3-[(4aS,5R,10bS)-9-bromo-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl]phenol;[(4aS,5S,10bR)-9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl]methanol;(4aS,5S,10bR)-9-tert-butyl-5-thiophen-3-yl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinoline;3-[(4aS,5S,10bR)-9-methyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl]phenol;3-(9-bromo-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl)phenol;(9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl)methanol

C116H130Br2N6O16S — CID 161226260

IUPAC3-[(4aS,5R,10bS)-9-bromo-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl]phenol;[(4aS,5S,10bR)-9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl]methanol;(4aS,5S,10bR)-9-tert-butyl-5-thiophen-3-yl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinoline;3-[(4aS,5S,10bR)-9-methyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl]phenol;3-(9-bromo-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl)phenol;(9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl)methanol
SMILESCC(C)(C)c1ccc2c(c1)C1OC(CO)COC1C(c1ccccc1)N2.CC(C)(C)c1ccc2c(c1)[C@H]1OC(CO)CO[C@H]1[C@H](c1ccccc1)N2.CC(C)(C)c1ccc2c(c1)[C@H]1OCCO[C@H]1[C@H](c1ccsc1)N2.Cc1ccc2c(c1)[C@H]1OCCO[C@H]1[C@H](c1cccc(O)c1)N2.Oc1cccc(C2Nc3ccc(Br)cc3C3OCCOC23)c1.Oc1cccc([C@@H]2Nc3ccc(Br)cc3[C@H]3OCCC[C@H]32)c1
InChIInChI=1S/2C22H27NO3.C19H23NO2S.C18H18BrNO2.C18H19NO3.C17H16BrNO3/c2*1-22(2,3)15-9-10-18-17(11-15)20-21(25-13-16(12-24)26-20)19(23-18)14-7-5-4-6-8-14;1-19(2,3)13-4-5-15-14(10-13)17-18(22-8-7-21-17)16(20-15)12-6-9-23-11-12;19-12-6-7-16-15(10-12)18-14(5-2-8-22-18)17(20-16)11-3-1-4-13(21)9-11;1-11-5-6-15-14(9-11)17-18(22-8-7-21-17)16(19-15)12-3-2-4-13(20)10-12;18-11-4-5-14-13(9-11)16-17(22-7-6-21-16)15(19-14)10-2-1-3-12(20)8-10/h2*4-11,16,19-21,23-24H,12-13H2,1-3H3;4-6,9-11,16-18,20H,7-8H2,1-3H3;1,3-4,6-7,9-10,14,17-18,20-21H,2,5,8H2;2-6,9-10,16-20H,7-8H2,1H3;1-5,8-9,15-17,19-20H,6-7H2/t16?,19-,20+,21-;;16-,17+,18-;14-,17-,18-;16-,17+,18-;/m0.000./s1
InChIKeyUYDXXXRUECSXBV-PJKPMQPBSA-N
MW2056.22 g/mol
LogP24.50
Rot. Bonds8

About 3-[(4aS,5R,10bS)-9-bromo-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl]phenol;[(4aS,5S,10bR)-9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl]methanol;(4aS,5S,10bR)-9-tert-butyl-5-thiophen-3-yl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinoline;3-[(4aS,5S,10bR)-9-methyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl]phenol;3-(9-bromo-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl)phenol;(9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl)methanol

3-[(4aS,5R,10bS)-9-bromo-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl]phenol;[(4aS,5S,10bR)-9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl]methanol;(4aS,5S,10bR)-9-tert-butyl-5-thiophen-3-yl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinoline;3-[(4aS,5S,10bR)-9-methyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl]phenol;3-(9-bromo-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl)phenol;(9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl)methanol (PubChem CID 161226260) has the molecular formula C116H130Br2N6O16S and a molecular weight of 2056.22 g/mol. Its IUPAC name is 3-[(4aS,5R,10bS)-9-bromo-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl]phenol;[(4aS,5S,10bR)-9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl]methanol;(4aS,5S,10bR)-9-tert-butyl-5-thiophen-3-yl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinoline;3-[(4aS,5S,10bR)-9-methyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl]phenol;3-(9-bromo-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl)phenol;(9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl)methanol.

Molecular Properties

Compound Name3-[(4aS,5R,10bS)-9-bromo-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl]phenol;[(4aS,5S,10bR)-9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl]methanol;(4aS,5S,10bR)-9-tert-butyl-5-thiophen-3-yl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinoline;3-[(4aS,5S,10bR)-9-methyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl]phenol;3-(9-bromo-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl)phenol;(9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl)methanol
PubChem CID161226260
Molecular FormulaC116H130Br2N6O16S
Molecular Weight2056.22 g/mol
Exact Mass2052.76
IUPAC Name3-[(4aS,5R,10bS)-9-bromo-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl]phenol;[(4aS,5S,10bR)-9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl]methanol;(4aS,5S,10bR)-9-tert-butyl-5-thiophen-3-yl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinoline;3-[(4aS,5S,10bR)-9-methyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl]phenol;3-(9-bromo-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl)phenol;(9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl)methanol
SMILESCC(C)(C)c1ccc2c(c1)C1OC(CO)COC1C(c1ccccc1)N2.CC(C)(C)c1ccc2c(c1)[C@H]1OC(CO)CO[C@H]1[C@H](c1ccccc1)N2.CC(C)(C)c1ccc2c(c1)[C@H]1OCCO[C@H]1[C@H](c1ccsc1)N2.Cc1ccc2c(c1)[C@H]1OCCO[C@H]1[C@H](c1cccc(O)c1)N2.Oc1cccc(C2Nc3ccc(Br)cc3C3OCCOC23)c1.Oc1cccc([C@@H]2Nc3ccc(Br)cc3[C@H]3OCCC[C@H]32)c1
InChIInChI=1S/2C22H27NO3.C19H23NO2S.C18H18BrNO2.C18H19NO3.C17H16BrNO3/c2*1-22(2,3)15-9-10-18-17(11-15)20-21(25-13-16(12-24)26-20)19(23-18)14-7-5-4-6-8-14;1-19(2,3)13-4-5-15-14(10-13)17-18(22-8-7-21-17)16(20-15)12-6-9-23-11-12;19-12-6-7-16-15(10-12)18-14(5-2-8-22-18)17(20-16)11-3-1-4-13(21)9-11;1-11-5-6-15-14(9-11)17-18(22-8-7-21-17)16(19-15)12-3-2-4-13(20)10-12;18-11-4-5-14-13(9-11)16-17(22-7-6-21-16)15(19-14)10-2-1-3-12(20)8-10/h2*4-11,16,19-21,23-24H,12-13H2,1-3H3;4-6,9-11,16-18,20H,7-8H2,1-3H3;1,3-4,6-7,9-10,14,17-18,20-21H,2,5,8H2;2-6,9-10,16-20H,7-8H2,1H3;1-5,8-9,15-17,19-20H,6-7H2/t16?,19-,20+,21-;;16-,17+,18-;14-,17-,18-;16-,17+,18-;/m0.000./s1
InChIKeyUYDXXXRUECSXBV-PJKPMQPBSA-N
XLogP24.50
TPSA274.86 Ų
H-Bond Donors11
H-Bond Acceptors23
Rotatable Bonds8
Heavy Atoms141
Complexity—

Lipinski Rule of Five

4 violations

RuleValue
MW ≤ 5002056.22
LogP ≤ 524.50
H-Bond Donors ≤ 511
H-Bond Acceptors ≤ 1023

Analyze 3-[(4aS,5R,10bS)-9-bromo-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl]phenol;[(4aS,5S,10bR)-9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl]methanol;(4aS,5S,10bR)-9-tert-butyl-5-thiophen-3-yl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinoline;3-[(4aS,5S,10bR)-9-methyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl]phenol;3-(9-bromo-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl)phenol;(9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl)methanol with MolForge

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Frequently Asked Questions

What is the IUPAC name of 3-[(4aS,5R,10bS)-9-bromo-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl]phenol;[(4aS,5S,10bR)-9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl]methanol;(4aS,5S,10bR)-9-tert-butyl-5-thiophen-3-yl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinoline;3-[(4aS,5S,10bR)-9-methyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl]phenol;3-(9-bromo-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl)phenol;(9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl)methanol?
The IUPAC name of 3-[(4aS,5R,10bS)-9-bromo-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl]phenol;[(4aS,5S,10bR)-9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl]methanol;(4aS,5S,10bR)-9-tert-butyl-5-thiophen-3-yl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinoline;3-[(4aS,5S,10bR)-9-methyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl]phenol;3-(9-bromo-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl)phenol;(9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl)methanol (CID 161226260) is 3-[(4aS,5R,10bS)-9-bromo-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl]phenol;[(4aS,5S,10bR)-9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl]methanol;(4aS,5S,10bR)-9-tert-butyl-5-thiophen-3-yl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinoline;3-[(4aS,5S,10bR)-9-methyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl]phenol;3-(9-bromo-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl)phenol;(9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl)methanol.
What is the SMILES notation for 3-[(4aS,5R,10bS)-9-bromo-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl]phenol;[(4aS,5S,10bR)-9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl]methanol;(4aS,5S,10bR)-9-tert-butyl-5-thiophen-3-yl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinoline;3-[(4aS,5S,10bR)-9-methyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl]phenol;3-(9-bromo-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl)phenol;(9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl)methanol?
The canonical SMILES for 3-[(4aS,5R,10bS)-9-bromo-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl]phenol;[(4aS,5S,10bR)-9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl]methanol;(4aS,5S,10bR)-9-tert-butyl-5-thiophen-3-yl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinoline;3-[(4aS,5S,10bR)-9-methyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl]phenol;3-(9-bromo-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl)phenol;(9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl)methanol is CC(C)(C)c1ccc2c(c1)C1OC(CO)COC1C(c1ccccc1)N2.CC(C)(C)c1ccc2c(c1)[C@H]1OC(CO)CO[C@H]1[C@H](c1ccccc1)N2.CC(C)(C)c1ccc2c(c1)[C@H]1OCCO[C@H]1[C@H](c1ccsc1)N2.Cc1ccc2c(c1)[C@H]1OCCO[C@H]1[C@H](c1cccc(O)c1)N2.Oc1cccc(C2Nc3ccc(Br)cc3C3OCCOC23)c1.Oc1cccc([C@@H]2Nc3ccc(Br)cc3[C@H]3OCCC[C@H]32)c1.
What is the InChIKey of 3-[(4aS,5R,10bS)-9-bromo-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl]phenol;[(4aS,5S,10bR)-9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl]methanol;(4aS,5S,10bR)-9-tert-butyl-5-thiophen-3-yl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinoline;3-[(4aS,5S,10bR)-9-methyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl]phenol;3-(9-bromo-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl)phenol;(9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl)methanol?
The InChIKey is UYDXXXRUECSXBV-PJKPMQPBSA-N. The full InChI is InChI=1S/2C22H27NO3.C19H23NO2S.C18H18BrNO2.C18H19NO3.C17H16BrNO3/c2*1-22(2,3)15-9-10-18-17(11-15)20-21(25-13-16(12-24)26-20)19(23-18)14-7-5-4-6-8-14;1-19(2,3)13-4-5-15-14(10-13)17-18(22-8-7-21-17)16(20-15)12-6-9-23-11-12;19-12-6-7-16-15(10-12)18-14(5-2-8-22-18)17(20-16)11-3-1-4-13(21)9-11;1-11-5-6-15-14(9-11)17-18(22-8-7-21-17)16(19-15)12-3-2-4-13(20)10-12;18-11-4-5-14-13(9-11)16-17(22-7-6-21-16)15(19-14)10-2-1-3-12(20)8-10/h2*4-11,16,19-21,23-24H,12-13H2,1-3H3;4-6,9-11,16-18,20H,7-8H2,1-3H3;1,3-4,6-7,9-10,14,17-18,20-21H,2,5,8H2;2-6,9-10,16-20H,7-8H2,1H3;1-5,8-9,15-17,19-20H,6-7H2/t16?,19-,20+,21-;;16-,17+,18-;14-,17-,18-;16-,17+,18-;/m0.000./s1.
What are the key properties of 3-[(4aS,5R,10bS)-9-bromo-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl]phenol;[(4aS,5S,10bR)-9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl]methanol;(4aS,5S,10bR)-9-tert-butyl-5-thiophen-3-yl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinoline;3-[(4aS,5S,10bR)-9-methyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl]phenol;3-(9-bromo-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl)phenol;(9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl)methanol?
3-[(4aS,5R,10bS)-9-bromo-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl]phenol;[(4aS,5S,10bR)-9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl]methanol;(4aS,5S,10bR)-9-tert-butyl-5-thiophen-3-yl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinoline;3-[(4aS,5S,10bR)-9-methyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl]phenol;3-(9-bromo-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl)phenol;(9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl)methanol has a molecular weight of 2056.22 g/mol, XLogP of 24.50, 8 rotatable bonds, 11 hydrogen bond donors, and 23 hydrogen bond acceptors.
Where does this data come from?
All data for 3-[(4aS,5R,10bS)-9-bromo-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl]phenol;[(4aS,5S,10bR)-9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl]methanol;(4aS,5S,10bR)-9-tert-butyl-5-thiophen-3-yl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinoline;3-[(4aS,5S,10bR)-9-methyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl]phenol;3-(9-bromo-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-5-yl)phenol;(9-tert-butyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-[1,4]dioxino[2,3-c]quinolin-2-yl)methanol is sourced from PubChem (CID 161226260), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).