N3290

Sigma-Aldrich

NKH 477

≥98% (HPLC), powder

Synonym(s):
Colforsin dapropate hydrochloride, N,N-dimethyl-, (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-5-(acetyloxy)-3-ethenyldodecahydro-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-1H-naphtho[2,1-b]pyran-6-yl ester b-Alanine hydrochloride, 6-[3-(dimethylamino)propionyl]-forskolin
Empirical Formula (Hill Notation):
C27H43NO8·HCl
CAS Number:
Molecular Weight:
546.09
MDL number:
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 3 mg/mL, clear to slightly hazy (warmed)

storage temp.

2-8°C

SMILES string

Cl.CN(C)CCC(=O)O[C@@H]1[C@H](OC(C)=O)[C@@]2(C)O[C@](C)(CC(=O)[C@]2(O)[C@@]3(C)[C@@H](O)CCC(C)(C)[C@H]13)C=C

InChI

1S/C27H43NO8.ClH/c1-10-24(5)15-18(31)27(33)25(6)17(30)11-13-23(3,4)21(25)20(35-19(32)12-14-28(8)9)22(34-16(2)29)26(27,7)36-24;/h10,17,20-22,30,33H,1,11-15H2,2-9H3;1H/t17-,20-,21-,22-,24-,25-,26+,27-;/m0./s1

InChI key

VIRRLEDAYYYTOD-YHEOSNBFSA-N

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

NKH 477 is a potent, orally active adenylyl cyclase activator. It is a water soluble derivative of forskolin, and dose dependentyl increases cAMP and blocks potassium-induced contraction concetrations in smooth muscle strips (IC50 = 80 nM). NKH 477 causes relaxation of histamine treated guinea pig smooth muscle (IC50 = 32 nM).

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Preparation Note

A clear to slightly hazy solution is possible.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Precautionary Statements

RIDADR

UN 2811 6.1 / PGII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Mika Takarada-Iemata et al.
Journal of neurochemistry, 130(3), 374-387 (2014-04-05)
N-myc downstream-regulated gene 2 (Ndrg2) is a differentiation- and stress-associated molecule predominantly expressed in astrocytes in the CNS. In this study, we examined the expression and the role of Ndrg2 after cortical stab injury. We observed that Ndrg2 expression was...
Lakshmi T Sunkara et al.
Molecular immunology, 57(2), 171-180 (2013-10-22)
Host defense peptides (HDP) have both microbicidal and immunomodulatory properties. Specific induction of endogenous HDP synthesis has emerged as a novel approach to antimicrobial therapy. Cyclic adenosine monophosphate (cAMP) and butyrate have been implicated in HDP induction in humans. However...
Saw Marlar et al.
American journal of physiology. Cell physiology, 306(6), C598-C606 (2014-01-24)
Regulated urine concentration takes place in the renal collecting duct upon arginine vasopressin (AVP) stimulation, where subapical vesicles containing aquaporin-2 (AQP2) are inserted into the apical membrane instantly increasing water reabsorption and urine concentration. The reabsorped water exits via basolateral...
Li-Hua Hang et al.
Pharmacological reports : PR, 65(3), 710-716 (2013-08-21)
It has been shown that spinal PKA/CREB signaling pathway is involved in neuropathic and inflammatory pain, but its effects on bone cancer pain have not previously been investigated. The aim of this study was to examine the potential role of...
Chin-San Loo et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(42), 17119-17124 (2013-10-03)
In kidney collecting duct cells, filamentous actin (F-actin) depolymerization is a critical step in vasopressin-induced trafficking of aquaporin-2 to the apical plasma membrane. However, the molecular components of this response are largely unknown. Using stable isotope-based quantitative protein mass spectrometry...
Related Content
Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.
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