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Chemical Structure| 1047-16-1 Chemical Structure| 1047-16-1

Structure of Quinacridone
CAS No.: 1047-16-1

Chemical Structure| 1047-16-1

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Product Details of [ 1047-16-1 ]

CAS No. :1047-16-1
Formula : C20H12N2O2
M.W : 312.32
SMILES Code : O=C(C(C=C1NC2=C3C=CC=C2)=C4C=C1C3=O)C5=C(N4)C=CC=C5
MDL No. :MFCD00059956
InChI Key :NRCMAYZCPIVABH-UHFFFAOYSA-N
Pubchem ID :13976

Safety of [ 1047-16-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P261-P302+P352-P305+P351+P338

Computational Chemistry of [ 1047-16-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 24
Num. arom. heavy atoms 22
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 97.71
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

65.72 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.31
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

4.03
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

3.68
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.15
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

5.18
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.47

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-4.99
Solubility 0.00317 mg/ml ; 0.0000101 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-5.11
Solubility 0.00241 mg/ml ; 0.0000077 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-8.15
Solubility 0.0000022 mg/ml ; 0.000000007 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

Yes
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.34 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.95

Application In Synthesis of [ 1047-16-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1047-16-1 ]

[ 1047-16-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 50-00-0 ]
  • [ 1047-16-1 ]
  • [ 130-14-3 ]
  • [ 532-02-5 ]
  • quinacridone/naphthalene sulfonic acid formaldehyde polymer [ No CAS ]
YieldReaction ConditionsOperation in experiment
A one-liter flask equipped with a stirrer, thermometer, condenser and drying tube is charged with 200 mi concentrated (95-98%) sulfuric acid. 31.2 G unsubstituted quinacridone (CROMOPHTALS RED 2020, Ciba Specialty Chemicals Inc.) is added at a temperature below 45C and the mixture is stirred for 10 minutes at 40-45C to dissolve the pigment. 39.7 G of a wet naphthalene SULFONIC acid sodium salt presscake with a solid content of 58%, a mixture containing 80% 1-naphthalene sulfonic acid sodium salt and 20% <strong>[532-02-5]2-naphthalene sulfonic acid sodium salt</strong> (Shanghai Shen Li Chemical Factory) is added at a temperature below 45C and the mixture is stirred for 15 minutes at 40 to 45C followed by the rapid addition of 3.2 G para formaldehyde. The reaction mixture is stirred for one hour at 58-60C, then poured into 2.5 I of ice water. The violet precipitate is stirred for 1 hour at 5-20 C, then filtered. The residue is washed with water to a pH of 2.5 and kept as presscake with a solid content of 13% by weight. Around 0. 5 G of the press cake are reslurried in 20 mi hot water yielding a bluish red colored liquid. It is filtered to remove little aggregated material. The filtrate is red and appears a dye solution. However, the electron micrograph shows the quinacridone in nanosize particle form with an average particle size of 4 to 25 nm.
  • 2
  • [ 50-00-0 ]
  • [ 1047-16-1 ]
  • [ 130-14-3 ]
  • [ 532-02-5 ]
  • poly(formaldehyde-co-1-naphtalene sulfonic acid sodium salt-co-2-naphtalene sulfonic acid sodium salt); quinacridone; naphtalene sulfonic acid methyl metacridone; mixture of [ No CAS ]
YieldReaction ConditionsOperation in experiment
A one liter flask equipped with a stirrer, thermometer, condenser and drying tube is charged with 200 ml concentrated (95-98%) sulfuric acid. 31.2 G unsubstituted quinacridone (CROMOPHTALO Red 2020, Ciba Specialty Chemicals Inc.) are added at a temperature BELOW 45C and the mixture is stirred for 10 minutes at 40-45C to dissolve the pigment. 39.7 G of a wet naphthalene sulfonic acid sodium SALT PRESSCAKE with a solid content of 58%, a mixture containing 80% 1-naphthalene sulfonic acid sodium salt and 20% 2- naphthalene SULFONIC acid sodium salt (Shanghai Shen Li Chemical Factory) are added at a temperature below 45C and the mixture is stirred for 15 minutes at 40-45C followed by the rapid addition of 3.2 G para formaldehyde. The reaction mixture is stirred for one hour at 58-60C then poured into 2. 5 1 ice water. The violet precipitate is stirred for 1 hours at 5-20C, then filtered. The violet press cake is washed with water to a pH of about 2.5 and kept as presscake. About 0.5 G of the press cake are RESLURRIED in 20 mi hot water yielding a red colored liquid which is filtered through paper to remove little aggregated material. The filtrate is red and appears like a dye solution. However, the electron micrograph shows the quinacridone in nanosize particle form with an average particle size of 4 to 25 nm. A small sample of the violet presscake is further washed to a pH of 5 and dried and analytically tested by MALDI. When measured in positive mode, it shows as main component quinacridone (m/z 314 peak), and only a trace of naphthalene SULFONIC acid methyl quinacridone (m/z 535 peak) is found as shown in Figure 1. When measured in negative mode, again the quinacridone is visible (m/z 312 peak) and the polymeric structure of the naphthalene sulfonic acid-formaldehyde polymer is clearly visible with the main molecular weight peaks at 428,649, 870,1091, 1312, 1534,1755 and 1976. The negative mode MALDI spectrum is shown in Figure 2.
 

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