IMPPAT Phytochemical information: 
(1|A,2|A)-crinan-1,2-diol

(1|A,2|A)-crinan-1,2-diol
Summary

SMILES: O[C@@H]1CC[C@@H]2[C@]3([C@@H]1O)CCN2Cc1c3cc2OCOc2c1
InChI: InChI=1S/C16H19NO4/c18-11-1-2-14-16(15(11)19)3-4-17(14)7-9-5-12-13(6-10(9)16)21-8-20-12/h5-6,11,14-15,18-19H,1-4,7-8H2/t11-,14-,15-,16+/m1/s1
InChIKey: DLYIURZCCWSUKD-MPESAESLSA-N
DeepSMILES: O[C@@H]CC[C@@H][C@][C@@H]6O))CCN5Ccc7ccOCOc5c9
Scaffold Graph/Node/Bond level: c1c2c(cc3c1OCO3)C13CCCCC1N(CC3)C2
Scaffold Graph/Node level: C1CCC23CCN(CC4CC5OCOC5CC42)C3C1
Scaffold Graph level: C1CC2CC3CC4CCC5(CCCCC45)C3CC2C1
Functional groups: CO; CN(C)C; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolines and derivatives
ClassyFire Subclass: Benzoquinolines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids
Synonymous chemical names:
(-)-amabiline
External chemical identifiers:
CID:CID_399199; ChEMBL:CHEMBL456315
Chemical structure download


(1|A,2|A)-crinan-1,2-diol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 289.33
Log P RDKit 0.76
Topological polar surface area (Å2) RDKit 62.16
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.62
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
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 5


(1|A,2|A)-crinan-1,2-diol
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 0.74


(1|A,2|A)-crinan-1,2-diol
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 -7.45
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes