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Spdph

HCID 157808
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Basic information

CAS
158913-22-5
Standard SMILES
O=C(CCSSc1ccccn1)NCCCCCC(=O)ON1C(=O)CCC1=O
InChIKey
QYEAAMBIUQLHFQ-UHFFFAOYSA-N
Molecular formula
C18H23N3O5S2
Average molar mass
425.5 g/mol
Monoisotopic mass
425.10791319

Names & identifiers

Preferred name
Spdph
IUPAC
(2,5-dioxopyrrolidin-1-yl) 6-[3-(pyridin-2-yldisulfanyl)propanoylamino]hexanoate
English name
Succinimidyl 6-[3-(2-Pyridyldithio)propionamido]hexanoate
Molecular formula
C18H23N3O5S2
Molecular weight
425.52

Names & synonyms

158913-22-5SPDPHDTXSID70166541N-Succinimidyl 6-(3-(2-pyridyldithio)propionamido)hexanoateRefChem:408360DTXCID8089032SPDP-C6-NHS esterSuccinimidyl 6-[3-(2-Pyridyldithio)propionamido]hexanoateLC-SPDP CrosslinkerMFCD00083163N-Succinimydyl-(3-(2-Pyridyldithio)propionate) Hexanate2,5-dioxopyrrolidin-1-yl 6-(3-(pyridin-2-yldisulfaneyl)propanamido)hexanoate
Show more names
SPDP-C6-NHS(2,5-dioxopyrrolidin-1-yl) 6-[3-(2-pyridyldisulfanyl)propanoylamino]hexanoate
(2,5-dioxopyrrolidin-1-yl) 6-[3-(pyridin-2-yldisulfanyl)propanoylamino]hexanoate(Succinimidyl 6-[3-(2-pyridyldithio)propionamido]hexanoate)succinimidyl 6-(3-[2-pyridyldithio]-propionamido)hexanoateN-[6-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-6-oxohexyl]-3-(2-pyridinyldithio)propanamideSuccinimidyl 6-[3-(2-pyridylthio)propionamidohexanoateC18H23N3O5S2Hexanoic acid, 6-[[1-oxo-3-(2-pyridinyldithio)propyl]amino]-, 2,5-dioxo-1-pyrrolidinyl esterN-(6-((2,5-Dioxo-1-pyrrolidinyl)oxy)-6-oxohexyl)-3-(2-pyridinyldithio)propanamide

Database identifiers

CAS
158913-22-5
PubChem CID
157808
DTXSID
DTXSID70166541
EC Number
968-854-5
Nikkaji
J850.936K

Properties

Computed structural properties

XLogP
1
Topological polar surface area
156 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
8
Rotatable bonds
13
Heavy atoms
28
Formal charge
0
Complexity
545

Physicochemical properties

Melting point
82 · 82-84°C
Density
1.36 · 1.36±0.1 g/cm3(Predicted)
storage temp.
2 · 2-8°C
solubility
100 mg/mL · DMSO: 100 mg/mL (235.01 mM)
form
Solid
pka
15.67 · 15.67±0.46(Predicted)
color
White
InChI
1S/C18H23N3O5S2/c22-14(10-13-27-28-15-6-3-5-12-20-15)19-11-4-1-2-7-18(25)26-21-16(23)8-9-17(21)24/h3,5-6,12H,1-2,4,7-11,13H2,(H,19,22)
InChIKey
QYEAAMBIUQLHFQ-UHFFFAOYSA-N
SMILES
O=C1CCC(N1OC(CCCCCNC(CCSSC2=CC=CC=N2)=O)=O)=O
UNSPSC Code
12352200 · 12352200
NACRES
22 · NA.22
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
261 · P261-P280-P271

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 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)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Safety data

wgk
WGK 3
hs_code
2928009090
Signal word
Warning
Symbol(GHS)
GHS07
Storage Class
11 - Combustible Solids
Hazard statements
H315-H319-H335
Precautionary statements
P261-P280-P271

Chemistry & industry

Applications · 3 items

DescriptionSPDP-C6-NHS ester contains a disulfide bond which is cleavable upon reduction. The NHS ester is reactive toward primary amine and sulfhydryl groups. SPDP-C6-NHS ester is commonly used for bioconjugation and reversible crosslinkings.

UsesA sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent.

General DescriptionThe amine-reactive portion of SPDP reagents is the N-hydroxysuccinimide (NHS) ester. Reactions are most commonly performed in phosphate, carbonate/bicarbonate, or borate buffers at pH 7-8. Other buffers can be used provided they do not contain primary amines (or thiols or disulfide reducing reagents – see discussion of the sulfhydryl reactivity). The rate of reaction and degradation by hydrolysis increases with increasing pH; for example, the half-life of the NHS ester is several hours at pH 7 and less than 10 minutes at pH 9. NHS-ester reagents like SPDP and LC-SPDP have limited aqueous solubility and must be dissolved in organic solvent before adding them to a reaction mixture. Sulfo-NHS-ester reagents like Sulfo-LC-SPDP are water-soluble and can be added directly to aqueous reaction mixtures.

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Compound notes

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WGK Germany
3 · WGK 3
HS Code
2928009090 · 2928009090
Storage Class
11 · 11 - Combustible Solids