InChI=1/C21H32O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-15,18,22-23,26H,3-11H2,1-2H3/t12-,13-,14+,15+,18-,19+,20+,21+/m1/s1

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Inherent Properties, Identifiers and References

ChemSpider ID:	5657
Empirical Formula:	C₂₁H₃₂O₅
Molecular Weight:	364.4758
Nominal Mass:	364 Da
Average Mass:	364.4758 Da
Monoisotopic Mass:	364.224974 Da

Systematic Name:

(3R,5R,8S,9S,10S,13S,14S,17R)-3,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,3,4,5,6,7,8,9,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-11-one

SMILES:

O=C2[C@H]3[C@H]([C@@H]1CC[C@](O)(C(=O)CO)[C@@]1(C)C2)CC[C@@H]4C[C@H](O)CC[C@]34C

InChI:

InChI=1/C21H32O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-15,18,22-23,26H,3-11H2,1-2H3/t12-,13-,14+,15+,18-,19+,20+,21+/m1/s1

InChIKey:

SYGWGHVTLUBCEM-ZIZPXRJBBU

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Names and Synonyms

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

(3a,5b)-3,17,21-trihydroxy-pregnane-11,20-dione

11,20-Pregnanedione-3a,17a,21-triol

200-161-9 [EINECS/ELINCS]

3.alpha.,17.alpha.,21-trihydroxy-5.beta.-pregnane-11,20-dione

3a,17,21-trihydroxy-5b-pregnane-11,20-dione

3a,17a,21-Pregnanetriol-11,20-dione

3a,17a,21-Trihydroxy-5b-pregnane-11,20-dione

3alpha,17,21-trihydroxy-5beta-Pregnane-11,20-dione

5.beta.-Pregnane-11,20-dione, 3.alpha.,17,21-trihydroxy-

53-05-4 [RN]

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Database ID(s)

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

Predicted Properties

LogP:	ACD/LogP: 1.85 XLogP: 1.40	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	1.85	ACD/LogD (pH 7.4):	1.85
ACD/BCF (pH 5.5):	14.89	ACD/BCF (pH 7.4):	14.89
ACD/KOC (pH 5.5):	240.51	ACD/KOC (pH 7.4):	240.51
#H bond acceptors:	5	#H bond donors:	3
#Freely Rotating Bonds:	5	Polar Surface Area:	61.83 Å²
Index of Refraction:	1.569	Molar Refractivity:	95.73 cm³
Molar Volume:	291.7 cm³	Polarizability:	37.95 10^-24cm³
Surface Tension:	54.6 dyne/cm	Density:	1.249 g/cm³
Flash Point:	297.1 °C	Enthalpy of Vaporization:	94.63 kJ/mol
Boiling Point:	544.5 °C at 760 mmHg	Vapour Pressure:	4E-14 mmHg at 25°C

MeSH

EPI Summary

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  2.12

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  500.25  (Adapted Stein & Brown method)
    Melting Pt (deg C):  212.72  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.9E-013  (Modified Grain method)
    MP  (exp database):  213 deg C
    Subcooled liquid VP: 1.9E-011 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):  78.9
       log Kow used: 2.12 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  2213.4 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.04E-007  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.155E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.12  (KowWin est)
  Log Kaw used:  -5.371  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  7.491
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3534
   Biowin2 (Non-Linear Model)     :   0.0025
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0323  (months      )
   Biowin4 (Primary Survey Model) :   3.0760  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6587
   Biowin6 (MITI Non-Linear Model):   0.1960
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.5809
 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):  2.53E-009 Pa (1.9E-011 mm Hg)
  Log Koa (Koawin est  ): 7.491
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.18E+003 
       Octanol/air (Koa) model:  7.6E-006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.000608 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  44.7460 E-12 cm3/molecule-sec
      Half-Life =     0.239 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.868 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   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    :  36.36
      Log Koc:  1.561 

 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 = 0.929 (BCF = 8.5)
       log Kow used: 2.12 (estimated)

 Volatilization from Water:
    Henry LC:  1.04E-007 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.075E+004  hours   (447.9 days)
    Half-Life from Model Lake : 1.174E+005  hours   (4893 days)

 Removal In Wastewater Treatment:
    Total removal:               2.38  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.27  percent
    Total to Air:                0.01  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.173           5.74         1000       
   Water     25.9            1.44e+003    1000       
   Soil      73.9            2.88e+003    1000       
   Sediment  0.119           1.3e+004     0          
     Persistence Time: 1.27e+003 hr

SimBioSys LASSO

Descriptors: 0, 0, 0, 0, 0, 0, 0, 4, 0, 0, 3, 6, 26, 0, 3, 0, 0, 0, 2, 2, 0, 0, 0, 0

Category	Target	PDB Code	LASSO Score
Metalloenzymes	ACE, angiotensin-converting enzyme;	1o86	0.03
Other Enzymes	AChE, acetylcholinesterase;	1eve	0.00
Metalloenzymes	ADA, adenosine deaminase;	1stw	0.14
Other Enzymes	ALR2, aldose reductase;	1ah3	0.00
Other Enzymes	AmpC, AmpC beta-lactamase;	1xgj	0.00
Nuclear Hormone Receptors	AR, androgen receptor;	1xq2	0.00
Kinases	CDK2, cyclindependent kinase 2;	1ckp	0.00
Metalloenzymes	COMT, catechol O-methyltransferase;	1h1d	0.00
Other Enzymes	cyclooxygenase-2	1cx2	0.00
Folate Enzymes	DHFR, dihydrofolate reductase;	3dfr	0.00
Kinases	EGFr, epidermal growth factor receptor;	1m17	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.30
Kinases	FGFr1, fibroblast growth factor receptor kinase;	1agw	0.00
Serine Proteases	FXa, factor Xa;	1f0r	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase;	1c2t	0.00
Other Enzymes	GPB, glycogen phosphorylase â;	1a8i	0.00
Other Enzymes	HIVPR, HIV protease;	1hpx	0.01
Other Enzymes	HIVRT, HIV reverse transcriptase;	1rt1	0.00
Other Enzymes	HMGR, hydroxymethylglutaryl-CoA reductase;	1hw8	0.01
Kinases	HSP90, human heat shock protein 90;	1uy6	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor;	2aa2	0.88
Other Enzymes	NA, neuraminidase;	1a4g	0.00
Kinases	P38 MAP, P38 mitogen activated protein;	1kv2	0.00
Other Enzymes	PARP, poly(ADP-ribose) polymerase;	1efy	0.01
Metalloenzymes	PDE5, phosphodiesterase 5;	1xp0	0.01
Kinases	PDGFrb, platelet derived growth factor receptor kinase;		0.00
Other Enzymes	PNP, purine nucleoside phosphorylase;	1b8o	0.00
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor ç;	1fm9	0.03
Nuclear Hormone Receptors	PR, progesterone receptor;	1sr7	0.00
Nuclear Hormone Receptors	RXRa, retinoic X receptor R;	1mvc	0.03
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase;	1a7a	0.03
Kinases	SRC, tyrosine kinase SRC;	2src	0.01
Serine Proteases	Thrombin	1ba8	0.01
Kinases	TK, thymidine kinase;	1kim	0.00
Serine Proteases	Trypsin	1bju	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor;	1vr2	0.00