IMPPAT Phytochemical information: 
Dehydronobilin

Dehydronobilin
Summary

SMILES: C/C=C(\C(=O)O[C@H]1CC(=CCC(=O)/C(=C/[C@H]2[C@@H]1C(=C)C(=O)O2)/C)C)/C
InChI: InChI=1S/C20H24O5/c1-6-12(3)19(22)24-16-9-11(2)7-8-15(21)13(4)10-17-18(16)14(5)20(23)25-17/h6-7,10,16-18H,5,8-9H2,1-4H3/b11-7?,12-6-,13-10+/t16-,17-,18+/m0/s1
InChIKey: FKDIIXZIKCNXAT-QQWVOQOZSA-N
DeepSMILES: C/C=C\C=O)O[C@H]CC=CCC=O)/C=C/[C@H][C@@H]%10C=C)C=O)O5))))))/C)))))C))))))/C
Scaffold Graph/Node/Bond level: C=C1C(=O)OC2C=CC(=O)CC=CCCC12
Scaffold Graph/Node level: CC1C(O)OC2CCC(O)CCCCCC21
Scaffold Graph level: CC1CCCCCC2C(CC1)CC(C)C2C
Functional groups: C/C=C(/C)C(=O)OC; CC=C(C)C; CC(=O)/C(C)=C/C; C=C1CCOC1=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Germacrane sesquiterpenoids
Synonymous chemical names:
3-dehydronobilin
External chemical identifiers:
CID:CID_44579900
Chemical structure download


Dehydronobilin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 344.41
Log P RDKit 3.22
Topological polar surface area (Å2) RDKit 69.67
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.45
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
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 2


Dehydronobilin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.436943


Dehydronobilin
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.31
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No