IMPPAT Phytochemical information: 
Yohimbic Acid

Yohimbic Acid
Summary

SMILES: OC(=O)[C@H]1[C@@H](O)CC[C@@H]2[C@@H]1C[C@@H]1N(C2)CCc2c1[nH]c1c2cccc1
InChI: InChI=1S/C20H24N2O3/c23-17-6-5-11-10-22-8-7-13-12-3-1-2-4-15(12)21-19(13)16(22)9-14(11)18(17)20(24)25/h1-4,11,14,16-18,21,23H,5-10H2,(H,24,25)/t11-,14-,16-,17-,18+/m0/s1
InChIKey: AADVZSXPNRLYLV-GKMXPDSGSA-N
DeepSMILES: OC=O)[C@H][C@@H]O)CC[C@@H][C@@H]6C[C@@H]NC6)CCcc6[nH]cc5cccc6
Scaffold Graph/Node/Bond level: c1ccc2c3c([nH]c2c1)C1CC2CCCCC2CN1CC3
Scaffold Graph/Node level: C1CCC2CN3CCC4C5CCCCC5NC4C3CC2C1
Scaffold Graph level: C1CCC2CC3C(CCC4C5CCCCC5CC34)CC2C1
Functional groups: CC(=O)O; CO; CN(C)C; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Corynanthean-type alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Yohimbine-like alkaloids
Synonymous chemical names:
yohimbinic acid
External chemical identifiers:
CID:CID_72131; ChEMBL:CHEMBL148824; ChEBI:CHEBI:35633; ZINC:ZINC000003881708; FDASRS:35FAV1EVEG; SureChEMBL:SCHEMBL571103; MolPort-002-507-235
Chemical structure download


Yohimbic Acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 340.42
Log P RDKit 2.56
Topological polar surface area (Å2) RDKit 76.56
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Yohimbic Acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.75


Yohimbic Acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.14
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes