naloxone
C₁₉H₂₁NO₄·327.400 g/mol·CID 5284596
IUPAC: (4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
Also known as: 465-65-6, l-Naloxone, (-)-Naloxone, n-Allylnoroxymorphone, Naloxona (+14 more)
Molecular Structure
Molecular Propertiesmass · H-bonds · stereo
Molecular Weight
327.400g/mol
Exact Mass
327.147058Da
Monoisotopic Mass
327.147058Da
XLogP
2.1
Polar Surface Area
70.0Ų
Complexity
594
Formal Charge
0
H-Bond Donors
2
H-Bond Acceptors
5
Rotatable Bonds
2
Heavy Atoms
24
Stereo Centers
4
Bond Stereo
0
Drug-Likeness (Lipinski's Rule of Five)
✓ 327.4 g/mol
MW ≤ 500
✓ 2.1
LogP ≤ 5
✓ 2
H-bond donors ≤ 5
✓ 5
H-bond acceptors ≤ 10
Passes all rules — good oral bioavailability predicted
GHS Hazard Classification
Danger
Hazards
H302Harmful if swallowedH315Causes skin irritationH318Causes serious eye damageH319Causes serious eye irritationH335May cause respiratory irritation
Source: PubChem GHS Classification. Always consult the SDS for handling.
Chemical IdentifiersSMILES · InChI
InChI
InChI=1S/C19H21NO4/c1-2-8-20-9-7-18-15-11-3-4-12(21)16(15)24-17(18)13(22)5-6-19(18,23)14(20)10-11/h2-4,14,17,21,23H,1,5-10H2/t14-,17+,18+,19-/m1/s1
Isomers8 compounds with formula C₁₉H₂₁NO₄
(6aS)-1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol
CID 10154 · 327.4 g/mol
[(4R,4aR,7S,7aR,12bS)-9-hydroxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl] acetate
CID 5462507 · 327.4 g/mol
(1S,9R)-3-hydroxy-4,13-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,10,13-pentaen-12-one
CID 5408233 · 327.4 g/mol
(13aS)-3,9-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,10-diol
CID 6917970 · 327.4 g/mol
(13aS)-3,10-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,9-diol
CID 439654 · 327.4 g/mol
3,10-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,9-diol
CID 22955 · 327.4 g/mol
1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol
CID 248507 · 327.4 g/mol
(6aS)-2,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1,9-diol
CID 133323 · 327.4 g/mol