IMPPAT Phytochemical information: 
4,5-Dihydroxy-2-hydroxymethyl-1,3,6,8-tetranitroanthraquinone

4,5-Dihydroxy-2-hydroxymethyl-1,3,6,8-tetranitroanthraquinone
Summary

SMILES: OCc1c([N+](=O)[O-])c(O)c2c(c1[N+](=O)[O-])C(=O)c1c(C2=O)c(O)c(cc1[N+](=O)[O-])[N+](=O)[O-]
InChI: InChI=1S/C15H6N4O13/c20-2-3-10(18(29)30)7-9(15(24)11(3)19(31)32)14(23)8-6(13(7)22)4(16(25)26)1-5(12(8)21)17(27)28/h1,20-21,24H,2H2
InChIKey: QFCNNIIPXGJBQT-UHFFFAOYSA-N
DeepSMILES: OCcc[N+]=O)[O-]))cO)ccc6[N+]=O)[O-])))C=O)ccC6=O))cO)ccc6[N+]=O)[O-]))))[N+]=O)[O-]
Scaffold Graph/Node/Bond level: O=C1c2ccccc2C(=O)c2ccccc21
Scaffold Graph/Node level: OC1C2CCCCC2C(O)C2CCCCC12
Scaffold Graph level: CC1C2CCCCC2C(C)C2CCCCC12
Functional groups: CO; c[N+](=O)[O-]; cO; cC(=O)c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Anthracenes
ClassyFire Subclass: Anthraquinones
Synonymous chemical names:
1,3,6,8-tetranitro-4,5-dihydroxy-2-hydroxymethylanthraquinone
External chemical identifiers:
CID:CID_5464178; ZINC:ZINC000085584148
Chemical structure download


4,5-Dihydroxy-2-hydroxymethyl-1,3,6,8-tetranitroanthraquinone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 450.23
Log P RDKit 1
Topological polar surface area (Å2) RDKit 267.39
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 17
Number of nitrogen atoms RDKit 4
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 14
Number of sp3 hybridized carbon atoms RDKit 1
Shape complexity RDKit 0.07
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3


4,5-Dihydroxy-2-hydroxymethyl-1,3,6,8-tetranitroanthraquinone
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 0
Ghose rule RDKit Passed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.36


4,5-Dihydroxy-2-hydroxymethyl-1,3,6,8-tetranitroanthraquinone
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 Low
Log Kp (Skin permeation, cm/s) SwissADME -7.85
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes