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Chemical Structure| 768-95-6 Chemical Structure| 768-95-6

Structure of 1-Adamantanol
CAS No.: 768-95-6

Chemical Structure| 768-95-6

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Product Details of [ 768-95-6 ]

CAS No. :768-95-6
Formula : C10H16O
M.W : 152.23
SMILES Code : OC12CC3CC(C2)CC(C3)C1
MDL No. :MFCD00074729
InChI Key :VLLNJDMHDJRNFK-UHFFFAOYSA-N
Pubchem ID :64152

Safety of [ 768-95-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H315-H319-H335-H228
Precautionary Statements:P240-P210-P264-P280-P370+P378-P337+P313
Class:4.1
UN#:1325
Packing Group:

Computational Chemistry of [ 768-95-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 45.04
TPSA ?

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

20.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.12
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

2.14
Log Po/w (WLOGP)?

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

1.95
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.

2.45
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

2.15
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.16

Water Solubility

Log S (ESOL):?

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

-2.13
Solubility 1.12 mg/ml ; 0.00738 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-2.2
Solubility 0.968 mg/ml ; 0.00636 mol/l
Class?

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

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

-1.35
Solubility 6.74 mg/ml ; 0.0443 mol/l
Class?

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

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

No
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.

-5.71 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

2.0
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

0.0 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)

3.69

Application In Synthesis of [ 768-95-6 ]

* 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 [ 768-95-6 ]

[ 768-95-6 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 75-76-3 ]
  • [ 768-95-6 ]
  • [ 702-79-4 ]
  • [ 281-23-2 ]
  • [ 1687-36-1 ]
  • [ 707-35-7 ]
  • [ 768-91-2 ]
  • 3
  • [ 39998-25-9 ]
  • [ 768-95-6 ]
  • [ 145958-61-8 ]
  • 4
  • [ 768-95-6 ]
  • [ 34334-96-8 ]
  • 1-(1-adamantyl)-5-methyl-3-nitropyrazole [ No CAS ]
  • 4-(1-adamantyl)-5-methyl-3-nitropyrazole [ No CAS ]
  • 1,4-di(1-adamantyl)-5-methyl-3-nitropyrazole [ No CAS ]
  • 5
  • [ 768-95-6 ]
  • [ 1835-65-0 ]
  • [ 921206-52-2 ]
  • 7
  • [ 15231-91-1 ]
  • [ 768-95-6 ]
  • [ 128272-29-7 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; In diethyl ether; n-heptane; dichloromethane; (a) Preparation of 3-(1-adamantyl)-6-bromo-2-naphthol 56 g (0.25 mol) of 6-bromo-2-naphthol, 38.2 g (0.25 mol) of 1-adamantanol and 500 ml of a mixture of dichloromethane and heptane (40/60) were introduced into a round-bottomed flask. 15 ml of concentrated sulfuric acid were added and the reaction mixture was stirred at room temperature for 48 hours. The solid was filtered off, washed with heptane (3*100 ml) and dissolved in ethyl ether and the organic phase was washed with water, separated by settling, dried over magnesium sulfate and evaporated. 60.1 g (67%) of the expected compound were collected, which compound had a melting point of 215-6 C.
With hydrogenchloride; In n-heptane; dichloromethane; water; (a) Synthesis of 7-(1-adamantyl)-6-hydroxy-2-bromonaphthalene: 22.3 g (0.1 mol) of 6-bromo-2-naphthol, 15.2 g (0.1 mol) of 1-adamantanol and 100 ml of dichloromethane were introduced into a round-bottomed flask. 5.5 ml of concentrated hydrochloric acid were added and the mixture was stirred at room temperature for twelve hours. The mixture was evaporated to dryness and the residue was taken up in water and neutralized with sodium bicarbonate. The resulting mixture was extracted with ethyl acetate and the organic phase was separated out after settling of the phases had taken place, dried over magnesium sulfate and evaporated. The residue obtained was triturated in a mixture of dichloromethane and heptane (30/70), filtered and dried. 19 g (53%) of the expected compound, with a melting point of 215-6 C., were collected.
  • 8
  • [ 6154-04-7 ]
  • [ 768-95-6 ]
  • 1-(1-adamantyl)-5-amino-3-methyltetrazol-3-ium perchlorate [ No CAS ]
  • 9
  • [ 33893-89-9 ]
  • [ 768-95-6 ]
  • 2-[2-(adamantan-1-yl)-2H-tetrazol-5-yl]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With sulfuric acid; at 20℃; for 0.666667h; General procedure: Compound 3a-3j, 10 mmol, and adamantan-1-ol, 10 mmol, were dissolved in 25 mL of 94% sulfuric acid. The mixture was kept for 40 min at room temperature and poured into 150 mL of an ice-water mixture. The product was extracted with chloroform (2*20 mL), the extract was washed with a 5% aqueous solution of Na2CO3 and with water and dried over anhydrous MgSO4, and the solvent was evaporated under reduced pressure.
  • 10
  • [ 768-95-6 ]
  • [ 16687-60-8 ]
  • 2-(adamantan-1-yl)-5-(4-nitrophenyl)-2H-tetrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With sulfuric acid; at 20℃; for 0.666667h; General procedure: Compound 3a-3j, 10 mmol, and adamantan-1-ol, 10 mmol, were dissolved in 25 mL of 94% sulfuric acid. The mixture was kept for 40 min at room temperature and poured into 150 mL of an ice-water mixture. The product was extracted with chloroform (2*20 mL), the extract was washed with a 5% aqueous solution of Na2CO3 and with water and dried over anhydrous MgSO4, and the solvent was evaporated under reduced pressure.
 

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Technical Information

Categories

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