[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(1,3-dihydroisoindol-2-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-morpholin-4-ylmethanone

C72H84Cl3N17O10 — CID 158522368

IUPAC[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(1,3-dihydroisoindol-2-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-morpholin-4-ylmethanone
SMILESCOc1ccc(CNc2nc(N3CCC[C@@H]3CO)ncc2C(=O)N2CCOCC2)cc1Cl.COc1ccc(CNc2nc(N3CCC[C@@H]3CO)ncc2C(=O)N2Cc3ccccc3C2)cc1Cl.COc1ccc(CNc2nc(N3CCC[C@H]3CO)ncc2C(=O)N2CCn3ccnc3C2)cc1Cl
InChIInChI=1S/C26H28ClN5O3.C24H28ClN7O3.C22H28ClN5O4/c1-35-23-9-8-17(11-22(23)27)12-28-24-21(13-29-26(30-24)32-10-4-7-20(32)16-33)25(34)31-14-18-5-2-3-6-19(18)15-31;1-35-20-5-4-16(11-19(20)25)12-27-22-18(13-28-24(29-22)32-7-2-3-17(32)15-33)23(34)31-10-9-30-8-6-26-21(30)14-31;1-31-19-5-4-15(11-18(19)23)12-24-20-17(21(30)27-7-9-32-10-8-27)13-25-22(26-20)28-6-2-3-16(28)14-29/h2-3,5-6,8-9,11,13,20,33H,4,7,10,12,14-16H2,1H3,(H,28,29,30);4-6,8,11,13,17,33H,2-3,7,9-10,12,14-15H2,1H3,(H,27,28,29);4-5,11,13,16,29H,2-3,6-10,12,14H2,1H3,(H,24,25,26)/t20-;17-;16-/m101/s1
InChIKeyHMJGUZHNNAQKER-HLPONZGOSA-N
MW1453.93 g/mol
LogP8.62
Rot. Bonds21

About [4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(1,3-dihydroisoindol-2-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-morpholin-4-ylmethanone

[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(1,3-dihydroisoindol-2-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-morpholin-4-ylmethanone (PubChem CID 158522368) has the molecular formula C72H84Cl3N17O10 and a molecular weight of 1453.93 g/mol. Its IUPAC name is [4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(1,3-dihydroisoindol-2-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-morpholin-4-ylmethanone.

Molecular Properties

Compound Name[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(1,3-dihydroisoindol-2-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-morpholin-4-ylmethanone
PubChem CID158522368
Molecular FormulaC72H84Cl3N17O10
Molecular Weight1453.93 g/mol
Exact Mass1451.57
IUPAC Name[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(1,3-dihydroisoindol-2-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-morpholin-4-ylmethanone
SMILESCOc1ccc(CNc2nc(N3CCC[C@@H]3CO)ncc2C(=O)N2CCOCC2)cc1Cl.COc1ccc(CNc2nc(N3CCC[C@@H]3CO)ncc2C(=O)N2Cc3ccccc3C2)cc1Cl.COc1ccc(CNc2nc(N3CCC[C@H]3CO)ncc2C(=O)N2CCn3ccnc3C2)cc1Cl
InChIInChI=1S/C26H28ClN5O3.C24H28ClN7O3.C22H28ClN5O4/c1-35-23-9-8-17(11-22(23)27)12-28-24-21(13-29-26(30-24)32-10-4-7-20(32)16-33)25(34)31-14-18-5-2-3-6-19(18)15-31;1-35-20-5-4-16(11-19(20)25)12-27-22-18(13-28-24(29-22)32-7-2-3-17(32)15-33)23(34)31-10-9-30-8-6-26-21(30)14-31;1-31-19-5-4-15(11-18(19)23)12-24-20-17(21(30)27-7-9-32-10-8-27)13-25-22(26-20)28-6-2-3-16(28)14-29/h2-3,5-6,8-9,11,13,20,33H,4,7,10,12,14-16H2,1H3,(H,28,29,30);4-6,8,11,13,17,33H,2-3,7,9-10,12,14-15H2,1H3,(H,27,28,29);4-5,11,13,16,29H,2-3,6-10,12,14H2,1H3,(H,24,25,26)/t20-;17-;16-/m101/s1
InChIKeyHMJGUZHNNAQKER-HLPONZGOSA-N
XLogP8.62
TPSA299.51 Ų
H-Bond Donors6
H-Bond Acceptors24
Rotatable Bonds21
Heavy Atoms102
Complexity—

Lipinski Rule of Five

4 violations

RuleValue
MW ≤ 5001453.93
LogP ≤ 58.62
H-Bond Donors ≤ 56
H-Bond Acceptors ≤ 1024

Analyze [4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(1,3-dihydroisoindol-2-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-morpholin-4-ylmethanone with MolForge

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Related Compounds

3-chloro-N-[(2S)-1-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-3-[4-(8-methylimidazo[1,2-a]pyridin-2-yl)phenyl]propan-2-yl]-4-propan-2-yloxybenzamide;3-chloro-N-[(2S)-1-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]-3-[4-(8-methylimidazo[1,2-a]pyridin-2-yl)phenyl]propan-2-yl]-4-propan-2-yloxybenzamide;3-chloro-N-[(2S)-1-(4-hydroxypiperidin-1-yl)-3-[4-(8-methylimidazo[1,2-a]pyridin-2-yl)phenyl]propan-2-yl]-4-propan-2-yloxybenzamide;3-chloro-N-[(2S)-1-(3-hydroxypyrrolidin-1-yl)-3-[4-(8-methylimidazo[1,2-a]pyridin-2-yl)phenyl]propan-2-yl]-4-propan-2-yloxybenzamide;3-chloro-N-[(2S)-1-[4-(8-methylimidazo[1,2-a]pyridin-2-yl)phenyl]-3-(2,2,2-trifluoroethylamino)propan-2-yl]-4-propan-2-yloxybenzamide
CID 173100787
4-[(3-chloro-4-methoxyphenyl)methylamino]-2-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)-N-(2-morpholin-4-ylethyl)pyrimidine-5-carboxamide
CID 22665589
[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)methanone
CID 58962795
N-[(3-chloro-4-methoxyphenyl)methyl]-4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-N-[2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-(pyrimidin-2-ylmethylcarbamoyl)pyrimidin-4-yl]pyrimidine-5-carboxamide
CID 117780068
N-[(3-chloro-4-methoxyphenyl)methyl]-4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-N-[2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-[methyl(pyrimidin-2-yl)carbamoyl]pyrimidin-4-yl]pyrimidine-5-carboxamide
CID 117780070
N-[(3-chloro-4-methoxyphenyl)methyl]-4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[2-(hydroxymethyl)pyrrolidin-1-yl]-N-[2-[2-(hydroxymethyl)pyrrolidin-1-yl]-5-(pyrimidin-2-ylmethylcarbamoyl)pyrimidin-4-yl]pyrimidine-5-carboxamide
CID 117780072
N-[(3-chloro-4-methoxyphenyl)methyl]-4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-N-[5-(pyrimidin-2-ylmethylcarbamoyl)-2-pyrrolidin-1-ylpyrimidin-4-yl]pyrimidine-5-carboxamide
CID 117804881
N-[(3-chloro-4-methoxyphenyl)methyl]-4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[2-(hydroxymethyl)pyrrolidin-1-yl]-N-[5-(pyrimidin-2-ylmethylcarbamoyl)-2-pyrrolidin-1-ylpyrimidin-4-yl]pyrimidine-5-carboxamide
CID 123610546
N-(3-chloro-4-methoxybenzyl)-4-((3-chloro-4-methoxybenzyl)amino)-2-((S)-2-(hydroxymethyl)pyrrolidin-1-yl)-N-(2-((R)-2-(hydroxymethyl)pyrrolidin-1-yl)-5-((pyrimidin-2-ylmethyl)carbamoyl)pyrimidin-4-yl)pyrimidine-5-carboxamide
CID 154631370
[2-[7-(3-aminopropyl)imidazo[1,2-a]pyridin-2-yl]-4-chloro-5-methoxyphenyl]methanol;3-chloro-N,N-dimethylpropan-1-amine;1-[2-[5-chloro-2-(hydroxymethyl)-4-methoxyphenyl]imidazo[1,2-a]pyridin-7-yl]-3-[3-(dimethylamino)propyl]imidazolidin-2-one;1-[2-[5-chloro-2-(hydroxymethyl)-4-methoxyphenyl]imidazo[1,2-a]pyridin-7-yl]imidazolidin-2-one
CID 157124522
sodium;(3S,4S)-4-amino-1-[2-[5-chloro-2-(hydroxymethyl)-4-methoxyphenyl]imidazo[1,2-a]pyridin-7-yl]pyrrolidin-3-ol;(3S,4S)-4-azidopyrrolidin-3-ol;tert-butyl (3S,4S)-3-azido-4-hydroxypyrrolidine-1-carboxylate;tert-butyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate;[4-chloro-2-(7-chloroimidazo[1,2-a]pyridin-2-yl)-5-methoxyphenyl]methanol;(3S,4S)-1-[2-[5-chloro-2-(hydroxymethyl)-4-methoxyphenyl]imidazo[1,2-a]pyridin-7-yl]-4-(pyridin-4-ylmethylamino)pyrrolidin-3-ol;pyridine-4-carbaldehyde;azide
CID 157359797
6-chloro-N-ethyl-8-[(4-methoxyphenyl)methyl-methylamino]imidazo[1,2-b]pyridazine-3-carboxamide;6-chloro-N-(3-hydroxycyclobutyl)-8-[(4-methoxyphenyl)methyl-methylamino]imidazo[1,2-b]pyridazine-3-carboxamide;6-chloro-8-[(4-methoxyphenyl)methyl-methylamino]-N-(2-methylpropyl)imidazo[1,2-b]pyridazine-3-carboxamide;6-chloro-8-[(4-methoxyphenyl)methyl-methylamino]-N-(oxetan-3-yl)imidazo[1,2-b]pyridazine-3-carboxamide;6-chloro-8-[(4-methoxyphenyl)methyl-methylamino]-N-propan-2-ylimidazo[1,2-b]pyridazine-3-carboxamide
CID 161469266

Frequently Asked Questions

What is the IUPAC name of [4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(1,3-dihydroisoindol-2-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-morpholin-4-ylmethanone?
The IUPAC name of [4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(1,3-dihydroisoindol-2-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-morpholin-4-ylmethanone (CID 158522368) is [4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(1,3-dihydroisoindol-2-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-morpholin-4-ylmethanone.
What is the SMILES notation for [4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(1,3-dihydroisoindol-2-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-morpholin-4-ylmethanone?
The canonical SMILES for [4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(1,3-dihydroisoindol-2-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-morpholin-4-ylmethanone is COc1ccc(CNc2nc(N3CCC[C@@H]3CO)ncc2C(=O)N2CCOCC2)cc1Cl.COc1ccc(CNc2nc(N3CCC[C@@H]3CO)ncc2C(=O)N2Cc3ccccc3C2)cc1Cl.COc1ccc(CNc2nc(N3CCC[C@H]3CO)ncc2C(=O)N2CCn3ccnc3C2)cc1Cl.
What is the InChIKey of [4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(1,3-dihydroisoindol-2-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-morpholin-4-ylmethanone?
The InChIKey is HMJGUZHNNAQKER-HLPONZGOSA-N. The full InChI is InChI=1S/C26H28ClN5O3.C24H28ClN7O3.C22H28ClN5O4/c1-35-23-9-8-17(11-22(23)27)12-28-24-21(13-29-26(30-24)32-10-4-7-20(32)16-33)25(34)31-14-18-5-2-3-6-19(18)15-31;1-35-20-5-4-16(11-19(20)25)12-27-22-18(13-28-24(29-22)32-7-2-3-17(32)15-33)23(34)31-10-9-30-8-6-26-21(30)14-31;1-31-19-5-4-15(11-18(19)23)12-24-20-17(21(30)27-7-9-32-10-8-27)13-25-22(26-20)28-6-2-3-16(28)14-29/h2-3,5-6,8-9,11,13,20,33H,4,7,10,12,14-16H2,1H3,(H,28,29,30);4-6,8,11,13,17,33H,2-3,7,9-10,12,14-15H2,1H3,(H,27,28,29);4-5,11,13,16,29H,2-3,6-10,12,14H2,1H3,(H,24,25,26)/t20-;17-;16-/m101/s1.
What are the key properties of [4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(1,3-dihydroisoindol-2-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-morpholin-4-ylmethanone?
[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(1,3-dihydroisoindol-2-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-morpholin-4-ylmethanone has a molecular weight of 1453.93 g/mol, XLogP of 8.62, 21 rotatable bonds, 6 hydrogen bond donors, and 24 hydrogen bond acceptors.
Where does this data come from?
All data for [4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-(1,3-dihydroisoindol-2-yl)methanone;[4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl]-morpholin-4-ylmethanone is sourced from PubChem (CID 158522368), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).