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DJ2830000

Molecular FormulaC₂₇H₃₃NO₄
Average mass435.555 Da
Monoisotopic mass435.240967 Da
ChemSpider ID94753

- 6 of 6 defined stereocentres

More details:

Names and Synonyms
Database ID(s)

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(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)-on [German] [ACD/IUPAC Name]

(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 [ACD/IUPAC Name]

(2R,4bS,6aS,12bS,12cR,14aS)-4b-Hydroxy-2-(2-hydroxy-2-propanyl)-12b,12c-diméthyl-5,6,6a,7,12,12b,12c,13,14,14a-décahydro-2H-chroméno[5',6':6,7]indéno[1,2-b]indol-3(4bH)-one [French] [ACD/IUPAC Name]

(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

1233509-81-3 [RN]

200-835-2 [EINECS]

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)- [ACD/Index Name]

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)-

3T9U9Z96L7

57186-25-1 [RN]

More...

DJ2830000

MFCD00083464

Paxilline

(+)-paxilline

(1S,2R,5S,7R,11S,14S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0^2,11.0^5,10.0^16,24.0^17,22]tetracosa-9,16(24),17,19,21-pentaen-8-one

(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-[1]benzopyrano[5',6':6,7]indeno[1,2-b]indol-3(4bH)-one

(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

[57186-25-1] [RN]

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-, (2-α,4b-β,6a-α,12b-β,12c-α,14a-β)-

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-, (2-α,4b-β,6a-α,12b-β,12c-α,14a-β)-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)-

5,6,6a,7,12,12bS,12cR,13,14,14aS-decahydro-4bS-hydroxy-2R-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-2H-1-benzopyrano[5?,6?:6,7]indeno[1,2-b]indole-3(4bH)-one

5,6,6a,7,12,12bS,12cR,13,14,14aS-decahydro-4bS-hydroxy-2R-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-2H-1-benzopyrano[5’,6’:6,7]indeno[1,2-b]indole-3(4bH)-one

5,6,6a,7,12,12bS,12cR,13,14,14aS-decahydro-4bS-hydroxy-2R-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-2H-1-benzopyrano[5Õ,6Õ:6,7]indeno[1,2-b]indole-3(4bH)-one

57186-25-1_x000B

BSPBio_001427

cid_105008

IDI1_033897

paxiline

paxillin

Paxilline from Penicillium paxilli

Paxilline, Penicillium paxilli

Paxillinemissing

Spectrum5_001975

UNII:3T9U9Z96L7

UNII-3T9U9Z96L7

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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

Bio1_000128 [DBID]

Bio1_000617 [DBID]

Bio1_001106 [DBID]

Bio2_000147 [DBID]

Bio2_000627 [DBID]

BRN 5317894 [DBID]

C13782 [DBID]

CBiol_001842 [DBID]

KBio2_000147 [DBID]

KBio2_002715 [DBID]

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Experimental data
Predicted - ACD/Labs
Predicted - EPISuite
Predicted - ChemAxon
Predicted - Mcule

Spectroscopy
- Lambda Max:
  
  280 FooDB FDB002165
Experimental Physico-chemical Properties
- Experimental Melting Point:
  
  252 °C FooDB FDB002165
- Experimental Solubility:
  
  Soluble to 100 mM in DMSO and to 20 mM in ethanol Tocris Bioscience 2006

Miscellaneous

Chemical Class:

Bio Activity:

ATPase Tocris Bioscience 2006

ATPases/GTPases Tocris Bioscience 2006

Cell signaling/Ca2+ signaling/Ca2+-ATPase (SERCA) Hello Bio HB1056

Enzymes Tocris Bioscience 2006

Enzymes/ATPase / GTPase/Ca2+-ATPase (SERCA) Hello Bio HB1056

Ion channels/Voltage-gated ion channel/Potassium Channels/Calcium activated (KCa) Hello Bio HB1056

Potent blocker of high-conductance Ca2+-activated K+ (BKCa, KCa1.1) channels. Binds to the ?-subunit of BKCa (Ki = 1.9 nM for block of currents in ?-subunit-expressing oocytes) and enhances binding of charybdotoxin to BKCa channels in vascular smooth muscle. Also inhibits sarco/endoplasmic reticulum Ca2+-ATPase (IC50 = 5 - 50 ?M). Tocris Bioscience 2006

Potent blocker of high-conductance Ca2+-activated K+ (BKCa, KCa1.1) channels. Binds to the alpha-subunit of BKCa (Ki = 1.9 nM for block of currents in alpha-subunit-expressing oocytes) and enhances binding of charybdotoxin to BKCa channels in vascular smooth muscle. Also inhibits sarco/endoplasmic reticulum Ca2+-ATPase (IC50 = 5 - 50 muM). Tocris Bioscience 2006

Potent, reversible and selective KCa channel inhibitor (Ki = 1.9 nM at ?-subunit). Also sarco/endoplasmic reticulum Ca2+ ATPase (SERCA) inhibitor (IC50 = 5-50 ÂµM). Indole alkaloid mycotoxin from Penicillium paxilli. Displays anticonvulsant properties. Hello Bio HB1056

Potent, reversible and selective KCa channel inhibitor (Ki = 1.9 nM at Å¾Â¤-subunit). Also sarco/endoplasmic reticulum Ca2+ ATPase (SERCA) inhibitor (IC50 = 5-50 Ã´â€˜M). Indole alkaloid mycotoxin from Penicillium paxilli. Displays anticonvulsant properties. Hello Bio HB1056

Potent, reversible, selective KCa channel inhibitor. Also SERCA inhibitor. Hello Bio HB1056

SERCA ATPase blocker. Also potent BKCa channel blocker Tocris Bioscience 2006

Type/Biochemicals & small molecules/Antagonists & inhibitors Hello Bio HB1056

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density:	1.3±0.1 g/cm³
Boiling Point:	648.8±55.0 °C at 760 mmHg
Vapour Pressure:	0.0±2.0 mmHg at 25°C
Enthalpy of Vaporization:	100.5±3.0 kJ/mol
Flash Point:	346.2±31.5 °C
Index of Refraction:	1.661
Molar Refractivity:	122.6±0.4 cm³
#H bond acceptors:	5
#H bond donors:	3
#Freely Rotating Bonds:	1
#Rule of 5 Violations:	0

ACD/LogP:	3.77
ACD/LogD (pH 5.5):	3.87
ACD/BCF (pH 5.5):	512.93
ACD/KOC (pH 5.5):	3030.13
ACD/LogD (pH 7.4):	3.87
ACD/BCF (pH 7.4):	512.93
ACD/KOC (pH 7.4):	3030.13
Polar Surface Area:	83 Å²
Polarizability:	48.6±0.5 10^-24cm³
Surface Tension:	62.8±5.0 dyne/cm
Molar Volume:	331.7±5.0 cm³

Predicted data is generated using the US Environmental Protection Agency�s EPISuite™

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  4.13

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  580.71  (Adapted Stein & Brown method)
    Melting Pt (deg C):  250.30  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.41E-016  (Modified Grain method)
    Subcooled liquid VP: 1.52E-013 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  0.5445
       log Kow used: 4.13 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  31.807 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Vinyl/Allyl Ketones
       Vinyl/Allyl Ethers
       Vinyl/Allyl Alcohols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.88E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.694E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.13  (KowWin est)
  Log Kaw used:  -14.440  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.570
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.4814
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.2821  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.5051  (weeks-months)
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0927
   Biowin6 (MITI Non-Linear Model):   0.0012
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.4070
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  2.03E-011 Pa (1.52E-013 mm Hg)
  Log Koa (Koawin est  ): 18.570
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.48E+005 
       Octanol/air (Koa) model:  9.12E+005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 339.7912 E-12 cm3/molecule-sec
      Half-Life =     0.031 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    22.664 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.137500 E-17 cm3/molecule-sec
      Half-Life =     1.007 Days (at 7E11 mol/cm3)
      Half-Life =     24.179 Hrs
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1125
      Log Koc:  3.051 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 2.481 (BCF = 302.8)
       log Kow used: 4.13 (estimated)

 Volatilization from Water:
    Henry LC:  8.88E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.376E+013  hours   (5.733E+011 days)
    Half-Life from Model Lake : 1.501E+014  hours   (6.255E+012 days)

 Removal In Wastewater Treatment:
    Total removal:              36.33  percent
    Total biodegradation:        0.37  percent
    Total sludge adsorption:    35.96  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.00121         0.733        1000       
   Water     4.31            4.32e+003    1000       
   Soil      93.1            8.64e+003    1000       
   Sediment  2.6             3.89e+004    0          
     Persistence Time: 7.29e+003 hr

Click to predict properties on the Chemicalize site

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DJ2830000

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Experimental Melting Point:

Experimental Solubility:

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