NP-MRD: Showing NP-Card for NP25302 (NP0004917)

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Record Information

Version

2.0

Created at

2020-12-09 02:18:44 UTC

Updated at

2021-07-15 16:50:32 UTC

NP-MRD ID

NP0004917

Secondary Accession Numbers

None

Natural Product Identification

Common Name

NP25302

Provided By

NPAtlas

Description

N-[(5S,7aS)-5,7a-dimethyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizin-3-yl]-3-methylbut-2-enamide belongs to the class of organic compounds known as pyrrolizines. Pyrrolizines are compounds containing a pyrrolizine moiety, which consists of a pyrrole ring fused to a pyrrolidine ring. NP25302 is found in Streptomyces, Streptomyces sp. UMA-044 and Streptomyces spinoverrucosus. NP25302 was first documented in 2003 (PMID: 14563155). Based on a literature review very few articles have been published on N-[(5S,7aS)-5,7a-dimethyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizin-3-yl]-3-methylbut-2-enamide (PMID: 22007707) (PMID: 17064037).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118153D          

 38 39  0  0  0  0            999 V2000
    4.7715    1.1490   -0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4375   -0.2733   -0.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5669   -1.2561   -0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2074   -0.7389   -0.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0432    0.1320   -0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2262    1.3544   -0.0255 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7318   -0.3914    0.0161 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4025    0.4606    0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4987    1.7805    0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9292    2.1443    0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3967    3.2054    0.6780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6354    0.9767   -0.2500 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7095    0.9377   -1.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9377    0.6873    0.4136 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9403   -0.8251    0.4666 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5060   -1.2575    0.5208 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1233   -1.8552    1.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458   -0.0861    0.1853 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8628    1.2966   -0.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034    1.7361   -1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4006    1.6120    0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1993   -2.1888   -0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4303   -0.8457   -0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8816   -1.5379    0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0268   -1.8068   -0.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5847   -1.4475   -0.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3322    2.4730    0.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7487    0.5223   -2.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5188    0.2530   -2.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8287    1.9683   -2.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9852    1.1590    1.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7784    1.0389   -0.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5584   -1.2175    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3572   -1.2064   -0.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2658   -2.0317   -0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6359   -1.0477    2.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4352   -2.7248    1.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0690   -2.1487    2.3719 H   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
  2  4  2  3  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18  8  1  0  0  0  0
 18 12  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  3 22  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  4 25  1  0  0  0  0
  7 26  1  0  0  0  0
  9 27  1  0  0  0  0
 13 28  1  0  0  0  0
 13 29  1  0  0  0  0
 13 30  1  0  0  0  0
 14 31  1  0  0  0  0
 14 32  1  0  0  0  0
 15 33  1  0  0  0  0
 15 34  1  0  0  0  0
 16 35  1  6  0  0  0
 17 36  1  0  0  0  0
 17 37  1  0  0  0  0
 17 38  1  0  0  0  0
M  END

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
    4.7715    1.1490   -0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4375   -0.2733   -0.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5669   -1.2561   -0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2074   -0.7389   -0.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0432    0.1320   -0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2262    1.3544   -0.0255 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7318   -0.3914    0.0161 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4025    0.4606    0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4987    1.7805    0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9292    2.1443    0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3967    3.2054    0.6780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6354    0.9767   -0.2500 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7095    0.9377   -1.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9377    0.6873    0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9403   -0.8251    0.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5060   -1.2575    0.5208 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1233   -1.8552    1.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458   -0.0861    0.1853 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8628    1.2966   -0.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034    1.7361   -1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4006    1.6120    0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1993   -2.1888   -0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4303   -0.8457   -0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8816   -1.5379    0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0268   -1.8068   -0.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5847   -1.4475   -0.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3322    2.4730    0.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7487    0.5223   -2.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5188    0.2530   -2.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8287    1.9683   -2.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9852    1.1590    1.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7784    1.0389   -0.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5584   -1.2175    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3572   -1.2064   -0.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2658   -2.0317   -0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6359   -1.0477    2.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4352   -2.7248    1.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0690   -2.1487    2.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18  8  1  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  7 26  1  0
  9 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  6
 17 36  1  0
 17 37  1  0
 17 38  1  0
M  END


  Mrv1652306242118153D          

 38 39  0  0  0  0            999 V2000
    4.7715    1.1490   -0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4375   -0.2733   -0.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5669   -1.2561   -0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2074   -0.7389   -0.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0432    0.1320   -0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2262    1.3544   -0.0255 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7318   -0.3914    0.0161 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4025    0.4606    0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4987    1.7805    0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9292    2.1443    0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3967    3.2054    0.6780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6354    0.9767   -0.2500 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7095    0.9377   -1.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9377    0.6873    0.4136 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9403   -0.8251    0.4666 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5060   -1.2575    0.5208 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1233   -1.8552    1.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458   -0.0861    0.1853 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8628    1.2966   -0.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034    1.7361   -1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4006    1.6120    0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1993   -2.1888   -0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4303   -0.8457   -0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8816   -1.5379    0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0268   -1.8068   -0.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5847   -1.4475   -0.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3322    2.4730    0.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7487    0.5223   -2.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5188    0.2530   -2.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8287    1.9683   -2.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9852    1.1590    1.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7784    1.0389   -0.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5584   -1.2175    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3572   -1.2064   -0.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2658   -2.0317   -0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6359   -1.0477    2.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4352   -2.7248    1.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0690   -2.1487    2.3719 H   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
  2  4  2  3  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18  8  1  0  0  0  0
 18 12  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  3 22  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  4 25  1  0  0  0  0
  7 26  1  0  0  0  0
  9 27  1  0  0  0  0
 13 28  1  0  0  0  0
 13 29  1  0  0  0  0
 13 30  1  0  0  0  0
 14 31  1  0  0  0  0
 14 32  1  0  0  0  0
 15 33  1  0  0  0  0
 15 34  1  0  0  0  0
 16 35  1  6  0  0  0
 17 36  1  0  0  0  0
 17 37  1  0  0  0  0
 17 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004917

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N(C(=O)C([H])=C(C([H])([H])[H])C([H])([H])[H])C1=C([H])C(=O)[C@]2(N1[C@@]([H])(C([H])([H])[H])C([H])([H])C2([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C14H20N2O2/c1-9(2)7-13(18)15-12-8-11(17)14(4)6-5-10(3)16(12)14/h7-8,10H,5-6H2,1-4H3,(H,15,18)/t10-,14-/m0/s1

> <INCHI_KEY>
HPPZJYLVFCHDDX-HZMBPMFUSA-N

> <FORMULA>
C14H20N2O2

> <MOLECULAR_WEIGHT>
248.326

> <EXACT_MASS>
248.152477892

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.60454561240423

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(5S,7aS)-5,7a-dimethyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizin-3-yl]-3-methylbut-2-enamide

> <ALOGPS_LOGP>
1.62

> <JCHEM_LOGP>
2.4650679846666663

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.599305240897941

> <JCHEM_PKA_STRONGEST_BASIC>
-0.24059381660784107

> <JCHEM_POLAR_SURFACE_AREA>
49.410000000000004

> <JCHEM_REFRACTIVITY>
81.38929999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.99e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(5S,7aS)-5,7a-dimethyl-1-oxo-6,7-dihydro-5H-pyrrolizin-3-yl]-3-methylbut-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
    4.7715    1.1490   -0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4375   -0.2733   -0.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5669   -1.2561   -0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2074   -0.7389   -0.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0432    0.1320   -0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2262    1.3544   -0.0255 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7318   -0.3914    0.0161 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4025    0.4606    0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4987    1.7805    0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9292    2.1443    0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3967    3.2054    0.6780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6354    0.9767   -0.2500 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7095    0.9377   -1.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9377    0.6873    0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9403   -0.8251    0.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5060   -1.2575    0.5208 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1233   -1.8552    1.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458   -0.0861    0.1853 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8628    1.2966   -0.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034    1.7361   -1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4006    1.6120    0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1993   -2.1888   -0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4303   -0.8457   -0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8816   -1.5379    0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0268   -1.8068   -0.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5847   -1.4475   -0.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3322    2.4730    0.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7487    0.5223   -2.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5188    0.2530   -2.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8287    1.9683   -2.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9852    1.1590    1.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7784    1.0389   -0.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5584   -1.2175    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3572   -1.2064   -0.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2658   -2.0317   -0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6359   -1.0477    2.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4352   -2.7248    1.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0690   -2.1487    2.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18  8  1  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  7 26  1  0
  9 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  6
 17 36  1  0
 17 37  1  0
 17 38  1  0
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       4.771   1.149  -0.191  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.438  -0.273  -0.212  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.567  -1.256  -0.311  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.207  -0.739  -0.149  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.043   0.132  -0.050  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.226   1.354  -0.026  0.00  0.00           O+0
HETATM    7  N   UNK     0       0.732  -0.391   0.016  0.00  0.00           N+0
HETATM    8  C   UNK     0      -0.403   0.461   0.112  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.499   1.781   0.159  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.929   2.144   0.257  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.397   3.205   0.678  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.635   0.977  -0.250  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.709   0.938  -1.758  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.938   0.687   0.414  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.940  -0.825   0.467  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.506  -1.258   0.521  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.123  -1.855   1.853  0.00  0.00           C+0
HETATM   18  N   UNK     0      -1.746  -0.086   0.185  0.00  0.00           N+0
HETATM   19  H   UNK     0       5.863   1.297  -0.297  0.00  0.00           H+0
HETATM   20  H   UNK     0       4.303   1.736  -1.005  0.00  0.00           H+0
HETATM   21  H   UNK     0       4.401   1.612   0.771  0.00  0.00           H+0
HETATM   22  H   UNK     0       5.199  -2.189  -0.778  0.00  0.00           H+0
HETATM   23  H   UNK     0       6.430  -0.846  -0.852  0.00  0.00           H+0
HETATM   24  H   UNK     0       5.882  -1.538   0.731  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.027  -1.807  -0.169  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.585  -1.448  -0.006  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.332   2.473   0.130  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.749   0.522  -2.126  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.519   0.253  -2.053  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.829   1.968  -2.158  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.985   1.159   1.403  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.778   1.039  -0.238  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.558  -1.218   1.293  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.357  -1.206  -0.506  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.266  -2.032  -0.259  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.636  -1.048   2.455  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.435  -2.725   1.744  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.069  -2.149   2.372  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2    1    3    4                                                  
CONECT    3    2   22   23   24                                             
CONECT    4    2    5   25                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   26                                                  
CONECT    8    7    9   18                                                  
CONECT    9    8   10   27                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   18                                             
CONECT   13   12   28   29   30                                             
CONECT   14   12   15   31   32                                             
CONECT   15   14   16   33   34                                             
CONECT   16   15   17   18   35                                             
CONECT   17   16   36   37   38                                             
CONECT   18   16    8   12                                                  
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    3                                                            
CONECT   23    3                                                            
CONECT   24    3                                                            
CONECT   25    4                                                            
CONECT   26    7                                                            
CONECT   27    9                                                            
CONECT   28   13                                                            
CONECT   29   13                                                            
CONECT   30   13                                                            
CONECT   31   14                                                            
CONECT   32   14                                                            
CONECT   33   15                                                            
CONECT   34   15                                                            
CONECT   35   16                                                            
CONECT   36   17                                                            
CONECT   37   17                                                            
CONECT   38   17                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

RDKit          3D

38 39  0  0  0  0  0  0  0  0999 V2000
    4.7715    1.1490   -0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4375   -0.2733   -0.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5669   -1.2561   -0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2074   -0.7389   -0.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0432    0.1320   -0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2262    1.3544   -0.0255 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7318   -0.3914    0.0161 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4025    0.4606    0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4987    1.7805    0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9292    2.1443    0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3967    3.2054    0.6780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6354    0.9767   -0.2500 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7095    0.9377   -1.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9377    0.6873    0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9403   -0.8251    0.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5060   -1.2575    0.5208 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1233   -1.8552    1.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458   -0.0861    0.1853 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8628    1.2966   -0.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034    1.7361   -1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4006    1.6120    0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1993   -2.1888   -0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4303   -0.8457   -0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8816   -1.5379    0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0268   -1.8068   -0.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5847   -1.4475   -0.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3322    2.4730    0.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7487    0.5223   -2.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5188    0.2530   -2.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8287    1.9683   -2.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9852    1.1590    1.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7784    1.0389   -0.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5584   -1.2175    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3572   -1.2064   -0.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2658   -2.0317   -0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6359   -1.0477    2.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4352   -2.7248    1.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0690   -2.1487    2.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18  8  1  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  7 26  1  0
  9 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  6
 17 36  1  0
 17 37  1  0
 17 38  1  0
M  END

View in JSmol View NMR Assignments View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₁₄H₂₀N₂O₂

Average Mass

248.3260 Da

Monoisotopic Mass

248.15248 Da

IUPAC Name

N-[(5S,7aS)-5,7a-dimethyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizin-3-yl]-3-methylbut-2-enamide

Traditional Name

N-[(5S,7aS)-5,7a-dimethyl-1-oxo-6,7-dihydro-5H-pyrrolizin-3-yl]-3-methylbut-2-enamide

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@]2(C)N1C(NC(=O)C=C(C)C)=CC2=O

InChI Identifier

InChI=1S/C14H20N2O2/c1-9(2)7-13(18)15-12-8-11(17)14(4)6-5-10(3)16(12)14/h7-8,10H,5-6H2,1-4H3,(H,15,18)/t10-,14-/m0/s1

InChI Key

HPPZJYLVFCHDDX-HZMBPMFUSA-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
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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	NPAtlas	14563155
Streptomyces sp. UMA-044	Bacteria	KNApSAcK
Streptomyces spinoverrucosus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolizines. Pyrrolizines are compounds containing a pyrrolizine moiety, which consists of a pyrrole ring fused to a pyrrolidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolizines

Sub Class

Not Available

Direct Parent

Pyrrolizines

Alternative Parents

Substituents

Pyrrolizine
N-acyl-amine
Pyrrolidine
Pyrroline
Vinylogous amide
Carboxamide group
Secondary carboxylic acid amide
Ketone
Ketene acetal or derivatives
Carboxylic acid derivative
Azacycle
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.62	ALOGPS
logP	2.47	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	13.6	ChemAxon
pKa (Strongest Basic)	-0.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.41 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.39 m³·mol⁻¹	ChemAxon
Polarizability	27.6 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

NPAtlas ID

NPA003143

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8507725

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10332265

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang Q, Schrader KK, ElSohly HN, Takamatsu S: New cell-cell adhesion inhibitors from Streptomyces sp. UMA-044. J Antibiot (Tokyo). 2003 Aug;56(8):673-81. doi: 10.7164/antibiotics.56.673. [PubMed:14563155 ]
Stevens K, Tyrrell AJ, Skerratt S, Robertson J: Synthesis of NP25302. Org Lett. 2011 Nov 18;13(22):5964-7. doi: 10.1021/ol202381m. Epub 2011 Oct 18. [PubMed:22007707 ]
Duvall JR, Wu F, Snider BB: Structure reassignment and synthesis of Jenamidines A1/A2, synthesis of (+)-NP25302, and formal synthesis of SB-311009 analogues. J Org Chem. 2006 Oct 27;71(22):8579-90. doi: 10.1021/jo061650+. [PubMed:17064037 ]

Showing NP-Card for NP25302 (NP0004917)

MOL for NP0004917 (NP25302)

3D MOL for NP0004917 (NP25302)

3D SDF for NP0004917 (NP25302)

3D-SDF for NP0004917 (NP25302)

PDB for NP0004917 (NP25302)

3D PDB for NP0004917 (NP25302)

SMILES for NP0004917 (NP25302)

INCHI for NP0004917 (NP25302)

Structure for NP0004917 (NP25302)

3D Structure for NP0004917 (NP25302)