4BW

2-amino-9-[(2R,3R,3aS,5R,7aR,9R,10R,10aS,12R,14aR)-9-(6-amino-9H-purin-9-yl)-3,5,10,12-tetrahydroxy-5,12-dioxidooctahydro-2H,7H-difuro[3,2-d:3',2'-j][1,3,7,9,2,8]tetraoxadiphosphacyclododecin-2-yl]-1,9-dihydro-6H-purin-6-one

Created: 2015-02-25
Last modified:  2020-05-26

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Chemical Details

Formal Charge0
Atom Count69
Chiral Atom Count8
Bond Count75
Aromatic Bond Count15
2D diagram of 4BW
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Chemical Component Summary

Name2-amino-9-[(2R,3R,3aS,5R,7aR,9R,10R,10aS,12R,14aR)-9-(6-amino-9H-purin-9-yl)-3,5,10,12-tetrahydroxy-5,12-dioxidooctahydro-2H,7H-difuro[3,2-d:3',2'-j][1,3,7,9,2,8]tetraoxadiphosphacyclododecin-2-yl]-1,9-dihydro-6H-purin-6-one
Synonyms3',3' cGAMP; c-GMP-AMP; c[G(3',5')pA(3',5')p]
Systematic Name (OpenEye OEToolkits)n/a
FormulaC20 H24 N10 O13 P2
Molecular Weight674.411
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01O=C7NC(=Nc1c7ncn1C6OC5COP(=O)(O)OC4C(OC(n2c3ncnc(N)c3nc2)C4O)COP(=O)(OC5C6O)O)N
SMILESCACTVS3.385NC1=Nc2n(cnc2C(=O)N1)[CH]3O[CH]4CO[P](O)(=O)O[CH]5[CH](O)[CH](O[CH]5CO[P](O)(=O)O[CH]4[CH]3O)n6cnc7c(N)ncnc67
SMILESOpenEye OEToolkits1.9.2c1nc(c2c(n1)n(cn2)C3C(C4C(O3)COP(=O)(OC5C(COP(=O)(O4)O)OC(C5O)n6cnc7c6N=C(NC7=O)N)O)O)N
Canonical SMILESCACTVS3.385 NC1=Nc2n(cnc2C(=O)N1)[C@@H]3O[C@@H]4CO[P](O)(=O)O[C@H]5[C@@H](O)[C@@H](O[C@@H]5CO[P](O)(=O)O[C@H]4[C@H]3O)n6cnc7c(N)ncnc67
Canonical SMILESOpenEye OEToolkits1.9.2 c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@H]4[C@H](O3)COP(=O)(O[C@@H]5[C@@H](COP(=O)(O4)O)O[C@H]([C@@H]5O)n6cnc7c6N=C(NC7=O)N)O)O)N
InChIInChI1.03 InChI=1S/C20H24N10O13P2/c21-14-8-15(24-3-23-14)29(4-25-8)18-10(31)12-6(40-18)1-38-45(36,37)43-13-7(2-39-44(34,35)42-12)41-19(11(13)32)30-5-26-9-16(30)27-20(22)28-17(9)33/h3-7,10-13,18-19,31-32H,1-2H2,(H,34,35)(H,36,37)(H2,21,23,24)(H3,22,27,28,33)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1
InChIKeyInChI1.03 RFCBNSCSPXMEBK-INFSMZHSSA-N

Related Resource References

Resource NameReference
PubChem 11181459, 135471108
ChEBI CHEBI:71580