NP-MRD: Showing NP-Card for n-allylnormorphine (NP0261994)

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Record Information

Version

2.0

Created at

2022-09-08 04:35:45 UTC

Updated at

2022-09-08 04:35:45 UTC

NP-MRD ID

NP0261994

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-allylnormorphine

Description

Nalorphine, also known as nalorphine serb or lethidrone, belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic. Nalorphine has a number of analogues including niconalorphine (the nicomorphine analogue), diacetylnalorphine (heroin analogue), dihydronalorphine (dihydromorphine) and a number of others and a number of codeine-based ones as well. Nalorphine is a drug which is used to reverse opioid overdose. Due to potent activation of the KOR, nalorphine produces side effects such as dysphoria, anxiety, confusion, and hallucinations, and for this reason, is no longer used medically. Nalorphine is a very strong basic compound (based on its pKa). Nalorphine was the second opioid antagonist to be introduced, preceded by nalodeine (N-allylnorcodeine) in 1915 and followed by naloxone in 1960 and naltrexone in 1963. More recently, it has become much more commonplace to use ethyl chloroformate instead of cyanogen bromide for the Von Braun degradation demethylation step. See for example the list of phenyltropanes or the synthesis of paroxetine for further examples of this. It acts at two opioid receptors — the μ-opioid receptor (MOR) where it has antagonistic effects, and at the κ-opioid receptor (KOR) (Ki 1.6 NM; EC50483nM; Emax 95%) where it exerts high-efficacy partial agonist/near-full agonist characteristics. n-allylnormorphine is found in Papaver somniferum. It was introduced in 1954 and was used as an antidote to reverse opioid overdose and in a challenge test to determine opioid dependence.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1572001261622422D          

 26 30  0  0  0  0            999 V2000
    0.2388   -0.6527    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5292   -0.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6178    0.0020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9477   -1.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6080   -1.3912    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1008   -1.9180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2388    0.7061    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9428   -0.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4499    0.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7558    1.2821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5292    0.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166   -0.5148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9028   -0.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4647   -1.3912    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7552   -1.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3711    0.8144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7552   -0.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1687   -0.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4942    2.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2130    2.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7558    2.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2130   -2.0952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8881   -2.1297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2427    1.7851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792   -2.5131    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2238    1.0165    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  1  0  0  0  0
  8  2  2  0  0  0  0
  9  3  1  0  0  0  0
 10 16  1  0  0  0  0
 11  7  1  0  0  0  0
  1 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14  5  1  0  0  0  0
 15  4  2  0  0  0  0
 16 12  1  0  0  0  0
 17  8  1  0  0  0  0
 18 17  2  0  0  0  0
 19 21  1  0  0  0  0
 20 19  2  0  0  0  0
 21 10  1  0  0  0  0
 22 15  1  0  0  0  0
 14 23  1  6  0  0  0
  7 24  1  6  0  0  0
  4  6  1  0  0  0  0
  7 10  1  0  0  0  0
  9 13  2  0  0  0  0
  8 11  1  0  0  0  0
 15 18  1  0  0  0  0
  5 25  1  1  0  0  0
  3 26  1  1  0  0  0
M  END

     RDKit          3D

 44 48  0  0  0  0  0  0  0  0999 V2000
    5.3513   -0.1644    0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3361   -0.7831    1.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1471   -1.1410    0.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9844   -0.5204    0.8246 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9106    0.8874    0.6765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7958    1.3946   -0.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5288    0.8186    0.1644 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1751    0.0931   -0.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6519   -1.0509   -1.4254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3257   -1.6873   -2.4732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4997   -1.1281   -2.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0025    0.0425   -2.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1663    0.5766   -2.9475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3088    0.6633   -1.3888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5136    1.8127   -0.6283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5840    1.8153    0.4939 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3758    1.3812    1.6933 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5896    2.0640    1.8008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6243   -0.0831    1.6901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5988   -0.8931    1.4506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2994   -0.2654    1.2071 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7288   -1.2077    0.6211 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5878   -1.5876   -0.8043 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2233    0.0966    1.1623 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3341    0.0998   -0.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3650   -1.0356    2.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3162   -0.7300   -0.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1018   -2.2503    0.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8654    1.2107    0.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9136    1.4595    1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7326    2.5046   -0.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0185    1.3066   -1.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9242   -2.5974   -2.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9936   -1.6552   -3.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5163    1.4366   -2.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    2.8479    0.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7858    1.6973    2.5837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4754    2.9000    2.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6286   -0.4736    1.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7695   -1.9718    1.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1109    0.1116    2.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6600   -2.1381    1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4249   -1.1711   -1.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6348   -2.6854   -0.9826 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 22  1  0
 22 23  1  0
 22 21  1  0
 21 20  1  0
 20 19  2  0
 19 17  1  0
 17 18  1  0
  7 16  1  0
 21  7  1  0
 17 16  1  0
  8 14  1  0
 23  9  1  0
 16 36  1  1
 13 35  1  0
 11 34  1  0
 10 33  1  0
  6 31  1  0
  6 32  1  0
  5 29  1  0
  5 30  1  0
  3 27  1  0
  3 28  1  0
  2 26  1  0
  1 24  1  0
  1 25  1  0
 22 42  1  1
 23 43  1  0
 23 44  1  0
 21 41  1  1
 20 40  1  0
 19 39  1  0
 17 37  1  1
 18 38  1  0
M  END


  Mrv1572001261622422D          

 26 30  0  0  0  0            999 V2000
    0.2388   -0.6527    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5292   -0.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6178    0.0020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9477   -1.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6080   -1.3912    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1008   -1.9180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2388    0.7061    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9428   -0.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4499    0.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7558    1.2821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5292    0.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166   -0.5148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9028   -0.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4647   -1.3912    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7552   -1.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3711    0.8144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7552   -0.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1687   -0.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4942    2.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2130    2.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7558    2.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2130   -2.0952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8881   -2.1297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2427    1.7851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792   -2.5131    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2238    1.0165    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  1  0  0  0  0
  8  2  2  0  0  0  0
  9  3  1  0  0  0  0
 10 16  1  0  0  0  0
 11  7  1  0  0  0  0
  1 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14  5  1  0  0  0  0
 15  4  2  0  0  0  0
 16 12  1  0  0  0  0
 17  8  1  0  0  0  0
 18 17  2  0  0  0  0
 19 21  1  0  0  0  0
 20 19  2  0  0  0  0
 21 10  1  0  0  0  0
 22 15  1  0  0  0  0
 14 23  1  6  0  0  0
  7 24  1  6  0  0  0
  4  6  1  0  0  0  0
  7 10  1  0  0  0  0
  9 13  2  0  0  0  0
  8 11  1  0  0  0  0
 15 18  1  0  0  0  0
  5 25  1  1  0  0  0
  3 26  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0261994

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(CC=C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C19H21NO3/c1-2-8-20-9-7-19-12-4-6-15(22)18(19)23-17-14(21)5-3-11(16(17)19)10-13(12)20/h2-6,12-13,15,18,21-22H,1,7-10H2/t12-,13+,15-,18-,19-/m0/s1

> <INCHI_KEY>
UIQMVEYFGZJHCZ-SSTWWWIQSA-N

> <FORMULA>
C19H21NO3

> <MOLECULAR_WEIGHT>
311.381

> <EXACT_MASS>
311.15214354

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
33.03135165951679

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,13R,14S,17R)-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraene-10,14-diol

> <ALOGPS_LOGP>
1.55

> <JCHEM_LOGP>
1.675260432701913

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.783094950352542

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.204004409255173

> <JCHEM_PKA_STRONGEST_BASIC>
8.805023536658458

> <JCHEM_POLAR_SURFACE_AREA>
52.93000000000001

> <JCHEM_REFRACTIVITY>
89.2851

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nalorphine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-JAN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-JAN-16         0                                  
HETATM    1  C   UNK     0       0.446  -1.218   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.988  -1.218   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.153   0.004   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.769  -2.597   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.135  -2.597   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.188  -3.580   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.446   1.318   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.760  -0.033   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.706   0.004   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       1.411   2.393   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -0.988   1.318   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.898  -0.961   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.552  -1.264   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.734  -2.597   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.276  -2.597   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.559   1.520   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.276  -0.033   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.048  -1.264   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.789   4.691   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.131   3.882   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.411   3.947   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.131  -3.911   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.524  -3.975   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0      -0.453   3.332   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.828  -4.691   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.284   1.898   0.000  0.00  0.00           H+0
CONECT    1    2    3    5   12                                             
CONECT    2    1    4    8                                                  
CONECT    3    1    7    9   26                                             
CONECT    4    2   15    6                                                  
CONECT    5    1    6   14   25                                             
CONECT    6    5    4                                                       
CONECT    7    3   11   24   10                                             
CONECT    8    2   17   11                                                  
CONECT    9    3   13                                                       
CONECT   10   16   21    7                                                  
CONECT   11    7    8                                                       
CONECT   12    1   16                                                       
CONECT   13   14    9                                                       
CONECT   14   13    5   23                                                  
CONECT   15    4   22   18                                                  
CONECT   16   10   12                                                       
CONECT   17    8   18                                                       
CONECT   18   17   15                                                       
CONECT   19   21   20                                                       
CONECT   20   19                                                            
CONECT   21   19   10                                                       
CONECT   22   15                                                            
CONECT   23   14                                                            
CONECT   24    7                                                            
CONECT   25    5                                                            
CONECT   26    3                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Value	Source
Nalorphine serb	Kegg
Hydrobromide, nalorphine	MeSH
Lethidrone	MeSH
Nalorphine hydrochloride	MeSH
Nalorphine, L-tartrate (1:1)	MeSH
Nalorphine hydrobromide	MeSH
Nalorphine, (14 alpha)-isomer	MeSH
Allylnormorphine	MeSH
Hydrochloride, nalorphine	MeSH
Nalorphine	MeSH

Chemical Formula

C₁₉H₂₁NO₃

Average Mass

311.3810 Da

Monoisotopic Mass

311.15214 Da

IUPAC Name

(1S,5R,13R,14S,17R)-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraene-10,14-diol

Traditional Name

nalorphine

CAS Registry Number

Not Available

SMILES

[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(CC=C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O

InChI Identifier

InChI=1S/C19H21NO3/c1-2-8-20-9-7-19-12-4-6-15(22)18(19)23-17-14(21)5-3-11(16(17)19)10-13(12)20/h2-6,12-13,15,18,21-22H,1,7-10H2/t12-,13+,15-,18-,19-/m0/s1

InChI Key

UIQMVEYFGZJHCZ-SSTWWWIQSA-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 morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Morphinans

Sub Class

Not Available

Direct Parent

Morphinans

Alternative Parents

Substituents

Morphinan
Phenanthrene
Tetralin
Coumaran
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Piperidine
Benzenoid
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

morphinane alkaloid (CHEBI:7458 )

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	1.55	ALOGPS
logP	1.68	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	10.2	ChemAxon
pKa (Strongest Basic)	8.81	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.93 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	89.29 m³·mol⁻¹	ChemAxon
Polarizability	33.03 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

Not Available

DrugBank ID

DB11490

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C11787

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nalorphine

METLIN ID

Not Available

PubChem Compound

5284595

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-allylnormorphine (NP0261994)

MOL for NP0261994 (n-allylnormorphine)

3D MOL for NP0261994 (n-allylnormorphine)

3D SDF for NP0261994 (n-allylnormorphine)

3D-SDF for NP0261994 (n-allylnormorphine)

PDB for NP0261994 (n-allylnormorphine)

3D PDB for NP0261994 (n-allylnormorphine)

SMILES for NP0261994 (n-allylnormorphine)

INCHI for NP0261994 (n-allylnormorphine)

Structure for NP0261994 (n-allylnormorphine)

3D Structure for NP0261994 (n-allylnormorphine)