IMPPAT Phytochemical information: 
Hautriwaic acid

Hautriwaic acid
Summary

SMILES: OC[C@]12CC[C@H]([C@]([C@H]2CCC=C1C(=O)O)(C)CCc1ccoc1)C
InChI: InChI=1S/C20H28O4/c1-14-6-10-20(13-21)16(18(22)23)4-3-5-17(20)19(14,2)9-7-15-8-11-24-12-15/h4,8,11-12,14,17,21H,3,5-7,9-10,13H2,1-2H3,(H,22,23)/t14-,17-,19+,20-/m1/s1
InChIKey: PHKSUFCCGLWIMC-SIKIZQCASA-N
DeepSMILES: OC[C@@]CC[C@H][C@][C@H]6CCC=C%10C=O)O)))))))C)CCcccoc5))))))))C
Scaffold Graph/Node/Bond level: C1=CC2CCCC(CCc3ccoc3)C2CC1
Scaffold Graph/Node level: C1CCC2C(C1)CCCC2CCC1CCOC1
Scaffold Graph level: C1CCC(CCC2CCCC3CCCCC32)C1
Functional groups: CO; CC=C(C(=O)O)C; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Diterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Colensane and Clerodane diterpenoids
Synonymous chemical names:
Hautriwaic acid, hautriwaic acid
External chemical identifiers:
CID:CID_12310372; ZINC:ZINC000039205618; MolPort-039-338-295
Chemical structure download


Hautriwaic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 332.44
Log P RDKit 4.05
Topological polar surface area (Å2) RDKit 70.67
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.65
Number of rotatable bonds RDKit 5
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 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Hautriwaic 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 0.853213


Hautriwaic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.33
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 Yes