NP-MRD: Showing NP-Card for 11beta-Hydroxyandrost-4-ene-3,17-dione (NP0087632)

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Record Information

Version

2.0

Created at

2022-05-11 16:55:20 UTC

Updated at

2022-05-11 16:55:20 UTC

NP-MRD ID

NP0087632

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11beta-Hydroxyandrost-4-ene-3,17-dione

Description

Phenmetrazine, also known as oxazimedrine or preludin, belongs to the class of organic compounds known as phenylmorpholines. These are aromatic compounds containing a morpholine ring and a benzene ring linked to each other through a CC or a CN bond. Phenmetrazine also acts as a monoamine oxidase inhibitor. Phenmetrazine is a drug which is used as an anorectic in the treatment of obesity. Phenmetrazine is a very strong basic compound (based on its pKa). Its actions and mechanisms are similar to dextroamphetamine. Phenmetrazine is a potentially toxic compound. It is this latter effect on the tubero-infundibular systm that seems to lead to reduced food intake. 11beta-Hydroxyandrost-4-ene-3,17-dione was first documented in 1964 (PMID: 14196928). Metabolism involves deamination to para-hydroxyamphetamine and phenylacetone; this latter compound is subsequently oxidize to benzoic acid and excreted as glucuronide or glycine (hippuric acid) conjugate (PMID: 23211394) (PMID: 4125018) (PMID: 5356063).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231220512D          

 25 28  0  0  1  0            999 V2000
   15.4067   -9.3235    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9753   -9.3037    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5022   -8.2401    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0446   -8.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1934   -6.9103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8585  -10.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5730   -9.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0721   -8.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5570   -8.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7151   -8.9402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4295   -8.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4295  -10.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5730   -7.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1440   -9.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7151   -9.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5730   -8.9402    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.2875   -8.5277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.8585   -7.7027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.0721   -7.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8585   -8.5277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1440   -8.9402    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.3571   -7.7921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0006  -10.1777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1441   -7.2902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3270   -6.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 21  4  1  1  0  0  0
 22  5  1  1  0  0  0
  6 14  1  0  0  0  0
  6  7  1  0  0  0  0
 16  7  1  0  0  0  0
 17  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 19  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 21  1  0  0  0  0
 12 15  1  0  0  0  0
 12 14  2  0  0  0  0
 13 22  1  0  0  0  0
 13 18  1  0  0  0  0
 14 21  1  0  0  0  0
 15 23  2  0  0  0  0
 16 17  1  0  0  0  0
 16 20  1  0  0  0  0
 17 22  1  0  0  0  0
 18 24  1  1  0  0  0
 18 20  1  0  0  0  0
 19 25  2  0  0  0  0
 19 22  1  0  0  0  0
 20 21  1  0  0  0  0
 16  3  1  1  0  0  0
 20  2  1  6  0  0  0
 17  1  1  6  0  0  0
M  END

     RDKit          3D

 48 51  0  0  0  0  0  0  0  0999 V2000
   -2.6079    1.2668   -0.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4493    0.2736    0.5326 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6754    0.7691    1.6843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2859    1.1061    1.2594 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2813    2.3141    0.5482 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4021   -0.0074    0.5802 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3935   -0.7655   -0.4275 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2998   -2.1290   -0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7282   -1.9511   -1.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4346   -0.8435   -0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6738   -1.0077    0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3699    0.0775    0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3048   -0.1426    1.5303 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9030    1.4628    0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4208    1.4652    0.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6973    0.4075   -0.1009 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3920    0.9908   -1.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7713   -1.0125    0.0376 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7596   -1.4534   -0.9810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0839   -1.2471   -0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7815   -0.2783    0.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4631    0.0157    1.7899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9175    1.1175   -1.4145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6534    1.2428   -1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5112    2.2859   -0.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1317    1.7024    2.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6508    0.0082    2.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2911    1.3360    2.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4537    3.0530    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173   -0.7509    1.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4026   -0.3299   -1.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3099   -2.6034    0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2142   -2.7536   -1.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2569   -2.9211   -0.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7398   -1.8520   -2.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2136   -1.9619   -0.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0412    1.6068   -0.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027    2.2323    0.9719 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0419    2.4634    0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2808    1.3695    1.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1949    1.7131   -1.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4478    0.1857   -2.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4436    1.5238   -1.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8088   -1.7127    0.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7528   -0.7311   -1.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6495   -2.4689   -1.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4439   -2.2232    0.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8654   -0.8426   -0.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21  2  1  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
  2 18  1  0
 16  6  1  0
  7 18  1  0
 16 10  1  0
 18 44  1  1
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  1
  5 29  1  0
  6 30  1  1
  7 31  1  6
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 11 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
M  END


  Mrv0541 02231220512D          

 25 28  0  0  1  0            999 V2000
   15.4067   -9.3235    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9753   -9.3037    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5022   -8.2401    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0446   -8.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1934   -6.9103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8585  -10.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5730   -9.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0721   -8.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5570   -8.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7151   -8.9402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4295   -8.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4295  -10.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5730   -7.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1440   -9.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7151   -9.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5730   -8.9402    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.2875   -8.5277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.8585   -7.7027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.0721   -7.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8585   -8.5277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1440   -8.9402    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.3571   -7.7921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0006  -10.1777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1441   -7.2902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3270   -6.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 21  4  1  1  0  0  0
 22  5  1  1  0  0  0
  6 14  1  0  0  0  0
  6  7  1  0  0  0  0
 16  7  1  0  0  0  0
 17  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 19  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 21  1  0  0  0  0
 12 15  1  0  0  0  0
 12 14  2  0  0  0  0
 13 22  1  0  0  0  0
 13 18  1  0  0  0  0
 14 21  1  0  0  0  0
 15 23  2  0  0  0  0
 16 17  1  0  0  0  0
 16 20  1  0  0  0  0
 17 22  1  0  0  0  0
 18 24  1  1  0  0  0
 18 20  1  0  0  0  0
 19 25  2  0  0  0  0
 19 22  1  0  0  0  0
 20 21  1  0  0  0  0
 16  3  1  1  0  0  0
 20  2  1  6  0  0  0
 17  1  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0087632

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CCC(=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-15,17,21H,3-8,10H2,1-2H3/t13-,14-,15-,17+,18-,19-/m0/s1

> <INCHI_KEY>
WSCUHXPGYUMQEX-KCZNZURUSA-N

> <FORMULA>
C19H26O3

> <MOLECULAR_WEIGHT>
302.4079

> <EXACT_MASS>
302.188194698

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.99813627846605

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10S,11S,15S,17S)-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14-dione

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
2.620186206333334

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.841125104395207

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.879147304952422

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8516370857036666

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
85.19999999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-androsten-11β-ol-3,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  H   UNK     0      28.759 -17.404   0.000  0.00  0.00           H+0
HETATM    2  H   UNK     0      26.087 -17.367   0.000  0.00  0.00           H+0
HETATM    3  H   UNK     0      27.071 -15.382   0.000  0.00  0.00           H+0
HETATM    4  C   UNK     0      24.350 -15.148   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.361 -12.899   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.869 -18.998   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.203 -18.228   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.001 -16.394   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      30.906 -15.148   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.868 -16.688   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.202 -15.918   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.202 -18.998   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.203 -13.608   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.535 -18.228   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.868 -18.228   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.203 -16.688   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.537 -15.918   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      25.869 -14.378   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.001 -13.902   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      25.869 -15.918   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.535 -16.688   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      28.667 -14.545   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      20.534 -18.998   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      24.536 -13.608   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      30.477 -12.438   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   20                                                            
CONECT    3   16                                                            
CONECT    4   21                                                            
CONECT    5   22                                                            
CONECT    6   14    7                                                       
CONECT    7    6   16                                                       
CONECT    8   17    9                                                       
CONECT    9    8   19                                                       
CONECT   10   11   15                                                       
CONECT   11   10   21                                                       
CONECT   12   15   14                                                       
CONECT   13   22   18                                                       
CONECT   14    6   12   21                                                  
CONECT   15   10   12   23                                                  
CONECT   16    7   17   20    3                                             
CONECT   17    8   16   22    1                                             
CONECT   18   13   24   20                                                  
CONECT   19    9   25   22                                                  
CONECT   20   16   18   21    2                                             
CONECT   21    4   11   14   20                                             
CONECT   22    5   13   17   19                                             
CONECT   23   15                                                            
CONECT   24   18                                                            
CONECT   25   19                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
2-Phenyl-3-methylmorpholine	ChEBI
3-Methyl-2-phenylmorpholine	HMDB
Defenmetrazin	HMDB
Dexphenmetrazine	HMDB
Fenmetrazin	HMDB
Oxazimedrine	HMDB
USAF ge-1	HMDB
Hydrochloride, phenmetrazine	HMDB
Phenmetraline	HMDB
Phenmetrazine hydrochloride	HMDB
Preludin	HMDB
11beta-Hydroxy-4-androstene-3,17-dione	ChEBI
4-Androsten-11beta-ol-3,17-dione	ChEBI
Androst-4-ene-3,17-dione-11beta-ol	ChEBI
11b-Hydroxy-4-androstene-3,17-dione	Generator
11β-hydroxy-4-androstene-3,17-dione	Generator
4-Androsten-11b-ol-3,17-dione	Generator
4-Androsten-11β-ol-3,17-dione	Generator
Androst-4-ene-3,17-dione-11b-ol	Generator
Androst-4-ene-3,17-dione-11β-ol	Generator
11beta-Hydroxyandrost-4-ene-3,17-dione	HMDB
11b-Hydroxyandrost-4-ene-3,17-dione	Generator
11Β-hydroxyandrost-4-ene-3,17-dione	Generator
11-Hydroxy-4-androstene-3,17-dione	MeSH
11-Hydroxyandrostenedione, (11alpha)-isomer	MeSH
11-Hydroxyandrostenedione, (11beta)-isomer	MeSH
11-Hydroxyandrostenedione	MeSH
11-Hydroxyandrostenedione, (9beta,10alpha,11alpha)-isomer	MeSH
11 beta-Hydroxyandrostenedione	MeSH
11-Hydroxyandrostenedione, (9beta,10alpha,11beta)-isomer	MeSH

Chemical Formula

C₁₉H₂₆O₃

Average Mass

302.4079 Da

Monoisotopic Mass

302.18819 Da

IUPAC Name

(1S,2R,10S,11S,15S,17S)-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14-dione

Traditional Name

4-androsten-11β-ol-3,17-dione

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C19H26O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-15,17,21H,3-8,10H2,1-2H3/t13-,14-,15-,17+,18-,19-/m0/s1

InChI Key

WSCUHXPGYUMQEX-KCZNZURUSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylmorpholines. These are aromatic compounds containing a morpholine ring and a benzene ring linked to each other through a CC or a CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxazinanes

Sub Class

Morpholines

Direct Parent

Phenylmorpholines

Alternative Parents

Substituents

Phenylmorpholine
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Dialkyl ether
Secondary aliphatic amine
Ether
Secondary amine
Azacycle
Oxacycle
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

morpholines (CHEBI:8067 )

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	2	ALOGPS
logP	2.62	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	14.88	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.2 m³·mol⁻¹	ChemAxon
Polarizability	34 Å³	ChemAxon
Number of Rings	4	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

HMDB0014968

DrugBank ID

DB00830

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4598

KEGG Compound ID

C07432

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenmetrazine

METLIN ID

Not Available

PubChem Compound

4762

PDB ID

Not Available

ChEBI ID

8067

Good Scents ID

Not Available

References

General References

BALAZ V: GLUCOTROPIC ACTION OF PHENMETRAZINE. Fed Proc Transl Suppl. 1964 Jul-Aug;23:769-71. [PubMed:14196928 ]
Banks ML, Blough BE, Fennell TR, Snyder RW, Negus SS: Role of phenmetrazine as an active metabolite of phendimetrazine: evidence from studies of drug discrimination and pharmacokinetics in rhesus monkeys. Drug Alcohol Depend. 2013 Jun 1;130(1-3):158-66. doi: 10.1016/j.drugalcdep.2012.10.026. Epub 2012 Dec 1. [PubMed:23211394 ]
Aloia JF: Phenmetrazine in diabetes insipidus. Lancet. 1973 Sep 1;2(7827):501-2. doi: 10.1016/s0140-6736(73)92099-0. [PubMed:4125018 ]
Negulici-Baliff E, Christodorescu D, Gheorghiu D: [Psychoses induced by phenmetrazine]. Neurol Psihiatr Neurochir. 1969 Jul-Aug;14(4):371-6. [PubMed:5356063 ]

Showing NP-Card for 11beta-Hydroxyandrost-4-ene-3,17-dione (NP0087632)

MOL for NP0087632 (11beta-Hydroxyandrost-4-ene-3,17-dione)

3D MOL for NP0087632 (11beta-Hydroxyandrost-4-ene-3,17-dione)

3D SDF for NP0087632 (11beta-Hydroxyandrost-4-ene-3,17-dione)

3D-SDF for NP0087632 (11beta-Hydroxyandrost-4-ene-3,17-dione)

PDB for NP0087632 (11beta-Hydroxyandrost-4-ene-3,17-dione)

3D PDB for NP0087632 (11beta-Hydroxyandrost-4-ene-3,17-dione)

SMILES for NP0087632 (11beta-Hydroxyandrost-4-ene-3,17-dione)

INCHI for NP0087632 (11beta-Hydroxyandrost-4-ene-3,17-dione)

Structure for NP0087632 (11beta-Hydroxyandrost-4-ene-3,17-dione)

3D Structure for NP0087632 (11beta-Hydroxyandrost-4-ene-3,17-dione)