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Upadacitinib

C17H19F3N6O — CID 58557659

💊View drug profile → upadacitinib

Data last refreshed: (MolForge compound catalog, from PubChem)

IUPAC(3S,4R)-3-ethyl-4-(1,5,7,10-tetrazatricyclo[7.3.0.02,6]dodeca-2(6),3,7,9,11-pentaen-12-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide
SMILESCC[C@@H]1CN(C(=O)NCC(F)(F)F)C[C@@H]1c1cnc2cnc3[nH]ccc3n12
InChIInChI=1S/C17H19F3N6O/c1-2-10-7-25(16(27)24-9-17(18,19)20)8-11(10)13-5-22-14-6-23-15-12(26(13)14)3-4-21-15/h3-6,10-11,21H,2,7-9H2,1H3,(H,24,27)/t10-,11+/m1/s1
InChIKeyWYQFJHHDOKWSHR-MNOVXSKESA-N
MW380.37 g/mol
LogP2.91
Rot. Bonds3

About Upadacitinib

Upadacitinib (PubChem CID 58557659) has the molecular formula C17H19F3N6O and a molecular weight of 380.37 g/mol. Its IUPAC name is (3S,4R)-3-ethyl-4-(1,5,7,10-tetrazatricyclo[7.3.0.02,6]dodeca-2(6),3,7,9,11-pentaen-12-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide.

Molecular Properties

Compound NameUpadacitinib
PubChem CID58557659
Molecular FormulaC17H19F3N6O
Molecular Weight380.37 g/mol
Exact Mass380.16
IUPAC Name(3S,4R)-3-ethyl-4-(1,5,7,10-tetrazatricyclo[7.3.0.02,6]dodeca-2(6),3,7,9,11-pentaen-12-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide
SMILESCC[C@@H]1CN(C(=O)NCC(F)(F)F)C[C@@H]1c1cnc2cnc3[nH]ccc3n12
InChIInChI=1S/C17H19F3N6O/c1-2-10-7-25(16(27)24-9-17(18,19)20)8-11(10)13-5-22-14-6-23-15-12(26(13)14)3-4-21-15/h3-6,10-11,21H,2,7-9H2,1H3,(H,24,27)/t10-,11+/m1/s1
InChIKeyWYQFJHHDOKWSHR-MNOVXSKESA-N
XLogP2.91
TPSA78.32 Ų
H-Bond Donors2
H-Bond Acceptors4
Rotatable Bonds3
Heavy Atoms27
Complexity—

Lipinski Rule of Five

Passes Rule of Five

RuleValue
MW ≤ 500380.37
LogP ≤ 52.91
H-Bond Donors ≤ 52
H-Bond Acceptors ≤ 104

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Related Compounds

1-cyclohexyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine
CID 50906783
8-cyclohexyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine
CID 58010265
N-(cyanomethyl)-N-methyl-7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,7-diazaspiro[4.4]nonane-1-carboxamide
CID 58293348
N-propyl-7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,7-diazaspiro[4.4]nonane-1-carboxamide
CID 58293383
3-[9,9-difluoro-4-methyl-7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,7-diazaspiro[4.4]nonan-1-yl]-3-oxopropanenitrile
CID 58293398
8-((3R,4S)-4-ethylpyrrolidin-3-yl)-3H-imidazo(1,2-a)pyrrolo(2,3-e)pyrazine
CID 118036111
Upadacitinib hemihydrate
CID 133053456

Frequently Asked Questions

What is the IUPAC name of Upadacitinib?
The IUPAC name of Upadacitinib (CID 58557659) is (3S,4R)-3-ethyl-4-(1,5,7,10-tetrazatricyclo[7.3.0.02,6]dodeca-2(6),3,7,9,11-pentaen-12-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide.
What is the SMILES notation for Upadacitinib?
The canonical SMILES for Upadacitinib is CC[C@@H]1CN(C(=O)NCC(F)(F)F)C[C@@H]1c1cnc2cnc3[nH]ccc3n12.
What is the InChIKey of Upadacitinib?
The InChIKey is WYQFJHHDOKWSHR-MNOVXSKESA-N. The full InChI is InChI=1S/C17H19F3N6O/c1-2-10-7-25(16(27)24-9-17(18,19)20)8-11(10)13-5-22-14-6-23-15-12(26(13)14)3-4-21-15/h3-6,10-11,21H,2,7-9H2,1H3,(H,24,27)/t10-,11+/m1/s1.
What are the key properties of Upadacitinib?
Upadacitinib has a molecular weight of 380.37 g/mol, XLogP of 2.91, 3 rotatable bonds, 2 hydrogen bond donors, and 4 hydrogen bond acceptors.
Where does this data come from?
All data for Upadacitinib is sourced from PubChem (CID 58557659), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).

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