InChI=1/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)

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Inherent Properties, Identifiers and References

ChemSpider ID:	2010
Empirical Formula:	C₅H₄N₄O
Molecular Weight:	136.1115
Nominal Mass:	136 Da
Average Mass:	136.1115 Da
Monoisotopic Mass:	136.038511 Da

Systematic Name:

1,2-dihydropyrazolo[4,3-e]pyrimidin-4-one

SMILES:

O=C2/N=C\N=C/1\NN\C=C\12

InChI:

InChI=1/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)

InChIKey:

OFCNXPDARWKPPY-UHFFFAOYAL

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Wikipedia Article(s)

Allopurinol is a drug used primarily to treat hyperuricemia (excess uric acid in blood plasma) and its complications, including chronic gout. Read more... or Edit at Wikipedia...

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Supplemental Information

Links & References

Jansson et al.. A mammalian functional nitrate reductase that regulates nitrite and nitric oxide homeostasis , Nature Chemical Biology, doi: 10.1038/nchembio.92, published online 30 May 2008.

[DOI: 10.1038/nchembio.92]

E. L. Willighagen, H. M. G. W. Denissen, R. Wehrens, and L. M. C. Buydens. On the Use of 1H and 13C 1D NMR Spectra as QSPR Descriptors, J. Chem. Inf. Model., 46 (2), 487-494, 2006

[PubMed: 16562976] [DOI: 10.1021/ci050282s]

K. Avasthi, D.S. Rawat, S. Sarkhel, P.R. Maulik. A dimeric layered structure of a 4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine compoundCDRI communication No. 6217., Acta Cryst C 2002 Volume 58 Part 6 Page o325-o327

User Data

experimental physchem properties

Melting Point: >300

The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. See also: Melting Point

Solubility: -2.38

No description available

miscellaneous

Safety: DANGER: POISON, teratogen, mutagen, GI/liver/kidney damage

See Chemical Safety

Source: synthetic

No description available

Names and Synonyms

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

1,5-Dihydro-4H-pyrazolo(3,4-d)pyrimidin-4-one

1,5-Dihydro-4H-pyrazolo(3,4-d)pyrimidin-4-one (9CI)

1,5-Dihydro-4H-pyrazolo(3,4-d)pyrimidine-4-one

1,5-Dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

1,5-Dihydro-pyrazolo[3,4-d]pyrimidin-4-one

1H-Pyrazolo[3,4-d]pyrimidin-4-ol

4H-Pyrazolo(3,4-d)pyrimidin-4-one, 1,5-dihydro-

4H-Pyrazolo[3,4-d]pyrimidin-4-one, 1,5-dihydro-

Allopurinol [Wiki]

Sigapurol

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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: -0.95 XLogP: -1.00	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	-1.52	ACD/LogD (pH 7.4):	-0.97
ACD/BCF (pH 5.5):	1	ACD/BCF (pH 7.4):	1
ACD/KOC (pH 5.5):	1.95	ACD/KOC (pH 7.4):	6.96
#H bond acceptors:	5	#H bond donors:	2
#Freely Rotating Bonds:	0	Polar Surface Area:	48.27 Å²
Index of Refraction:	1.902	Molar Refractivity:	33.55 cm³
Molar Volume:	71.9 cm³	Polarizability:	13.3 10^-24cm³
Surface Tension:	91.4 dyne/cm	Density:	1.89 g/cm³
Flash Point:	129.7 °C	Enthalpy of Vaporization:	53.02 kJ/mol
Boiling Point:	290.8 °C at 760 mmHg	Vapour Pressure:	0.00203 mmHg at 25°C

MeSH

EPI Summary

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  -1.14

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  396.36  (Adapted Stein & Brown method)
    Melting Pt (deg C):  164.18  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.77E-007  (Modified Grain method)
    Subcooled liquid VP: 1.02E-005 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):  8.234e+005
       log Kow used: -1.14 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.48E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.200E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.14  (KowWin est)
  Log Kaw used:  -11.460  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.320
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6827
   Biowin2 (Non-Linear Model)     :   0.7457
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8984  (weeks       )
   Biowin4 (Primary Survey Model) :   3.6514  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0471
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.8020
 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):  0.00136 Pa (1.02E-005 mm Hg)
  Log Koa (Koawin est  ): 10.320
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00221 
       Octanol/air (Koa) model:  0.00513 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0738 
       Mackay model           :  0.15 
       Octanol/air (Koa) model:  0.291 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 146.1890 E-12 cm3/molecule-sec
      Half-Life =     0.073 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.878 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.175000 E-17 cm3/molecule-sec
      Half-Life =     6.549 Days (at 7E11 mol/cm3)
   Fraction sorbed to airborne particulates (phi): 0.112 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  929.6
      Log Koc:  2.968 

 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 = 0.500 (BCF = 3.162)
       log Kow used: -1.14 (estimated)

 Volatilization from Water:
    Henry LC:  8.48E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 8.055E+009  hours   (3.356E+008 days)
    Half-Life from Model Lake : 8.787E+010  hours   (3.661E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  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       2.2e-006        1.74         1000       
   Water     39              360          1000       
   Soil      61              720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr

SimBioSys LASSO

Descriptors: 0, 0, 0, 2, 2, 0, 0, 4, 0, 0, 0, 0, 0, 0, 0, 0, 9, 1, 0, 0, 0, 0, 0, 0

Category	Target	PDB Code	LASSO Score
Other Enzymes	ALR2, aldose reductase	1ah3	1.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.97
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.95
Kinases	HSP90, human heat shock protein 90	1uy6	0.94
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.90
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.89
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.87
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.84
Kinases	SRC, tyrosine kinase SRC	2src	0.81
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.77
Other Enzymes	InhA, enoyl ACP reductase	1p44	0.36
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.15
Metalloenzymes	ADA, adenosine deaminase	1stw	0.07
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.07
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.07
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.05
Kinases	TK, thymidine kinase	1kim	0.03
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.03
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.02
Other Enzymes	NA, neuraminidase	1a4g	0.02
Serine Proteases	FXa, factor Xa	1f0r	0.02
Other Enzymes	HMGR, hydroxymethylglutaryl-CoA reductase	1hw8	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.01
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.00
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.00
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.00
Other Enzymes	HIVPR, HIV protease	1hpx	0.00
Other Enzymes	COX-1, cyclooxygenase-1	1p4g	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Serine Proteases	Thrombin	1ba8	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	0.00
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.00