IMPPAT Phytochemical information: 
[(1S,2R,3R,4S,5R,6S,8R,9S,10S,13S,16S,17R,18S)-8,9-dihydroxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadec-11-en-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate
[(1S,2R,3R,4S,5R,6S,8R,9S,10S,13S,16S,17R,18S)-8,9-dihydroxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadec-11-en-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate
Summary

SMILES: CO[C@H]1C[C@@]2(O)[C@H]3[C@H]([C@@H]1C[C@H]3[C@@]13[C@H]4[C@]2(O)[C@@H](OC)[C@@H]1[C@](C=N4)(CC[C@@H]3OC)COC(=O)c1ccccc1N1C(=O)C[C@@H](C1=O)C)OC
InChI: InChI=1S/C35H44N2O10/c1-17-12-24(38)37(29(17)39)21-9-7-6-8-18(21)30(40)47-16-32-11-10-23(44-3)34-20-13-19-22(43-2)14-33(41,25(20)26(19)45-4)35(42,31(34)36-15-32)28(46-5)27(32)34/h6-9,15,17,19-20,22-23,25-28,31,41-42H,10-14,16H2,1-5H3/t17-,19+,20+,22-,23-,25+,26-,27+,28-,31-,32-,33+,34-,35+/m0/s1
InChIKey: ZXTOPWJFZABXSX-JVBPJWSTSA-N
DeepSMILES: CO[C@H]C[C@@]O)[C@H][C@H][C@@H]6C[C@H]5[C@@][C@H][C@]9O)[C@@H]OC))[C@@H]5[C@]C=N7))CC[C@@H]9OC)))))COC=O)cccccc6NC=O)C[C@@H]C5=O))C)))))))))))))))))))))))OC
Scaffold Graph/Node/Bond level: O=C(OCC12C=NC3C4CC1C3(CCC2)C1CC2CCC4C1C2)c1ccccc1N1C(=O)CCC1=O
Scaffold Graph/Node level: OC(OCC12CCCC34C5CC6CCC(C5C6)C(CC13)C4NC2)C1CCCCC1N1C(O)CCC1O
Scaffold Graph level: CC(CCC12CCCC34C(CC1)C(CC23)C1CCC2CC1C4C2)C1CCCCC1C1C(C)CCC1C
Functional groups: COC; CO; cN1C(=O)CCC1=O; CC=NC; cC(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Benzene and substituted derivatives
ClassyFire Subclass: Benzoic acids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids|Terpenoids
NP Classifier Superclass: Pseudoalkaloids
NP Classifier Class: Terpenoid alkaloids
Synonymous chemical names:
anhweidelphinine
External chemical identifiers:
CID:CID_101631699; ZINC:ZINC000169361635
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(1S,2R,3R,4S,5R,6S,8R,9S,10S,13S,16S,17R,18S)-8,9-dihydroxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadec-11-en-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 652.74
Log P RDKit 1.78
Topological polar surface area (Å2) RDKit 153.42
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 35
Number of heavy atoms RDKit 47
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 14
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 25
Shape complexity RDKit 0.71
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 8
Number of saturated carbocycles RDKit 5
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 8
[(1S,2R,3R,4S,5R,6S,8R,9S,10S,13S,16S,17R,18S)-8,9-dihydroxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadec-11-en-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.31
[(1S,2R,3R,4S,5R,6S,8R,9S,10S,13S,16S,17R,18S)-8,9-dihydroxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadec-11-en-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.53
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes