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Succinimidyl 4-(N-maleimidomethyl)cyclohexanecarboxylate

HCID 125175
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
64987-85-5
Standard SMILES
O=C(ON1C(=O)CCC1=O)C1CCC(CN2C(=O)C=CC2=O)CC1
InChIKey
JJAHTWIKCUJRDK-UHFFFAOYSA-N
Molecular formula
C16H18N2O6
Average molar mass
334.32 g/mol
Monoisotopic mass
334.1164863

Overview

Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate is an N-hydroxysuccinimide ester derived from 4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid. It is a N-hydroxysuccinimide ester and a member of maleimides.

Names & identifiers

Preferred name
Succinimidyl 4-(N-maleimidomethyl)cyclohexanecarboxylate
IUPAC
(2,5-dioxopyrrolidin-1-yl) 4-[(2,5-dioxopyrrol-1-yl)methyl]cyclohexane-1-carboxylate
English name
SMCC crosslinker
Molecular formula
C16H18N2O6
Molecular weight
334.32

Names & synonyms

64987-85-5N-Smc-carboxylateB357P1G1IFN-(4-Carboxycyclohexylmethyl)maleimide N-hydroxysuccinimide esterN-Hydroxysuccinimidyl 4-(N-maleimidomethylcyclohexane)-1-carboxylateDTXSID30215307N-Succinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid1H-Pyrrole-2,5-dione, 1-((4-(((2,5-dioxo-1-pyrrolidinyl)oxy)carbonyl)cyclohexyl)methyl)-Succinimidyl 4-(N-maleimidomethyl)cyclohexanecarboxylateSMCC compoundRefChem:394650DTXCID90137798
Show more names
N-Succinimidyl 4-(maleimidomethyl)cyclohexanecarboxylate, SMCCNSC 344483LKAR3-RM1SMCC,98%SMCC[573114]25MG/100MG/10G
SMCC71875-81-52,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylateTRANS-4-(MALEIMIDOMETHYL)CYCLOHEXANECARBOXYLIC ACID-NHSN-Succinimidyl 4-(Maleimidomethyl)cyclohexane-1-carboxylateSMCC crosslinkerN-Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylatetrans-2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate

Properties

Computed structural properties

XLogP
-0.1
Topological polar surface area
101 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
6
Rotatable bonds
5
Heavy atoms
24
Formal charge
0
Complexity
598

Physicochemical properties

Melting point
180 · 180-182 °C (lit.)
Boiling point
501.7 · 501.7±42.0 °C(Predicted)
Density
1.42 · 1.42±0.1 g/cm3(Predicted)
storage temp.
-20 °C · -20°C
solubility
50 mg/mL · chloroform: 50 mg/mL
form
powder
pka
-2.24 · -2.24±0.20(Predicted)
color
White to Off-White
Sensitive
Moisture & Light Sensitive
BRN
1555271 · 1555271
InChI
InChI=1S/C16H18N2O6/c19-12-5-6-13(20)17(12)9-10-1-3-11(4-2-10)16(23)24-18-14(21)7-8-15(18)22/h5-6,10-11H,1-4,7-9H2
InChIKey
JJAHTWIKCUJRDK-UHFFFAOYSA-N
SMILES
C1(C(ON2C(=O)CCC2=O)=O)CCC(CN2C(=O)C=CC2=O)CC1
CAS DataBase Reference
64987 · 64987-85-5(CAS DataBase Reference)
FDA UNII
357 P1G1IF · B357P1G1IF

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 82 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

Hazard information

Hazard Classes and Categories · 2 items

Skin Irrit. 2 (100%)

Skin Irrit. 2 (100%)

Safety data

F
10-21
PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
hs_code
29280000
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26-36-60-37
Storage Class
11 - Combustible Solids
Hazard statements
H315-H319-H335
Precautionary statements
P261-P280a-P304+P340-P305+P351+P338-P405-P501a

Chemistry & industry

Applications · 3 items

DescriptionSMCC crosslinker is a hetero-bifunctional crosslinker that contain N-hydroxysuccinimide (NHS) ester and maleimide groups that allow covalent conjugation of amine- and sulfhydryl-containing molecules. SMCC crosslinker must be dissolved in an organic solvent, such as DMSO or DMF, and then can be added to an aqueous crosslinking reaction. SMCC crosslinking reagent is permeable across the lipid bilayer of the cell membrane and can be used to crosslink intracellular proteins and peptides.

UsesA sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent. It conjugates anti-digoxin F(abTaIII)2 fragments to l-B-galactosidase. Conjugates hIgG to alkaline phosphatase.Spacer Arm: 11.6 Angstroms.

General Description4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester (SMCC) is a heterobifunctional cross-linking reagent incorporating an extended spacer with amine and sulfhydryl reactivity. It is typically coupled initially to molecules containing primary amine by amide bond buffered at pH 7.5 (6.5-8.5). The second coupling is specific for molecules containing free sulfhydryl by thioether linkage buffered at pH 6.8 (6.5-7.0). SMCC contains nine atom linker. An extended aliphatic spacer stabilizes the maleimide prior to coupling compared to aromatic spacers.

Upstream & downstream products

Downstream products

Doxorubicin-SMCC

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.

Related reactions

12 records
New reaction record
HRID 260225 reaction equation
HRID 260225As reactantuspto-grants-1996_06
HRID 330754 reaction equation
HRID 330754As productAs reactantuspto-grants-2014_11
HRID 526284 reaction equation
HRID 526284As productAs reactantuspto-grants-2016_05
HRID 538911 reaction equation
HRID 538911As reactantuspto-grants-2014_10
HRID 574010 reaction equation
HRID 574010As reactantuspto-grants-2015_05
HRID 628598 reaction equation
HRID 628598As productAs reactantuspto-grants-2016_04
HRID 1458504 reaction equation
HRID 1458504As reactantuspto-grants-1998_12
HRID 1458505 reaction equation
HRID 1458505As reactantuspto-grants-1998_12
Page 1 of 2

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
64987-85-5
PubChem CID
125175
DTXSID
DTXSID30215307
ChEBI
CHEBI:63174
UNII
B357P1G1IF
EC Number
613-734-7、694-914-2
Nikkaji
J416.284F、J555.938C
UNSPSC Code
41116133 · 41116133
NACRES
7 · NC.07
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
26 · 26-36-60-37
WGK Germany
3 · 3
F
10 · 10-21
HS Code
29280000 · 29280000
Storage Class
11 · 11 - Combustible Solids
+86-0571-88938639 17705817739 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
北京安司莫森技术有限公司010-82954736 13391601435 · [email protected]
上海超悦化学科技有限公司(原上海斯比德化学)21-65679720 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
北京华威锐科化工有限公司0757-86329057 18934348241 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
阿法埃莎(中国)化学有限公司400-6106006 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海钰康生物科技有限公司+86-18930848214 +86-021-56762820 · [email protected]
上海相辉医药科技有限公司13761987713 · [email protected]
Zhejiang J&C Biological Technology Co.,Limited+1-2135480471 · [email protected]
上海瀚香生物科技有限公司177-54423994 17754423994 · [email protected]
ChemPep, Inc.+1 (888) 615-9178 / (561) 791-8787 · [email protected]
济南精合医药科技有限公司0531-88811783 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
河南多贝化工有限公司0370-2785118 17550508557 · [email protected]
上海源叶生物科技有限公司13636370518 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
深圳市茵诺圣生物科技有限公司0755-28351685 18503098468 · [email protected]
深圳康特腾科技有限公司86-0755-86635001 · [email protected]
上海睿升化工科技有限公司+86-021-50935922
上海金赛生物科技有限公司189-1821-4718 18918214718
天津卡普希科技有限公司022-66211079 13212288319 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
上海昶衍化工科技有限公司021-20242659 18930833303 · [email protected]
苏州宏雄生物科技有限公司18051745768
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
海杰亚(成都)医药科技有限公司028-84502008 13568869383 · [email protected]
上海笛柏生物科技有限公司400-008-9730,021-54359730 400-008-9730 · [email protected]
CovaChem, LLC.+1815.714.8421 (direct) · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
湖南华腾制药有限公司400-8592883 · [email protected]
上海馨远医药科技有限公司021-24206007 13764915196 · [email protected]
山东君泰药业有限公司15006412179 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
赫利森(厦门)生物科技有限公司0592-5667290 18649641090
上海寰川实业有限公司021-61478794 · [email protected]
上海嵩爰化工科技有限公司010-1234567 18521000990 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
ALB Technology Limited702-983-3769 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]

Additional notes

DefinitionChEBI: Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate is an N-hydroxysuccinimide ester derived from 4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid. It is a member of maleimides and a N-hydroxysuccinimide ester.