IMPPAT Phytochemical information: 
(3S)-3-hydroxycyclocitral

(3S)-3-hydroxycyclocitral
Summary

SMILES: O=CC1=C(C)C[C@H](CC1(C)C)O
InChI: InChI=1S/C10H16O2/c1-7-4-8(12)5-10(2,3)9(7)6-11/h6,8,12H,4-5H2,1-3H3/t8-/m1/s1
InChIKey: SWPMTVXRLXPNDP-MRVPVSSYSA-N
DeepSMILES: O=CC=CC)C[C@H]CC6C)C)))O
Scaffold Graph/Node/Bond level: C1=CCCCC1
Scaffold Graph/Node level: C1CCCCC1
Scaffold Graph level: C1CCCCC1
Functional groups: CC(=C(C=O)C)C; 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: Apocarotenoids
NP Classifier Class: Apocarotenoids (β-)
Synonymous chemical names:
4-hydroxy-2,6,6-trimethyl-cyclohex-1-ene-carboxaldehyde
External chemical identifiers:
CID:CID_25201359; ChEBI:CHEBI:53167; SureChEMBL:SCHEMBL10452597
Chemical structure download


(3S)-3-hydroxycyclocitral
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 168.24
Log P RDKit 1.68
Topological polar surface area (Å2) RDKit 37.3
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 12
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.7
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 1


(3S)-3-hydroxycyclocitral
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.604755


(3S)-3-hydroxycyclocitral
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.55
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 No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No