[ CAS No. 72040-64-3 ] {[proInfo.proName]}

Name: 72040-64-3|6-(5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)hexanoic acid|95%
Brand: Ambeed
SKU: A291733
Rating: 94 (32 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 72040-64-3 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 72040-64-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 72040-64-3 ]

SDS Specification

Alternatived Products of [ 72040-64-3 ]

Product Details of [ 72040-64-3 ]

CAS No. :	72040-64-3	MDL No. :	MFCD00144853
Formula :	C₁₆H₂₇N₃O₄S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CMUGHZFPFWNUQT-HUBLWGQQSA-N
M.W :	357.47	Pubchem ID :	446905
Synonyms :	N-(+)-Biotinyl-6-aminohexanoic acid	Chemical Name :	6-(5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)hexanoic acid

Calculated chemistry of [ 72040-64-3 ]

Physicochemical Properties

Num. heavy atoms :	24
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.81
Num. rotatable bonds :	12
Num. H-bond acceptors :	4.0
Num. H-bond donors :	4.0
Molar Refractivity :	101.18
TPSA :	132.83 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.02 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.96
Log Po/w (XLOGP3) :	0.65
Log Po/w (WLOGP) :	0.71
Log Po/w (MLOGP) :	1.05
Log Po/w (SILICOS-IT) :	1.78
Consensus Log Po/w :	1.23

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.67
Solubility :	7.58 mg/ml ; 0.0212 mol/l
Class :	Very soluble
Log S (Ali) :	-3.02
Solubility :	0.345 mg/ml ; 0.000966 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.65
Solubility :	0.081 mg/ml ; 0.000226 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	4.02

Safety of [ 72040-64-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 72040-64-3 ]

* 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.

Upstream synthesis route of [ 72040-64-3 ]
Downstream synthetic route of [ 72040-64-3 ]

[ 72040-64-3 ] Synthesis Path-Upstream 1~8

1
[ 6066-82-6 ]
[ 72040-64-3 ]
[ 72040-63-2 ]

Reference： [1] Bioconjugate Chemistry, 2010, vol. 21, # 9, p. 1642 - 1655

2
[ 58-85-5 ]
[ 60-32-2 ]
[ 72040-64-3 ]

Reference： [1] Journal of the American Chemical Society, 2004, vol. 126, # 44, p. 14411 - 14418

3
[ 35013-72-0 ]
[ 60-32-2 ]
[ 72040-64-3 ]

Yield	Reaction Conditions	Operation in experiment
1.455 g	With sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 20℃; for 16 h;	ε-Aminocaproic acid (966mg, 8.4mmol) was dissolved in 30mL 1M aqueous NaHCO₃ solution. Then N-hydroxysuccinimidobiotin (3.09g) in 35mL DMF was added dropwise to the solution and the mixture was stirred at room temperature for 16h. The solution was concentrated under reduced pressure to remove partial solvent and 150mL aqueous citric acid (100g/L) was then added and stirred at 60°C for 30min. The precipitate was collected by filtration and washed with distilled water. The precipitate was dissolved in a mixture of isopropanol and water (8:2, v/v) and kept at 4°C to give pure 3 (1.455g, 50percent) as a yellowish crystal; IR cm⁻¹ (KBr): 3200–3500, 3070, 2932, 2859, 1696, 1644, 1543, 1475, 1391, 1324, 1265, 1118; ¹H NMR (600MHz, DMSO-d₆): δ 7.75 (1H, t, J=5.4Hz, C6–NH), 6.45 (1H, s, C13–NH), 6.38 (1H, s, C14–NH), 4.35–4.27 (1H, m, H-14), 4.12 (1H, m, H-13), 3.09 (1H, m, H-12), 3.00 (1H, m, H-6) 2.82 (1H, dd, J=12.4, 5.1Hz, H-15a), 2.57 (1H, d, J=12.4Hz, H-15b), 2.19 (2H, t, J=7.4Hz, H-2), 2.04 (2H, t, J=7.3Hz, H-8), 1.20–1.67 (14H, m). ¹³C NMR (150MHz, DMSO-d₆): δ 171.84 (C-1, C-7), 162.74 (C-16), 61.06 (C-13), 59.20 (C-14), 55.44 (C-12), 39.68 (C-15), 38.25 (C-6), 35.21 (C-8), 29.05 (C-2), 28.92, 28.21, 28.04, 26.04, 25.73, 25.36.

Reference： [1] Chemical Communications, 2009, # 33, p. 5030 - 5032
[2] European Journal of Medicinal Chemistry, 2014, vol. 71, p. 219 - 228
[3] RSC Advances, 2018, vol. 8, # 57, p. 32775 - 32793

4
[ 1306616-52-3 ]
[ 60-32-2 ]
[ 72040-64-3 ]

Reference： [1] Patent: US2012/232262, 2012, A1, . Location in patent: Page/Page column 3

5
[ 58-85-5 ]
[ 72040-64-3 ]

Reference： [1] Patent: US2012/232262, 2012, A1,
[2] European Journal of Medicinal Chemistry, 2014, vol. 71, p. 219 - 228
[3] Organic and Biomolecular Chemistry, 2016, vol. 14, # 32, p. 7676 - 7690
[4] RSC Advances, 2018, vol. 8, # 57, p. 32775 - 32793

6
[ 1926-80-3 ]
[ 72040-64-3 ]

Reference： [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2000, vol. 43, # 4, p. 309 - 322
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 15, p. 3591 - 3594

7
[ 120550-35-8 ]
[ 72040-64-3 ]

Reference： [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2000, vol. 43, # 4, p. 309 - 322

8
[ 60-32-2 ]
[ 72040-64-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 15, p. 3591 - 3594

[ 72040-64-3 ] Synthesis Path-Downstream 1~88

1
[ 7689-03-4 ]
[ 72040-64-3 ]
6-biotinylaminocaproic acid-(20s)-camptothecin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With dmap; diisopropyl-carbodiimide; In N,N-dimethyl-formamide; at 20℃; for 48h;Inert atmosphere;	General procedure: To a mixture of Biotin or 6-biotinylaminocaproic acid (0.3 mmol), camptothecin analogues (0.1 mmol) and DMF (2.5 mL) was added, 4-Dimethylaminopyridine (DMAP) (0.01 mmol) was added and N, N'-Diisopropylcarbodiimide) (DIC) (0.6 mmol) dropwise. The reaction mixture was stirred at room temperature for 2 days under N2. Solvent were removed under a reduced. The residue was purified on a silica gel chromatography (CHCl3:CH3OH = 15:1?9:1) to afford the product Biotin-(20s)-camptothecin (11). Yellow amorphous powder, yield 60percent;

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 234 - 237
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4846 - 4849

2
glycine rapamycin ester [ No CAS ]
[ 72040-64-3 ]
C₆₉H₁₀₇N₅O₁₇S [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 4715 - 4721

3
[ 56-41-7 ]
[ 72040-64-3 ]
(S)-2-{6-[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-propionic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 927 - 933

4
[ 61-90-5 ]
[ 72040-64-3 ]
(S)-4-Methyl-2-{6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-pentanoic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 927 - 933

5
[ 63-68-3 ]
[ 72040-64-3 ]
[ 217655-55-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 927 - 933

6
[ 56-85-9 ]
[ 72040-64-3 ]
(S)-4-Carbamoyl-2-{6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-butyric acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 927 - 933

7
[ 74-79-3 ]
[ 72040-64-3 ]
(S)-5-Guanidino-2-{6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-pentanoic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 927 - 933

8
[ 63-91-2 ]
[ 72040-64-3 ]
(S)-2-{6-[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-3-phenyl-propionic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 927 - 933

9
[ 912557-14-3 ]
[ 72040-64-3 ]
[(S)-2-((S)-3-Methyl-2-{6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-butyrylamino)-propionylamino]-acetic acid (2E,4E)-hexa-2,4-dienyl ester [ No CAS ]

Reference： [1]Chemistry - A European Journal,2006,vol. 12,p. 6095 - 6109

10
[ 861640-70-2 ]
[ 72040-64-3 ]
[ 861640-71-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 4200 - 4208

11
p-aminophenyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-nonulosyl-2-onic acid-(2->3)-β-D-galactopyranoside-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside [ No CAS ]
[ 72040-64-3 ]
[(6-biotinylamido)hexanoylamido]-phenyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-nonulosyl-2-onic acid-(2->3)-β-D-galactopyranoside-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside [ No CAS ]

Reference： [1]Carbohydrate Research,2007,vol. 342,p. 1244 - 1248

12
p-aminophenyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-nonulosyl-2-onic acid-(2->6)-β-D-galactopyranoside-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside [ No CAS ]
[ 72040-64-3 ]
[(6-biotinylamido)hexanoylamido]-phenyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-nonulosyl-2-onic acid-(2->6)-β-D-galactopyranoside-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside [ No CAS ]

Reference： [1]Carbohydrate Research,2007,vol. 342,p. 1244 - 1248

13
C₂₁H₂₂N₂O₂ [ No CAS ]
[ 72040-64-3 ]
C₃₇H₄₇N₅O₅S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4703 - 4707

14
[ 72040-64-3 ]
(S)-4-Methylsulfanyl-2-{6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-butyric acid 4-nitro-phenyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 927 - 933

15
[ 72040-64-3 ]
(S)-4-Methylsulfanyl-2-{6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 927 - 933

16
[ 72040-64-3 ]
[ 446878-26-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 927 - 933

17
[ 72040-64-3 ]
[ 446878-23-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 927 - 933

18
[ 72040-64-3 ]
[ 446878-21-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 927 - 933

19
[ 72040-64-3 ]
[ 446878-22-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 927 - 933

20
[ 72040-64-3 ]
[ 446878-24-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 927 - 933

21
[ 72040-64-3 ]
14-hydroxy-3β-{6-[5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido]hexanoyloxy}-5β,14β-card-20(22)-enolide [ No CAS ]

Reference： [1]Tetrahedron,2000,vol. 56,p. 9625 - 9632

22
[ 72040-64-3 ]
22-(4-benzoylbenzoyloxy)-14-hydroxy-3β-{6-[5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido]hexanoyloxy}-5β,14β-card-20(22)-enolide [ No CAS ]

Reference： [1]Tetrahedron,2000,vol. 56,p. 9625 - 9632

23
[ 1926-80-3 ]
[ 72040-64-3 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2000,vol. 43,p. 309 - 322
[2]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 3591 - 3594

24
[ 72040-64-3 ]
[ 223733-86-6 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1836 - 1841

25
[ 72040-64-3 ]
1-O-(α-D-galactopyranosyl)-2-<N-12-(6-(biotinoylamino)hexanoylamino)dodecanoylamino>-octadecanol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1836 - 1841

26
[ 72040-64-3 ]
(2S,3R)-1-O-(α-D-galactopyranosyl)-2-<N-12-(6-(biotinoylamino)hexanoylamino)dodecanoylamino>-1,3-octadecanediol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1836 - 1841

27
[ 72040-64-3 ]
(2S,3S,4R)-1-O-(β-D-galactopyranosyl)-2-<N-12-(6-(biotinoylamino)hexanoylamino)dodecanoylamino>-1,3,4-octadecanetriol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1836 - 1841

28
[ 72040-64-3 ]
(2S,3S,4R)-1-O-(α-D-galactopyranosyl)-2-<N-12-(6-(biotinoylamino)hexanoylamino)dodecanoylamino>-1,3,4-octadecanetriol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1836 - 1841

29
[ 648903-77-9 ]
[ 72040-64-3 ]
2-{4-[6-(biotinamido)hexanamido]phenylamino}-6-(2,6-dichlorophenyl)-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;N,N-dimethyl-formamide; In dichloromethane; for 12h;	2- (4-AMINOPHENYLAMINO)-6- (2, 6-DICHLOROPHENYL)-8-METHYL-8H-PYRIDO [2, 3-D] PYRIMIDIN-7- one, SKI DV1-10, (55 mg, 0.133 mmol), N- (+)-BIOTINYL-6-AMINOCAPROIC acid (57.2 mg, 0.160 mmol), 1- [3- (DIMETHYLAMINO) PROPYL]-3-ETHYLCARBODIIMIDE hydrochloride (123 mg, 0.64 mmol), and 4-dimethylaminopyridine (78 mg, 0.64 mmol) were combined in a 10 mL flame-dried round bottomed flask under argon. The solids were suspended in 5 mL of methylene chloride and a few drops of dimethylformamide. The solution was stirred for 12 hours. The reaction was poured into a separatory funnel containing 50 mL of methylene chloride. The organic layer was washed with three 50 mL portions of water and once with 50 mL of saturated brine. The organic layer was dried over magnesium sulfate, the drying agent removed by filtration and the solvent removed. The crude residue was purified by gradient silica gel column chromatography (0-15 percent 7M ammonia/ methanol in methylene chloride). The product containing fractions were combined and evaporated. The product was pure by standard analytical techniques.

Reference： [1]Patent: WO2004/63195,2004,A1 .Location in patent: Page 58

30
[ 883720-36-3 ]
[ 72040-64-3 ]
[ 883720-37-4 ]

Yield	Reaction Conditions	Operation in experiment
73.4%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 0.5h;	Benzophenone-biotin: N-(+)-Biotinyl-6-aminohexanoic acid (239 mg) and 4~benzoyl-L-phenylalanyl-6-aminoxehanoic acid methyl ester (237 mg) were dissolved in DMF, 230 mul of DIPEA were added to the reaction mixture, followed by 237 mg of HBTU. The reaction mixture was stirred at RT for 30 min. LC-MS analysis showed complete reaction. The solvent and excess of DIPEA were removed under high vacuum. The crude product was dissolved in CHCl3 and extracted 2X with 1percent HCl. Organic phase was separated, solvent was removed and the product was purified using rotary chromatography (SiO2 solid phase). Yield 325 mg (73.4percent).

Reference： [1]Patent: WO2007/41341,2007,A2 .Location in patent: Page/Page column 68

31
[ 72040-64-3 ]
[ 518-28-5 ]
[ 1041187-72-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 5815 - 5825

32
[ 5680-79-5 ]
[ 72040-64-3 ]
C₁₉H₃₂N₄O₅S [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 7119 - 7122

33
[ 1176084-23-3 ]
[ 1176084-10-8 ]
[ 72040-64-3 ]
C₁₃₃H₂₅₄N₂₂O₄₆S₆ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 11683 - 11685

34
C₃₀H₃₅N₂O₄Pol [ No CAS ]
[ 72040-64-3 ]
C₄₆H₆₀N₅O₇PolS [ No CAS ]