InChI=1/C9H11NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,10-12H,5H2,1H3

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Search term: C9H11NO3
Found by conversion query string to chemical structure (full match)

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Inherent Properties, Identifiers and References

ChemSpider ID:	7158
Empirical Formula:	C₉H₁₁NO₃
Molecular Weight:	181.1885
Nominal Mass:	181 Da
Average Mass:	181.1885 Da
Monoisotopic Mass:	181.073893 Da

Systematic Name:

1-(3,4-dihydroxyphenyl)-2-methylamino-ethanone

SMILES:

O=C(c1cc(O)c(O)cc1)CNC

InChI:

InChI=1/C9H11NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,10-12H,5H2,1H3

InChIKey:

PZMVOUYYNKPMSI-UHFFFAOYAW

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Wikipedia Article(s)

Adrenalone is an adrenergic agent used as a topical vasoconstrictor and hemostatic. It is the ketone form of epinephrine. Category:Catecholamines Category:Sympathomimetics Read more... or Edit at Wikipedia...

Associated Data Sources and Commercial Suppliers

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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

202-756-9 [EINECS/ELINCS]

3,4-Dihydroxy-a-methylaminoacetophenone

4-Methylaminocetopyrocatechol

62-13-5 [RN]

Adrenalona [Spanish]

adrenalone

Adrenalone (USAN)

Adrenalonum [Latin]

Adrenolone

Stryphnonasal

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Database ID(s)

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Predicted Properties

LogP:	ACD/LogP: 0.67 ALOGPS: -0.55	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	-1.39	ACD/LogD (pH 7.4):	-0.01
ACD/BCF (pH 5.5):	1	ACD/BCF (pH 7.4):	1
ACD/KOC (pH 5.5):	1	ACD/KOC (pH 7.4):	11.57
#H bond acceptors:	4	#H bond donors:	3
#Freely Rotating Bonds:	5	Polar Surface Area:	38.77 Å²
Index of Refraction:	1.589	Molar Refractivity:	48.27 cm³
Molar Volume:	143.1 cm³	Polarizability:	19.13 10^-24cm³
Surface Tension:	55.2 dyne/cm	Density:	1.265 g/cm³
Flash Point:	199.1 °C	Enthalpy of Vaporization:	68.28 kJ/mol
Boiling Point:	405.6 °C at 760 mmHg	Vapour Pressure:	3.7E-07 mmHg at 25°C

MeSH

EPI Summary

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  0.47

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  334.97  (Adapted Stein & Brown method)
    Melting Pt (deg C):  119.64  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.51E-007  (Modified Grain method)
    MP  (exp database):  235.5 dec deg C
    Subcooled liquid VP: 2.81E-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):  8.355e+005
       log Kow used: 0.47 (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:
       Aliphatic Amines
       Phenols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.79E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.309E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.47  (KowWin est)
  Log Kaw used:  -13.708  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.178
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0536
   Biowin2 (Non-Linear Model)     :   0.9483
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.9135  (weeks       )
   Biowin4 (Primary Survey Model) :   3.6868  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5271
   Biowin6 (MITI Non-Linear Model):   0.4085
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.4431
 Ready Biodegradability Prediction:   YES

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

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  0.00375 Pa (2.81E-005 mm Hg)
  Log Koa (Koawin est  ): 14.178
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000801 
       Octanol/air (Koa) model:  37 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0281 
       Mackay model           :  0.0602 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  91.9746 E-12 cm3/molecule-sec
      Half-Life =     0.116 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.396 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.0442 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  248.8
      Log Koc:  2.396 

 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: 0.47 (estimated)

 Volatilization from Water:
    Henry LC:  4.79E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.645E+012  hours   (6.855E+010 days)
    Half-Life from Model Lake : 1.795E+013  hours   (7.479E+011 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.77  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       1.88e-008       2.79         1000       
   Water     37.5            360          1000       
   Soil      62.4            720          1000       
   Sediment  0.0705          3.24e+003    0          
     Persistence Time: 589 hr

SimBioSys LASSO

Descriptors: 0, 0, 0, 1, 0, 0, 0, 2, 0, 0, 2, 4, 0, 3, 5, 0, 6, 0, 1, 2, 0, 0, 0, 0

Category	Target	PDB Code	LASSO Score
Metalloenzymes	ADA, adenosine deaminase	1stw	0.35
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.24
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.03
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.02
Kinases	SRC, tyrosine kinase SRC	2src	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
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	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
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.00
Kinases	TK, thymidine kinase	1kim	0.00
Other Enzymes	COX-1, cyclooxygenase-1	1p4g	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Serine Proteases	Thrombin	1ba8	0.00
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.00
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00

Feedback

Date	Severity	Status	Feedback
5/4/2007 1:34:48 PM	Low	Fixed	The chemical names 3,4-Dihydroxy-.alpha.-methylaminoacetophenone and 3,4-Dihydroxy-alpha-methylaminoacetophenone (why are these in capitals ?) are confusing and technically incorrect. Use of the term acetophenone requires substituents on the phenyl ring to have primes after the substituent position, thus 3',4'-Dihydroxy-2-(methylamino)acetophenone Also, many of the names (chemical and other) refer to the hydrochloride and should not be present in this record Any questions/comments send to BARKInfSer@aol.com Verdict: Edits made