5'-O-[(R)-{[(R)-{[(5aR,6R,7R,8R,9aR)-2-Amino-4-oxo-6,7-disulfanyl-1,5a,6,7,8,9a-hexahydro-4H-pyrano[3,2-g]pteridin-8-yl]methoxy}(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]guanosine

ChemSpider ID: 5290546
Molecular Formula: C₂₀H₂₆N₁₀O₁₃P₂S₂
Average mass: 740.55719 Da
Monoisotopic mass: 740.059753 Da
Systematic name

5'-O-[(R)-{[(R)-{[(5aR,6R,7R,8R,9aR)-2-Amino-4-oxo-6,7-disulfanyl-1,5a,6,7,8,9a-hexahydro-4H-pyrano[3,2-g]pteridin-8-yl]methoxy}(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]guanosine
SMILES and InChIs

SMILES:

O=C/1\N=C(\N)NC2=N/[C@@H]3O[C@@H]([C@@H](S)[C@H](S)[C@@H]3/N=C\12)COP(=O)(O)OP(=O)(O)OC[C@H]6O[C@@H](n4cnc5c4NC(=N/C5=O)\N)[C@H](O)[C@@H]6O Copied

Std. InChI:

InChI=1S/C20H26N10O13P2S2/c21-19-26-13-7(15(33)28-19)24-6-12(47)11(46)5(41-17(6)25-13)2-40-45(37,38)43-44(35,36)39-1-4-9(31)10(32)18(42-4)30-3-23-8-14(30)27-20(22)29-16(8)34/h3-6,9-12,17-18,31-32,46-47H,1-2H2,(H,35,36)(H,37,38)(H3,22,27,29,34)(H3,21,25,26,28,33)/t4-,5-,6+,9-,10-,11-,12-,17-,18-/m1/s1 Copied

Std. InChIKey:

FDXWPXAMGMKUHE-VPOIRQIFSA-N Copied
Cite this record
CSID:5290546, http://www.chemspider.com/Chemical-Structure.5290546.html (accessed 16:55, May 25, 2013) Copied

Names and Identifiers

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

ACD/LogP:	-0.583	# of Rule of 5 Violations:	3
ACD/LogD (pH 5.5):	-5.07	ACD/LogD (pH 7.4):	-5.10
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:	23	#H bond donors:	10
#Freely Rotating Bonds:	13	Polar Surface Area:	435.93 Å²
Index of Refraction:	2.069	Molar Refractivity:	150.716 cm³
Molar Volume:	288.55 cm³	Polarizability:	59.749 10^-24cm³
Surface Tension:	161.042007446289 dyne/cm	Density:	2.566 g/cm³
Flash Point:	625.01 °C	Enthalpy of Vaporization:	170.951 kJ/mol
Boiling Point:	1109.843 °C at 760 mmHg	Vapour Pressure:	0 mmHg at 25°C

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Spectra

CIFs

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Pharmacological Links

SimBioSys LASSO

Category	Target	PDB Code	LASSO Score
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.47
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.18
Kinases	TK, thymidine kinase	1kim	0.08
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.07
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.03
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	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
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Nuclear Hormone Receptors	ER, estrogen receptor; antagonist	3ert	0.01
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.00
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.00
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.00
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.00
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.00
Other Enzymes	ALR2, aldose reductase	1ah3	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	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-2, cyclooxygenase-2	1cx2	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Other Enzymes	COX-1, cyclooxygenase-1	1p4g	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	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
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.00
Serine Proteases	Thrombin	1ba8	0.00
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.00
Serine Proteases	Trypsin	1bju	0.00

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5'-O-[(R)-{[(R)-{[(5aR,6R,7R,8R,9aR)-2-Amino-4-oxo-6,7-disulfanyl-1,5a,6,7,8,9a-hexahydro-4H-pyrano[3,2-g]pteridin-8-yl]methoxy}(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]guanosine

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SimBioSys LASSO

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5'-O-[(R)-{[(R)-{[(5aR,6R,7R,8R,9aR)-2-Amino-4-oxo-6,7-disulfanyl-1,5a,6,7,8,9a-hexahydro-4H-pyrano[3,2-g]pteridin-8-yl]methoxy}(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]guanosine

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