IMPPAT Phytochemical information: 
Orotidine

Orotidine
Summary

SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1c(=O)[nH]c(=O)cc1C(=O)O
InChI: InChI=1S/C10H12N2O8/c13-2-4-6(15)7(16)8(20-4)12-3(9(17)18)1-5(14)11-10(12)19/h1,4,6-8,13,15-16H,2H2,(H,17,18)(H,11,14,19)/t4-,6-,7-,8-/m1/s1
InChIKey: FKCRAVPPBFWEJD-XVFCMESISA-N
DeepSMILES: OC[C@H]O[C@H][C@@H][C@@H]5O))O))nc=O)[nH]c=O)cc6C=O)O
Scaffold Graph/Node/Bond level: O=c1ccn(C2CCCO2)c(=O)[nH]1
Scaffold Graph/Node level: OC1CCN(C2CCCO2)C(O)N1
Scaffold Graph level: CC1CCC(C2CCCC2)C(C)C1
Functional groups: CO; COC; cn(C)c; c=O; c[nH]c; cC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Nucleosides, nucleotides, and analogues
ClassyFire Class: Pyrimidine nucleosides
NP Classifier Biosynthetic pathway: Carbohydrates
NP Classifier Superclass: Nucleosides
NP Classifier Class: Pyrimidine nucleos(t)ides
Synonymous chemical names:
orotidine
External chemical identifiers:
CID:CID_92751; ChEBI:CHEBI:25722; ZINC:ZINC000006090924; FDASRS:B350MC02GZ; SureChEMBL:SCHEMBL20894; MolPort-016-580-883
Chemical structure download


Orotidine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 288.21
Log P RDKit -3.15
Topological polar surface area (Å2) RDKit 162.08
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


Orotidine
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 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.389088


Orotidine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.88
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 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


Orotidine
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000293404NAGS828
ENSP00000232607UMPS816
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.