IMPPAT Phytochemical information: 
Deoxycholic acid

Deoxycholic acid
Summary

SMILES: O[C@@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2C[C@H](O)[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)O)C)C)C
InChI: InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1
InChIKey: KXGVEGMKQFWNSR-LLQZFEROSA-N
DeepSMILES: O[C@@H]CC[C@][C@@H]C6)CC[C@@H][C@@H]6C[C@H]O)[C@][C@H]6CC[C@@H]5[C@@H]CCC=O)O))))C))))))C)))))))))C
Scaffold Graph/Node/Bond level: C1CCC2C(C1)CCC1C3CCCC3CCC21
Scaffold Graph/Node level: C1CCC2C(C1)CCC1C3CCCC3CCC21
Scaffold Graph level: C1CCC2C(C1)CCC1C3CCCC3CCC21
Functional groups: CC(=O)O; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Bile acids, alcohols and derivatives
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Cholane steroids
Synonymous chemical names:
choleic acid
External chemical identifiers:
CID:222528; ChEMBL:CHEMBL406393; ChEBI:28834; ZINC:ZINC000003914810; FDASRS:005990WHZZ; SureChEMBL:SCHEMBL4300; MolPort-002-507-414
Chemical structure download


Deoxycholic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 392.58
Log P RDKit 4.48
Topological polar surface area (Å2) RDKit 77.76
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.42
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 23
Shape complexity RDKit 0.96
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


Deoxycholic acid
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 0
Ghose filter RDKit Passed
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 0.6592


Deoxycholic acid
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.21
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes


Deoxycholic acid
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000019103SCTR900
ENSP00000053469GUCA1A700
ENSP00000176195SCT900
ENSP00000215832MAPK1743
ENSP00000216117HMOX1726
ENSP00000216797NFKBIA721
ENSP00000226574NFKB1700
ENSP00000229328PRKAB1700
ENSP00000231656CDX1818
ENSP00000232975TNNC1800
ENSP00000237527GHRH900
ENSP00000240652IAPP900
ENSP00000243911MC3R900
ENSP00000245457PTGER2900
ENSP00000247668TRAF2700
ENSP00000251849RAF1765
ENSP00000254235ADCY7900
ENSP00000256958SLCO1B1700
ENSP00000260600ADCY3900
ENSP00000261196SLCO1B3700
ENSP00000261769CDH1772
ENSP00000262178VIPR2900
ENSP00000262441GLP2R900
ENSP00000263025MAPK3756
ENSP00000264487AREG700
ENSP00000264708POMC900
ENSP00000265164CASP6700
ENSP00000268206EFTUD1800
ENSP00000269305TP53859
ENSP00000269571ERBB2832
ENSP00000270631PTH2900
ENSP00000272847PTH2R900
ENSP00000275216TAAR1900
ENSP00000275493EGFR954
ENSP00000276571CRH900
ENSP00000278175ADM900
ENSP00000282091PTH900
ENSP00000285238ABCC3700
ENSP00000286355ADCY8900
ENSP00000289753HTR6900
ENSP00000291294PTGIR900
ENSP00000294016ADCY9900
ENSP00000294954LHCGR900
ENSP00000297323ADCY1900
ENSP00000298171TSHR900
ENSP00000298386RXFP2900
ENSP00000299766MC4R900
ENSP00000301522PRDX2700
ENSP00000301645CYP7A1745
ENSP00000302846PTGER4900
ENSP00000303248RXFP1900
ENSP00000303424PTGDR900
ENSP00000304501ADORA2B908
ENSP00000305355PRKCB700
ENSP00000305372ADRB2900
ENSP00000306124PRKCE700
ENSP00000306129DRD5900
ENSP00000309845HRAS744
ENSP00000311032CASP3820
ENSP00000311405ADCY6900
ENSP00000312126ADCY4900
ENSP00000318077MC5R900
ENSP00000320180GHRHR900
ENSP00000321999PTH1R900
ENSP00000324173HSPA5742
ENSP00000327246VIPR1900
ENSP00000327652900
ENSP00000329623BCL2743
ENSP00000330237CASP9749
ENSP00000331746CALCA900
ENSP00000333821MC2R900
ENSP00000334448GNG2900
ENSP00000335333PIP5K1C700
ENSP00000336630ADORA2A910
ENSP00000337949HTR7900
ENSP00000338072AVPR2900
ENSP00000340943CRHR2900
ENSP00000342952ADCY2900
ENSP00000343782ADRB3900
ENSP00000344456CTNNB1847
ENSP00000346017CALCB900
ENSP00000350005GIP900
ENSP00000352561CALCR900
ENSP00000352839NPSR1900
ENSP00000353915HTR4900
ENSP00000354499MT-CO1723
ENSP00000355759PARP1745
ENSP00000356213VIP900
ENSP00000356438PTGS2846
ENSP00000357283LMNA739
ENSP00000358301ADRB1900
ENSP00000358727GSTO1900
ENSP00000360141GNAS900
ENSP00000362353GLP1R900
ENSP00000366506HRH2900
ENSP00000367830PRKCZ700
ENSP00000367869900
ENSP00000368646PRDX4700
ENSP00000369647AVP900
ENSP00000370408CDX2818
ENSP00000372221SERPINB5726
ENSP00000379086ADM2900
ENSP00000379213PTHLH900
ENSP00000379514ADCYAP1R1900
ENSP00000381105NPS900
ENSP00000381333CRHR1900
ENSP00000381607GSTP1746
ENSP00000383558GCGR900
ENSP00000384273RELA738
ENSP00000384708FSHR900
ENSP00000387662GCG915
ENSP00000387699CREB1827
ENSP00000411658ADCYAP1900
ENSP00000419361ADCY5900
ENSP00000428657NAIP700
ENSP00000428824GPBAR1957
ENSP00000447149NR1H4826
ENSP00000451605MC1R900
ENSP00000467494GIPR900
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.