IMPPAT | IMPPAT: Indian Medicinal Plants, Phytochemistry And Therapeutics

1-[(12S,13R,18R)-7-[[(12S,13R,18R)-16-hydroxy-3,16,20-trimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4,6,8-tetraen-17-yl]methyl]-6-methoxy-3,20-dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4(9),5,7,16-pentaen-17-yl]ethanone

Summary

SMILES: COc1cc2c(cc1CC1[C@@H]3CC4N([C@H]([C@@H]3COC1(C)O)Cc1c4n(C)c3c1cccc3)C)c1c(n2C)C2C[C@@H]3[C@H]([C@H](C1)N2C)COC=C3C(=O)C
InChI: InChI=1S/C43H52N4O5/c1-22(48)30-19-51-20-31-25(30)14-38-42-29(17-35(31)44(38)3)27-12-23(40(50-7)18-37(27)47(42)6)13-33-26-15-39-41-28(24-10-8-9-11-34(24)46(41)5)16-36(45(39)4)32(26)21-52-43(33,2)49/h8-12,18-19,25-26,31-33,35-36,38-39,49H,13-17,20-21H2,1-7H3/t25-,26+,31+,32+,33?,35-,36-,38?,39?,43?/m0/s1
InChIKey: JGXFRVOHTXTCCH-BKNHQHATSA-N
DeepSMILES: COcccccc6CC[C@@H]CCN[C@H][C@@H]6COC%10C)O)))))Ccc6nC)cc5cccc6)))))))))))C)))))))))ccn5C))CC[C@@H][C@H][C@H]C8)N6C)))COC=C6C=O)C
Scaffold Graph/Node/Bond level: C1=CC2CC3NC(Cc4c3[nH]c3ccc(CC5COCC6C7Cc8c([nH]c9ccccc89)C(CC56)N7)cc43)C2CO1
Scaffold Graph/Node level: C1CCC2C(C1)NC1C3CC4C(CC5CCC6NC7C8CC9CCOCC9C(CC7C6C5)N8)COCC4C(CC21)N3
Scaffold Graph level: C1CCC2C(C1)CC1CC2CC2C3CC(CC4CCCC5C6CC(CC45)C4CC5CCCCC5C4C6)CCC3CC12
Functional groups: cOC; cn(C)c; CN(C)C; COC=C(C(C)=O)C; COC(C)(O)C

Chemical classification

ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Macroline alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Carboline alkaloids

Synonymous chemical names:
Macralstonine, macralstonine

External chemical identifiers:
CID:CID_102069292

Chemical structure download

2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT

Physicochemical properties

Property name	Tool	Property value
Molecular weight (g/mol)	RDKit	704.91
Log P	RDKit	5.85
Topological polar surface area (Å²)	RDKit	81.33
Number of hydrogen bond acceptors	RDKit	9
Number of hydrogen bond donors	RDKit	1
Number of carbon atoms	RDKit	43
Number of heavy atoms	RDKit	52
Number of heteroatoms	RDKit	9
Number of nitrogen atoms	RDKit	4
Number of sulfur atoms	RDKit	0
Number of chiral carbon atoms	RDKit	10
Stereochemical complexity	RDKit	0.23
Number of sp hybridized carbon atoms	RDKit	0
Number of sp² hybridized carbon atoms	RDKit	19
Number of sp³ hybridized carbon atoms	RDKit	24
Shape complexity	RDKit	0.56
Number of rotatable bonds	RDKit	4
Number of aliphatic carbocycles	RDKit	0
Number of aliphatic heterocycles	RDKit	6
Number of aliphatic rings	RDKit	6
Number of aromatic carbocycles	RDKit	2
Number of aromatic heterocycles	RDKit	2
Number of aromatic rings	RDKit	4
Total number of rings	RDKit	10
Number of saturated carbocycles	RDKit	0
Number of saturated heterocycles	RDKit	3
Number of saturated rings	RDKit	3
Number of Smallest Set of Smallest Rings (SSSR)	RDKit	10

Drug-likeness properties

Property name	Tool	Property value
Number of Lipinski’s rule of 5 violations	RDKit	2
Lipinski’s rule of 5 filter	RDKit	Failed
Number of Ghose filter violations	RDKit	4
Ghose filter	RDKit	Failed
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	0.28589

ADME properties

Property name	Tool	Property value
Bioavailability score	SwissADME	0.55
Solubility class [ESOL]	SwissADME	Poorly soluble
Solubility class [Silicos-IT]	SwissADME	Poorly soluble
Blood Brain Barrier permeation	SwissADME	No
Gastrointestinal absorption	SwissADME	High
Log K_p (Skin permeation, cm/s)	SwissADME	-7.50
Number of PAINS structural alerts	SwissADME	1
Number of Brenk structural alerts	SwissADME	0
CYP1A2 inhibitor	SwissADME	No
CYP2C19 inhibitor	SwissADME	Yes
CYP2C9 inhibitor	SwissADME	No
CYP2D6 inhibitor	SwissADME	No
CYP3A4 inhibitor	SwissADME	No
P-glycoprotein substrate	SwissADME	Yes