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Chemical Structure| 2885-00-9 Chemical Structure| 2885-00-9

Structure of 1-Octadecanethiol
CAS No.: 2885-00-9

Chemical Structure| 2885-00-9

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Product Details of [ 2885-00-9 ]

CAS No. :2885-00-9
Formula : C18H38S
M.W : 286.56
SMILES Code : CCCCCCCCCCCCCCCCCCS
English Name :Octadecane-1-thiol
MDL No. :MFCD00004886
InChI Key :QJAOYSPHSNGHNC-UHFFFAOYSA-N
Pubchem ID :17905

Safety of [ 2885-00-9 ]

Computational Chemistry of [ 2885-00-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 19
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 16
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 96.57
TPSA ?

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

38.8 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

5.1
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

9.17
Log Po/w (WLOGP)?

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

7.18
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.

6.01
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

7.29
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

6.95

Water Solubility

Log S (ESOL):?

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

-6.34
Solubility 0.000132 mg/ml ; 0.000000459 mol/l
Class?

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

Poorly soluble
Log S (Ali)?

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

-9.88
Solubility 0.0000000376 mg/ml ; 0.0000000001 mol/l
Class?

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

Poorly 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

-7.25
Solubility 0.000016 mg/ml ; 0.0000000557 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

Low
BBB permeant?

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

No
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

No
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.

-1.54 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

1.0
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

1.0
Egan?

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

1.0
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

3.0
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<2.0
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)

3.4

Application In Synthesis of [ 2885-00-9 ]

* 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 [ 2885-00-9 ]

[ 2885-00-9 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 32980-25-9 ]
  • [ 2885-00-9 ]
  • [ 155800-04-7 ]
YieldReaction ConditionsOperation in experiment
58% With dmap; dicyclohexyl-carbodiimide In dichloromethane for 18h; Ambient temperature;
  • 2
  • [ 2885-00-9 ]
  • [ 13380-67-1 ]
  • [ 1596302-56-5 ]
YieldReaction ConditionsOperation in experiment
91% With cetyltrimethylammonim bromide; In water; at 20℃; for 1h;Green chemistry; General procedure: To a 100-mL round-bottom flask containing (40 mL) of distilled water, wereadded CTAB or CPB (10 mmol%) and stirred at room temperature. To this mixture1- dodecanethiol (0.35 g, 1.56 mmol) was added in one portion, followed byN-phenylmaleimide (1) (0.3 g, 1.56 mmol) added portionwise. Stirring was continuedfor an additional 1 h at room temperature. As the reaction completed (monitoredby thin-layer chromatography, TLC) the precipitated product was collected by vacuumfiltration and dried at room temperature. Thereafter it was crystallized fromethanol / ethyl acetate as a white crystalline solid.
  • 3
  • [ 2885-00-9 ]
  • [ 593-45-3 ]
YieldReaction ConditionsOperation in experiment
85% With molybdenum hexacarbonyl In acetone at 120℃; for 6h; Inert atmosphere; Molybdenum-Mediated Desulfurization of Thiols (1mmol Scale); Typical Procedure General procedure: A mixture of 2-mercapto-N-methyl-N-phenylbenzamide(1a) (243 mg, 1.00 mmol), Mo(CO)6 (264 mg, 1.00 mmol),and acetone (10.0 mL) in a pressure-resistant glass tube wasstirred at 120 °C for 6 h. The mixture was filtered through ashort pad of Celite and the precipitate was washed withEtOAc (200 mL). The solvent was removed in vacuo and theresidue was subjected to column chromatography on silicagel (hexane- EtOAc, 3:1) to give N-methyl-Nphenylbenzamide(2a) (154 mg, 73%) as a yellow solid.
  • 4
  • [ 2885-00-9 ]
  • [ 1805773-37-8 ]
  • [ 1805774-14-4 ]
YieldReaction ConditionsOperation in experiment
85% In 1,2-dichloro-ethane at 80℃; Schlenk technique; Prepatation of disulfides (1a-e,1f-q) General procedure: A 25 mL Shlenk tube charged with thiol (2.0 mmol) and N-(difluoromethylthio)phthalimide (3.0 mmol) was added 1, 2-dichloroethane (6.0 mL). The mixture wasstirred at 80 oC for 16-24 h. The solvent was removed under vacuum and the residuewas purified by flask column chromatography (petroleum) to givedifluoromethyl-substituted dithioether.
 

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