NP-MRD: Showing NP-Card for naloxone (NP0217877)

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Record Information

Version

2.0

Created at

2022-09-05 18:21:51 UTC

Updated at

2022-09-05 18:21:51 UTC

NP-MRD ID

NP0217877

Secondary Accession Numbers

None

Natural Product Identification

Common Name

naloxone

Description

Naloxone, also known as MRZ 2593BR or naloxonum, belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. Naloxone is a drug which is used for the complete or partial reversal of narcotic depression, including respiratory depression, induced by opioids including natural and synthetic narcotics, propoxyphene, methadone and the narcotic-antagonist analgesics: Nalbuphine, pentazocine and butorphanol. It is also indicated for the diagnosis of suspected acute opioid overdose. It may also be used as an adjunctive agent to increase blood pressure in the management of septic shock. Naloxone is a very strong basic compound (based on its pKa). naloxone is found in Papaver somniferum. naloxone was first documented in 2006 (PMID: 17023477). In humans, naloxone is involved in naloxone action pathway (PMID: 25468814) (PMID: 26469689) (PMID: 26604818).

Structure

MOL 3D MOL SDF PDB SMILES InChI

1183
  Mrv0541 02231215182D          

 26 30  0  0  1  0            999 V2000
    1.9356   -0.2231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4727   -1.7584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349   -2.3527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349    1.8149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3440   -1.0939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -0.6814    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9151   -1.0939    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6296   -0.6814    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4861   -1.0939    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6773   -0.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    0.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151   -1.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6296    0.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8506   -0.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    0.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -2.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861   -1.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861    0.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9350   -1.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    1.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861    1.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    1.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7804   -1.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3713   -2.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675   -1.3334    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8196   -1.2870    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 18  1  0  0  0  0
  7  2  1  1  0  0  0
  3 17  2  0  0  0  0
  4 21  1  0  0  0  0
  5  8  1  0  0  0  0
  5 14  1  0  0  0  0
  5 19  1  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  1  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 25  1  6  0  0  0
  9 17  1  0  0  0  0
  9 26  1  1  0  0  0
 10 14  1  0  0  0  0
 11 15  2  0  0  0  0
 11 18  1  0  0  0  0
 12 16  1  0  0  0  0
 13 15  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 18 21  2  0  0  0  0
 19 23  1  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
 23 24  2  0  0  0  0
M  END

     RDKit          3D

 45 49  0  0  0  0  0  0  0  0999 V2000
   -5.4169    0.0301    0.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3020    0.7102    0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0471    0.3647    0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9817    0.0429   -0.0553 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4990    1.1455   -0.8057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3469    0.8453   -1.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6277   -0.1127   -1.0949 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3595    0.5431   -0.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9585    0.5951    1.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7721    1.2907    2.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9302    1.8904    1.7123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2873    1.8009    0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4467    2.3979   -0.0870 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4860    1.1075   -0.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5122    0.8045   -1.8776 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7638   -0.4319   -2.0383 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5812   -1.4913   -1.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6184   -1.8087   -2.0156 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2488   -2.1925   -0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7718   -2.4216   -0.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0827   -1.2870   -0.5397 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9769   -1.7495   -1.5297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9849   -0.7476    0.5781 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2690   -0.0941    1.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3877   -0.8133    0.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3198    0.2992   -0.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2931    1.5456   -0.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2798   -0.5488    1.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7322    1.1979    1.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3471    1.4858   -1.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2820    2.0529   -0.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875    1.7933   -1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6846    0.4337   -2.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4595    1.3379    3.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5817    2.4404    2.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0560    2.9120    0.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4751   -0.6084   -3.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6557   -1.6737    0.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7357   -3.2134   -0.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5611   -3.3460   -0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4794   -2.7462    0.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8735   -1.8918   -1.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5026   -1.6641    0.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9269    0.6628    2.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0195   -0.8878    2.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 12  2  0
 12 13  1  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  1  6
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  4 23  1  0
 23 24  1  0
 23 21  1  0
 21 22  1  6
 21 20  1  0
 20 19  1  0
 19 17  1  0
 17 18  2  0
  7 16  1  0
 21  7  1  0
 17 16  1  0
  8 14  1  0
 24  9  1  0
 16 37  1  6
 13 36  1  0
 11 35  1  0
 10 34  1  0
  6 32  1  0
  6 33  1  0
  5 30  1  0
  5 31  1  0
  3 28  1  0
  3 29  1  0
  2 27  1  0
  1 25  1  0
  1 26  1  0
 23 43  1  1
 24 44  1  0
 24 45  1  0
 22 42  1  0
 20 40  1  0
 20 41  1  0
 19 38  1  0
 19 39  1  0
M  END

1183
  Mrv0541 02231215182D          

 26 30  0  0  1  0            999 V2000
    1.9356   -0.2231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4727   -1.7584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349   -2.3527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349    1.8149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3440   -1.0939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -0.6814    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9151   -1.0939    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6296   -0.6814    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4861   -1.0939    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6773   -0.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    0.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151   -1.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6296    0.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8506   -0.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    0.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -2.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861   -1.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861    0.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9350   -1.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    1.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861    1.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    1.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7804   -1.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3713   -2.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675   -1.3334    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8196   -1.2870    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 18  1  0  0  0  0
  7  2  1  1  0  0  0
  3 17  2  0  0  0  0
  4 21  1  0  0  0  0
  5  8  1  0  0  0  0
  5 14  1  0  0  0  0
  5 19  1  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  1  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 25  1  6  0  0  0
  9 17  1  0  0  0  0
  9 26  1  1  0  0  0
 10 14  1  0  0  0  0
 11 15  2  0  0  0  0
 11 18  1  0  0  0  0
 12 16  1  0  0  0  0
 13 15  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 18 21  2  0  0  0  0
 19 23  1  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0217877

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(CC=C)[C@]([H])(C4)[C@]1(O)CCC2=O

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
UZHSEJADLWPNLE-GRGSLBFTSA-N

> <FORMULA>
C19H21NO4

> <MOLECULAR_WEIGHT>
327.3743

> <EXACT_MASS>
327.147058165

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
33.802113519777905

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,13R,17S)-10,17-dihydroxy-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-one

> <ALOGPS_LOGP>
1.47

> <JCHEM_LOGP>
1.620221160000001

> <ALOGPS_LOGS>
-1.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.580259045446617

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.2696665202107935

> <JCHEM_PKA_STRONGEST_BASIC>
10.630340131165019

> <JCHEM_POLAR_SURFACE_AREA>
70

> <JCHEM_REFRACTIVITY>
88.72220000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.64e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
naloxone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1183                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.613  -0.416   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.349  -3.282   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.238  -4.392   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.238   3.388   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       9.975  -2.042   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.974  -1.272   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.308  -2.042   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.642  -1.272   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.641  -2.042   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.864  -0.143   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.974   0.268   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.308  -3.582   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.642   0.268   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.054  -0.143   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.308   1.038   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.974  -4.352   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.641  -3.582   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.641   1.038   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.079  -3.227   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.308   2.578   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.641   2.578   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.974   3.348   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.657  -2.865   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.760  -4.050   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0       9.086  -2.489   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.397  -2.402   0.000  0.00  0.00           H+0
CONECT    1    9   18                                                       
CONECT    2    7                                                            
CONECT    3   17                                                            
CONECT    4   21                                                            
CONECT    5    8   14   19                                                  
CONECT    6    7    9   10   11                                             
CONECT    7    2    6    8   12                                             
CONECT    8    5    7   13   25                                             
CONECT    9    1    6   17   26                                             
CONECT   10    6   14                                                       
CONECT   11    6   15   18                                                  
CONECT   12    7   16                                                       
CONECT   13    8   15                                                       
CONECT   14    5   10                                                       
CONECT   15   11   13   20                                                  
CONECT   16   12   17                                                       
CONECT   17    3    9   16                                                  
CONECT   18    1   11   21                                                  
CONECT   19    5   23                                                       
CONECT   20   15   22                                                       
CONECT   21    4   18   22                                                  
CONECT   22   20   21                                                       
CONECT   23   19   24                                                       
CONECT   24   23                                                            
CONECT   25    8                                                            
CONECT   26    9                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Value	Source
(-)-Naloxone	ChEBI
1-N-Allyl-14-hydroxynordihydromorphinone	ChEBI
17-Allyl-3,14-dihydroxy-4,5alpha-epoxymorphinan-6-one	ChEBI
Naloxona	ChEBI
Naloxonum	ChEBI
DBL Naloxone	Kegg
17-Allyl-3,14-dihydroxy-4,5a-epoxymorphinan-6-one	Generator
17-Allyl-3,14-dihydroxy-4,5α-epoxymorphinan-6-one	Generator
EN 1530 base	HMDB
L-Naloxone	HMDB
N-Allylnoroxymorphone	HMDB
Nalossone	HMDB
Abello brand OF naloxone hydrochloride	HMDB
Abello, naloxone	HMDB
Boots brand OF naloxone hydrochloride	HMDB
Bristol-myers squibb brand OF naloxone hydrochloride	HMDB
Curamed brand OF naloxone hydrochloride	HMDB
endo Brand OF naloxone hydrochloride	HMDB
Narcanti	HMDB
Ratiopharm brand OF naloxone hydrochloride	HMDB
Dihydride, naloxone hydrochloride	HMDB
Naloxon ratiopharm	HMDB
Naloxone hydrochloride	HMDB
Naloxone hydrochloride, (5 beta,9 alpha,13 alpha,14 alpha)-isomer	HMDB
SERB brand OF naloxone hydrochloride	HMDB
Bristol myers squibb brand OF naloxone hydrochloride	HMDB
Curamed, naloxon	HMDB
Lamepro brand OF naloxone hydrochloride	HMDB
MRZ 2593BR	HMDB
Nalone	HMDB
Naloxon-ratiopharm	HMDB
Hydrobromide, naloxone	HMDB
Hydrochloride dihydride, naloxone	HMDB
Hydrochloride, naloxone	HMDB
MRZ 2593 BR	HMDB
MRZ 2593-BR	HMDB
Naloxon curamed	HMDB
Naloxone abello	HMDB
Naloxone hydrochloride dihydride	HMDB
Naloxone, (5 beta,9 alpha,13 alpha,14 alpha)-isomer	HMDB
Naloxonratiopharm	HMDB
Naloxone hydrobromide	HMDB
Narcan	HMDB
United drug brand OF naloxone hydrochloride	HMDB

Chemical Formula

C₁₉H₂₁NO₄

Average Mass

327.3743 Da

Monoisotopic Mass

327.14706 Da

IUPAC Name

(1S,5R,13R,17S)-10,17-dihydroxy-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-one

Traditional Name

naloxone

CAS Registry Number

Not Available

SMILES

[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(CC=C)[C@]([H])(C4)[C@]1(O)CCC2=O

InChI Identifier

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

InChI Key

UZHSEJADLWPNLE-GRGSLBFTSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Papaver somniferum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Isoquinolone
Tetralin
Coumaran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Aralkylamine
Piperidine
Cyclic alcohol
Tertiary alcohol
1,2-aminoalcohol
Ketone
Tertiary aliphatic amine
Tertiary amine
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Organooxygen compound
Alcohol
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

morphinane alkaloid (CHEBI:7459 )
organic heteropentacyclic compound (CHEBI:7459 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.47	ALOGPS
logP	1.62	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	7.27	ChemAxon
pKa (Strongest Basic)	10.63	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	88.72 m³·mol⁻¹	ChemAxon
Polarizability	33.8 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0015314

DrugBank ID

DB01183

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4447644

KEGG Compound ID

C07252

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Naloxone

METLIN ID

Not Available

PubChem Compound

5284596

PDB ID

Not Available

ChEBI ID

7459

Good Scents ID

Not Available

References

General References

Brewer C: Emergency naloxone for heroin overdose: naloxone is not the only opioid antagonist. BMJ. 2006 Oct 7;333(7571):754-5. doi: 10.1136/bmj.333.7571.754-b. [PubMed:17023477 ]
Ray B, O'Donnell D, Kahre K: Police officer attitudes towards intranasal naloxone training. Drug Alcohol Depend. 2015 Jan 1;146:107-10. doi: 10.1016/j.drugalcdep.2014.10.026. Epub 2014 Nov 8. [PubMed:25468814 ]
Sivilotti ML: Flumazenil, naloxone and the 'coma cocktail'. Br J Clin Pharmacol. 2016 Mar;81(3):428-36. doi: 10.1111/bcp.12731. Epub 2015 Sep 21. [PubMed:26469689 ]
Webster LR, Smith MD, Unal C, Finn A: Low-dose naloxone provides an abuse-deterrent effect to buprenorphine. J Pain Res. 2015 Nov 4;8:791-8. doi: 10.2147/JPR.S90780. eCollection 2015. [PubMed:26604818 ]
LOTUS database [Link]

Showing NP-Card for naloxone (NP0217877)

MOL for NP0217877 (naloxone)

3D MOL for NP0217877 (naloxone)

3D SDF for NP0217877 (naloxone)

3D-SDF for NP0217877 (naloxone)

PDB for NP0217877 (naloxone)

3D PDB for NP0217877 (naloxone)

SMILES for NP0217877 (naloxone)

INCHI for NP0217877 (naloxone)

Structure for NP0217877 (naloxone)

3D Structure for NP0217877 (naloxone)