57186-25-1

57186-25-1 structure

Name: Paxilline
Chemical Name: Paxilline,(2R,4bS,6aS,12bS,12cR,14aS)-5,6,6a,7,12,12b,12c,13,14,14a-Decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-2H-pyrano[2'',3'':5',6']benz[1',2':6,7]indeno[1,2-b]indol-3(4bH)-one
CAS Number: 57186-25-1
Molecular Formula: C₂₇H₃₃NO₄
Molecular Weight: 435.555
Catalog: analytical chemistry Standard Food and cosmetics standards
Create Date: 2017-02-28 14:10:43
Modify Date: 2025-08-25 18:21:46
Paxilline is an indole alkaloid mycotoxin from Penicillium paxilli, acts as a potent BK channels inhibitor by an almost exclusively closed-channel block mechanism. Paxilline also inhibits the sarco/endoplasmic reticulum Ca2+ ATPase (SERCA) with IC50s between 5μM and 50μM for differing isoforms. Paxilline possesses significant anticonvulsant activity[1][2][3].

Name	Paxilline,(2R,4bS,6aS,12bS,12cR,14aS)-5,6,6a,7,12,12b,12c,13,14,14a-Decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-2H-pyrano[2'',3'':5',6']benz[1',2':6,7]indeno[1,2-b]indol-3(4bH)-one
Synonyms	2H-Pyrano(2'',3'':5',6')benz(1',2':6,7)indeno(1,2-b)indol-3(4bH)-one, 5,6,6a,7,12,12b,12c,13,14,14a-decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-, (2R,4bS,6aS,12bS,12cR,14aS)- PAXILINE 2H-1-Benzopyrano[5',6':6,7]indeno[1,2-b]indol-3(4bH)-one, 5,6,6a,7,12,12b,12c,13,14,14a-decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-, (2R,4bS,6aS,12bS,12cR,14aS)- PAXILLINE,PENICILLIUM PAXILLI DPNI-caged-GABA (2R,4bS,6aS,12bS,12cR,14aS)-4b-Hydroxy-2-(2-hydroxy-2-propanyl)-12b,12c-dimethyl-5,6,6a,7,12,12b,12c,13,14,14a-decahydro-2H-chromeno[5',6':6,7]indeno[1,2-b]indol-3(4bH)-one MFCD00083464 (2R,4bS,6aS,12bS,12cR,14aS)-4b-Hydroxy-2-(2-hydroxypropan-2-yl)-12b,12c-dimethyl-5,6,6a,7,12,12b,12c,13,14,14a-decahydro-2H-chromeno[5',6':6,7]indeno[1,2-b]indol-3(4bH)-one paxilline from penicillium paxilli Paxilline 1 Paxilline

Description	Paxilline is an indole alkaloid mycotoxin from Penicillium paxilli, acts as a potent BK channels inhibitor by an almost exclusively closed-channel block mechanism. Paxilline also inhibits the sarco/endoplasmic reticulum Ca2+ ATPase (SERCA) with IC50s between 5μM and 50μM for differing isoforms. Paxilline possesses significant anticonvulsant activity[1][2][3].
Related Catalog	Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel Research Areas >> Neurological Disease
Target	IC50: 5-50 μM (SERCA)[2], BK channel[1]
References	[1]. Zhou Y, et al. Paxilline inhibits BK channels by an almost exclusively closed-channel block mechanism. J Gen Physiol. 2014 Nov;144(5):415-40. [2]. Bilmen JG, et al. The mechanism of inhibition of the sarco/endoplasmic reticulum Ca2+ ATPase by paxilline. Arch Biochem Biophys. 2002 Oct 1;406(1):55-64. [3]. Sheehan JJ, et al. Anticonvulsant effects of the BK-channel antagonist paxilline. Epilepsia. 2009 Apr;50(4):711-20.

Density	1.3±0.1 g/cm3
Boiling Point	648.8±55.0 °C at 760 mmHg
Melting Point	252ºC
Molecular Formula	C₂₇H₃₃NO₄
Molecular Weight	435.555
Flash Point	346.2±31.5 °C
Exact Mass	435.240967
PSA	82.55000
LogP	3.77
Vapour Pressure	0.0±2.0 mmHg at 25°C
Index of Refraction	1.661
Storage condition	2-8°C
Water Solubility	Soluble in DMSO, acetone or chloroform.

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 41,1868,1988

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 41KEAL "Toxicology, Biochemistry and Pathology of Mycotoxins," Uraguchi, K. and M. Yamazaki, eds., New York, John Wiley & Sons, Inc., 1978 Volume(issue)/page/year: -,108,1978

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 41,1868,1988

Symbol	GHS05, GHS06
Signal Word	Danger
Hazard Statements	H301-H311-H315-H318-H331-H335
Precautionary Statements	P261-P280-P301 + P310-P305 + P351 + P338-P311
Personal Protective Equipment	Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes	T: Toxic;
Risk Phrases	R23/24/25
Safety Phrases	26-36/37/39-45
RIDADR	UN 2811 6
WGK Germany	3
RTECS	DJ2830000
Packaging Group	III
Hazard Class	6.1(b)
HS Code	29419090

Precursor 0
DownStream 2
12627-35-9 121998-08-1