(5-chloro-2-propan-2-yloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(2-cyclopentyloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(7-fluoro-2,3-dimethylquinoxalin-5-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(5-methyl-1H-indazol-7-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;8-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]-4H-1,4-benzoxazin-3-one

C136H164ClFN30O9 — CID 159905728

About (5-chloro-2-propan-2-yloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(2-cyclopentyloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(7-fluoro-2,3-dimethylquinoxalin-5-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(5-methyl-1H-indazol-7-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;8-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]-4H-1,4-benzoxazin-3-one

(5-chloro-2-propan-2-yloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(2-cyclopentyloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(7-fluoro-2,3-dimethylquinoxalin-5-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(5-methyl-1H-indazol-7-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;8-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]-4H-1,4-benzoxazin-3-one (PubChem CID 159905728) has the molecular formula C136H164ClFN30O9 and a molecular weight of 2417.46 g/mol. Its IUPAC name is (5-chloro-2-propan-2-yloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(2-cyclopentyloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(7-fluoro-2,3-dimethylquinoxalin-5-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(5-methyl-1H-indazol-7-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;8-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]-4H-1,4-benzoxazin-3-one.

Molecular Properties

• Compound Name: (5-chloro-2-propan-2-yloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(2-cyclopentyloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(7-fluoro-2,3-dimethylquinoxalin-5-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(5-methyl-1H-indazol-7-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;8-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]-4H-1,4-benzoxazin-3-one
• PubChem CID: 159905728
• Molecular Formula: C136H164ClFN30O9
• Molecular Weight: 2417.46 g/mol
• Exact Mass: 2415.30
• IUPAC Name: (5-chloro-2-propan-2-yloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(2-cyclopentyloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(7-fluoro-2,3-dimethylquinoxalin-5-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(5-methyl-1H-indazol-7-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;8-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]-4H-1,4-benzoxazin-3-one
• SMILES: Cc1cc(C(=O)N2CCCC[C@H]2c2cc3nc(N4CC[C@H](C)C4)c(C)cn3n2)c2[nH]ncc2c1.Cc1cn2nc([C@@H]3CCCCN3C(=O)c3cc(Cl)ccc3OC(C)C)cc2nc1N1CC[C@H](C)C1.Cc1cn2nc([C@@H]3CCCCN3C(=O)c3cc(F)cc4nc(C)c(C)nc34)cc2nc1N1CC[C@H](C)C1.Cc1cn2nc([C@@H]3CCCCN3C(=O)c3cccc4c3OCC(=O)N4)cc2nc1N1CC[C@H](C)C1.Cc1cn2nc([C@@H]3CCCCN3C(=O)c3ccccc3OC3CCCC3)cc2nc1N1CC[C@H](C)C1
• InChI: InChI=1S/C29H37N5O2.C28H32FN7O.C27H34ClN5O2.C26H31N7O.C26H30N6O3/c1-20-14-16-32(18-20)28-21(2)19-34-27(30-28)17-24(31-34)25-12-7-8-15-33(25)29(35)23-11-5-6-13-26(23)36-22-9-3-4-10-22;1-16-8-10-34(14-16)27-17(2)15-36-25(32-27)13-22(33-36)24-7-5-6-9-35(24)28(37)21-11-20(29)12-23-26(21)31-19(4)18(3)30-23;1-17(2)35-24-9-8-20(28)13-21(24)27(34)32-11-6-5-7-23(32)22-14-25-29-26(19(4)16-33(25)30-22)31-12-10-18(3)15-31;1-16-7-9-31(14-16)25-18(3)15-33-23(28-25)12-21(30-33)22-6-4-5-8-32(22)26(34)20-11-17(2)10-19-13-27-29-24(19)20;1-16-9-11-30(13-16)25-17(2)14-32-22(28-25)12-20(29-32)21-8-3-4-10-31(21)26(34)18-6-5-7-19-24(18)35-15-23(33)27-19/h5-6,11,13,17,19-20,22,25H,3-4,7-10,12,14-16,18H2,1-2H3;11-13,15-16,24H,5-10,14H2,1-4H3;8-9,13-14,16-18,23H,5-7,10-12,15H2,1-4H3;10-13,15-16,22H,4-9,14H2,1-3H3,(H,27,29);5-7,12,14,16,21H,3-4,8-11,13,15H2,1-2H3,(H,27,33)/t20-,25-;16-,24-;18-,23-;16-,22-;16-,21-/m00000/s1
• InChIKey: NWNUINRXTJCMFJ-RLBNUHBESA-N
• XLogP: 24.23
• TPSA: 379.95 Ų
• H-Bond Donors: 2
• H-Bond Acceptors: 32
• Rotatable Bonds: 19
• Heavy Atoms: 177
• Complexity: —

Lipinski Rule of Five

3 violations

Rule	Value
MW ≤ 500	2417.46
LogP ≤ 5	24.23
H-Bond Donors ≤ 5	2
H-Bond Acceptors ≤ 10	32

Frequently Asked Questions

What is the IUPAC name of (5-chloro-2-propan-2-yloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(2-cyclopentyloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(7-fluoro-2,3-dimethylquinoxalin-5-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(5-methyl-1H-indazol-7-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;8-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]-4H-1,4-benzoxazin-3-one?

The IUPAC name of (5-chloro-2-propan-2-yloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(2-cyclopentyloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(7-fluoro-2,3-dimethylquinoxalin-5-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(5-methyl-1H-indazol-7-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;8-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]-4H-1,4-benzoxazin-3-one (CID 159905728) is (5-chloro-2-propan-2-yloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(2-cyclopentyloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(7-fluoro-2,3-dimethylquinoxalin-5-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(5-methyl-1H-indazol-7-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;8-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]-4H-1,4-benzoxazin-3-one.

What is the SMILES notation for (5-chloro-2-propan-2-yloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(2-cyclopentyloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(7-fluoro-2,3-dimethylquinoxalin-5-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(5-methyl-1H-indazol-7-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;8-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]-4H-1,4-benzoxazin-3-one?

The canonical SMILES for (5-chloro-2-propan-2-yloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(2-cyclopentyloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(7-fluoro-2,3-dimethylquinoxalin-5-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(5-methyl-1H-indazol-7-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;8-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]-4H-1,4-benzoxazin-3-one is Cc1cc(C(=O)N2CCCC[C@H]2c2cc3nc(N4CC[C@H](C)C4)c(C)cn3n2)c2[nH]ncc2c1.Cc1cn2nc([C@@H]3CCCCN3C(=O)c3cc(Cl)ccc3OC(C)C)cc2nc1N1CC[C@H](C)C1.Cc1cn2nc([C@@H]3CCCCN3C(=O)c3cc(F)cc4nc(C)c(C)nc34)cc2nc1N1CC[C@H](C)C1.Cc1cn2nc([C@@H]3CCCCN3C(=O)c3cccc4c3OCC(=O)N4)cc2nc1N1CC[C@H](C)C1.Cc1cn2nc([C@@H]3CCCCN3C(=O)c3ccccc3OC3CCCC3)cc2nc1N1CC[C@H](C)C1.

What is the InChIKey of (5-chloro-2-propan-2-yloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(2-cyclopentyloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(7-fluoro-2,3-dimethylquinoxalin-5-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(5-methyl-1H-indazol-7-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;8-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]-4H-1,4-benzoxazin-3-one?

The InChIKey is NWNUINRXTJCMFJ-RLBNUHBESA-N. The full InChI is InChI=1S/C29H37N5O2.C28H32FN7O.C27H34ClN5O2.C26H31N7O.C26H30N6O3/c1-20-14-16-32(18-20)28-21(2)19-34-27(30-28)17-24(31-34)25-12-7-8-15-33(25)29(35)23-11-5-6-13-26(23)36-22-9-3-4-10-22;1-16-8-10-34(14-16)27-17(2)15-36-25(32-27)13-22(33-36)24-7-5-6-9-35(24)28(37)21-11-20(29)12-23-26(21)31-19(4)18(3)30-23;1-17(2)35-24-9-8-20(28)13-21(24)27(34)32-11-6-5-7-23(32)22-14-25-29-26(19(4)16-33(25)30-22)31-12-10-18(3)15-31;1-16-7-9-31(14-16)25-18(3)15-33-23(28-25)12-21(30-33)22-6-4-5-8-32(22)26(34)20-11-17(2)10-19-13-27-29-24(19)20;1-16-9-11-30(13-16)25-17(2)14-32-22(28-25)12-20(29-32)21-8-3-4-10-31(21)26(34)18-6-5-7-19-24(18)35-15-23(33)27-19/h5-6,11,13,17,19-20,22,25H,3-4,7-10,12,14-16,18H2,1-2H3;11-13,15-16,24H,5-10,14H2,1-4H3;8-9,13-14,16-18,23H,5-7,10-12,15H2,1-4H3;10-13,15-16,22H,4-9,14H2,1-3H3,(H,27,29);5-7,12,14,16,21H,3-4,8-11,13,15H2,1-2H3,(H,27,33)/t20-,25-;16-,24-;18-,23-;16-,22-;16-,21-/m00000/s1.

What are the key properties of (5-chloro-2-propan-2-yloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(2-cyclopentyloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(7-fluoro-2,3-dimethylquinoxalin-5-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(5-methyl-1H-indazol-7-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;8-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]-4H-1,4-benzoxazin-3-one?

(5-chloro-2-propan-2-yloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(2-cyclopentyloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(7-fluoro-2,3-dimethylquinoxalin-5-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(5-methyl-1H-indazol-7-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;8-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]-4H-1,4-benzoxazin-3-one has a molecular weight of 2417.46 g/mol, XLogP of 24.23, 19 rotatable bonds, 2 hydrogen bond donors, and 32 hydrogen bond acceptors.

Where does this data come from?

All data for (5-chloro-2-propan-2-yloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(2-cyclopentyloxyphenyl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(7-fluoro-2,3-dimethylquinoxalin-5-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;(5-methyl-1H-indazol-7-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone;8-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]-4H-1,4-benzoxazin-3-one is sourced from PubChem (CID 159905728), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).