InChI=1/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)

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Inherent Properties, Identifiers and References

ChemSpider ID:	810
Empirical Formula:	C₆H₁₃N₃O₃
Molecular Weight:	175.1857
Nominal Mass:	175 Da
Average Mass:	175.1857 Da
Monoisotopic Mass:	175.095691 Da

Systematic Name:

2-amino-5-ureido-pentanoic acid

SMILES:

O=C(O)C(N)CCCNC(=O)N

InChI:

InChI=1/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)

InChIKey:

RHGKLRLOHDJJDR-UHFFFAOYAQ

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Supplemental Information

Links & References

Cheng Bai, Charles C. Reilly and Bruce W. Wood . Identification and Quantitation of Asparagine and Citrulline Using High-Performance Liquid Chromatography (HPLC), Analytical Chemistry Insights 2007:2 31-36

Abstract: High-performance liquid chromatography (HPLC) analysis was used for identification of two problematic ureides, asparagine and citrulline. We report here a technique that takes advantage of the predictable delay in retention time of the co-asparagine/citrulline peak to enable both qualitative and quantitative analysis of asparagine and citrulline.

User Data

miscellaneous

Safety: CAUTION: May irritate eyes, skin, and respiratory tract

See Chemical Safety

Source: Citrullis vulgaris and the alga Grateloupia filicina

No description available

Drug Status: undetermined activity

No description available

Chemical Class: amino acid

No description available

Names and Synonyms

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

211-012-2 [EINECS/ELINCS]

2-Amino-5-ureidovaleric acid

alpha-Amino-delta-ureidovaleric acid

Citrulline [Wiki]

N~5~-(aminocarbonyl)ornithine

N5-(aminocarbonyl)-Ornithine

N5-carbamoylornithine

N5-carbamylornithine

ornithine, N~5~-(aminocarbonyl)-

Ornithine, N5-(aminocarbonyl)-

More...

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: -1.53 XLogP: -3.90 ALOGPS: -3.27	# of Rule of 5 Violations:	1
ACD/LogD (pH 5.5):	-4.03	ACD/LogD (pH 7.4):	-4.03
ACD/BCF (pH 5.5):	1	ACD/BCF (pH 7.4):	1
ACD/KOC (pH 5.5):	1	ACD/KOC (pH 7.4):	1
#H bond acceptors:	6	#H bond donors:	6
#Freely Rotating Bonds:	6	Polar Surface Area:	53.09 Å²
Index of Refraction:	1.531	Molar Refractivity:	42.06 cm³
Molar Volume:	135.8 cm³	Polarizability:	16.67 10^-24cm³
Surface Tension:	61.9 dyne/cm	Density:	1.289 g/cm³
Flash Point:	187.7 °C	Enthalpy of Vaporization:	69.78 kJ/mol
Boiling Point:	386.7 °C at 760 mmHg	Vapour Pressure:	4.7E-07 mmHg at 25°C

MeSH

EPI Summary

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  -3.93
    Log Kow (Exper. database match) =  -3.19
       Exper. Ref:  Sangster (1994)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  399.96  (Adapted Stein & Brown method)
    Melting Pt (deg C):  292.35  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.48E-008  (Modified Grain method)
    MP  (exp database):  235.5 deg C
    Subcooled liquid VP: 8.33E-006 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):  1.283e+004
       log Kow used: -3.19 (expkow database)
       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-acid
       Neutral Organics-acid
       Ureas(substituted)-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.86E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.049E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -3.19  (exp database)
  Log Kaw used:  -14.932  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.742
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8907
   Biowin2 (Non-Linear Model)     :   0.9067
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.2011  (weeks       )
   Biowin4 (Primary Survey Model) :   4.0238  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5030
   Biowin6 (MITI Non-Linear Model):   0.3792
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.1123
 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):  0.00111 Pa (8.33E-006 mm Hg)
  Log Koa (Koawin est  ): 11.742
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0027 
       Octanol/air (Koa) model:  0.136 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0889 
       Mackay model           :  0.178 
       Octanol/air (Koa) model:  0.916 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  47.7000 E-12 cm3/molecule-sec
      Half-Life =     0.224 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.691 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.133 (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 = 0.500 (BCF = 3.162)
       log Kow used: -3.19 (expkow database)

 Volatilization from Water:
    Henry LC:  2.86E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  2.71E+013  hours   (1.129E+012 days)
    Half-Life from Model Lake : 2.956E+014  hours   (1.232E+013 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       7.05e-010       5.38         1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr

SimBioSys LASSO

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

Category	Target	PDB Code	LASSO Score
Metalloenzymes	ACE, angiotensin-converting enzyme;	1o86	0.05
Other Enzymes	AChE, acetylcholinesterase;	1eve	0.00
Metalloenzymes	ADA, adenosine deaminase;	1stw	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	0.03
Metalloenzymes	COMT, catechol O-methyltransferase;	1h1d	0.00
Other Enzymes	COX-1, cyclooxygenase-1;	1p4g	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	0.00
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	0.00
Other Enzymes	InhA, enoyl ACP reductase;	1p44	0.00
Nuclear Hormone Receptors	MR, mineralocorticoid receptor;	2aa2	0.01
Other Enzymes	NA, neuraminidase;	1a4g	0.05
Kinases	P38 MAP, P38 mitogen activated protein;	1kv2	0.00
Other Enzymes	PARP, poly(ADP-ribose) polymerase;	1efy	0.00
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	0.00
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase;	1a7a	0.00
Kinases	SRC, tyrosine kinase SRC;	2src	0.01
Serine Proteases	Thrombin	1ba8	0.00
Kinases	TK, thymidine kinase;	1kim	0.00
Serine Proteases	Trypsin	1bju	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor;	1vr2	0.00

Spectra

Type: HNMR

Associated Hyperlink: http://mmcd.nmrfam.wisc.edu/rawnmr/expnmr_00071_1.tar

Comments: Madison Metabolomics Consortium Database Spectrum, Q. Cui, et al; "Metabolite identification via the Madison Metabolomics Consortium Database", Nature Biotechnology, 26,162 (2008)

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Type: CNMR

Associated Hyperlink: http://mmcd.nmrfam.wisc.edu/rawnmr/expnmr_00071_3.tar

Comments: Madison Metabolomics Consortium Database Spectrum, Q. Cui, et al; "Metabolite identification via the Madison Metabolomics Consortium Database", Nature Biotechnology, 26,162 (2008)

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