InChI=1/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(17)7(4(1-16)21-10)22-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1

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Inherent Properties, Identifiers and References

ChemSpider ID:	37610
Empirical Formula:	C₁₀H₁₄N₅O₇P
Molecular Weight:	347.2212
Nominal Mass:	347 Da
Average Mass:	347.2212 Da
Monoisotopic Mass:	347.063084 Da

Systematic Name:

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl] dihydrogen phosphate

SMILES:

O=P(O)(O)O[C@@H]3[C@H](O[C@@H](n2cnc1c(ncnc12)N)[C@@H]3O)CO

InChI:

InChI=1/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(17)7(4(1-16)21-10)22-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1

InChIKey:

LNQVTSROQXJCDD-KQYNXXCUBU

Std. InChI:

InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(17)7(4(1-16)21-10)22-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1

Std. InChIKey:

LNQVTSROQXJCDD-KQYNXXCUSA-N

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Supplemental Information

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identifiers

SMILES: OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(=O)(O)O)n1cnc2c(N)ncnc12

The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. See also: SMILES

Names and Synonyms

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

Adenosine-3'-phosphoric Acid

Adenylic Acid b

h-Adenylic Acid

201-521-8 [EINECS/ELINCS]

3'-Adenosine monophosphate

3'-ADENYLIC ACID

3'-AMP

4-26-00-03607

4-26-00-03607 (Beilstein Handbook Reference) [Beilstein]

84-21-9 [RN]

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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: -1.46 XLogP: -3.50	# of Rule of 5 Violations:	2
ACD/LogD (pH 5.5):	-4.76	ACD/LogD (pH 7.4):	-5.72
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:	12	#H bond donors:	6
#Freely Rotating Bonds:	6	Polar Surface Area:	129.1 Å²
Index of Refraction:	1.905	Molar Refractivity:	69.9 cm³
Molar Volume:	149.6 cm³	Polarizability:	27.71 10^-24cm³
Surface Tension:	140.9 dyne/cm	Density:	2.32 g/cm³
Flash Point:	447 °C	Enthalpy of Vaporization:	124.27 kJ/mol
Boiling Point:	815.5 °C at 760 mmHg	Vapour Pressure:	4.06E-28 mmHg at 25°C

EPI Summary

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  -1.68

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  480.00  (Adapted Stein & Brown method)
    Melting Pt (deg C):  90.27  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.35E-012  (Modified Grain method)
    MP  (exp database):  197 deg C
    Subcooled liquid VP: 8.76E-011 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):  8510
       log Kow used: -1.68 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  500 mg/L (15 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L
    Wat Sol (Exper. database match) =  500.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aromatic Amines
       Imidazoles

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.00E-031  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  7.248E-017 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.68  (KowWin est)
  Log Kaw used:  -29.388  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  27.708
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3186
   Biowin2 (Non-Linear Model)     :   0.0065
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6082  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.4876  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0392
   Biowin6 (MITI Non-Linear Model):   0.0013
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5595
 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):  1.17E-008 Pa (8.76E-011 mm Hg)
  Log Koa (Koawin est  ): 27.708
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  257 
       Octanol/air (Koa) model:  1.25E+015 
   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 = 270.4370 E-12 cm3/molecule-sec
      Half-Life =     0.040 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    28.477 Min
   Ozone Reaction:
      No Ozone Reaction Estimation
   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: -1.68 (estimated)

 Volatilization from Water:
    Henry LC:  1E-031 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.091E+028  hours   (4.546E+026 days)
    Half-Life from Model Lake :  1.19E+029  hours   (4.959E+027 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       2.12e-019       0.949        1000       
   Water     46.4            900          1000       
   Soil      53.5            1.8e+003     1000       
   Sediment  0.0891          8.1e+003     0          
     Persistence Time: 973 hr

SimBioSys LASSO

Descriptors: 0, 0, 0, 2, 2, 0, 0, 9, 0, 0, 4, 8, 0, 0, 6, 0, 9, 0, 0, 2, 0, 0, 0, 0

Category	Target	PDB Code	LASSO Score
Metalloenzymes	ADA, adenosine deaminase	1stw	0.99
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.60
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.43
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.17
Kinases	TK, thymidine kinase	1kim	0.09
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.03
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.03
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.03
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.02
Kinases	EGFr, epidermal growth factor receptor	1m17	0.02
Kinases	SRC, tyrosine kinase SRC	2src	0.01
Other Enzymes	HMGR, hydroxymethylglutaryl-CoA reductase	1hw8	0.01
Kinases	HSP90, human heat shock protein 90	1uy6	0.01
Other Enzymes	HIVPR, HIV protease	1hpx	0.01
Metalloenzymes	PDE5, phosphodiesterase 5	1xp0	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.01
Nuclear Hormone Receptors	ER, estrogen receptor; antagonist	3ert	0.01
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.00
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.00
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.00
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.00
Nuclear Hormone Receptors	GR, glucocorticoid receptor	1m2z	0.00
Other Enzymes	COX-1, cyclooxygenase-1	1p4g	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	0.00
Other Enzymes	ALR2, aldose reductase	1ah3	0.00
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.00
Other Enzymes	InhA, enoyl ACP reductase	1p44	0.00
Serine Proteases	Thrombin	1ba8	0.00
Serine Proteases	Trypsin	1bju	0.00