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Cyclic diguanosine monophosphate

CAT: 0926-NC46014-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0926-NC46014-01Size:1 mg
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CAS Number
61093-23-0
Synonyms
C-di-GMP; Cyclic-di-GMP; Cyclic bis (3',5') diguanylic acid; Cyclic diguanylate; c-diGMP
Smiles
C1[C@@H]2[C@H] ([C@H] ([C@@H] (O2) N3C=NC4=C3N=C (NC4=O) N) O) OP (=O) (OC[C@@H]5[C@H] ([C@H] ([C@@H] (O5) N6C=NC7=C6N=C (NC7=O) N) O) OP (=O) (O1) O) O
Molecular Formula
C20H24N10O14P2
Molecular Weight
690.41 g/mol
Controlled
No

Chemical Information

c-di-GMP

C-di-GMP is a cyclic purine dinucleotide that is the 3',5'-cyclic dimer of MP. It has a role as an immunomodulator and a signalling molecule. It is a cyclic purine dinucleotide and a guanyl ribonucleotide. It is a conjugate acid of a c-di-GMP(2-).

CAS Number61093-23-0
PubChem CID135440063
IUPAC Name2-amino-9-[(1S,6R,8R,9R,10S,15R,17R,18R)-17-(2-amino-6-oxo-1H-purin-9-yl)-3,9,12,18-tetrahydroxy-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.3.0.06,10]octadecan-8-yl]-1H-purin-6-one
Molecular FormulaC20H24N10O14P2
Molecular Weight690.4
XLogP-6.8
Topological Polar Surface Area341
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count18
Rotatable Bond Count2
Heavy Atom Count46
Formal Charge0
Complexity1340
SMILES
C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C3N=C(NC4=O)N)O)OP(=O)(OC[C@@H]5[C@H]([C@H]([C@@H](O5)N6C=NC7=C6N=C(NC7=O)N)O)OP(=O)(O1)O)O
InChI
InChI=1S/C20H24N10O14P2/c21-19-25-13-7(15(33)27-19)23-3-29(13)17-9(31)11-5(41-17)1-39-45(35,36)44-12-6(2-40-46(37,38)43-11)42-18(10(12)32)30-4-24-8-14(30)26-20(22)28-16(8)34/h3-6,9-12,17-18,31-32H,1-2H2,(H,35,36)(H,37,38)(H3,21,25,27,33)(H3,22,26,28,34)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1
InChIKey
PKFDLKSEZWEFGL-MHARETSRSA-N
Chemical Structure
2D Structure
2D structure of c-di-GMP
CAS: 61093-23-0
CID: 135440063
Formula: C20H24N10O14P2
MW: 690.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight690.4
XLogP3-6.8
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count18
Rotatable Bond Count2
Exact Mass690.09486947
Monoisotopic Mass690.09486947
Topological Polar Surface Area341 Ų
Heavy Atom Count46
Formal Charge0
Complexity1340
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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A 232-0018- (2- Aminoethylthio) - cyclic diguanosine monophosphate (8-AET-c-diGMP), sodium salt
M 102-0052'- O- (N'- Methylanthraniloyl) - cyclic diguanosine monophosphate (MANT-c-diGMP), sodium salt
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