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(RS)-(11b,16a)-16,17-[Butylidenebis(oxy)]-11,21-dihydroxypregna-1,4-diene-3,20-dione

ChemSpider ID: 36566
Molecular Formula: C₂₅H₃₄O₆
Average mass: 430.533905 Da
Monoisotopic mass: 430.235535 Da
Systematic name

(4aR,4bS,5S,6aS,6bS,8R,9aR,10aS,10bS)-6b-Glycoloyl-5-hydroxy-4a,6a-dimethyl-8-propyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one
SMILES and InChIs

SMILES:

O=C(CO)[C@]25O[C@@H](O[C@@H]5C[C@H]1[C@H]4[C@H]([C@@H](O)C[C@@]12C)[C@]/3(/C=C\C(=O)\C=C\3CC4)C)CCC Copied

Std. InChI:

InChI=1S/C25H34O6/c1-4-5-21-30-20-11-17-16-7-6-14-10-15(27)8-9-23(14,2)22(16)18(28)12-24(17,3)25(20,31-21)19(29)13-26/h8-10,16-18,20-22,26,28H,4-7,11-13H2,1-3H3/t16-,17-,18-,20+,21+,22+,23-,24-,25+/m0/s1 Copied

Std. InChIKey:

VOVIALXJUBGFJZ-VXKMTNQYSA-N Copied
Cite this record
CSID:36566, http://www.chemspider.com/Chemical-Structure.36566.html (accessed 04:24, May 23, 2013) Copied

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

(4aR,4bS,5S,6aS,6bS,8R,9aR,10aS,10bS)-5-Hydroxy-6b-(hydroxyacetyl)-4a,6a-dimethyl-8-propyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-on

(4aR,4bS,5S,6aS,6bS,8R,9aR,10aS,10bS)-5-hydroxy-6b-(hydroxyacetyl)-4a,6a-dimethyl-8-propyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one

(4aR,4bS,5S,6aS,6bS,8R,9aR,10aS,10bS)-5-hydroxy-6b-(hydroxyacétyl)-4a,6a-diméthyl-8-propyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodécahydro-2H-naphto[2',1':4,5]indéno[1,2-d][1,3]dioxol-2-one

(4aR,4bS,5S,6aS,6bS,8R,9aR,10aS,10bS)-6b-Glycoloyl-5-hydroxy-4a,6a-dimethyl-8-propyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one [ACD/IUPAC Name]

(RS)-(11b,16a)-16,17-[Butylidenebis(oxy)]-11,21-dihydroxypregna-1,4-diene-3,20-dione

257-139-7 [EINECS]

2H-naphth[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one, 4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-5-hydroxy-6b-(2-hydroxyacetyl)-4a,6a-dimethyl-8-propyl-, (4aR,4bS,5S,6aS,6bS,8R,9aR,10aS,10bS)-

2H-naphth[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one, 4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-5-hydroxy-6b-(hydroxyacetyl)-4a,6a-dimethyl-8-propyl-, (4aR,4bS,5S,6aS,6bS,8R,9aR,10aS,10bS)-

(11β,16α)-16,17-(Butylidenebis(oxy))-11,21-dihydroxypregna-1,4-diene-3,20-dione

(4aR,4bS,5S,6aS,6bS,9aR,10aS,10bS)-5-hydroxy-6b-(hydroxyacetyl)-4a,6a-dimethyl-8-propyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one

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Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

S 1320 [DBID]

CCRIS 5230 [DBID]

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Properties

Predicted - ACD/Labs
Predicted - EPISuite
Predicted - ChemAxon

Predicted data is generated using the ACD/Labs’ ACD/PhysChem Suite, for more information see their website.

ACD/LogP:	3.204	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	3.20	ACD/LogD (pH 7.4):	3.20
ACD/BCF (pH 5.5):	160.32	ACD/BCF (pH 7.4):	160.32
ACD/KOC (pH 5.5):	1318.06	ACD/KOC (pH 7.4):	1318.06
#H bond acceptors:	6	#H bond donors:	2
#Freely Rotating Bonds:	6	Polar Surface Area:	93.06 Å²
Index of Refraction:	1.592	Molar Refractivity:	113.865 cm³
Molar Volume:	336.446 cm³	Polarizability:	45.14 10^-24cm³
Surface Tension:	55.2480010986328 dyne/cm	Density:	1.28 g/cm³
Flash Point:	201.79 °C	Enthalpy of Vaporization:	102.439 kJ/mol
Boiling Point:	599.743 °C at 760 mmHg	Vapour Pressure:	0 mmHg at 25°C

Predicted data is generated using the US Environmental Protection Agency’s EPISuite™, for more information see their website.

                    
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  3.98

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  545.88  (Adapted Stein & Brown method)
    Melting Pt (deg C):  234.03  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.15E-014  (Modified Grain method)
    Subcooled liquid VP: 2.05E-012 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):  0.7874
       log Kow used: 3.98 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.16369 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.56E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.274E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.98  (KowWin est)
  Log Kaw used:  -10.572  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.552
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.3728
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.8690  (months      )
   Biowin4 (Primary Survey Model) :   2.9612  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5164
   Biowin6 (MITI Non-Linear Model):   0.0255
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.8240
 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):  2.73E-010 Pa (2.05E-012 mm Hg)
  Log Koa (Koawin est  ): 14.552
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.1E+004 
       Octanol/air (Koa) model:  87.5 
   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 = 101.0144 E-12 cm3/molecule-sec
      Half-Life =     0.106 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.271 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.312500 E-17 cm3/molecule-sec
      Half-Life =     0.873 Days (at 7E11 mol/cm3)
      Half-Life =     20.955 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    :  10
      Log Koc:  1.000 

 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 = 2.365 (BCF = 231.8)
       log Kow used: 3.98 (estimated)

 Volatilization from Water:
    Henry LC:  6.56E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.852E+009  hours   (7.716E+007 days)
    Half-Life from Model Lake :  2.02E+010  hours   (8.418E+008 days)

 Removal In Wastewater Treatment:
    Total removal:              29.16  percent
    Total biodegradation:        0.31  percent
    Total sludge adsorption:    28.84  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       0.0531          2.27         1000       
   Water     12.7            1.44e+003    1000       
   Soil      83.6            2.88e+003    1000       
   Sediment  3.63            1.3e+004     0          
     Persistence Time: 1.79e+003 hr

Click to predict properties on the Chemicalize site

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Category	Target	PDB Code	LASSO Score
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.03
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.03
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.03
Kinases	SRC, tyrosine kinase SRC	2src	0.01
Serine Proteases	Thrombin	1ba8	0.01
Other Enzymes	HMGR, hydroxymethylglutaryl-CoA reductase	1hw8	0.01
Other Enzymes	HIVPR, HIV protease	1hpx	0.01
Kinases	HSP90, human heat shock protein 90	1uy6	0.01
Metalloenzymes	PDE5, phosphodiesterase 5	1xp0	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.01
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.00
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.00
Serine Proteases	Trypsin	1bju	0.00
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.00
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.00
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.00
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00
Other Enzymes	ALR2, aldose reductase	1ah3	0.00
Kinases	TK, thymidine kinase	1kim	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Other Enzymes	COX-1, cyclooxygenase-1	1p4g	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	0.00
Nuclear Hormone Receptors	GR, glucocorticoid receptor	1m2z	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; antagonist	3ert	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Other Enzymes	InhA, enoyl ACP reductase	1p44	0.00
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00

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(RS)-(11b,16a)-16,17-[Butylidenebis(oxy)]-11,21-dihydroxypregna-1,4-diene-3,20-dione

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Std. InChI:

Std. InChIKey:

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(RS)-(11b,16a)-16,17-[Butylidenebis(oxy)]-11,21-dihydroxypregna-1,4-diene-3,20-dione

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