IMPPAT Phytochemical information: 
Graecunin D
Graecunin D
Summary

SMILES: [NH3+]CC(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)O)Cc1c[nH]c2c1cccc2)[C@H](O)C)[C@H](O)C)CCC(=O)O)CC(=O)O)Cc1ccc(cc1)O
InChI: InChI=1S/C48H63N11O18/c1-23(60)40(46(75)51-21-36(64)57-41(24(2)61)47(76)55-32(42(71)52-22-39(69)70)17-26-20-50-29-7-4-3-6-28(26)29)58-43(72)30(13-14-37(65)66)54-45(74)34-8-5-15-59(34)48(77)33(18-38(67)68)56-44(73)31(53-35(63)19-49)16-25-9-11-27(62)12-10-25/h3-4,6-7,9-12,20,23-24,30-34,40-41,50,60-62H,5,8,13-19,21-22,49H2,1-2H3,(H,51,75)(H,52,71)(H,53,63)(H,54,74)(H,55,76)(H,56,73)(H,57,64)(H,58,72)(H,65,66)(H,67,68)(H,69,70)/p+1/t23-,24-,30+,31+,32+,33+,34+,40+,41+/m1/s1
InChIKey: YYYJTUAEGPSBSQ-GZCAAYOFSA-O
DeepSMILES: [NH3+]CC=O)N[C@H]C=O)N[C@H]C=O)NCCC[C@H]5C=O)N[C@H]C=O)N[C@H]C=O)NCC=O)N[C@H]C=O)N[C@H]C=O)NCC=O)O)))))Ccc[nH]cc5cccc6)))))))))))))[C@H]O)C))))))))[C@H]O)C)))))CCC=O)O)))))))))))))CC=O)O))))))Ccccccc6))O
Scaffold Graph/Node/Bond level: O=C(CCc1ccccc1)NCC(=O)N1CCCC1C(=O)NCC(=O)NCC(=O)NCC(=O)NCC(=O)NCCc1c[nH]c2ccccc12
Scaffold Graph/Node level: OC(CCC1CCCCC1)NCC(O)N1CCCC1C(O)NCC(O)NCC(O)NCC(O)NCC(O)NCCC1CNC2CCCCC12
Scaffold Graph level: CC(CCCC1CCC2CCCCC21)CCC(C)CCC(C)CCC(C)CCC(C)C1CCCC1C(C)CCC(C)CCC1CCCCC1
Functional groups: CC(=O)NC; CC(=O)O; CN(C)C(C)=O; CNC(C)=O; CO; C[NH3+]; cO; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Amino acids, peptides, and analogues
NP Classifier Biosynthetic pathway: Amino acids and Peptides
NP Classifier Superclass: Oligopeptides
NP Classifier Class: Linear peptides
Synonymous chemical names:
graecunin d
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Graecunin D
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 1083.1
Log P RDKit -5.78
Topological polar surface area (Å2) RDKit 469.13
Number of hydrogen bond acceptors RDKit 15
Number of hydrogen bond donors RDKit 16
Number of carbon atoms RDKit 48
Number of heavy atoms RDKit 77
Number of heteroatoms RDKit 29
Number of nitrogen atoms RDKit 11
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 26
Number of sp3 hybridized carbon atoms RDKit 22
Shape complexity RDKit 0.46
Number of rotatable bonds RDKit 29
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
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 4
Graecunin D
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.0308
Graecunin D
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Very 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 -17.3
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
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