Tryptophan
C₁₁H₁₂N₂O₂·204.229 g/mol·Amino Acids·CID 6305
Amino AcidEssential
An essential amino acid with a large indole side chain. Precursor to serotonin and melatonin. The least abundant amino acid in most proteins. Often cited (incorrectly) as the cause of post-Thanksgiving drowsiness.
IUPAC: (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
Also known as: tryptophan, 73-22-3, L-Tryptophane, Tryptophane, (S)-Tryptophan (+14 more)
Molecular Structure
Molecular Propertiesmass · H-bonds · stereo
Molecular Weight
204.220g/mol
Exact Mass
204.089878Da
Monoisotopic Mass
204.089878Da
XLogP
-1.1
Polar Surface Area
79.1Ų
Complexity
245
Formal Charge
0
H-Bond Donors
3
H-Bond Acceptors
3
Rotatable Bonds
3
Heavy Atoms
15
Stereo Centers
1
Bond Stereo
0
Drug-Likeness (Lipinski's Rule of Five)
✓ 204.2 g/mol
MW ≤ 500
✓ -1.1
LogP ≤ 5
✓ 3
H-bond donors ≤ 5
✓ 3
H-bond acceptors ≤ 10
Passes all rules — good oral bioavailability predicted
Chemical IdentifiersSMILES · InChI
InChI
InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1
Constituent Elements
Isomers8 compounds with formula C₁₁H₁₂N₂O₂
3-ethyl-5-phenylimidazolidine-2,4-dione
CID 3292 · 204.2 g/mol
(2R)-2-amino-3-(1H-indol-3-yl)propanoic acid
CID 9060 · 204.2 g/mol
2-amino-3-(1H-indol-3-yl)propanoic acid
CID 1148 · 204.2 g/mol
2-(2,3-dihydro-1,4-benzodioxin-3-yl)-4,5-dihydro-1H-imidazole
CID 54459 · 204.2 g/mol
2-azaniumyl-3-(1H-indol-3-yl)propanoate
CID 4099458 · 204.2 g/mol
5-ethyl-5-phenylimidazolidine-2,4-dione
CID 91480 · 204.2 g/mol
(2S)-2-azaniumyl-3-(1H-indol-3-yl)propanoate
CID 6923516 · 204.2 g/mol
4-hydroxy-1,5-dimethyl-2-phenylpyrazol-3-one
CID 98889 · 204.2 g/mol