IMPPAT Phytochemical information: 
Dihydrophaseic acid

Dihydrophaseic acid
Summary

SMILES: OC(=O)/C=C(\C=C\[C@]1(O)[C@@]2(C)CO[C@]1(C)C[C@H](C2)O)/C
InChI: InChI=1S/C15H22O5/c1-10(6-12(17)18)4-5-15(19)13(2)7-11(16)8-14(15,3)20-9-13/h4-6,11,16,19H,7-9H2,1-3H3,(H,17,18)/b5-4+,10-6-/t11-,13+,14+,15-/m0/s1
InChIKey: XIVFQYWMMJWUCD-VSTJRZLJSA-N
DeepSMILES: OC=O)/C=C\C=C\[C@]O)[C@@]C)CO[C@]5C)C[C@H]C7)O))))))))))/C
Scaffold Graph/Node/Bond level: C1CC2COC(C1)C2
Scaffold Graph/Node level: C1CC2COC(C1)C2
Scaffold Graph level: C1CC2CCC(C1)C2
Functional groups: CC(=C/C(=O)O)/C=C/C; CO; COC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Sesquiterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Apocarotenoids
NP Classifier Class: Apocarotenoids(ε-)
Synonymous chemical names:
dihydrophaseic acid, epidihydrophaseic acid, 4'-dihydrophaseic-acid
External chemical identifiers:
CID:CID_11988272; ChEMBL:CHEMBL3594246; ChEBI:CHEBI:23757; ZINC:ZINC000030730129; SureChEMBL:SCHEMBL9990748
Chemical structure download


Dihydrophaseic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 282.34
Log P RDKit 1.25
Topological polar surface area (Å2) RDKit 86.99
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.27
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.67
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
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 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


Dihydrophaseic 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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.535562


Dihydrophaseic 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 -8.11
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
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