NP-MRD: Showing NP-Card for (2e)-3-[(3r)-3-nonyloxiran-2-yl]-1-[(3r,4s,5s)-2,3,4-trihydroxy-5-(hydroxymethyl)-4,5-dihydropyrrol-3-yl]prop-2-en-1-one (NP0242701)

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Record Information

Version

1.0

Created at

2022-09-07 03:04:43 UTC

Updated at

2022-09-07 03:04:44 UTC

NP-MRD ID

NP0242701

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-3-[(3r)-3-nonyloxiran-2-yl]-1-[(3r,4s,5s)-2,3,4-trihydroxy-5-(hydroxymethyl)-4,5-dihydropyrrol-3-yl]prop-2-en-1-one

Description

Pramanicin belongs to the class of organic compounds known as b'-hydroxy-alpha,beta-unsaturated ketones. These are alpha,beta-unsaturated ketones that carry a hydroxyl group at the beta'-position. It was first documented in 2013 (PMID: 23441183). Based on a literature review a significant number of articles have been published on Pramanicin (PMID: 33250887) (PMID: 28169387) (PMID: 25647715) (PMID: 24514071).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072205042D          

 26 27  0  0  1  0            999 V2000
    5.1448   -5.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8592   -4.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5737   -5.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2882   -4.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0027   -5.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7171   -4.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4316   -5.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1461   -4.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8605   -5.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5750   -4.6776    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.9875   -3.9631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4000   -4.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1145   -5.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1145   -5.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8290   -6.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5434   -5.9151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8290   -7.1526    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0085   -7.0664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6494   -7.0664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0619   -6.3519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9850   -7.8200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3719   -8.3721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.4581   -9.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2118   -9.5281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6574   -7.9596    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.9038   -8.2951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 15  1  6  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 17 25  1  0  0  0  0
 25 26  1  6  0  0  0
M  END

     RDKit          3D

 57 58  0  0  0  0  0  0  0  0999 V2000
   -6.2514    2.3241    0.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3185    0.8195    0.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2035    0.4044   -0.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2547   -1.0479   -1.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3078   -1.9762   -0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8577   -1.9065   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2189   -0.6601   -0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7138   -0.5858   -0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0204   -1.7121    0.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4858   -1.6779   -0.0206 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0010   -1.7397   -1.2900 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0032   -0.4691   -0.7288 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2937    0.0590   -0.1684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4379    0.3458    1.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6373    0.8582    1.7452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5103    1.0663    3.0104 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9186    1.1451    1.1027 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7537    1.7392    2.0737 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8743    2.0828   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575    3.3274    0.0168 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4865    1.6096   -1.0750 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0167    0.3085   -0.8045 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5379    0.3078   -0.9104 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9077    0.6814   -2.1829 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6526   -0.0752    0.5983 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8531   -1.1995    0.7004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2312    2.8067    0.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8632    2.5382    1.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4696    2.6941    0.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2635    0.4209    1.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4914    0.3898    1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5194    1.0136   -1.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2342    0.7832   -1.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3006   -1.3836   -0.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3012   -1.1851   -2.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6233   -3.0297   -0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5257   -2.0698    0.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3231   -2.7754   -0.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5844   -2.0863   -1.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7000    0.2828   -0.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2633   -0.6402    0.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4109    0.4045   -0.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5376   -0.5399   -1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4014   -2.7221   -0.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1678   -1.6010    1.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0634   -2.1840    0.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3103    0.2690   -1.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1253    0.2133   -0.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5273    0.1610    1.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1716    2.3212    2.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7390    3.6962   -0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6021   -0.4772   -1.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9586   -0.6745   -0.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9271    1.0111   -0.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7997    0.2796   -2.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5735   -0.2240    1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9327   -1.7213   -0.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  1
 17 25  1  0
 25 26  1  0
 25 22  1  0
 22 23  1  0
 23 24  1  0
 22 21  1  0
 21 19  2  0
 19 20  1  0
 12 10  1  0
 19 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  1
 12 47  1  6
 13 48  1  0
 14 49  1  0
 18 50  1  0
 25 56  1  1
 26 57  1  0
 22 52  1  6
 23 53  1  0
 23 54  1  0
 24 55  1  0
 20 51  1  0
M  END


  Mrv1652309072205042D          

 26 27  0  0  1  0            999 V2000
    5.1448   -5.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8592   -4.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5737   -5.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2882   -4.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0027   -5.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7171   -4.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4316   -5.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1461   -4.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8605   -5.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5750   -4.6776    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.9875   -3.9631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4000   -4.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1145   -5.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1145   -5.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8290   -6.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5434   -5.9151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8290   -7.1526    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0085   -7.0664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6494   -7.0664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0619   -6.3519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9850   -7.8200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3719   -8.3721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.4581   -9.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2118   -9.5281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6574   -7.9596    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.9038   -8.2951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 15  1  6  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 17 25  1  0  0  0  0
 25 26  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0242701

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCC[C@H]1OC1\C=C\C(=O)[C@@]1(O)[C@@H](O)[C@H](CO)N=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H31NO6/c1-2-3-4-5-6-7-8-9-14-15(26-14)10-11-16(22)19(25)17(23)13(12-21)20-18(19)24/h10-11,13-15,17,21,23,25H,2-9,12H2,1H3,(H,20,24)/b11-10+/t13-,14+,15?,17-,19+/m0/s1

> <INCHI_KEY>
BOWRHOKHYKPEAR-BSYQFINISA-N

> <FORMULA>
C19H31NO6

> <MOLECULAR_WEIGHT>
369.458

> <EXACT_MASS>
369.215137722

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.32167986401657

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-[(3R)-3-nonyloxiran-2-yl]-1-[(2S,3S,4R)-3,4,5-trihydroxy-2-(hydroxymethyl)-3,4-dihydro-2H-pyrrol-4-yl]prop-2-en-1-one

> <JCHEM_LOGP>
1.7977885606903499

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.403670752466715

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.2974357918739292

> <JCHEM_PKA_STRONGEST_BASIC>
2.6161662616879795

> <JCHEM_POLAR_SURFACE_AREA>
122.88000000000001

> <JCHEM_REFRACTIVITY>
96.73649999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[(3R)-3-nonyloxiran-2-yl]-1-[(3R,4S,5S)-2,3,4-trihydroxy-5-(hydroxymethyl)-4,5-dihydropyrrol-3-yl]prop-2-en-1-one

> <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  C   UNK     0       9.604  -9.502   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.937  -8.732   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.271  -9.502   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.605  -8.732   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.938  -9.502   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.272  -8.732   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.606  -9.502   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.939  -8.732   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.273  -9.502   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.607  -8.732   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      22.377  -7.398   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      23.147  -8.732   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.480  -9.502   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.480 -11.042   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.814 -11.812   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      27.148 -11.042   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      25.814 -13.352   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      24.282 -13.191   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      27.346 -13.191   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      28.116 -11.857   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0      27.972 -14.597   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      26.828 -15.628   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.989 -17.159   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      28.395 -17.786   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      25.494 -14.858   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      24.087 -15.484   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10   12                                                       
CONECT   12   11   10   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   25                                             
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   17   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₃₁NO₆

Average Mass

369.4580 Da

Monoisotopic Mass

369.21514 Da

IUPAC Name

(2E)-3-[(3R)-3-nonyloxiran-2-yl]-1-[(2S,3S,4R)-3,4,5-trihydroxy-2-(hydroxymethyl)-3,4-dihydro-2H-pyrrol-4-yl]prop-2-en-1-one

Traditional Name

(2E)-3-[(3R)-3-nonyloxiran-2-yl]-1-[(3R,4S,5S)-2,3,4-trihydroxy-5-(hydroxymethyl)-4,5-dihydropyrrol-3-yl]prop-2-en-1-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCC[C@H]1OC1\C=C\C(=O)[C@@]1(O)[C@@H](O)[C@H](CO)N=C1O

InChI Identifier

InChI=1S/C19H31NO6/c1-2-3-4-5-6-7-8-9-14-15(26-14)10-11-16(22)19(25)17(23)13(12-21)20-18(19)24/h10-11,13-15,17,21,23,25H,2-9,12H2,1H3,(H,20,24)/b11-10+/t13-,14+,15?,17-,19+/m0/s1

InChI Key

BOWRHOKHYKPEAR-BSYQFINISA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as b'-hydroxy-alpha,beta-unsaturated ketones. These are alpha,beta-unsaturated ketones that carry a hydroxyl group at the beta'-position.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

b'-hydroxy-alpha,beta-unsaturated ketones

Alternative Parents

Substituents

B'-hydroxy-alpha,beta-unsaturated-ketone
Cyclic carboximidic acid
Tertiary alcohol
Pyrroline
Enone
Alpha-hydroxy ketone
Acryloyl-group
Lactim
Secondary alcohol
Ketone
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Ether
Oxirane
Dialkyl ether
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organonitrogen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	1.8	ChemAxon
pKa (Strongest Acidic)	0.3	ChemAxon
pKa (Strongest Basic)	2.62	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	122.88 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	96.74 m³·mol⁻¹	ChemAxon
Polarizability	41.32 Å³	ChemAxon
Number of Rings	2	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

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

134715044

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gao Y, Stuhldreier F, Schmitt L, Wesselborg S, Guo Z, Zou K, Mandi A, Kurtan T, Liu Z, Proksch P: Induction of New Lactam Derivatives From the Endophytic Fungus Aplosporella javeedii Through an OSMAC Approach. Front Microbiol. 2020 Nov 4;11:600983. doi: 10.3389/fmicb.2020.600983. eCollection 2020. [PubMed:33250887 ]
Tan SW, Chai CL, Moloney MG: Mimics of pramanicin derived from pyroglutamic acid and their antibacterial activity. Org Biomol Chem. 2017 Feb 22;15(8):1889-1912. doi: 10.1039/c6ob02828d. [PubMed:28169387 ]
Tan SW, Chai CL, Moloney MG, Thompson AL: Synthesis of mimics of pramanicin from pyroglutamic acid and their antibacterial activity. J Org Chem. 2015 Mar 6;80(5):2661-75. doi: 10.1021/jo502810b. Epub 2015 Feb 23. [PubMed:25647715 ]
Tan SW, Chai CL, Moloney MG: Synthesis of 3-acyltetramates by side chain manipulation and their antibacterial activity. Org Biomol Chem. 2014 Mar 21;12(11):1711-6. doi: 10.1039/c4ob00095a. [PubMed:24514071 ]
Bodur C, Kutuk O, Karsli-Uzunbas G, Isimjan TT, Harrison P, Basaga H: Pramanicin analog induces apoptosis in human colon cancer cells: critical roles for Bcl-2, Bim, and p38 MAPK signaling. PLoS One. 2013;8(2):e56369. doi: 10.1371/journal.pone.0056369. Epub 2013 Feb 18. [PubMed:23441183 ]
LOTUS database [Link]

Showing NP-Card for (2e)-3-[(3r)-3-nonyloxiran-2-yl]-1-[(3r,4s,5s)-2,3,4-trihydroxy-5-(hydroxymethyl)-4,5-dihydropyrrol-3-yl]prop-2-en-1-one (NP0242701)

MOL for NP0242701 ((2e)-3-[(3r)-3-nonyloxiran-2-yl]-1-[(3r,4s,5s)-2,3,4-trihydroxy-5-(hydroxymethyl)-4,5-dihydropyrrol-3-yl]prop-2-en-1-one)

3D MOL for NP0242701 ((2e)-3-[(3r)-3-nonyloxiran-2-yl]-1-[(3r,4s,5s)-2,3,4-trihydroxy-5-(hydroxymethyl)-4,5-dihydropyrrol-3-yl]prop-2-en-1-one)

3D SDF for NP0242701 ((2e)-3-[(3r)-3-nonyloxiran-2-yl]-1-[(3r,4s,5s)-2,3,4-trihydroxy-5-(hydroxymethyl)-4,5-dihydropyrrol-3-yl]prop-2-en-1-one)

3D-SDF for NP0242701 ((2e)-3-[(3r)-3-nonyloxiran-2-yl]-1-[(3r,4s,5s)-2,3,4-trihydroxy-5-(hydroxymethyl)-4,5-dihydropyrrol-3-yl]prop-2-en-1-one)

PDB for NP0242701 ((2e)-3-[(3r)-3-nonyloxiran-2-yl]-1-[(3r,4s,5s)-2,3,4-trihydroxy-5-(hydroxymethyl)-4,5-dihydropyrrol-3-yl]prop-2-en-1-one)

3D PDB for NP0242701 ((2e)-3-[(3r)-3-nonyloxiran-2-yl]-1-[(3r,4s,5s)-2,3,4-trihydroxy-5-(hydroxymethyl)-4,5-dihydropyrrol-3-yl]prop-2-en-1-one)

SMILES for NP0242701 ((2e)-3-[(3r)-3-nonyloxiran-2-yl]-1-[(3r,4s,5s)-2,3,4-trihydroxy-5-(hydroxymethyl)-4,5-dihydropyrrol-3-yl]prop-2-en-1-one)

INCHI for NP0242701 ((2e)-3-[(3r)-3-nonyloxiran-2-yl]-1-[(3r,4s,5s)-2,3,4-trihydroxy-5-(hydroxymethyl)-4,5-dihydropyrrol-3-yl]prop-2-en-1-one)

Structure for NP0242701 ((2e)-3-[(3r)-3-nonyloxiran-2-yl]-1-[(3r,4s,5s)-2,3,4-trihydroxy-5-(hydroxymethyl)-4,5-dihydropyrrol-3-yl]prop-2-en-1-one)

3D Structure for NP0242701 ((2e)-3-[(3r)-3-nonyloxiran-2-yl]-1-[(3r,4s,5s)-2,3,4-trihydroxy-5-(hydroxymethyl)-4,5-dihydropyrrol-3-yl]prop-2-en-1-one)