IMPPAT Phytochemical information: 
Dracorubin

Dracorubin
Summary

SMILES: COc1cc2oc3c4c(c2c2c1CC[C@H](O2)c1ccccc1)cc(oc4cc(=O)c3C)c1ccccc1
InChI: InChI=1S/C32H24O5/c1-18-23(33)16-27-29-22(15-25(35-27)20-11-7-4-8-12-20)30-28(37-31(18)29)17-26(34-2)21-13-14-24(36-32(21)30)19-9-5-3-6-10-19/h3-12,15-17,24H,13-14H2,1-2H3/t24-/m0/s1
InChIKey: FWKBXSPDFCAHFN-DEOSSOPVSA-N
DeepSMILES: COcccocccc6cc%10CC[C@H]O6)cccccc6))))))))))))ccoc6cc=O)c%10C))))))cccccc6
Scaffold Graph/Node/Bond level: O=c1cc2oc(-c3ccccc3)cc3c4c5c(ccc4oc(c1)c23)CCC(c1ccccc1)O5
Scaffold Graph/Node level: OC1CC2OC(C3CCCCC3)CC3C2C(C1)OC1CCC2CCC(C4CCCCC4)OC2C13
Scaffold Graph level: CC1CC2CC(C3CCCCC3)CC3C2C(C1)CC1CCC2CCC(C4CCCCC4)CC2C13
Functional groups: cOC; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Biflavonoids and polyflavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavans
Synonymous chemical names:
dracocarmin, dracorubin
External chemical identifiers:
CID:CID_160270; ChEMBL:CHEMBL485799; ChEBI:CHEBI:4714; ZINC:ZINC000004098302
Chemical structure download


Dracorubin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 488.54
Log P RDKit 7.74
Topological polar surface area (Å2) RDKit 61.81
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 37
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.03
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 27
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.16
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 6
Total number of rings RDKit 7
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 7


Dracorubin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.19


Dracorubin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Insoluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -5.49
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No