IMPPAT Phytochemical information: 
Haematoxylin

Haematoxylin
Summary

SMILES: Oc1cc2C[C@@]3([C@H](c2cc1O)c1ccc(c(c1OC3)O)O)O
InChI: InChI=1S/C16H14O6/c17-10-2-1-8-13-9-4-12(19)11(18)3-7(9)5-16(13,21)6-22-15(8)14(10)20/h1-4,13,17-21H,5-6H2/t13-,16+/m0/s1
InChIKey: WZUVPPKBWHMQCE-XJKSGUPXSA-N
DeepSMILES: OcccC[C@@][C@H]c5cc9O))))cccccc6OC%10)))O))O))))))O
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CC1COc3ccccc3C21
Scaffold Graph/Node level: C1CCC2C(C1)CC1COC3CCCCC3C12
Scaffold Graph level: C1CCC2C(C1)CCC1CC3CCCCC3C12
Functional groups: cO; cOC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
Synonymous chemical names:
hematoxylin, haematoxylin
External chemical identifiers:
CID:CID_442514; ChEMBL:CHEMBL477197; ChEBI:CHEBI:5601; ZINC:ZINC000000155806; FDASRS:YKM8PY2Z55; SureChEMBL:SCHEMBL19654; MolPort-002-507-295
Chemical structure download


Haematoxylin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 302.28
Log P RDKit 1.32
Topological polar surface area (Å2) RDKit 110.38
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.12
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.25
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
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


Haematoxylin
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.469461


Haematoxylin
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.30
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes