NP-MRD: Showing NP-Card for 3-{4-[(2s,3s,6r)-5-hydroxy-3-(hydroxymethyl)-6-(1h-indol-3-yl)-3,6-dihydro-2h-1,4-oxazin-2-yl]phenoxy}propanenitrile (NP0256218)

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Record Information

Version

1.0

Created at

2022-09-07 20:57:48 UTC

Updated at

2022-09-07 20:57:49 UTC

NP-MRD ID

NP0256218

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{4-[(2s,3s,6r)-5-hydroxy-3-(hydroxymethyl)-6-(1h-indol-3-yl)-3,6-dihydro-2h-1,4-oxazin-2-yl]phenoxy}propanenitrile

Description

3-{4-[(2S,3S,6R)-5-hydroxy-3-(hydroxymethyl)-6-(1H-indol-3-yl)-3,6-dihydro-2H-1,4-oxazin-2-yl]phenoxy}propanenitrile belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. 3-{4-[(2s,3s,6r)-5-hydroxy-3-(hydroxymethyl)-6-(1h-indol-3-yl)-3,6-dihydro-2h-1,4-oxazin-2-yl]phenoxy}propanenitrile is found in Mytilus galloprovincialis. It was first documented in 2002 (PMID: 35412727). Based on a literature review a significant number of articles have been published on 3-{4-[(2S,3S,6R)-5-hydroxy-3-(hydroxymethyl)-6-(1H-indol-3-yl)-3,6-dihydro-2H-1,4-oxazin-2-yl]phenoxy}propanenitrile (PMID: 36099392) (PMID: 31661213) (PMID: 31593386) (PMID: 29589881).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072222572D          

 29 32  0  0  1  0            999 V2000
   -4.9778   -6.3177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7229   -5.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4679   -4.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6610   -4.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4060   -3.7923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5990   -3.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441   -2.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -2.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -2.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -2.5916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -3.5477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1190   -4.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6880   -4.6754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -4.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0470   -4.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 13 21  1  0  0  0  0
 16 21  1  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 10 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
  9 28  1  0  0  0  0
 28 29  2  0  0  0  0
  6 29  1  0  0  0  0
M  END

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
    8.9782    0.9481   -1.0241 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9150    0.9900   -0.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5394    1.0237   -0.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3209   -0.1612    0.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1071   -0.2919    1.4717 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8554   -0.4742    0.9710 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5893   -0.5917   -0.3668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2744   -0.7737   -0.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2021   -0.8445    0.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1488   -1.0381   -0.4999 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0902   -0.1765    0.1021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1820   -0.1450   -0.7355 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3619    0.5021   -0.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2305   -0.0835    0.8371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1487    0.8406    1.2070 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9014    1.9993    0.5817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5504    3.2159    0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0535    4.2437   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9320    4.0657   -0.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2998    2.8411   -0.9797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7808    1.8056   -0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6471   -1.4678   -1.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8877   -1.5397   -1.8807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452   -2.5138   -1.0016 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6898   -2.4196   -0.3130 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2377   -3.4842   -0.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3757   -4.7265   -0.6282 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4805   -0.7266    1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7593   -0.5468    1.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8802    1.1467   -0.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4595    1.9268    0.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0967   -0.0664    1.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6648   -1.1188    0.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4006   -0.5614   -1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1330   -0.8588   -1.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1718   -0.7831   -1.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8884    0.4706   -1.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1476   -1.1004    1.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9389    0.6881    1.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4224    3.3937    1.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5645    5.1915   -0.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5566    4.8806   -1.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4282    2.6447   -1.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0560   -0.9124   -2.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8818   -2.6068    0.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3317   -3.3977   -1.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2367   -3.4319   -0.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8330   -4.7465    0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6660   -0.7770    2.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9860   -0.4522    2.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 26  1  0
 26 25  1  0
 25 24  1  0
 24 22  2  0
 22 23  1  0
 22 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  3  0
  6 29  1  0
 29 28  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 10 25  1  0
 28  9  1  0
 21 13  1  0
 21 16  1  0
 27 48  1  0
 26 46  1  0
 26 47  1  0
 25 45  1  1
 23 44  1  0
 12 37  1  6
 10 36  1  6
  8 35  1  0
  7 34  1  0
  4 32  1  0
  4 33  1  0
  3 30  1  0
  3 31  1  0
 29 50  1  0
 28 49  1  0
 14 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
M  END


  Mrv1652309072222572D          

 29 32  0  0  1  0            999 V2000
   -4.9778   -6.3177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7229   -5.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4679   -4.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6610   -4.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4060   -3.7923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5990   -3.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441   -2.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -2.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -2.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -2.5916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -3.5477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1190   -4.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6880   -4.6754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -4.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0470   -4.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 13 21  1  0  0  0  0
 16 21  1  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 10 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
  9 28  1  0  0  0  0
 28 29  2  0  0  0  0
  6 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256218

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@H]1N=C(O)[C@H](O[C@H]1C1=CC=C(OCCC#N)C=C1)C1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C22H21N3O4/c23-10-3-11-28-15-8-6-14(7-9-15)20-19(13-26)25-22(27)21(29-20)17-12-24-18-5-2-1-4-16(17)18/h1-2,4-9,12,19-21,24,26H,3,11,13H2,(H,25,27)/t19-,20-,21+/m0/s1

> <INCHI_KEY>
GMCSPTIRNYGHRP-PCCBWWKXSA-N

> <FORMULA>
C22H21N3O4

> <MOLECULAR_WEIGHT>
391.427

> <EXACT_MASS>
391.153206168

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
42.13419367230699

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{4-[(2S,3S,6R)-5-hydroxy-3-(hydroxymethyl)-6-(1H-indol-3-yl)-3,6-dihydro-2H-1,4-oxazin-2-yl]phenoxy}propanenitrile

> <JCHEM_LOGP>
2.471715668

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.579179380486156

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3718345835471473

> <JCHEM_PKA_STRONGEST_BASIC>
1.2349934069354043

> <JCHEM_POLAR_SURFACE_AREA>
110.86

> <JCHEM_REFRACTIVITY>
106.28490000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-{4-[(2S,3S,6R)-5-hydroxy-3-(hydroxymethyl)-6-(1H-indol-3-yl)-3,6-dihydro-2H-1,4-oxazin-2-yl]phenoxy}propanenitrile

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  N   UNK     0      -9.292 -11.793   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -8.816 -10.328   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.340  -8.864   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.834  -8.544   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -6.358  -7.079   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.852  -6.759   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.376  -5.294   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.869  -4.974   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.143  -4.334   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.680  -5.158   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.187  -4.838   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       2.204  -6.622   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       0.698  -6.943   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.222  -8.407   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.284  -8.727   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.315  -7.583   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.821  -7.903   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   29                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   28                                                  
CONECT   10    9   11   25                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   13   16                                                  
CONECT   22   12   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   10   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28    9   29                                                       
CONECT   29   28    6                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₁N₃O₄

Average Mass

391.4270 Da

Monoisotopic Mass

391.15321 Da

IUPAC Name

3-{4-[(2S,3S,6R)-5-hydroxy-3-(hydroxymethyl)-6-(1H-indol-3-yl)-3,6-dihydro-2H-1,4-oxazin-2-yl]phenoxy}propanenitrile

Traditional Name

3-{4-[(2S,3S,6R)-5-hydroxy-3-(hydroxymethyl)-6-(1H-indol-3-yl)-3,6-dihydro-2H-1,4-oxazin-2-yl]phenoxy}propanenitrile

CAS Registry Number

Not Available

SMILES

OC[C@@H]1N=C(O)[C@H](O[C@H]1C1=CC=C(OCCC#N)C=C1)C1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C22H21N3O4/c23-10-3-11-28-15-8-6-14(7-9-15)20-19(13-26)25-22(27)21(29-20)17-12-24-18-5-2-1-4-16(17)18/h1-2,4-9,12,19-21,24,26H,3,11,13H2,(H,25,27)/t19-,20-,21+/m0/s1

InChI Key

GMCSPTIRNYGHRP-PCCBWWKXSA-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
Mytilus galloprovincialis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Phenoxy compound
Phenol ether
Alkyl aryl ether
Para-oxazine
Monocyclic benzene moiety
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrole
Cyclic carboximidic acid
Dialkyl ether
Ether
Carbonitrile
Nitrile
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Primary alcohol
Organopnictogen compound
Organic nitrogen compound
Alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	2.47	ChemAxon
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	1.23	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	110.86 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	106.28 m³·mol⁻¹	ChemAxon
Polarizability	42.13 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163190889

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Freebody J: "The Root of All Evil is Inactivity": The Response of French Psychiatrists to New Approaches to Patient Work and Occupation, 1918-1939. 2021. [PubMed:36099392 ]
Authors unspecified: Childhood Pulmonary Inflammatory Myofibroblastic Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:35412727 ]
Authors unspecified: Childhood Adrenocortical Carcinoma Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:31661213 ]
Authors unspecified: Childhood Breast Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:31593386 ]
Authors unspecified: Cognitive Impairment in Adults with Non-Central Nervous System Cancers (PDQ(R)): Patient Version. 2002. [PubMed:29589881 ]
LOTUS database [Link]

Showing NP-Card for 3-{4-[(2s,3s,6r)-5-hydroxy-3-(hydroxymethyl)-6-(1h-indol-3-yl)-3,6-dihydro-2h-1,4-oxazin-2-yl]phenoxy}propanenitrile (NP0256218)

MOL for NP0256218 (3-{4-[(2s,3s,6r)-5-hydroxy-3-(hydroxymethyl)-6-(1h-indol-3-yl)-3,6-dihydro-2h-1,4-oxazin-2-yl]phenoxy}propanenitrile)

3D MOL for NP0256218 (3-{4-[(2s,3s,6r)-5-hydroxy-3-(hydroxymethyl)-6-(1h-indol-3-yl)-3,6-dihydro-2h-1,4-oxazin-2-yl]phenoxy}propanenitrile)

3D SDF for NP0256218 (3-{4-[(2s,3s,6r)-5-hydroxy-3-(hydroxymethyl)-6-(1h-indol-3-yl)-3,6-dihydro-2h-1,4-oxazin-2-yl]phenoxy}propanenitrile)

3D-SDF for NP0256218 (3-{4-[(2s,3s,6r)-5-hydroxy-3-(hydroxymethyl)-6-(1h-indol-3-yl)-3,6-dihydro-2h-1,4-oxazin-2-yl]phenoxy}propanenitrile)

PDB for NP0256218 (3-{4-[(2s,3s,6r)-5-hydroxy-3-(hydroxymethyl)-6-(1h-indol-3-yl)-3,6-dihydro-2h-1,4-oxazin-2-yl]phenoxy}propanenitrile)

3D PDB for NP0256218 (3-{4-[(2s,3s,6r)-5-hydroxy-3-(hydroxymethyl)-6-(1h-indol-3-yl)-3,6-dihydro-2h-1,4-oxazin-2-yl]phenoxy}propanenitrile)

SMILES for NP0256218 (3-{4-[(2s,3s,6r)-5-hydroxy-3-(hydroxymethyl)-6-(1h-indol-3-yl)-3,6-dihydro-2h-1,4-oxazin-2-yl]phenoxy}propanenitrile)

INCHI for NP0256218 (3-{4-[(2s,3s,6r)-5-hydroxy-3-(hydroxymethyl)-6-(1h-indol-3-yl)-3,6-dihydro-2h-1,4-oxazin-2-yl]phenoxy}propanenitrile)

Structure for NP0256218 (3-{4-[(2s,3s,6r)-5-hydroxy-3-(hydroxymethyl)-6-(1h-indol-3-yl)-3,6-dihydro-2h-1,4-oxazin-2-yl]phenoxy}propanenitrile)

3D Structure for NP0256218 (3-{4-[(2s,3s,6r)-5-hydroxy-3-(hydroxymethyl)-6-(1h-indol-3-yl)-3,6-dihydro-2h-1,4-oxazin-2-yl]phenoxy}propanenitrile)