IMPPAT Phytochemical information: 
Secocrispiolide

Secocrispiolide
Summary

SMILES: C=C1[C@H](CCOC1=O)Cc1c(C)cccc1C
InChI: InChI=1S/C15H18O2/c1-10-5-4-6-11(2)14(10)9-13-7-8-17-15(16)12(13)3/h4-6,13H,3,7-9H2,1-2H3/t13-/m1/s1
InChIKey: KXYKHKYNFWGGQW-CYBMUJFWSA-N
DeepSMILES: C=C[C@H]CCOC6=O)))))CccC)cccc6C
Scaffold Graph/Node/Bond level: C=C1C(=O)OCCC1Cc1ccccc1
Scaffold Graph/Node level: CC1C(CC2CCCCC2)CCOC1O
Scaffold Graph level: CC1CCCC(CC2CCCCC2)C1C
Functional groups: C=C(C)C(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Benzene and substituted derivatives
ClassyFire Subclass: Xylenes
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Germacrane sesquiterpenoids
Synonymous chemical names:
Secocrispiolide, secocrispiolide
External chemical identifiers:
CID:CID_90475612; ZINC:ZINC000014693727
Chemical structure download


Secocrispiolide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 230.31
Log P RDKit 2.97
Topological polar surface area (Å2) RDKit 26.3
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 17
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 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.4
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


Secocrispiolide
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 0.58


Secocrispiolide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -5.16
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No