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Adenosine cyclic 3',5'-monophosphate

ChemSpider ID: 5851
Molecular Formula: C₁₀H₁₂N₅O₆P
Average mass: 329.205902 Da
Monoisotopic mass: 329.052521 Da
Systematic name

(4aR,6R,7R,7aS)-6-(6-Amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 2-oxide
SMILES and InChIs

SMILES:

c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@H]4[C@H](O3)COP(=O)(O4)O)O)N Copied

Std. InChI:

InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1 Copied

Std. InChIKey:

IVOMOUWHDPKRLL-KQYNXXCUSA-N Copied
Cite this record
CSID:5851, http://www.chemspider.com/Chemical-Structure.5851.html (accessed 15:38, May 21, 2013) Copied

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

Adenosine cyclic 3',5'-monophosphate

(4aR,6R,7R,7aS)-6-(6-Amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2,7-diol-2-oxid [ACD/IUPAC Name]

(4aR,6R,7R,7aS)-6-(6-Amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 2-oxide [ACD/IUPAC Name]

3',5'-Cyclic AMP

3′,5′-Cyclic AMP

3'5'-cyclic ester of AMP

4H-furo[3,2-d]-1,3,2-dioxaphosphorin-7-ol, 6-(6-amino-9H-purin-9-yl)tetrahydro-2-hydroxy-, 2-oxide, (4aR,6R,7R,7aS)- [ACD/Index Name]

Adenosine 3',5'-cyclic monophosphate

Adenosine 3,5'-cyclic monophosphoric acid

Adenosine 3',5'-cyclic phosphate

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

CHEBI:17489 [DBID]

A9501_SIGMA [DBID]

AIDS008698 [DBID]

AIDS-008698 [DBID]

bmse000071 [DBID]

BRN 0052645 [DBID]

C00575 [DBID]

CCRIS 4291 [DBID]

EU-0100084 [DBID]

NSC 94017 [DBID]

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Properties

Experimental data
Predicted - ACD/Labs
Predicted - EPISuite
Predicted - ChemAxon

Data supplied by datasources and users.

Predicted Physico-chemical Properties
- Predicted Melting Point:
  
  260 deg C (260 °C) J and K Scientific
Miscellaneous
- Chemical Class:
  
  Phosphorylation (EU-OpenScreen [A 9501])

Predicted data is generated using the ACD/Labs’ ACD/PhysChem Suite, for more information see their website.

ACD/LogP:	1.221	# of Rule of 5 Violations:	1
ACD/LogD (pH 5.5):	-2.15	ACD/LogD (pH 7.4):	-2.28
ACD/BCF (pH 5.5):	1.00	ACD/BCF (pH 7.4):	1.00
ACD/KOC (pH 5.5):	1.00	ACD/KOC (pH 7.4):	1.00
#H bond acceptors:	11	#H bond donors:	4
#Freely Rotating Bonds:	2	Polar Surface Area:	164.65 Å²
Index of Refraction:	2.012	Molar Refractivity:	67.045 cm³
Molar Volume:	133.062 cm³	Polarizability:	26.579 10^-24cm³
Surface Tension:	153.837005615234 dyne/cm	Density:	2.474 g/cm³
Flash Point:	378.046 °C	Enthalpy of Vaporization:	107.817 kJ/mol
Boiling Point:	701.488 °C at 760 mmHg	Vapour Pressure:	0 mmHg at 25°C

Predicted data is generated using the US Environmental Protection Agency’s EPISuite™, for more information see their website.

                    
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  -2.36
    Log Kow (Exper. database match) =  -2.96
       Exper. Ref:  Hansch,C et al. (1995)

 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):  2.19E-012  (Modified Grain method)
    MP  (exp database):  219-220 deg C
    Subcooled liquid VP: 2.58E-010 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):  1.364e+005
       log Kow used: -2.96 (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:
       Aromatic Amines
       Imidazoles

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.92E-028  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.955E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -2.96  (exp database)
  Log Kaw used:  -25.923  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  22.963
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1684
   Biowin2 (Non-Linear Model)     :   0.0028
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4880  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3841  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1764
   Biowin6 (MITI Non-Linear Model):   0.0006
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.2807
 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):  3.44E-008 Pa (2.58E-010 mm Hg)
  Log Koa (Koawin est  ): 22.963
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  87.2 
       Octanol/air (Koa) model:  2.25E+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 = 289.6869 E-12 cm3/molecule-sec
      Half-Life =     0.037 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    26.584 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: -2.96 (expkow database)

 Volatilization from Water:
    Henry LC:  2.92E-028 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.638E+024  hours   (1.516E+023 days)
    Half-Life from Model Lake : 3.969E+025  hours   (1.654E+024 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       3.81e-016       0.886        1000       
   Water     46.5            900          1000       
   Soil      53.5            1.8e+003     1000       
   Sediment  0.0892          8.1e+003     0          
     Persistence Time: 973 hr

Click to predict properties on the Chemicalize site

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Category	Target	PDB Code	LASSO Score
Metalloenzymes	ADA, adenosine deaminase	1stw	0.99
Kinases	TK, thymidine kinase	1kim	0.91
Kinases	EGFr, epidermal growth factor receptor	1m17	0.89
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.64
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.46
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.42
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.35
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.18
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.03
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.02
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	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
Metalloenzymes	PDE5, phosphodiesterase 5	1xp0	0.01
Other Enzymes	HIVPR, HIV protease	1hpx	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
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	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
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00
Serine Proteases	Thrombin	1ba8	0.00

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Adenosine cyclic 3',5'-monophosphate

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Std. InChIKey:

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Adenosine cyclic 3',5'-monophosphate

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