IMPPAT Phytochemical information: 
Geosmin

Geosmin
Summary

SMILES: C[C@H]1CCC[C@@]2([C@]1(O)CCCC2)C
InChI: InChI=1S/C12H22O/c1-10-6-5-8-11(2)7-3-4-9-12(10,11)13/h10,13H,3-9H2,1-2H3/t10-,11+,12-/m0/s1
InChIKey: JLPUXFOGCDVKGO-TUAOUCFPSA-N
DeepSMILES: C[C@H]CCC[C@@][C@]6O)CCCC6)))))C
Scaffold Graph/Node/Bond level: C1CCC2CCCCC2C1
Scaffold Graph/Node level: C1CCC2CCCCC2C1
Scaffold Graph level: C1CCC2CCCCC2C1
Functional groups: CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Alcohols and polyols
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Eudesmane sesquiterpenoids|Noreudesmane sesquiterpenoids
Synonymous chemical names:
geosmin, Geosmin,(-)-, Geosmin
External chemical identifiers:
CID:CID_29746; ChEMBL:CHEMBL2374043; ChEBI:CHEBI:46702; ZINC:ZINC000003870304; FDASRS:MYW912WXJ4; SureChEMBL:SCHEMBL50009
Chemical structure download


Geosmin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 182.31
Log P RDKit 3.12
Topological polar surface area (Å2) RDKit 20.23
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 13
Number of heteroatoms RDKit 1
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 0
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 1
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


Geosmin
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.61


Geosmin
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.08
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