NP-MRD: Showing NP-Card for Hyperaspine (NP0025434)

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Record Information

Version

1.0

Created at

2021-06-19 17:33:49 UTC

Updated at

2021-06-29 23:50:23 UTC

NP-MRD ID

NP0025434

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hyperaspine

Provided By

JEOL Database JEOL Logo

Description

(3S,4aS,6R,8S)-3-methyl-8-pentyl-octahydropyrido[1,2-c][1,3]oxazin-6-yl 1H-pyrrole-2-carboxylate belongs to the class of organic compounds known as pyrrole carboxylic acids and derivatives. These are heterocyclic compounds containing a pyrrole ring bearing a carboxyl group (or a derivative thereof). Hyperaspine is found in Hyperaspis campestris. It was first documented in 2003 (PMID: 14682765). Based on a literature review very few articles have been published on (3S,4aS,6R,8S)-3-methyl-8-pentyl-octahydropyrido[1,2-c][1,3]oxazin-6-yl 1H-pyrrole-2-carboxylate (PMID: 16268544).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119333D          

 54 56  0  0  0  0            999 V2000
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   -0.3512   -3.4340   -4.7817 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.7733   -0.0761   -2.8289 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0543    0.6817   -1.6806 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3437   -0.0303   -0.3450 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306192119333D          

 54 56  0  0  0  0            999 V2000
   -0.4751   -4.5308   -3.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3512   -3.4340   -4.7817 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.0351   -1.0603   -0.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4265   -0.1178   -0.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1786    1.6983    0.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0536   -0.4099    4.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2023   -2.1970    6.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -2.9419    5.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8143   -1.6788    3.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2583   -0.1115    0.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2236    1.4466    1.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1590    1.4326   -0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7204    3.2199   -0.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3822    3.5521    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1115    3.6147   -2.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4837    5.1588   -2.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0730    5.7153   -1.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7593    5.4979   -3.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3088    1.0446   -3.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8338    1.4807   -3.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0  0  0  0
 18 19  1  0  0  0  0
 24 23  1  0  0  0  0
 23 22  1  0  0  0  0
 22 20  1  0  0  0  0
 20 19  1  0  0  0  0
 14 15  2  0  0  0  0
  8  9  1  0  0  0  0
  8 17  1  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
  7  6  1  0  0  0  0
 10 11  2  0  0  0  0
  6 24  1  0  0  0  0
  6  5  1  0  0  0  0
 18 17  1  0  0  0  0
 18 46  1  6  0  0  0
 18 24  1  0  0  0  0
  5  4  1  0  0  0  0
 15 16  1  0  0  0  0
  4  3  1  0  0  0  0
 16 12  1  0  0  0  0
  3  2  1  0  0  0  0
  8  7  1  0  0  0  0
  2  1  1  0  0  0  0
 12 13  2  0  0  0  0
 20 21  1  0  0  0  0
 13 40  1  0  0  0  0
 14 41  1  0  0  0  0
 15 42  1  0  0  0  0
 16 43  1  0  0  0  0
  8 39  1  1  0  0  0
  7 37  1  0  0  0  0
  7 38  1  0  0  0  0
  6 36  1  1  0  0  0
 17 44  1  0  0  0  0
 17 45  1  0  0  0  0
 23 53  1  0  0  0  0
 23 54  1  0  0  0  0
 20 49  1  6  0  0  0
 19 47  1  0  0  0  0
 19 48  1  0  0  0  0
  5 34  1  0  0  0  0
  5 35  1  0  0  0  0
  4 32  1  0  0  0  0
  4 33  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
  2 28  1  0  0  0  0
  2 29  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 21 50  1  0  0  0  0
 21 51  1  0  0  0  0
 21 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025434

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C([H])=C([H])C([H])=C1C(=O)O[C@]1([H])C([H])([H])[C@@]([H])(N2C([H])([H])O[C@@]([H])(C([H])([H])[H])C([H])([H])[C@@]2([H])C1([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H30N2O3/c1-3-4-5-7-15-11-17(24-19(22)18-8-6-9-20-18)12-16-10-14(2)23-13-21(15)16/h6,8-9,14-17,20H,3-5,7,10-13H2,1-2H3/t14-,15-,16-,17+/m0/s1

> <INCHI_KEY>
SGHXLRHVQDPMOF-LUKYLMHMSA-N

> <FORMULA>
C19H30N2O3

> <MOLECULAR_WEIGHT>
334.46

> <EXACT_MASS>
334.225642834

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.854943981501904

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4aS,6R,8S)-3-methyl-8-pentyl-octahydropyrido[1,2-c][1,3]oxazin-6-yl 1H-pyrrole-2-carboxylate

> <ALOGPS_LOGP>
3.90

> <JCHEM_LOGP>
3.704119882333333

> <ALOGPS_LOGS>
-2.66

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.640490367679497

> <JCHEM_PKA_STRONGEST_BASIC>
7.341199337914838

> <JCHEM_POLAR_SURFACE_AREA>
54.56000000000001

> <JCHEM_REFRACTIVITY>
93.75489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4aS,6R,8S)-3-methyl-8-pentyl-octahydropyrido[1,2-c][1,3]oxazin-6-yl 1H-pyrrole-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
   -0.4751   -4.5308   -3.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3512   -3.4340   -4.7817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9451   -2.0953   -4.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1976   -1.4598   -3.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7733   -0.0761   -2.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0543    0.6817   -1.6806 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3437   -0.0303   -0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2796    0.7101    0.8338 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1199   -0.0605    2.0414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0781    0.0770    2.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9920    0.8015    2.3118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0919   -0.7637    3.8529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0982   -0.9208    4.7922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6553   -1.8525    5.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3893   -2.2480    5.3965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0578   -1.5870    4.2441 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7751    0.8751    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0748    1.5384   -0.7558 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7678    3.0465   -0.7429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0377    3.6443   -2.1225 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5651    5.0888   -2.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3364    2.8929   -3.1142 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7506    1.5312   -3.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4067    0.8388   -1.8722 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1252   -5.4831   -4.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1293   -4.3116   -2.8504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5158   -4.6594   -3.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8715   -3.7599   -5.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7035   -3.3037   -5.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0015   -2.2307   -4.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9169   -1.4091   -5.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2770   -2.1113   -2.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8654   -1.3784   -3.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8325   -0.1917   -2.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7727    0.5452   -3.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5257    1.6727   -1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0351   -1.0603   -0.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4265   -0.1178   -0.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1786    1.6983    0.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0536   -0.4099    4.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2023   -2.1970    6.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -2.9419    5.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8143   -1.6788    3.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2583   -0.1115    0.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2236    1.4466    1.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1590    1.4326   -0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7204    3.2199   -0.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3822    3.5521    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1115    3.6147   -2.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4837    5.1588   -2.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0730    5.7153   -1.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7593    5.4979   -3.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3088    1.0446   -3.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8338    1.4807   -3.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 18 19  1  0
 24 23  1  0
 23 22  1  0
 22 20  1  0
 20 19  1  0
 14 15  2  0
  8  9  1  0
  8 17  1  0
  9 10  1  0
 10 12  1  0
  7  6  1  0
 10 11  2  0
  6 24  1  0
  6  5  1  0
 18 17  1  0
 18 46  1  6
 18 24  1  0
  5  4  1  0
 15 16  1  0
  4  3  1  0
 16 12  1  0
  3  2  1  0
  8  7  1  0
  2  1  1  0
 12 13  2  0
 20 21  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
  8 39  1  1
  7 37  1  0
  7 38  1  0
  6 36  1  1
 17 44  1  0
 17 45  1  0
 23 53  1  0
 23 54  1  0
 20 49  1  6
 19 47  1  0
 19 48  1  0
  5 34  1  0
  5 35  1  0
  4 32  1  0
  4 33  1  0
  3 30  1  0
  3 31  1  0
  2 28  1  0
  2 29  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.475  -4.531  -3.735  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.351  -3.434  -4.782  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.945  -2.095  -4.338  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.198  -1.460  -3.161  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.773  -0.076  -2.829  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.054   0.682  -1.681  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.344  -0.030  -0.345  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.280   0.710   0.834  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.120  -0.061   2.041  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.078   0.077   2.680  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.992   0.802   2.312  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.092  -0.764   3.853  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.098  -0.921   4.792  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.655  -1.853   5.761  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.389  -2.248   5.396  0.00  0.00           C+0
HETATM   16  N   UNK     0      -0.058  -1.587   4.244  0.00  0.00           N+0
HETATM   17  C   UNK     0       1.775   0.875   0.591  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.075   1.538  -0.756  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.768   3.046  -0.743  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.038   3.644  -2.123  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.565   5.089  -2.203  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.336   2.893  -3.114  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.751   1.531  -3.118  0.00  0.00           C+0
HETATM   24  N   UNK     0       1.407   0.839  -1.872  0.00  0.00           N+0
HETATM   25  H   UNK     0      -0.125  -5.483  -4.147  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.129  -4.312  -2.850  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.516  -4.659  -3.422  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.872  -3.760  -5.690  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.704  -3.304  -5.051  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.002  -2.231  -4.076  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.917  -1.409  -5.193  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.277  -2.111  -2.286  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.865  -1.378  -3.413  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.833  -0.192  -2.562  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.773   0.545  -3.733  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.526   1.673  -1.630  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.035  -1.060  -0.355  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.427  -0.118  -0.193  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.179   1.698   0.961  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.054  -0.410   4.772  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.202  -2.197   6.630  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.302  -2.942   5.856  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.814  -1.679   3.738  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.258  -0.112   0.628  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.224   1.447   1.414  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.159   1.433  -0.907  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.720   3.220  -0.470  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.382   3.552   0.012  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.111   3.615  -2.348  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.484   5.159  -2.041  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.073   5.715  -1.463  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.759   5.498  -3.200  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.309   1.045  -3.991  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.834   1.481  -3.293  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    3    1   28   29                                             
CONECT    3    4    2   30   31                                             
CONECT    4    5    3   32   33                                             
CONECT    5    6    4   34   35                                             
CONECT    6    7   24    5   36                                             
CONECT    7    6    8   37   38                                             
CONECT    8    9   17    7   39                                             
CONECT    9    8   10                                                       
CONECT   10    9   12   11                                                  
CONECT   11   10                                                            
CONECT   12   10   16   13                                                  
CONECT   13   14   12   40                                                  
CONECT   14   13   15   41                                                  
CONECT   15   14   16   42                                                  
CONECT   16   15   12   43                                                  
CONECT   17    8   18   44   45                                             
CONECT   18   19   17   46   24                                             
CONECT   19   18   20   47   48                                             
CONECT   20   22   19   21   49                                             
CONECT   21   20   50   51   52                                             
CONECT   22   23   20                                                       
CONECT   23   24   22   53   54                                             
CONECT   24   23    6   18                                                  
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    2                                                            
CONECT   29    2                                                            
CONECT   30    3                                                            
CONECT   31    3                                                            
CONECT   32    4                                                            
CONECT   33    4                                                            
CONECT   34    5                                                            
CONECT   35    5                                                            
CONECT   36    6                                                            
CONECT   37    7                                                            
CONECT   38    7                                                            
CONECT   39    8                                                            
CONECT   40   13                                                            
CONECT   41   14                                                            
CONECT   42   15                                                            
CONECT   43   16                                                            
CONECT   44   17                                                            
CONECT   45   17                                                            
CONECT   46   18                                                            
CONECT   47   19                                                            
CONECT   48   19                                                            
CONECT   49   20                                                            
CONECT   50   21                                                            
CONECT   51   21                                                            
CONECT   52   21                                                            
CONECT   53   23                                                            
CONECT   54   23                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  112    0
END

RDKit          3D

54 56  0  0  0  0  0  0  0  0999 V2000
   -0.4751   -4.5308   -3.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3512   -3.4340   -4.7817 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7733   -0.0761   -2.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0543    0.6817   -1.6806 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3437   -0.0303   -0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2796    0.7101    0.8338 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1199   -0.0605    2.0414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0781    0.0770    2.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9920    0.8015    2.3118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0919   -0.7637    3.8529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0982   -0.9208    4.7922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6553   -1.8525    5.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3893   -2.2480    5.3965 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0748    1.5384   -0.7558 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7678    3.0465   -0.7429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0377    3.6443   -2.1225 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5651    5.0888   -2.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3364    2.8929   -3.1142 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4067    0.8388   -1.8722 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1252   -5.4831   -4.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1293   -4.3116   -2.8504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5158   -4.6594   -3.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8715   -3.7599   -5.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7035   -3.3037   -5.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0015   -2.2307   -4.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9169   -1.4091   -5.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2770   -2.1113   -2.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8654   -1.3784   -3.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8325   -0.1917   -2.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7727    0.5452   -3.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5257    1.6727   -1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0351   -1.0603   -0.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4265   -0.1178   -0.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1786    1.6983    0.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0536   -0.4099    4.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2023   -2.1970    6.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -2.9419    5.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8143   -1.6788    3.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2583   -0.1115    0.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2236    1.4466    1.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1590    1.4326   -0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7204    3.2199   -0.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3822    3.5521    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1115    3.6147   -2.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4837    5.1588   -2.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0730    5.7153   -1.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7593    5.4979   -3.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3088    1.0446   -3.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8338    1.4807   -3.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 18 19  1  0
 24 23  1  0
 23 22  1  0
 22 20  1  0
 20 19  1  0
 14 15  2  0
  8  9  1  0
  8 17  1  0
  9 10  1  0
 10 12  1  0
  7  6  1  0
 10 11  2  0
  6 24  1  0
  6  5  1  0
 18 17  1  0
 18 46  1  6
 18 24  1  0
  5  4  1  0
 15 16  1  0
  4  3  1  0
 16 12  1  0
  3  2  1  0
  8  7  1  0
  2  1  1  0
 12 13  2  0
 20 21  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
  8 39  1  1
  7 37  1  0
  7 38  1  0
  6 36  1  1
 17 44  1  0
 17 45  1  0
 23 53  1  0
 23 54  1  0
 20 49  1  6
 19 47  1  0
 19 48  1  0
  5 34  1  0
  5 35  1  0
  4 32  1  0
  4 33  1  0
  3 30  1  0
  3 31  1  0
  2 28  1  0
  2 29  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
M  END

View in JSmol

Synonyms

Value	Source
(3S,4AS,6R,8S)-3-methyl-8-pentyl-octahydropyrido[1,2-c][1,3]oxazin-6-yl 1H-pyrrole-2-carboxylic acid	Generator

Chemical Formula

C₁₉H₃₀N₂O₃

Average Mass

334.4600 Da

Monoisotopic Mass

334.22564 Da

IUPAC Name

(3S,4aS,6R,8S)-3-methyl-8-pentyl-octahydropyrido[1,2-c][1,3]oxazin-6-yl 1H-pyrrole-2-carboxylate

Traditional Name

(3S,4aS,6R,8S)-3-methyl-8-pentyl-octahydropyrido[1,2-c][1,3]oxazin-6-yl 1H-pyrrole-2-carboxylate

CAS Registry Number

Not Available

SMILES

[H]N1C([H])=C([H])C([H])=C1C(=O)O[C@]1([H])C([H])([H])[C@@]([H])(N2C([H])([H])O[C@@]([H])(C([H])([H])[H])C([H])([H])[C@@]2([H])C1([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C19H30N2O3/c1-3-4-5-7-15-11-17(24-19(22)18-8-6-9-20-18)12-16-10-14(2)23-13-21(15)16/h6,8-9,14-17,20H,3-5,7,10-13H2,1-2H3/t14-,15-,16-,17+/m0/s1

InChI Key

SGHXLRHVQDPMOF-LUKYLMHMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hyperaspis campestris	JEOL database	Lebrun, B., et al, Tetrahedron Letts. 42, 4621 (2001)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrole carboxylic acids and derivatives. These are heterocyclic compounds containing a pyrrole ring bearing a carboxyl group (or a derivative thereof).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrroles

Sub Class

Pyrrole carboxylic acids and derivatives

Direct Parent

Pyrrole carboxylic acids and derivatives

Alternative Parents

Substituents

Pyrrole-2-carboxylic acid or derivatives
1,3-oxazinane
Hydropyridine
Oxazinane
Piperidine
Substituted pyrrole
Heteroaromatic compound
Hemiaminal
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
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	3.9	ALOGPS
logP	3.7	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	12.64	ChemAxon
pKa (Strongest Basic)	7.34	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.56 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	93.75 m³·mol⁻¹	ChemAxon
Polarizability	38.85 Å³	ChemAxon
Number of Rings	3	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

9419584

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11244548

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Comins DL, Sahn JJ: A six-step asymmetric synthesis of (+)-hyperaspine. Org Lett. 2005 Nov 10;7(23):5227-8. doi: 10.1021/ol052068v. [PubMed:16268544 ]
Zhu W, Ma D: Preparation of syn-delta-hydroxy-beta-amino esters via an intramolecular hydrogen bond directed diastereoselective hydrogenation. Total synthesis of (3S,4aS,6R,8S)-hyperaspine. Org Lett. 2003 Dec 25;5(26):5063-6. doi: 10.1021/ol036097m. [PubMed:14682765 ]
Lebrun, B., et al. (2001). Lebrun, B., et al, Tetrahedron Letts. 42, 4621 (2001). Tetrahedron Lett.

Showing NP-Card for Hyperaspine (NP0025434)

MOL for NP0025434 (Hyperaspine)

3D MOL for NP0025434 (Hyperaspine)

3D SDF for NP0025434 (Hyperaspine)

3D-SDF for NP0025434 (Hyperaspine)

PDB for NP0025434 (Hyperaspine)

3D PDB for NP0025434 (Hyperaspine)

SMILES for NP0025434 (Hyperaspine)

INCHI for NP0025434 (Hyperaspine)

Structure for NP0025434 (Hyperaspine)

3D Structure for NP0025434 (Hyperaspine)