InChI=1/C3H5N3O9/c7-4(8)13-1-3(15-6(11)12)2-14-5(9)10/h3H,1-2H2

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Search term: SNIOPGDIGTZGOP-UHFFFAOYAR
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Inherent Properties, Identifiers and References

ChemSpider ID:	4354
Empirical Formula:	C3H5N3O9
Molecular Weight:	227.09
Nominal Mass:	227 Da
Average Mass:	227.0865 Da
Monoisotopic Mass:	227.002579 Da

Systematic Name:

2,3-dinitrooxypropyl nitrate

SMILES:

C(C(CO[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-]

InChI:

InChI=1/C3H5N3O9/c7-4(8)13-1-3(15-6(11)12)2-14-5(9)10/h3H,1-2H2

InChIKey:

SNIOPGDIGTZGOP-UHFFFAOYAR

Std. InChI:

InChI=1S/C3H5N3O9/c7-4(8)13-1-3(15-6(11)12)2-14-5(9)10/h3H,1-2H2

Std. InChIKey:

SNIOPGDIGTZGOP-UHFFFAOYSA-N

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Wikipedia Article(s)

Glyceryl trinitrate (GTN) is an alternate name for the chemical nitroglycerin, which has been used to treat angina and heart failure since at least 1870. Despite this, the mechanism of nitric oxide (NO) generation from GTN and the metabolic consequences of this bioactivation are still not entirely understood. In medical circles it is often referred to as "nitro." Read more... or Edit at Wikipedia...

Nitroglycerin (NG), (United States spelling) also known as nitroglycerine, (UK spelling), trinitroglycerin, trinitroglycerine, 1,2,3-trinitroxypropane and glyceryl trinitrate, is a heavy, colorless, oily, explosive liquid obtained by nitrating glycerol. Since the 1860s, it has been used as an active ingredient in the manufacture of explosives, specifically dynamite, and as such is employed in the construction and demolition industries. Similarly, since the 1880s, it has been used by the military as an active ingredient, and a gellatinizer for nitrocellulose, in some solid propellants, such as Cordite and Ballistite. Nitroglycerin is also used medically as a vasodilator to treat heart conditions, such as angina and chronic heart failure. It is one of the oldest and most useful drugs for treating heart disease by shortening or even preventing attacks of angina pectoris. Nitroglycerin comes in forms of tablets, sprays or patches.Feb97, Vol. 7, Issue 6 An alternative IUPAC name is nitrate. Read more... or Edit at Wikipedia...

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Supplemental Information

Links & References

QSAR World - Datasets - GG - Peak Time

Kenneth E. Thummel and Danny D. Shen. Peak Time, "Goodman & Gilman's The Pharmacological Basis of Therapeutics", 10/e, Ed. by Joel G. Hardman, Lee E. Limbird and Alfred Goodman Gilman, McGraw-Hill, pp. 1917-2023

'Peak-Time' values have been taken from the Table A-II-1 given in Appendix II of the above mentioned reference. These are in hours unless otherwise indicated. Users are requested to go through the comments associated with these values, which have been given as footnotes in the table. Only drugs that had 'Peak-Time' values indicated for them have been provided in the files here. Structures (and values) for Clavulanate (1.3), Enoxaparin (3), Epoetin Alfa (SC: 18, IP:12), Etanercept (SC-SD:72(48-96)), Filgrastim (4-5.8), Heparin (3), Interferon Alfa (IM:3.8,SC:7.3), Interferon Beta (SC:1-8), Lithium (IR:0.5-3, SR:2-6), Mycophenolate (MPA: 1.1-2.2), Prednisolone (1.5+-0.5), Sargramostim (A,SC: 1-3, C,SC:1.5-4) and Streptokinase (0.9+-0.21) have not been provided here. In all, 270 drugs and their 'Peak-Time' values are given in the files here.

QSAR World - Datasets - GG - Urinary Excretion

Kenneth E. Thummel and Danny D. Shen. Urinary Excretion, "Goodman & Gilman's The Pharmacological Basis of Therapeutics", 10/e, Ed. by Joel G. Hardman, Lee E. Limbird and Alfred Goodman Gilman, McGraw-Hill, pp. 1917-2023

Urinary Excretion (%) values have been taken from the Table A-II-1 given in Appendix II of the above mentioned reference. Users are requested to go through the comments associated with these values, which have been given as footnotes in the table. Only drugs that had Urinary Excretion values indicated for them have been provided in the files here. Structures (and values) for Alteplase (t-PA) (Low), Clavulanate (43+-14), Enoxaparin (43), Epoetin alfa (<3), Etanercept (Negligible), Heparin (Negligible), Lithium (95+-15), Mycophenolate (MPA: <1), Prednisolone (26+-9), Rapacuronium (6-22) and Streptokinase (0) have not been provided here. In all, 297 drugs and their Urinary Excretion values (%) are given in the files here.

QSAR World - Datasets - GG - Volume of Distribution

Kenneth E. Thummel and Danny D. Shen. Volume of Distribution, "Goodman & Gilman's The Pharmacological Basis of Therapeutics", 10/e, Ed. by Joel G. Hardman, Lee E. Limbird and Alfred Goodman Gilman, McGraw-Hill, pp. 1917-2023

'Volume of Distribution' values have been taken from the Table A-II-1 given in Appendix II of the above mentioned reference. These are in liters/kg units unless otherwise indicated. Users are requested to go through the comments associated with these values, which have been given as footnotes in the table. Only drugs that had 'Volume of Distribution' values indicated for them have been provided in the files here. Structures (and values) for Alteplase (t-PA) (0.10+-0.01), Clavulanate (0.21+-0.05), Enoxaparin (0.12+-0.04), Epoetin Alfa (0.033+-0.013 (0.033-0.075)), Etanercept (0.11), Filgrastim (0.15), Heparin (0.058+-0.11) +- 0.1), Infliximab (0.043). Interferon Alfa (0.40+-0.19), Interferon Beta (2.9+-1.8), Lithium (0.66+-0.16), Mycophenolate (MPA: 3.6+-4), Prednisolone (0.42+-0.11), Rapacuronium (0.2-0.5), Sargramostim (A: -, C:2(0.4-18) liters/(m.m)) and Streptokinase (0.08+-0.04) have not been provided here. In all, 284 drugs and their 'Volume of Distribution' values are given in the files here.

QSAR World - Datasets - GG - Peak Concentration

Kenneth E. Thummel and Danny D. Shen. Peak Concentration, "Goodman & Gilman's The Pharmacological Basis of Therapeutics", 10/e, Ed. by Joel G. Hardman, Lee E. Limbird and Alfred Goodman Gilman, McGraw-Hill, pp. 1917-2023

'Peak-Concentrations' values have been taken from the Table A-II-1 given in Appendix II of the above mentioned reference. The units are indicated along with the values. Users are requested to go through the comments associated with these values, which have been given as footnotes in the table. Structures (and values) for Alteplase (t-PA) (973+-133 ng/ml), Clavulanate (2.8 micro g/ml), Enoxaparin (ACLM: 145+-45 ng/ml, BCLM: 414+-87 ng/ml), Epoetin Alfa (SC: 176+-75 U/l, IP: 375+-123 U/l), Etanercept (IV:2.32 micro-g/ml, SC-SD:1.2 micro-g/ml, SC-MD 3 micro-g/ml), Filgrastim (SC: 4 and 49 ng/ml), Heparin (70+-39 ng/ml), Infliximab (118 micro-g/ml), Interferon Alfa (IV: ~13 ng/ml, IM: 2.0 (1.5-2.6) ng/ml, SC: 1.7 (1.2-2.3) ng/ml), Interferon Beta (IV: 1491+-659 IU/ml, SC: 40+-20 IU/ml), Lithium (IR: 1-2 mM, SR: 0.7-1.2 mM), Mycophenolate (MPA: 8-19 micro-g/ml), Prednisolone (458+-150 ng/ml), Rapacuronium (6-20 micro-g/ml), Sargramostim (A, IV: 5ng/ml, A, SC: 1.5 ng/ml, C, IV: 100 ng/ml, C, SC: 10 ng/ml) and Streptokinase (188+-58 IU/ml) have not been provided here. In all, 304 drugs and their 'Peak-Concentration' values are given in the files here.

QSAR World - Datasets - GG - Clearance

Kenneth E. Thummel and Danny D. Shen. Clearance , "Goodman & Gilman's The Pharmacological Basis of Therapeutics", 10/e, Ed. by Joel G. Hardman, Lee E. Limbird and Alfred Goodman Gilman, McGraw-Hill, pp. 1917-2023

'Clearance' values have been taken from the Table A-II-1 given in Appendix II of the above mentioned reference. These are in (ml/min/kg) units unless otherwise indicated. Users are requested to go through the comments associated with these values, which have been given as footnotes in the table. Only drugs that had 'Clearance' values indicated for them have been provided in the files here. Structures (and values) for Alteplase (t-PA) (10+-4), Clavulanate (3.6+-1.0), Enoxaparin (0.3+-0.1), Epoetin Alfa (0.047+-0.017 (0.047-0.092)), Etanercept (0.02), Filgrastim (0.5-0.7), Heparin (1/(0.65 + 0/0.008D) +- 0.1), Interferon Alfa (2.8+-0.6), Interferon Beta (13+-5), Lithium (0.35+-0.11), Mycophenolate (MM: 120-163, MPA: 2.5+-0.4), Prednisolone (1.0+-0.16), Rapacuronium (7-11), Sargramostim (A: 420 ml/min/(m.m), C:49(15-118) ml/min/(m.m)) and Streptokinase (1.7+-0.7) have not been provided here. In all, 301 drugs and their 'Clearance' values are given in the files here.

QSAR World - Datasets - GG - Oral Availability

Kenneth E. Thummel and Danny D. Shen. Percentage Oral Availability, "Goodman & Gilman's The Pharmacological Basis of Therapeutics", 10/e, Ed. by Joel G. Hardman, Lee E. Limbird and Alfred Goodman Gilman, McGraw-Hill, pp. 1917-2023

Availability (Oral) % have been taken from the Table A-II-1 given in Appendix II of the above mentioned reference. Users are requested to go through the comments associated with these values, which have been given as footnotes in the table. Only drugs that had Availability values indicated for them have been provided in the files here. Structures (and values) for Clavulanate (75+-21), Enoxaparin (SC: 92), Epoetin alfa (SC: 22 (11-36), IP: 3 (1-7)), Etanercept (SC: 58), Filgrastim (SC: 49+-9), Interferon alfa (IM: 80-83, SC: 90), Interferon beta (SC: 51+-17), Lithium (100), Mycophenolate (MM: ~0, MPA: 94) and Prednisolone (82+-13) have not been provided here. In all, 242 drugs and their Availability (Oral) % are given in the files here.

Daniel F. Veber, Stephen R. Johnson, Hung-Yuan Cheng, Brian R. Smith, Keith W. Ward, and Kenneth D. Kopple. Molecular Properties That Influence the Oral Bioavailability of Drug Candidates, J. Med. Chem. 2002, 45(12), 2615-2623

[DOI: 10.1021/jm020017n]

275 drugs and their human oral bioavalability values have been given in the supplementary material of the paper. These values have in turn been taken from Goodman & Gilman's The Pharmacological Basis of Therapeutics, VIII and X Editions. The datasets are available from the QSAR World pages: http://www.qsarworld.com/qsar-datasets-veber.php

Igor V. Tetko, Vsevolod Yu. Tanchuk, Tamara N. Kasheva, and Alessandro E. P. Villa. Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices, J. Chem. Inf. Comput. Sci., 2001, 41 (6), pp 1488–1493

[DOI: 10.1021/ci000392t]

The molecular weight and electrotopological E-state indices were used to estimate by Artificial Neural Networks aqueous solubility for a diverse set of 1291 organic compounds. The neural network with 33-4-1 neurons provided highly predictive results with r2 = 0.91 and RMS = 0.62.

User Data

experimental physchem properties

Boiling Point: Begins to decompose at 122-140F

The boiling point of a liquid is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid. See also: Boiling Point

Flash Point: Explodes

The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture in air. See also: Flash Point

Freezing Point: 56F

No description available

Specific Gravity: 1.60

Specific gravity is defined as the ratio of the density of a given substance to the density of water, when both are at the same temperature. See also: Specific Gravity

Solubility: 0.1%

No description available

Ionization Potential: ?

No description available

Vapor Pressure: 0.0003 mmHg

No description available

miscellaneous

Appearance: Colorless to pale-yellow, viscous liquid or solid (below 56F). [Note: An explosive ingredient in dynamite (20-40%) with ethylene glycol dinitrate (80-60%).]

Visual appearance of the given substance.

First Aid: Eye: Irrigate immediately Skin: Soap wash immediately Breathing: Respiratory support Swallow: Medical attention immediately

No description available

Exposure Routes: inhalation, skin absorption, ingestion, skin and/or eye contact

No description available

Symptoms: Throbbing headache; dizziness; nausea, vomiting, abdominal pain; hypotension; flush; palpitations; methemoglobinemia; delirium, central nervous system depression; angina; skin irritation

No description available

Target Organs: cardiovascular system, blood, skin, central nervous system

No description available

Incompatibilities and Reactivities: Heat, ozone, shock, acids [Note: An OSHA Class A Explosive (1910.109).]

No description available

Personal protection and Sanitation: Skin: Prevent skin contact Eyes: Prevent eye contact Wash skin: When contaminated Remove: When wet (flammable) Change: Daily Provide: Quick drench

No description available

Exposure Limits: NIOSH REL : ST 0.1 mg/m 3 [skin] OSHA PEL ?: C 0.2 ppm (2 mg/m 3 ) [skin]

No description available

Names and Synonyms

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

1,2,3-propanetriol, trinitrate

1,2,3-Propanetriyl trinitrate

Aquo-Trinitrosan

Gilucor "Nitro"

Glycerol Nitric Acid Triester

nitran

Nitriderm

Nitro Mack

Nitrolande

Nitrolar

More...

Database ID(s)

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

ACD/Labs Predicted Properties

ACD/LogP:	2.32	# of Rule of 5 Violations:	1
ACD/LogD (pH 5.5):	2.32	ACD/LogD (pH 7.4):	2.32
ACD/BCF (pH 5.5):		ACD/BCF (pH 7.4):
ACD/KOC (pH 5.5):		ACD/KOC (pH 7.4):
#H bond acceptors:	12	#H bond donors:	0
#Freely Rotating Bonds:	8	Polar Surface Area:	165.15 Å²
Index of Refraction:	1.488	Molar Refractivity:	39.2 cm³
Molar Volume:	135.8 cm³	Polarizability:	15.54 10^-24cm³
Surface Tension:	63.5 dyne/cm	Density:	1.671 g/cm³
Flash Point:	145.7 °C	Enthalpy of Vaporization:	51.41 kJ/mol
Boiling Point:	295.8 °C at 760 mmHg	Vapour Pressure:	0.00263 mmHg at 25°C

MeSH

EPI Summary

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  1.51
    Log Kow (Exper. database match) =  1.62
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  281.84  (Adapted Stein & Brown method)
    Melting Pt (deg C):  50.21  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.0272  (Mean VP of Antoine & Grain methods)
    MP  (exp database):  13.5 deg C
    BP  (exp database):  250 deg C
    VP  (exp database):  4.00E-04 mm Hg at 25 deg C

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  1305
       log Kow used: 1.62 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  1380 mg/L (20 deg C)
        Exper. Ref:  SEIDELL,A (1941)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1409.1 mg/L
    Wat Sol (Exper. database match) =  1380.00
       Exper. Ref:  SEIDELL,A (1941)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.54E-009  atm-m3/mole
   Group Method:   Incomplete
   Exper Database: 9.87E-08  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  6.228E-006 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.62  (exp database)
  Log Kaw used:  -5.394  (exp database)
      Log Koa (KOAWIN v1.10 estimate):  7.014
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6394
   Biowin2 (Non-Linear Model)     :   0.4462
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6973  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5201  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0847
   Biowin6 (MITI Non-Linear Model):   0.0366
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.7222
 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):  0.0533 Pa (0.0004 mm Hg)
  Log Koa (Koawin est  ): 7.014
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.62E-005 
       Octanol/air (Koa) model:  2.54E-006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.00203 
       Mackay model           :  0.00448 
       Octanol/air (Koa) model:  0.000203 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =   1.0980 E-12 cm3/molecule-sec
      Half-Life =     9.741 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =   116.891 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.00325 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  130.8
      Log Koc:  2.117 

 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 = 0.547 (BCF = 3.527)
       log Kow used: 1.62 (expkow database)

 Volatilization from Water:
    Henry LC:  9.87E-008 atm-m3/mole  (Henry experimental database)
    Half-Life from Model River:       8941  hours   (372.5 days)
    Half-Life from Model Lake : 9.766E+004  hours   (4069 days)

 Removal In Wastewater Treatment:
    Total removal:               2.02  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.92  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       0.873           234          1000       
   Water     32.5            900          1000       
   Soil      66.6            1.8e+003     1000       
   Sediment  0.0884          8.1e+003     0          
     Persistence Time: 1.06e+003 hr

SimBioSys LASSO

Descriptors: 0, 0, 0, 0, 0, 0, 0, 6, 12, 0, 0, 0, 0, 0, 5, 0, 0, 9, 0, 0, 0, 0, 0, 0

Category	Target	PDB Code	LASSO Score
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.61
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.11
Other Enzymes	HIVPR, HIV protease	1hpx	0.11
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.09
Serine Proteases	FXa, factor Xa	1f0r	0.05
Other Enzymes	HMGR, hydroxymethylglutaryl-CoA reductase	1hw8	0.03
Other Enzymes	AChE, acetylcholinesterase	1eve	0.03
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.01
Kinases	SRC, tyrosine kinase SRC	2src	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.01
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Serine Proteases	Thrombin	1ba8	0.00
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.00
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.00
Kinases	TK, thymidine kinase	1kim	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.00
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Kinases	HSP90, human heat shock protein 90	1uy6	0.00
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.00
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.00