Zidovudine

C10H13N5O4 — CID 35370

IUPAC1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
SMILESCC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)N=[N+]=[N-]
InChIInChI=1S/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1
InChIKeyHBOMLICNUCNMMY-XLPZGREQSA-N
MW267.24 g/mol
LogP0.00
Rot. Bonds3

About Zidovudine

Zidovudine (PubChem CID 35370) has the molecular formula C10H13N5O4 and a molecular weight of 267.24 g/mol. Its IUPAC name is 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione.

Molecular Properties

Compound NameZidovudine
PubChem CID35370
Molecular FormulaC10H13N5O4
Molecular Weight267.24 g/mol
Exact Mass267.10
IUPAC Name1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
SMILESCC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)N=[N+]=[N-]
InChIInChI=1S/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1
InChIKeyHBOMLICNUCNMMY-XLPZGREQSA-N
XLogP0.00
TPSA93.20 Ų
H-Bond Donors2
H-Bond Acceptors6
Rotatable Bonds3
Heavy Atoms19
Complexity484

Lipinski Rule of Five

Passes Rule of Five

RuleValue
MW ≤ 500267.24
LogP ≤ 50.00
H-Bond Donors ≤ 52
H-Bond Acceptors ≤ 106

Computed Properties (RDKit)

Structural Alerts{'alert_name': 'azo_A(324)', 'substructure': 'N/A'}, {'alert_name': 'Azido_group', 'substructure': 'N/A'}, {'alert_name': 'diazo_group', 'substructure': 'N/A'}, {'alert_name': 'quaternary_nitrogen_3', 'substructure': 'N/A'}

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Related Compounds

Thymidine
CID 5789
Telbivudine
CID 159269
3'-Fluorothymidine
CID 33039
5-Methyluridine
CID 445408
1-(2-Deoxypentofuranosyl)-4-hydroxy-5-methylpyrimidin-2(1H)-one
CID 1134
Clevudine
CID 73115
1-beta-D-Arabinofuranosyl-5-methyl-2,4(1H,3H)-pyrimidinedione
CID 65049
Edoxudin
CID 66377
Zidovudine triphosphate
CID 72187
Navuridine
CID 55262
2',3'-Dideoxythymidine
CID 65119
Netivudine
CID 55281

Frequently Asked Questions

What is the IUPAC name of Zidovudine?
The IUPAC name of Zidovudine (CID 35370) is 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione.
What is the SMILES notation for Zidovudine?
The canonical SMILES for Zidovudine is CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)N=[N+]=[N-].
What is the InChIKey of Zidovudine?
The InChIKey is HBOMLICNUCNMMY-XLPZGREQSA-N. The full InChI is InChI=1S/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1.
What are the key properties of Zidovudine?
Zidovudine has a molecular weight of 267.24 g/mol, XLogP of 0.00, 3 rotatable bonds, 2 hydrogen bond donors, and 6 hydrogen bond acceptors.
Where does this data come from?
All data for Zidovudine is sourced from PubChem (CID 35370), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).