IMPPAT Phytochemical information: 
Phosphoserine

Phosphoserine
Summary

SMILES: OC(=O)[C@H](COP(=O)(O)O)N
InChI: InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)/t2-/m0/s1
InChIKey: BZQFBWGGLXLEPQ-REOHCLBHSA-N
DeepSMILES: OC=O)[C@H]COP=O)O)O))))N
Functional groups: CC(=O)O; CN; COP(=O)(O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Amino acids, peptides, and analogues
NP Classifier Biosynthetic pathway: Amino acids and Peptides
NP Classifier Superclass: Small peptides
NP Classifier Class: Aminoacids
Synonymous chemical names:
dexfosfoserine, phosphoserine
External chemical identifiers:
CID:68841; ChEMBL:CHEMBL284377; ChEBI:15811; ZINC:ZINC000003869280; FDASRS:VI4F0K069V; SureChEMBL:SCHEMBL6846; MolPort-003-939-112
Chemical structure download


Phosphoserine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 185.07
Log P RDKit -1.49
Topological polar surface area (Å2) RDKit 130.08
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 3
Number of heavy atoms RDKit 11
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.67
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 0
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 0


Phosphoserine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.3921


Phosphoserine
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Highly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.63
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No


Phosphoserine
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000003084CFTR957
ENSP00000156084OTUD5800
ENSP00000164139PYGM974
ENSP00000171111KEAP1795
ENSP00000216274RIPK3826
ENSP00000216392PYGL974
ENSP00000217182EEF1A2777
ENSP00000219548STUB1795
ENSP00000223366GCK800
ENSP00000225275MPO705
ENSP00000225371EPX705
ENSP00000229328PRKAB1800
ENSP00000231188GRM6872
ENSP00000233735REG1A800
ENSP00000238081YWHAQ908
ENSP00000242577DYNLL1800
ENSP00000245541GGA3800
ENSP00000245934SYMPK800
ENSP00000247970PIN1834
ENSP00000248975YWHAH908
ENSP00000256797ERN2704
ENSP00000257430APC800
ENSP00000258962SRSF1816
ENSP00000260404PAK6800
ENSP00000260810TOPBP1800
ENSP00000261205SYT1795
ENSP00000261716TAOK1741
ENSP00000261769CDH1795
ENSP00000262160SMAD2958
ENSP00000262265PIH1D1800
ENSP00000262290LPO794
ENSP00000262367CREBBP800
ENSP00000262848PRKX745
ENSP00000263125PRKCQ958
ENSP00000263270AP2S1795
ENSP00000264012CDH3735
ENSP00000264033CBL800
ENSP00000264335YWHAE908
ENSP00000264381BCHE800
ENSP00000265388TNPO3800
ENSP00000265563PRKAR2A820
ENSP00000265717PRKAR2B820
ENSP00000268607MAP1LC3B800
ENSP00000269260ARRB2705
ENSP00000272317RPS27A800
ENSP00000272444DUSP11701
ENSP00000273062CTDSP1800
ENSP00000275605PSPH990
ENSP00000281708FBXW7949
ENSP00000282441YAP1800
ENSP00000283752SERPINB3902
ENSP00000291386SSU72800
ENSP00000293813742
ENSP00000296271RHO800
ENSP00000300093PLK1845
ENSP00000301264DAPK3829
ENSP00000305355PRKCB800
ENSP00000306138GRM5825
ENSP00000306330YWHAG908
ENSP00000307241PDHB800
ENSP00000307863U2AF2800
ENSP00000308351MLKL826
ENSP00000308450CDC20783
ENSP00000309503YWHAZ919
ENSP00000309542PGA5712
ENSP00000309591PRKACA992
ENSP00000310094TAOK2957
ENSP00000310127IRF3800
ENSP00000311113JUP833
ENSP00000311538ARR3741
ENSP00000313967C1QB800
ENSP00000314414AP2B1800
ENSP00000315644TYMS773
ENSP00000318944TRAF7701
ENSP00000319060CAMK2G800
ENSP00000322192PGA3712
ENSP00000322957PAK7800
ENSP00000323511PNKP800
ENSP00000323867PRKAG1800
ENSP00000324806GSK3B893
ENSP00000329967TBK1800
ENSP00000330054EEF1A1824
ENSP00000332973SMAD3800
ENSP00000340989SFN908
ENSP00000341044ACACB800
ENSP00000341344GGA1800
ENSP00000341551SMAD4800
ENSP00000342105DYRK2818
ENSP00000342924MCPH1800
ENSP00000343325PKN1800
ENSP00000344173GRM8868
ENSP00000344220PDPK1967
ENSP00000344456CTNNB1833
ENSP00000344460CBS716
ENSP00000349955RPRD1A800
ENSP00000350132PLN795
ENSP00000350348GRM7874
ENSP00000351049PAK4800
ENSP00000351926AP2A1845
ENSP00000353099HLA-DRB1800
ENSP00000353344ETS2724
ENSP00000353415PRKAR1B930
ENSP00000354159NLRC4795
ENSP00000354621SMURF1814
ENSP00000356146SCAF8800
ENSP00000358417PHGDH908
ENSP00000358497RNGTT795
ENSP00000358770SLK800
ENSP00000358802KCNC4800
ENSP00000358813TTK800
ENSP00000359206BTRC800
ENSP00000359552PKN2800
ENSP00000359719PRKACB785
ENSP00000360124PGM1811
ENSP00000360290PRKAA2800
ENSP00000361423ABL1858
ENSP00000362532RPRD1B800
ENSP00000362608PIM1958
ENSP00000362931SRPK1826
ENSP00000363296GRM4946
ENSP00000363768C1QC800
ENSP00000363773C1QA800
ENSP00000364389CDC14B800
ENSP00000364912SPEN800
ENSP00000365588MDC1816
ENSP00000365773PSAT1940
ENSP00000366604SF1800
ENSP00000367391PGA4712
ENSP00000369134PDHA1836
ENSP00000370781CDC20B701
ENSP00000371475TP53BP1812
ENSP00000371535SEPSECS880
ENSP00000375881ALPP865
ENSP00000376436ETS1795
ENSP00000378529FZR1734
ENSP00000379364MOB1A823
ENSP00000379678PGM5734
ENSP00000380227ITGA4800
ENSP00000381220HDDC2800
ENSP00000381932DYRK1A800
ENSP00000383199NEDD4L817
ENSP00000384048PAXIP1859
ENSP00000385892PLEKHB2800
ENSP00000387699CREB1800
ENSP00000390651IRAK4800
ENSP00000394734CLK1862
ENSP00000401445ERN1704
ENSP00000408695PRKCA822
ENSP00000409581ARRB1795
ENSP00000413234AP2A2849
ENSP00000418960BRCA1819
ENSP00000425809PGM3752
ENSP00000430684IKBKB818
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.