IMPPAT Phytochemical information: 
Diosindigo B

Diosindigo B
Summary

SMILES: COC1=C/C(=C\2/C=C(OC)c3c(C2=O)cc(cc3O)C)/C(=O)c2c1c(O)cc(c2)C
InChI: InChI=1S/C24H20O6/c1-11-5-15-21(17(25)7-11)19(29-3)9-13(23(15)27)14-10-20(30-4)22-16(24(14)28)6-12(2)8-18(22)26/h5-10,25-26H,1-4H3/b14-13+
InChIKey: HVSMANGMDQFHLH-BUHFOSPRSA-N
DeepSMILES: COC=C/C=C/C=COC))ccC/6=O))cccc6O)))C))))))))/C=O)cc6cO)ccc6)C
Scaffold Graph/Node/Bond level: O=C1C(=C2C=Cc3ccccc3C2=O)C=Cc2ccccc21
Scaffold Graph/Node level: OC1C2CCCCC2CCC1C1CCC2CCCCC2C1O
Scaffold Graph level: CC1C2CCCCC2CCC1C1CCC2CCCCC2C1C
Functional groups: COC1=C/C(=C2/C=C(OC)ccC2=O)C(=O)cc1; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Naphthalenes
ClassyFire Subclass: Naphthols and derivatives
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Naphthalenes
NP Classifier Class: Bisnaphthalenes
Synonymous chemical names:
diosindigo b
External chemical identifiers:
CID:CID_11200524; ZINC:ZINC000015121605; SureChEMBL:SCHEMBL11919735
Chemical structure download


Diosindigo B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 404.42
Log P RDKit 4.08
Topological polar surface area (Å2) RDKit 93.06
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 20
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.17
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


Diosindigo B
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.73


Diosindigo B
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.08
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No