N-[3-[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]thiophen-2-yl]acetamide;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(5-ethyl-1,2-oxazol-3-yl)methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-[5-(1-hydroxycyclopentyl)-1,2-oxazol-3-yl]methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(1-methylimidazol-4-yl)methanone;(3-fluoro-7-methylimidazo[1,2-a]pyridin-2-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone

C117H149FN36O9S — CID 159359398

About N-[3-[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]thiophen-2-yl]acetamide;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(5-ethyl-1,2-oxazol-3-yl)methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-[5-(1-hydroxycyclopentyl)-1,2-oxazol-3-yl]methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(1-methylimidazol-4-yl)methanone;(3-fluoro-7-methylimidazo[1,2-a]pyridin-2-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone

N-[3-[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]thiophen-2-yl]acetamide;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(5-ethyl-1,2-oxazol-3-yl)methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-[5-(1-hydroxycyclopentyl)-1,2-oxazol-3-yl]methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(1-methylimidazol-4-yl)methanone;(3-fluoro-7-methylimidazo[1,2-a]pyridin-2-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone (PubChem CID 159359398) has the molecular formula C117H149FN36O9S and a molecular weight of 2254.79 g/mol. Its IUPAC name is N-[3-[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]thiophen-2-yl]acetamide;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(5-ethyl-1,2-oxazol-3-yl)methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-[5-(1-hydroxycyclopentyl)-1,2-oxazol-3-yl]methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(1-methylimidazol-4-yl)methanone;(3-fluoro-7-methylimidazo[1,2-a]pyridin-2-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone.

Molecular Properties

• Compound Name: N-[3-[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]thiophen-2-yl]acetamide;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(5-ethyl-1,2-oxazol-3-yl)methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-[5-(1-hydroxycyclopentyl)-1,2-oxazol-3-yl]methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(1-methylimidazol-4-yl)methanone;(3-fluoro-7-methylimidazo[1,2-a]pyridin-2-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone
• PubChem CID: 159359398
• Molecular Formula: C117H149FN36O9S
• Molecular Weight: 2254.79 g/mol
• Exact Mass: 2253.20
• IUPAC Name: N-[3-[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]thiophen-2-yl]acetamide;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(5-ethyl-1,2-oxazol-3-yl)methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-[5-(1-hydroxycyclopentyl)-1,2-oxazol-3-yl]methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(1-methylimidazol-4-yl)methanone;(3-fluoro-7-methylimidazo[1,2-a]pyridin-2-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone
• SMILES: CC(=O)Nc1sccc1C(=O)N1CCCC[C@H]1c1cc2nc(N3CC[C@H](N)C3)c(C)cn2n1.CCc1cc(C(=O)N2CCCC[C@H]2c2cc3nc(N4CC[C@H](N)C4)c(C)cn3n2)no1.Cc1ccn2c(F)c(C(=O)N3CCCC[C@H]3c3cc4nc(N5CC[C@H](C)C5)c(C)cn4n3)nc2c1.Cc1cn2nc([C@@H]3CCCCN3C(=O)c3cc(C4(O)CCCC4)on3)cc2nc1N1CC[C@H](N)C1.Cc1cn2nc([C@@H]3CCCCN3C(=O)c3cn(C)cn3)cc2nc1N1CC[C@H](N)C1
• InChI: InChI=1S/C26H30FN7O.C25H33N7O3.C23H29N7O2S.C22H29N7O2.C21H28N8O/c1-16-8-11-33-21(12-16)28-23(24(33)27)26(35)32-9-5-4-6-20(32)19-13-22-29-25(18(3)15-34(22)30-19)31-10-7-17(2)14-31;1-16-14-32-22(27-23(16)30-11-7-17(26)15-30)13-18(28-32)20-6-2-5-10-31(20)24(33)19-12-21(35-29-19)25(34)8-3-4-9-25;1-14-12-30-20(26-21(14)28-9-6-16(24)13-28)11-18(27-30)19-5-3-4-8-29(19)23(32)17-7-10-33-22(17)25-15(2)31;1-3-16-10-18(26-31-16)22(30)28-8-5-4-6-19(28)17-11-20-24-21(14(2)12-29(20)25-17)27-9-7-15(23)13-27;1-14-10-29-19(24-20(14)27-8-6-15(22)11-27)9-16(25-29)18-5-3-4-7-28(18)21(30)17-12-26(2)13-23-17/h8,11-13,15,17,20H,4-7,9-10,14H2,1-3H3;12-14,17,20,34H,2-11,15,26H2,1H3;7,10-12,16,19H,3-6,8-9,13,24H2,1-2H3,(H,25,31);10-12,15,19H,3-9,13,23H2,1-2H3;9-10,12-13,15,18H,3-8,11,22H2,1-2H3/t2*17-,20-;16-,19-;15-,19-;15-,18-/m00000/s1
• InChIKey: LIIMRYOSLDQLME-HSFOMWSWSA-N
• XLogP: 14.17
• TPSA: 509.29 Ų
• H-Bond Donors: 6
• H-Bond Acceptors: 40
• Rotatable Bonds: 18
• Heavy Atoms: 164
• Complexity: —

Lipinski Rule of Five

4 violations

Rule	Value
MW ≤ 500	2254.79
LogP ≤ 5	14.17
H-Bond Donors ≤ 5	6
H-Bond Acceptors ≤ 10	40

Frequently Asked Questions

What is the IUPAC name of N-[3-[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]thiophen-2-yl]acetamide;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(5-ethyl-1,2-oxazol-3-yl)methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-[5-(1-hydroxycyclopentyl)-1,2-oxazol-3-yl]methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(1-methylimidazol-4-yl)methanone;(3-fluoro-7-methylimidazo[1,2-a]pyridin-2-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone?

The IUPAC name of N-[3-[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]thiophen-2-yl]acetamide;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(5-ethyl-1,2-oxazol-3-yl)methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-[5-(1-hydroxycyclopentyl)-1,2-oxazol-3-yl]methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(1-methylimidazol-4-yl)methanone;(3-fluoro-7-methylimidazo[1,2-a]pyridin-2-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone (CID 159359398) is N-[3-[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]thiophen-2-yl]acetamide;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(5-ethyl-1,2-oxazol-3-yl)methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-[5-(1-hydroxycyclopentyl)-1,2-oxazol-3-yl]methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(1-methylimidazol-4-yl)methanone;(3-fluoro-7-methylimidazo[1,2-a]pyridin-2-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone.

What is the SMILES notation for N-[3-[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]thiophen-2-yl]acetamide;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(5-ethyl-1,2-oxazol-3-yl)methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-[5-(1-hydroxycyclopentyl)-1,2-oxazol-3-yl]methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(1-methylimidazol-4-yl)methanone;(3-fluoro-7-methylimidazo[1,2-a]pyridin-2-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone?

The canonical SMILES for N-[3-[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]thiophen-2-yl]acetamide;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(5-ethyl-1,2-oxazol-3-yl)methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-[5-(1-hydroxycyclopentyl)-1,2-oxazol-3-yl]methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(1-methylimidazol-4-yl)methanone;(3-fluoro-7-methylimidazo[1,2-a]pyridin-2-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone is CC(=O)Nc1sccc1C(=O)N1CCCC[C@H]1c1cc2nc(N3CC[C@H](N)C3)c(C)cn2n1.CCc1cc(C(=O)N2CCCC[C@H]2c2cc3nc(N4CC[C@H](N)C4)c(C)cn3n2)no1.Cc1ccn2c(F)c(C(=O)N3CCCC[C@H]3c3cc4nc(N5CC[C@H](C)C5)c(C)cn4n3)nc2c1.Cc1cn2nc([C@@H]3CCCCN3C(=O)c3cc(C4(O)CCCC4)on3)cc2nc1N1CC[C@H](N)C1.Cc1cn2nc([C@@H]3CCCCN3C(=O)c3cn(C)cn3)cc2nc1N1CC[C@H](N)C1.

What is the InChIKey of N-[3-[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]thiophen-2-yl]acetamide;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(5-ethyl-1,2-oxazol-3-yl)methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-[5-(1-hydroxycyclopentyl)-1,2-oxazol-3-yl]methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(1-methylimidazol-4-yl)methanone;(3-fluoro-7-methylimidazo[1,2-a]pyridin-2-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone?

The InChIKey is LIIMRYOSLDQLME-HSFOMWSWSA-N. The full InChI is InChI=1S/C26H30FN7O.C25H33N7O3.C23H29N7O2S.C22H29N7O2.C21H28N8O/c1-16-8-11-33-21(12-16)28-23(24(33)27)26(35)32-9-5-4-6-20(32)19-13-22-29-25(18(3)15-34(22)30-19)31-10-7-17(2)14-31;1-16-14-32-22(27-23(16)30-11-7-17(26)15-30)13-18(28-32)20-6-2-5-10-31(20)24(33)19-12-21(35-29-19)25(34)8-3-4-9-25;1-14-12-30-20(26-21(14)28-9-6-16(24)13-28)11-18(27-30)19-5-3-4-8-29(19)23(32)17-7-10-33-22(17)25-15(2)31;1-3-16-10-18(26-31-16)22(30)28-8-5-4-6-19(28)17-11-20-24-21(14(2)12-29(20)25-17)27-9-7-15(23)13-27;1-14-10-29-19(24-20(14)27-8-6-15(22)11-27)9-16(25-29)18-5-3-4-7-28(18)21(30)17-12-26(2)13-23-17/h8,11-13,15,17,20H,4-7,9-10,14H2,1-3H3;12-14,17,20,34H,2-11,15,26H2,1H3;7,10-12,16,19H,3-6,8-9,13,24H2,1-2H3,(H,25,31);10-12,15,19H,3-9,13,23H2,1-2H3;9-10,12-13,15,18H,3-8,11,22H2,1-2H3/t2*17-,20-;16-,19-;15-,19-;15-,18-/m00000/s1.

What are the key properties of N-[3-[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]thiophen-2-yl]acetamide;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(5-ethyl-1,2-oxazol-3-yl)methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-[5-(1-hydroxycyclopentyl)-1,2-oxazol-3-yl]methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(1-methylimidazol-4-yl)methanone;(3-fluoro-7-methylimidazo[1,2-a]pyridin-2-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone?

N-[3-[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]thiophen-2-yl]acetamide;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(5-ethyl-1,2-oxazol-3-yl)methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-[5-(1-hydroxycyclopentyl)-1,2-oxazol-3-yl]methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(1-methylimidazol-4-yl)methanone;(3-fluoro-7-methylimidazo[1,2-a]pyridin-2-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone has a molecular weight of 2254.79 g/mol, XLogP of 14.17, 18 rotatable bonds, 6 hydrogen bond donors, and 40 hydrogen bond acceptors.

Where does this data come from?

All data for N-[3-[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]thiophen-2-yl]acetamide;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(5-ethyl-1,2-oxazol-3-yl)methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-[5-(1-hydroxycyclopentyl)-1,2-oxazol-3-yl]methanone;[(2S)-2-[5-[(3S)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]-(1-methylimidazol-4-yl)methanone;(3-fluoro-7-methylimidazo[1,2-a]pyridin-2-yl)-[(2S)-2-[6-methyl-5-[(3S)-3-methylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl]piperidin-1-yl]methanone is sourced from PubChem (CID 159359398), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).