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5-acetylamino-4-guanidino-6-(1,2,3-trihydroxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid

5519 (ChemSpider ID)
C₁₂H₂₀N₄O₇
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Mass

Molecular weight:	332.3098
Nominal mass:	332 Da
Average mass:	332.3098 Da
Monoisotopic mass:	332.133199 Da

Machine readable identifiers

Systematic name:

5-(acetylamino)-2,6-anhydro-3,4,5-trideoxy-4-[(diaminomethylidene)amino]non-2-enonic acid

SMILES:

O=C(O)C=1OC(C(O)C(O)CO)C(NC(=O)C)C(/N=C(\N)N)C=1 Copied

InChI:

InChI=1/C12H20N4O7/c1-4(18)15-8-5(16-12(13)14)2-7(11(21)22)23-10(8)9(20)6(19)3-17/h2,5-6,8-10,17,19-20H,3H2,1H3,(H,15,18)(H,21,22)(H4,13,14,16) Copied

InChIKey:

ARAIBEBZBOPLMB-UHFFFAOYAD

Std. InChI:

InChI=1S/C12H20N4O7/c1-4(18)15-8-5(16-12(13)14)2-7(11(21)22)23-10(8)9(20)6(19)3-17/h2,5-6,8-10,17,19-20H,3H2,1H3,(H,15,18)(H,21,22)(H4,13,14,16) Copied

Std. InChIKey:

ARAIBEBZBOPLMB-UHFFFAOYSA-N

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Patents

Identifiers

Properties

Pred. Prop. (ACD/Labs)
Pred. Prop. (EPISuite)
NMRShiftDB
Pred. Prop. (ChemAxon)

ACD/LogP:	-3.63	# of Rule of 5 Violations:	2
ACD/LogD (pH 5.5):	-6.12	ACD/LogD (pH 7.4):	-6.13
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:	11	#H bond donors:	9
#Freely Rotating Bonds:	9	Polar Surface Area:	102.37 Å²
Index of Refraction:	1.678	Molar Refractivity:	71.55 cm³
Molar Volume:	189.6 cm³	Polarizability:	28.36 10^-24cm³
Surface Tension:	77.3 dyne/cm	Density:	1.75 g/cm³
Flash Point:	°C	Enthalpy of Vaporization:	kJ/mol
Boiling Point:	°C at 760 mmHg	Vapour Pressure:	mmHg at 25°C

                    
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  -4.58

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  606.39  (Adapted Stein & Brown method)
    Melting Pt (deg C):  262.30  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.33E-017  (Modified Grain method)
    Subcooled liquid VP: 5.27E-015 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):  1e+006
       log Kow used: -4.58 (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-acid
       Vinyl/Allyl Ethers-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.63E-030  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.816E-024 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -4.58  (KowWin est)
  Log Kaw used:  -27.723  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  23.143
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0010
   Biowin2 (Non-Linear Model)     :   0.8247
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.2464  (weeks       )
   Biowin4 (Primary Survey Model) :   4.3379  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5082
   Biowin6 (MITI Non-Linear Model):   0.0951
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.2556
 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):  7.03E-013 Pa (5.27E-015 mm Hg)
  Log Koa (Koawin est  ): 23.143
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.27E+006 
       Octanol/air (Koa) model:  3.41E+010 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 144.9710 E-12 cm3/molecule-sec
      Half-Life =     0.074 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.885 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     5.687500 E-17 cm3/molecule-sec
      Half-Life =     0.201 Days (at 7E11 mol/cm3)
      Half-Life =      4.836 Hrs
   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    :  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: -4.58 (estimated)

 Volatilization from Water:
    Henry LC:  4.63E-030 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.305E+026  hours   (9.605E+024 days)
    Half-Life from Model Lake : 2.515E+027  hours   (1.048E+026 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       3.32e-014       1.3          1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr

Calculate properties at chemicalize.org

Category	Target	PDB Code	LASSO Score
Other Enzymes	NA, neuraminidase	1a4g	0.11
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.03
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	ACE, angiotensin-converting enzyme	1o86	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.01
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.00
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Serine Proteases	Thrombin	1ba8	0.00
Kinases	TK, thymidine kinase	1kim	0.00
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.00
Other Enzymes	COX-1, cyclooxygenase-1	1p4g	0.00
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.00
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	0.00
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.00
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.00

5-acetylamino-4-guanidino-6-(1,2,3-trihydroxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid

Systematic name:

SMILES:

InChI:

InChIKey:

Std. InChI:

Std. InChIKey:

Associated Data Sources and Commercial Suppliers

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SimBioSys LASSO

5-acetylamino-4-guanidino-6-(1​,2,3-trihydroxypropyl)-5,6-dih​ydro-4H-pyran-2-carboxylic aci​d

Systematic name:

SMILES:

InChI:

InChIKey:

Std. InChI:

Std. InChIKey:

Associated Data Sources and Commercial Suppliers

Patents

Identifiers

Properties

Medical Subject Headings Classification

Pharmacological Links

SimBioSys LASSO

5-acetylamino-4-guanidino-6-(1,2,3-trihydroxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid