IMPPAT Phytochemical information: 
methyl (1S,10S,12S,13E)-13-ethylidene-4-hydroxy-18-(hydroxymethyl)-8,15-diazapentacyclo[10.5.1.01,9.02,7.010,15]octadeca-2(7),3,5,8-tetraene-18-carboxylate
methyl (1S,10S,12S,13E)-13-ethylidene-4-hydroxy-18-(hydroxymethyl)-8,15-diazapentacyclo[10.5.1.01,9.02,7.010,15]octadeca-2(7),3,5,8-tetraene-18-carboxylate
Summary

SMILES: COC(=O)C1(CO)[C@H]2C[C@H]3C4=Nc5c([C@@]14CCN3C/C/2=C/C)cc(O)cc5
InChI: InChI=1S/C21H24N2O4/c1-3-12-10-23-7-6-20-15-8-13(25)4-5-16(15)22-18(20)17(23)9-14(12)21(20,11-24)19(26)27-2/h3-5,8,14,17,24-25H,6-7,9-11H2,1-2H3/b12-3-/t14?,17-,20?,21?/m0/s1
InChIKey: CPAUEKXFXGFLCO-KTYHQEAQSA-N
DeepSMILES: COC=O)CCO))[C@H]C[C@H]C=Ncc[C@@]95CCN9C/C/%13=C/C))))))))ccO)cc6
Scaffold Graph/Node/Bond level: C=C1CN2CCC34CC1CC2C3=Nc1ccccc14
Scaffold Graph/Node level: CC1CN2CCC34CC1CC2C3NC1CCCCC14
Scaffold Graph level: CC1CC2CCC34CC1CC2C3CC1CCCCC14
Functional groups: COC(C)=O; CO; cN=C(C)C; CN(C)C; C/C=C(/C)C; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Corynanthean-type alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
10-hydroxy-deacetylakuammiline, 10-hydroxy-desacetyl-akuammiline, 10-hydroxy desacetyl-akuammiline
External chemical identifiers:
CID:CID_21627987
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
methyl (1S,10S,12S,13E)-13-ethylidene-4-hydroxy-18-(hydroxymethyl)-8,15-diazapentacyclo[10.5.1.01,9.02,7.010,15]octadeca-2(7),3,5,8-tetraene-18-carboxylate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 368.43
Log P RDKit 1.92
Topological polar surface area (Å2) RDKit 82.36
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.52
Number of rotatable bonds RDKit 3
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 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
methyl (1S,10S,12S,13E)-13-ethylidene-4-hydroxy-18-(hydroxymethyl)-8,15-diazapentacyclo[10.5.1.01,9.02,7.010,15]octadeca-2(7),3,5,8-tetraene-18-carboxylate
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.62
methyl (1S,10S,12S,13E)-13-ethylidene-4-hydroxy-18-(hydroxymethyl)-8,15-diazapentacyclo[10.5.1.01,9.02,7.010,15]octadeca-2(7),3,5,8-tetraene-18-carboxylate
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 -8.16
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes