O-{[4'-(6-amino-9H-purin-9-yl)-6'-({[hydroxy({[hydroxy(phosphonooxy)phosphoryl]oxy})phosphoryl]oxy}methyl)-2,6-dinitro-3'a,4',6',6'a-tetrahydrospiro[cyclohexane-1,2'-furo[3,4-d][1,3]dioxole]-2,5-dien-4-ylidene]nitroso}oxidanidolate

• ChemBase ID: 2256
• Molecular Formular: C16H16N8O19P3-
• Molecular Mass: 717.261723
• Monoisotopic Mass: 716.97445522
• SMILES: Nc1ncnc2c1ncn2C1OC(COP(=O)(O)OP(=O)(O)OP(=O)(O)O)C2OC3(OC12)C(=C/C(=N(/O)\[O-])/C=C3[N+](=O)[O-])[N+](=O)[O-]
• Canonical SMILES: [O-][N+](=O)C1=C/C(=N(\O)/[O-])/C=C(C21OC1C(O2)C(OC1COP(=O)(OP(=O)(OP(=O)(O)O)O)O)n1cnc2c1ncnc2N)[N+](=O)[O-]
• InChI: InChI=1S/C16H16N8O19P3/c17-13-10-14(19-4-18-13)21(5-20-10)15-12-11(7(39-15)3-38-45(34,35)43-46(36,37)42-44(31,32)33)40-16(41-12)8(23(27)28)1-6(22(25)26)2-9(16)24(29)30/h1-2,4-5,7,11-12,15H,3H2,(H6-,17,18,19,25,26,31,32,33,34,35,36,37)/q-1
• InChIKey: LQZBDVDATBCNNN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: O-{[4'-(6-amino-9H-purin-9-yl)-6'-({[hydroxy({[hydroxy(phosphonooxy)phosphoryl]oxy})phosphoryl]oxy}methyl)-2,6-dinitro-3'a,4',6',6'a-tetrahydrospiro[cyclohexane-1,2'-furo[3,4-d][1,3]dioxole]-2,5-dien-4-ylidene]nitroso}oxidanidolate
• IUPAC Traditional name: O-[4'-(6-aminopurin-9-yl)-6'-[({hydroxy[hydroxy(phosphonooxy)phosphoryl]oxyphosphoryl}oxy)methyl]-2,6-dinitro-3'a,4',6',6'a-tetrahydrospiro[cyclohexane-1,2'-furo[3,4-d][1,3]dioxole]-2,5-dien-4-ylidenenitroso]oxidanidolate
• Synonyms: Spiro(2,4,6-Trinitrobenzene[1,2a]-2o',3o'-Methylene-Adenine-Triphosphate

Database IDs

• PubChem SID: 160965709; 46507848
• PubChem CID: 0

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.8570134
• H Acceptors: 21
• H Donor: 5
• LogD (pH = 5.5): -11.1159
• LogD (pH = 7.4): -11.732449
• Log P: -5.879753
• Molar Refractivity: 149.0519 cm^3
• Polarizability: 53.822144 Å^3
• Polar Surface Area: 400.58 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.16
• LOG S: -2.36
• Solubility (Water): 3.22e+00 g/l

DETAILS

DrugBank - DB02524

Drug information: experimental