NP-MRD: Showing NP-Card for Nitropyrrolin E (NP0009579)

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Record Information

Version

2.0

Created at

2021-01-05 19:11:54 UTC

Updated at

2021-07-15 17:03:40 UTC

NP-MRD ID

NP0009579

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nitropyrrolin E

Provided By

NPAtlas

Description

(3R,10R,11R)-10-chloro-2,6,10-trimethyl-12-(5-nitro-1H-pyrrol-3-yl)dodec-6-ene-2,3,11-triol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Nitropyrrolin E is found in Streptomyces sp. CNQ-509. Based on a literature review very few articles have been published on (3R,10R,11R)-10-chloro-2,6,10-trimethyl-12-(5-nitro-1H-pyrrol-3-yl)dodec-6-ene-2,3,11-triol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106363D          

 58 58  0  0  0  0            999 V2000
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M  CHG  2  16   1  18  -1
M  END

     RDKit          3D

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M  CHG  2  16   1  18  -1
M  END


  Mrv1652306242106363D          

 58 58  0  0  0  0            999 V2000
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   -2.1723    0.4214    3.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3644   -0.7162    2.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0220    0.0238    0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2464   -1.0654   -0.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8919   -2.1281    1.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5621   -2.9749    0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7468   -3.7367   -1.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1266   -3.7525    0.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1979   -4.5121   -0.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2785   -0.3704   -1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4186   -2.0900   -2.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4920   -1.6274    0.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691   -0.4241    0.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4391   -0.6886   -1.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2600    1.6909   -1.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4838    2.1166    0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0524   -0.8069   -0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2109   -1.7023    0.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7597    1.3270    0.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9543    0.5590    1.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7802    0.2605   -1.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3871   -1.2014   -1.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5312    2.6723   -1.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7960    0.8979   -1.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3578    1.6720   -2.6504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2791    2.4162   -1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6561    3.6492   -1.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9455    2.9982    0.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3112    0.9141    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  6  8  1  6  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  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
 16 18  1  0  0  0  0
 15 19  2  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  1  0  0  0
 19 12  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  3 31  1  0  0  0  0
  4 32  1  0  0  0  0
  4 33  1  0  0  0  0
  5 34  1  0  0  0  0
  5 35  1  0  0  0  0
  7 36  1  0  0  0  0
  7 37  1  0  0  0  0
  7 38  1  0  0  0  0
  9 39  1  6  0  0  0
 10 40  1  0  0  0  0
 11 41  1  0  0  0  0
 11 42  1  0  0  0  0
 13 43  1  0  0  0  0
 14 44  1  0  0  0  0
 19 45  1  0  0  0  0
 20 46  1  0  0  0  0
 20 47  1  0  0  0  0
 21 48  1  0  0  0  0
 21 49  1  0  0  0  0
 22 50  1  6  0  0  0
 23 51  1  0  0  0  0
 25 52  1  0  0  0  0
 25 53  1  0  0  0  0
 25 54  1  0  0  0  0
 26 55  1  0  0  0  0
 26 56  1  0  0  0  0
 26 57  1  0  0  0  0
 27 58  1  0  0  0  0
M  CHG  2  16   1  18  -1
M  END
> <DATABASE_ID>
NP0009579

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]([H])(C([H])([H])C1=C([H])N([H])C(=C1[H])[N+]([O-])=O)[C@@](Cl)(C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(\C([H])([H])[H])C([H])([H])C([H])([H])[C@@]([H])(O[H])C(O[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H31ClN2O5/c1-13(7-8-15(23)18(2,3)25)6-5-9-19(4,20)16(24)10-14-11-17(21-12-14)22(26)27/h6,11-12,15-16,21,23-25H,5,7-10H2,1-4H3/b13-6-/t15-,16-,19-/m1/s1

> <INCHI_KEY>
CAJMFLABBNVXCD-GPMSIDNRSA-N

> <FORMULA>
C19H31ClN2O5

> <MOLECULAR_WEIGHT>
402.92

> <EXACT_MASS>
402.1921498

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
43.29149865136452

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
({4-[(2R,3R,6Z,10R)-3-chloro-2,10,11-trihydroxy-3,7,11-trimethyldodec-6-en-1-yl]-1H-pyrrol-2-yl}nitro)-lambda1-oxidanyl

> <ALOGPS_LOGP>
3.70

> <JCHEM_LOGP>
3.282068640666667

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.550835892799096

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.365591507807071

> <JCHEM_PKA_STRONGEST_BASIC>
-3.089266613900067

> <JCHEM_POLAR_SURFACE_AREA>
119.62

> <JCHEM_REFRACTIVITY>
105.9078

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{4-[(2R,3R,6Z,10R)-3-chloro-2,10,11-trihydroxy-3,7,11-trimethyldodec-6-en-1-yl]-1H-pyrrol-2-ylnitro}-lambda1-oxidanyl

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 58  0  0  0  0  0  0  0  0999 V2000
   -2.1466   -0.6411    3.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5849   -0.7485    1.8767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2864   -0.7744    1.7315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4073   -0.8755    0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2806   -2.1353    0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0665   -2.3807   -0.7145 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8570   -3.6457   -0.4764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9265   -2.6895   -2.0398 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9406   -1.2234   -1.1187 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6140   -1.5473   -2.2900 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8755   -0.7959   -0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7029    0.3473   -0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9167    0.2598   -1.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3463    1.4975   -1.3845 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4331    2.3691   -0.9367 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5401    3.7951   -1.0386 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.5290    4.3071   -1.5706 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5358    4.5748   -0.5404 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.3864    1.6812   -0.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5341   -0.8013    0.7615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4277    0.4559    0.7458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3869    0.3349   -0.4347 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1827   -0.7800   -0.3365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1839    1.6170   -0.5172 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0070    1.6936   -1.7672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1948    2.7659   -0.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9846    1.7880    0.6179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4213   -1.1535    3.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1301   -1.1171    3.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1723    0.4214    3.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3644   -0.7162    2.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0220    0.0238    0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2464   -1.0654   -0.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8919   -2.1281    1.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5621   -2.9749    0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7468   -3.7367   -1.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1266   -3.7525    0.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1979   -4.5121   -0.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2785   -0.3704   -1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4186   -2.0900   -2.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4920   -1.6274    0.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691   -0.4241    0.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4391   -0.6886   -1.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2600    1.6909   -1.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4838    2.1166    0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0524   -0.8069   -0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2109   -1.7023    0.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7597    1.3270    0.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9543    0.5590    1.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7802    0.2605   -1.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3871   -1.2014   -1.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5312    2.6723   -1.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7960    0.8979   -1.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3578    1.6720   -2.6504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2791    2.4162   -1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6561    3.6492   -1.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9455    2.9982    0.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3112    0.9141    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  6
  6  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  2  0
  2 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  1
 19 12  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  7 36  1  0
  7 37  1  0
  7 38  1  0
  9 39  1  6
 10 40  1  0
 11 41  1  0
 11 42  1  0
 13 43  1  0
 14 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  6
 23 51  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 26 55  1  0
 26 56  1  0
 26 57  1  0
 27 58  1  0
M  CHG  2  16   1  18  -1
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.147  -0.641   3.301  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.585  -0.749   1.877  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.286  -0.774   1.732  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.407  -0.876   0.443  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.281  -2.135   0.537  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.067  -2.381  -0.715  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.857  -3.646  -0.476  0.00  0.00           C+0
HETATM    8 Cl   UNK     0       0.927  -2.689  -2.040  0.00  0.00          Cl+0
HETATM    9  C   UNK     0       2.941  -1.223  -1.119  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.614  -1.547  -2.290  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.876  -0.796  -0.023  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.703   0.347  -0.491  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.917   0.260  -1.121  0.00  0.00           C+0
HETATM   14  N   UNK     0       6.346   1.498  -1.385  0.00  0.00           N+0
HETATM   15  C   UNK     0       5.433   2.369  -0.937  0.00  0.00           C+0
HETATM   16  N   UNK     0       5.540   3.795  -1.039  0.00  0.00           N+1
HETATM   17  O   UNK     0       6.529   4.307  -1.571  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.536   4.575  -0.540  0.00  0.00           O-1
HETATM   19  C   UNK     0       4.386   1.681  -0.369  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.534  -0.801   0.762  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.428   0.456   0.746  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.387   0.335  -0.435  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.183  -0.780  -0.337  0.00  0.00           O+0
HETATM   24  C   UNK     0      -5.184   1.617  -0.517  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.007   1.694  -1.767  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.195   2.766  -0.548  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.985   1.788   0.618  0.00  0.00           O+0
HETATM   28  H   UNK     0      -1.421  -1.153   3.956  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.130  -1.117   3.355  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.172   0.421   3.561  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.364  -0.716   2.652  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.022   0.024   0.210  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.246  -1.065  -0.415  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.892  -2.128   1.455  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.562  -2.975   0.646  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.747  -3.737  -1.107  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.127  -3.753   0.599  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.198  -4.512  -0.705  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.279  -0.370  -1.347  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.419  -2.090  -2.149  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.492  -1.627   0.373  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.269  -0.424   0.823  0.00  0.00           H+0
HETATM   43  H   UNK     0       6.439  -0.689  -1.362  0.00  0.00           H+0
HETATM   44  H   UNK     0       7.260   1.691  -1.867  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.484   2.117   0.087  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.052  -0.807  -0.213  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.211  -1.702   0.826  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.760   1.327   0.595  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.954   0.559   1.706  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.780   0.261  -1.353  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.387  -1.201  -1.215  0.00  0.00           H+0
HETATM   52  H   UNK     0      -6.531   2.672  -1.763  0.00  0.00           H+0
HETATM   53  H   UNK     0      -6.796   0.898  -1.787  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.358   1.672  -2.650  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.279   2.416  -1.050  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.656   3.649  -1.035  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.946   2.998   0.513  0.00  0.00           H+0
HETATM   58  H   UNK     0      -6.311   0.914   0.961  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    1    3   20                                                  
CONECT    3    2    4   31                                                  
CONECT    4    3    5   32   33                                             
CONECT    5    4    6   34   35                                             
CONECT    6    5    7    8    9                                             
CONECT    7    6   36   37   38                                             
CONECT    8    6                                                            
CONECT    9    6   10   11   39                                             
CONECT   10    9   40                                                       
CONECT   11    9   12   41   42                                             
CONECT   12   11   13   19                                                  
CONECT   13   12   14   43                                                  
CONECT   14   13   15   44                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   15   12   45                                                  
CONECT   20    2   21   46   47                                             
CONECT   21   20   22   48   49                                             
CONECT   22   21   23   24   50                                             
CONECT   23   22   51                                                       
CONECT   24   22   25   26   27                                             
CONECT   25   24   52   53   54                                             
CONECT   26   24   55   56   57                                             
CONECT   27   24   58                                                       
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    3                                                            
CONECT   32    4                                                            
CONECT   33    4                                                            
CONECT   34    5                                                            
CONECT   35    5                                                            
CONECT   36    7                                                            
CONECT   37    7                                                            
CONECT   38    7                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   11                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   19                                                            
CONECT   46   20                                                            
CONECT   47   20                                                            
CONECT   48   21                                                            
CONECT   49   21                                                            
CONECT   50   22                                                            
CONECT   51   23                                                            
CONECT   52   25                                                            
CONECT   53   25                                                            
CONECT   54   25                                                            
CONECT   55   26                                                            
CONECT   56   26                                                            
CONECT   57   26                                                            
CONECT   58   27                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  116    0
END

RDKit          3D

58 58  0  0  0  0  0  0  0  0999 V2000
   -2.1466   -0.6411    3.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5849   -0.7485    1.8767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2864   -0.7744    1.7315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4073   -0.8755    0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2806   -2.1353    0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0665   -2.3807   -0.7145 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8570   -3.6457   -0.4764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9265   -2.6895   -2.0398 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9406   -1.2234   -1.1187 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6140   -1.5473   -2.2900 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8755   -0.7959   -0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7029    0.3473   -0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9167    0.2598   -1.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3463    1.4975   -1.3845 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4331    2.3691   -0.9367 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5401    3.7951   -1.0386 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.5290    4.3071   -1.5706 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5358    4.5748   -0.5404 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.3864    1.6812   -0.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5341   -0.8013    0.7615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4277    0.4559    0.7458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3869    0.3349   -0.4347 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1827   -0.7800   -0.3365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1839    1.6170   -0.5172 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0070    1.6936   -1.7672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1948    2.7659   -0.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9846    1.7880    0.6179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4213   -1.1535    3.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1301   -1.1171    3.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1723    0.4214    3.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3644   -0.7162    2.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0220    0.0238    0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2464   -1.0654   -0.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8919   -2.1281    1.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5621   -2.9749    0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7468   -3.7367   -1.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1266   -3.7525    0.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1979   -4.5121   -0.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2785   -0.3704   -1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4186   -2.0900   -2.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4920   -1.6274    0.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691   -0.4241    0.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4391   -0.6886   -1.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2600    1.6909   -1.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4838    2.1166    0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0524   -0.8069   -0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2109   -1.7023    0.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7597    1.3270    0.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9543    0.5590    1.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7802    0.2605   -1.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3871   -1.2014   -1.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5312    2.6723   -1.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7960    0.8979   -1.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3578    1.6720   -2.6504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2791    2.4162   -1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6561    3.6492   -1.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9455    2.9982    0.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3112    0.9141    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  6
  6  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  2  0
  2 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  1
 19 12  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  7 36  1  0
  7 37  1  0
  7 38  1  0
  9 39  1  6
 10 40  1  0
 11 41  1  0
 11 42  1  0
 13 43  1  0
 14 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  6
 23 51  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 26 55  1  0
 26 56  1  0
 26 57  1  0
 27 58  1  0
M  CHG  2  16   1  18  -1
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₉H₃₁ClN₂O₅

Average Mass

402.9200 Da

Monoisotopic Mass

402.19215 Da

IUPAC Name

({4-[(2R,3R,6Z,10R)-3-chloro-2,10,11-trihydroxy-3,7,11-trimethyldodec-6-en-1-yl]-1H-pyrrol-2-yl}nitro)-lambda1-oxidanyl

Traditional Name

{4-[(2R,3R,6Z,10R)-3-chloro-2,10,11-trihydroxy-3,7,11-trimethyldodec-6-en-1-yl]-1H-pyrrol-2-ylnitro}-lambda1-oxidanyl

CAS Registry Number

Not Available

SMILES

CC(CC[C@@H](O)C(C)(C)O)=CCC[C@@](C)(Cl)[C@H](O)CC1=CNC(=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C19H31ClN2O5/c1-13(7-8-15(23)18(2,3)25)6-5-9-19(4,20)16(24)10-14-11-17(21-12-14)22(26)27/h6,11-12,15-16,21,23-25H,5,7-10H2,1-4H3/t15-,16-,19-/m1/s1

InChI Key

CAJMFLABBNVXCD-GPMSIDNRSA-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
Streptomyces sp. CNQ-509	NPAtlas	21090803

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Nitroaromatic compound
Substituted pyrrole
Heteroaromatic compound
Tertiary alcohol
Pyrrole
Organic nitro compound
Secondary alcohol
C-nitro compound
Halohydrin
Chlorohydrin
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Polyol
Organic oxoazanium
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Alkyl halide
Alkyl chloride
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	3.7	ALOGPS
logP	3.28	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	12.37	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	119.62 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	105.91 m³·mol⁻¹	ChemAxon
Polarizability	43.29 Å³	ChemAxon
Number of Rings	1	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

NPAtlas ID

NPA018545

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

139588259

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Nitropyrrolin E (NP0009579)

MOL for NP0009579 (Nitropyrrolin E)

3D MOL for NP0009579 (Nitropyrrolin E)

3D SDF for NP0009579 (Nitropyrrolin E)

3D-SDF for NP0009579 (Nitropyrrolin E)

PDB for NP0009579 (Nitropyrrolin E)

3D PDB for NP0009579 (Nitropyrrolin E)

SMILES for NP0009579 (Nitropyrrolin E)

INCHI for NP0009579 (Nitropyrrolin E)

Structure for NP0009579 (Nitropyrrolin E)

3D Structure for NP0009579 (Nitropyrrolin E)