potentiating toxic effect of NMDA. Bull Exp Biol Med. 2005 Jul;140(1):33-7. [PubMed:16254614 ]
  2. Piraud M, Vianey-Saban C, Bourdin C, Acquaviva-Bourdain C, Boyer S, Elfakir C, Bouchu D: A new reversed-phase liquid chromatographic/tandem mass spectrometric method for analysis of underivatised amino acids: evaluation for the diagnosis and the management of inherited disorders of amino acid metabolism. Rapid Commun Mass Spectrom. 2005;19(22):3287-97. [PubMed:16235234 ]
  3. Rawat V, Goux W, Piechaczyk M, D Mello SR: c-Fos Protects Neurons Through a Noncanonical Mechanism Involving HDAC3 Interaction: Identification of a 21-Amino Acid Fragment with Neuroprotective Activity. Mol Neurobiol. 2016 Mar;53(2):1165-1180. doi: 10.1007/s12035-014-9058-1. Epub 2015 Jan 16. [PubMed:25592718 ]
  4. McGee MA, Abdel-Rahman AA: N-Methyl-D-Aspartate Receptor Signaling and Function in Cardiovascular Tissues. J Cardiovasc Pharmacol. 2016 Aug;68(2):97-105. doi: 10.1097/FJC.0000000000000398. [PubMed:27046337 ]
  5. Cinelli E, Mutolo D, Pantaleo T, Bongianni F: Neural mechanisms underlying respiratory regulation within the preBotzinger complex of the rabbit. Respir Physiol Neurobiol. 2021 Nov;293:103736. doi: 10.1016/j.resp.2021.103736. Epub 2021 Jul 3. [PubMed:34224867 ]
  6. Salau VF, Erukainure OL, Koorbanally NA, Islam MS: Ferulic acid promotes muscle glucose uptake and modulate dysregulated redox balance and metabolic pathways in ferric-induced pancreatic oxidative injury. J Food Biochem. 2021 Feb 8:e13641. doi: 10.1111/jfbc.13641. [PubMed:33555086 ]