IMPPAT Phytochemical information: 
Betulinic acid
Betulinic acid
Summary

SMILES: CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O)C(=O)O
InChI: InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
InChIKey: QGJZLNKBHJESQX-FZFNOLFKSA-N
DeepSMILES: CC=C)[C@@H]CC[C@][C@H]5[C@H]CC[C@H][C@@][C@]6C)CC%10)))C)CC[C@@H][C@]6C)CC[C@@H]C6C)C))O))))))))))))))C=O)O
Scaffold Graph/Node/Bond level: C1CCC2C(C1)CCC1C2CCC2C3CCCC3CCC21
Scaffold Graph/Node level: C1CCC2C(C1)CCC1C2CCC2C3CCCC3CCC21
Scaffold Graph level: C1CCC2C(C1)CCC1C2CCC2C3CCCC3CCC21
Functional groups: CC(=O)O; C=C(C)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Triterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Lupane triterpenoids
Synonymous chemical names:
betulinicacid, betulinic acid, betulic-acid, betulinic acid, Betulinic acid, brtulinic acid, betullinic acid, betulinic-acid, betulic acid
External chemical identifiers:
CID:CID_64971; ChEMBL:CHEMBL269277; ChEBI:CHEBI:3087; ZINC:ZINC000004097714; FDASRS:4G6A18707N; SureChEMBL:SCHEMBL61767; MolPort-003-939-279
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Betulinic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 456.71
Log P RDKit 7.09
Topological polar surface area (Å2) RDKit 57.53
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 27
Shape complexity RDKit 0.9
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 5
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Betulinic acid
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
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 Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.436098
Betulinic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -3.26
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Betulinic acid
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_001172ENSG00000178467P4HTM54681ChEMBL, NPASS
TAR_EXP_001209ENSG00000166501PRKCB5579NPASS
TAR_EXP_001194ENSG00000132356PRKAA15562ChEMBL
TAR_EXP_001195ENSG00000162409PRKAA25563ChEMBL
TAR_EXP_001196ENSG00000111725PRKAB15564ChEMBL
TAR_EXP_001197ENSG00000131791PRKAB25565ChEMBL
TAR_EXP_001203ENSG00000181929PRKAG15571ChEMBL
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_001373ENSG00000239713APOBEC3G60489NPASS
TAR_EXP_001300ENSG00000160801PTH1R5745NPASS
TAR_EXP_001306ENSG00000196396PTPN15770BindingDB, ChEMBL
TAR_EXP_001362ENSG00000173039RELA5970ChEMBL, NPASS
TAR_EXP_001366ENSG00000117152RGS45999NPASS
TAR_EXP_001618ENSG00000198900TOP17150ChEMBL
TAR_EXP_001662ENSG00000131408NR1H27376ChEMBL, NPASS
TAR_EXP_001942ENSG00000012504NR1H49971NPASS
TAR_EXP_001164ENSG00000135766EGLN154583BindingDB, ChEMBL, NPASS
TAR_EXP_001280ENSG00000198074AKR1B1057016ChEMBL, NPASS
TAR_EXP_001151ENSG00000170734POLH5429NPASS
TAR_EXP_001213ENSG00000171132PRKCE5581NPASS
TAR_EXP_001140ENSG00000115592PRKAG353632ChEMBL
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000012ENSG00000142230SAE110055BindingDB, ChEMBL
TAR_EXP_000015ENSG00000025434NR1H310062ChEMBL, NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000069ENSG00000087237CETP1071ChEMBL, NPASS
TAR_EXP_000102ENSG00000091428RAPGEF411069NPASS
TAR_EXP_000123ENSG00000269858EGLN2112398ChEMBL, NPASS
TAR_EXP_000124ENSG00000129521EGLN3112399ChEMBL, NPASS
TAR_EXP_000252ENSG00000179921GPBAR1151306BindingDB, ChEMBL, NPASS
TAR_EXP_000312ENSG00000181019NQO11728ChEMBL, NPASS
TAR_EXP_000322ENSG00000197635DPP41803ChEMBL, NPASS
TAR_EXP_000361ENSG00000128394APOBEC3F200316NPASS
TAR_EXP_000401ENSG00000163631ALB213BindingDB, ChEMBL, NPASS
TAR_EXP_000456ENSG00000085662AKR1B1231ChEMBL, NPASS
TAR_EXP_000601ENSG00000111087GLI12735BindingDB, ChEMBL, NPASS
TAR_EXP_000604ENSG00000112164GLP1R2740NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000660ENSG00000082701GSK3B2932ChEMBL
TAR_EXP_000747ENSG00000138413IDH13417ChEMBL, NPASS
TAR_EXP_000991ENSG00000135318NT5E4907ChEMBL
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_001058ENSG00000106617PRKAG251422ChEMBL
TAR_EXP_001059ENSG00000122008POLK51426NPASS
TAR_EXP_001150ENSG00000070501POLB5423BindingDB, ChEMBL, NPASS
TAR_EXP_000011ENSG00000126261UBA210054ChEMBL, NPASS