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Pharmaceutical impurity

Brivudine 5'-Triphosphate

Brivudine 5'-Triphosphate is listed in the pharmaceutical impurity collection under CAS 77222-61-8. Its represented structure has formula C11H16BrN2O14P3 and a calculated molecular weight of 573.08 g/mol.

2D chemical structure

O N H O N H O O P O O H O P O O H O P O O H O H O B r ( R ) ( S ) ( R ) ( E )

Chemical identity

Catalog name
Brivudine 5'-Triphosphate
Common name
Brivudine 5'-Triphosphate
Chemical name
[[(2R,3S,5R)-5-[5-[(E)-2-bromoethenyl]-2,4-dioxopyrimidin-1-yl]-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
CAS
77222-61-8
SMILES
O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)cc1/C=C/Br
InChI
InChI=1S/C11H16BrN2O14P3/c12-2-1-6-4-14(11(17)13-10(6)16)9-3-7(15)8(26-9)5-25-30(21,22)28-31(23,24)27-29(18,19)20/h1-2,4,7-9,15H,3,5H2,(H,21,22)(H,23,24)(H,13,16,17)(H2,18,19,20)/b2-1+/t7-,8+,9+/m0/s1
InChIKey
BDKFDDMJXWAXHI-PIXDULNESA-N

Record ID: A1f5a45b9d18a

Computed properties

C11H16BrN2O14P3 Molecular formula
573.075 g/molMolecular weight
571.8998 DaMonoisotopic exact mass
244.14 ŲTopological polar surface area
-0.1061 Calculated LogP (Wildman–Crippen)
103.6342 cm³/molMolar refractivity (Wildman–Crippen)
10 countHydrogen-bond acceptors
6 countHydrogen-bond donors

Descriptors are calculated from the displayed SMILES. Calculated LogP is not a measured partition coefficient or a pH-specific LogD. 2 potential atom stereocenters have unspecified configuration.

Molecular descriptor profile

Descriptor radar

Mol. weight LogP TPSA HBA HBD Rotatable 25 50 75 100

Structural feature counts

0 3 6 9 Count H-bond acceptors H-bond donors Rotatable bonds Rings Aromatic rings Stereo centers

Element composition

Br C H N O P 0 4 8 12 16 Number of atoms

Radar scale: 0–100 percentile within 25,771 distinct represented structures in this release, using the midpoint rank for ties. Larger values indicate a higher descriptor rank, not greater safety or toxicity. Element counts include hydrogen and combine isotopes under each element.

Radar values and percentile reference
DescriptorValuePercentile
Molecular weight573.07590.59
Calculated LogP (Wildman–Crippen)-0.106113.20
Topological polar surface area244.1497.55
Hydrogen-bond acceptors1093.21
Hydrogen-bond donors696.36
Rotatable bonds (strict)986.25

Complete molecular descriptors

PropertyCalculated valueUnit / type
Molecular formulaC11H16BrN2O14P3dimensionless
Molecular weight573.075g/mol
Monoisotopic exact mass571.8998Da
Topological polar surface area244.14Ų
Calculated LogP (Wildman–Crippen)-0.1061dimensionless
Molar refractivity (Wildman–Crippen)103.6342cm³/mol
Hydrogen-bond acceptors10count
Hydrogen-bond donors6count
Rotatable bonds (strict)9count
Heavy atoms31count
Heteroatoms20count
Rings2count
Aromatic rings1count
Aliphatic rings1count
Saturated rings1count
Aromatic heterocycles1count
Aliphatic heterocycles1count
Saturated heterocycles1count
Aromatic carbocycles0count
Aliphatic carbocycles0count
Fraction of sp³ carbon atoms0.4545fraction
Formal charge0e
Disconnected components1count
Isotopically specified atoms0count
Potential atom stereocenters5count
Unspecified atom stereocenters2count
Spiro atoms0count
Bridgehead atoms0count
Labute approximate surface area180.2046Ų
Valence electrons176count
Radical electrons0count
Bertz complexity1,093.7131index
Balaban J2.0734index

Ring categories overlap and should not be summed. No toxicity result, PDE, HBEL or acceptable intake is inferred from these descriptors.

Toxicological services and resources for Brivudine 5'-Triphosphate

Qualification and safety assessment of Brivudine 5'-Triphosphate

Explore toxicological qualification of Brivudine 5'-Triphosphate and ICH M7 mutagenic impurity assessment of Brivudine 5'-Triphosphate for evaluation of this impurity in its pharmaceutical context.

Where data gaps need to be addressed, resources include read-across assessment for Brivudine 5'-Triphosphate and acceptable intake and limit justification for Brivudine 5'-Triphosphate. The relevant approach depends on the available evidence, exposure and duration of use.

Related Altox services and technical resources

Identity sources and calculation method

Identifiers originate from the source catalogues and available public identity records. InChI and InChIKey on this page are generated from the displayed SMILES. RDKit validation checks the molecular representation; it does not independently verify every catalogue assignment.

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