NP-MRD: Showing NP-Card for langkamide (NP0040702)

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Record Information

Version

2.0

Created at

2021-06-20 22:47:35 UTC

Updated at

2021-06-30 00:14:45 UTC

NP-MRD ID

NP0040702

Secondary Accession Numbers

None

Natural Product Identification

Common Name

langkamide

Provided By

JEOL Database JEOL Logo

Description

Langkamide belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid. langkamide is found in Piper sarmentosum. langkamide was first documented in 2011 (PMID: 21881266). Based on a literature review very few articles have been published on Langkamide.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100473D          

 39 40  0  0  0  0            999 V2000
   -0.2330   -0.0188   -5.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6989    0.9923   -4.3362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1163    1.0584   -3.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065    0.3227   -2.7054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5284    0.4503   -1.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6939   -0.3314   -0.9826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7415   -1.6723   -0.9287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5921   -2.5237   -1.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6176   -3.1259   -2.3796 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5427   -2.5978   -0.4113 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6837   -3.2319   -0.8070 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5227   -3.0811    0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8737   -2.4727    1.4061 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4821   -2.1692    0.9161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393   -1.6624    1.6171 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9261    1.3270   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2064    2.0554   -0.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7106    2.8764    0.1034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1274    2.8049    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022    1.9500   -2.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7916    2.6934   -2.5681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3497    3.9143   -3.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8574    0.0103   -6.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3352   -1.0148   -4.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7997    0.1752   -5.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4981   -0.3578   -3.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5571    0.2466   -0.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6326   -2.1974   -0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1071   -2.7143   -1.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5007   -4.2811   -1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5438   -3.4297    0.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2161   -2.2311    2.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3170    1.4259    0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3639    3.0249    1.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266    1.8096    0.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6110    3.5704   -0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2377    4.4911   -3.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651    4.5124   -2.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7707    3.7306   -4.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0  0  0  0
 10 11  1  0  0  0  0
  5 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 20  2  0  0  0  0
  5  6  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 10  1  0  0  0  0
  3  4  2  0  0  0  0
 14 15  2  0  0  0  0
  6  7  2  0  0  0  0
  3  2  1  0  0  0  0
  2  1  1  0  0  0  0
  7  8  1  0  0  0  0
 20 21  1  0  0  0  0
  4  5  1  0  0  0  0
 21 22  1  0  0  0  0
  8 10  1  0  0  0  0
 17 18  1  0  0  0  0
 20  3  1  0  0  0  0
 18 19  1  0  0  0  0
  4 26  1  0  0  0  0
 16 33  1  0  0  0  0
  6 27  1  0  0  0  0
  7 28  1  0  0  0  0
 11 29  1  0  0  0  0
 11 30  1  0  0  0  0
 12 31  1  0  0  0  0
 13 32  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
 22 37  1  0  0  0  0
 22 38  1  0  0  0  0
 22 39  1  0  0  0  0
 19 34  1  0  0  0  0
 19 35  1  0  0  0  0
 19 36  1  0  0  0  0
M  END

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.2330   -0.0188   -5.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6989    0.9923   -4.3362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1163    1.0584   -3.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065    0.3227   -2.7054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5284    0.4503   -1.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6939   -0.3314   -0.9826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7415   -1.6723   -0.9287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5921   -2.5237   -1.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6176   -3.1259   -2.3796 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5427   -2.5978   -0.4113 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6837   -3.2319   -0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5227   -3.0811    0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8737   -2.4727    1.4061 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4821   -2.1692    0.9161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393   -1.6624    1.6171 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9261    1.3270   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2064    2.0554   -0.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7106    2.8764    0.1034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1274    2.8049    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022    1.9500   -2.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7916    2.6934   -2.5681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3497    3.9143   -3.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8574    0.0103   -6.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3352   -1.0148   -4.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7997    0.1752   -5.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4981   -0.3578   -3.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5571    0.2466   -0.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6326   -2.1974   -0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1071   -2.7143   -1.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5007   -4.2811   -1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5438   -3.4297    0.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2161   -2.2311    2.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3170    1.4259    0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3639    3.0249    1.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266    1.8096    0.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6110    3.5704   -0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2377    4.4911   -3.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651    4.5124   -2.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7707    3.7306   -4.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
 10 11  1  0
  5 16  2  0
 16 17  1  0
 17 20  2  0
  5  6  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  1  0
  3  4  2  0
 14 15  2  0
  6  7  2  0
  3  2  1  0
  2  1  1  0
  7  8  1  0
 20 21  1  0
  4  5  1  0
 21 22  1  0
  8 10  1  0
 17 18  1  0
 20  3  1  0
 18 19  1  0
  4 26  1  0
 16 33  1  0
  6 27  1  0
  7 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 22 37  1  0
 22 38  1  0
 22 39  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
M  END


  Mrv1652306212100473D          

 39 40  0  0  0  0            999 V2000
   -0.2330   -0.0188   -5.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6989    0.9923   -4.3362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1163    1.0584   -3.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065    0.3227   -2.7054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5284    0.4503   -1.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6939   -0.3314   -0.9826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7415   -1.6723   -0.9287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5921   -2.5237   -1.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6176   -3.1259   -2.3796 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5427   -2.5978   -0.4113 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6837   -3.2319   -0.8070 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5227   -3.0811    0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8737   -2.4727    1.4061 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4821   -2.1692    0.9161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393   -1.6624    1.6171 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9261    1.3270   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2064    2.0554   -0.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7106    2.8764    0.1034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1274    2.8049    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022    1.9500   -2.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7916    2.6934   -2.5681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3497    3.9143   -3.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8574    0.0103   -6.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3352   -1.0148   -4.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7997    0.1752   -5.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4981   -0.3578   -3.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5571    0.2466   -0.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6326   -2.1974   -0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1071   -2.7143   -1.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5007   -4.2811   -1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5438   -3.4297    0.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2161   -2.2311    2.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3170    1.4259    0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3639    3.0249    1.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266    1.8096    0.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6110    3.5704   -0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2377    4.4911   -3.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651    4.5124   -2.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7707    3.7306   -4.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0  0  0  0
 10 11  1  0  0  0  0
  5 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 20  2  0  0  0  0
  5  6  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 10  1  0  0  0  0
  3  4  2  0  0  0  0
 14 15  2  0  0  0  0
  6  7  2  0  0  0  0
  3  2  1  0  0  0  0
  2  1  1  0  0  0  0
  7  8  1  0  0  0  0
 20 21  1  0  0  0  0
  4  5  1  0  0  0  0
 21 22  1  0  0  0  0
  8 10  1  0  0  0  0
 17 18  1  0  0  0  0
 20  3  1  0  0  0  0
 18 19  1  0  0  0  0
  4 26  1  0  0  0  0
 16 33  1  0  0  0  0
  6 27  1  0  0  0  0
  7 28  1  0  0  0  0
 11 29  1  0  0  0  0
 11 30  1  0  0  0  0
 12 31  1  0  0  0  0
 13 32  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
 22 37  1  0  0  0  0
 22 38  1  0  0  0  0
 22 39  1  0  0  0  0
 19 34  1  0  0  0  0
 19 35  1  0  0  0  0
 19 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040702

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(/[H])C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H])C(=O)N1C(=O)C([H])=C([H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H17NO5/c1-20-12-9-11(10-13(21-2)16(12)22-3)6-7-15(19)17-8-4-5-14(17)18/h4-7,9-10H,8H2,1-3H3/b7-6-

> <INCHI_KEY>
RZTXFCPQEOFMDN-SREVYHEPSA-N

> <FORMULA>
C16H17NO5

> <MOLECULAR_WEIGHT>
303.314

> <EXACT_MASS>
303.110672651

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
30.07424758838333

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(2Z)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,5-dihydro-1H-pyrrol-2-one

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
1.4491481343333332

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.064669130540178

> <JCHEM_PKA_STRONGEST_BASIC>
-3.657025076880157

> <JCHEM_POLAR_SURFACE_AREA>
65.07000000000001

> <JCHEM_REFRACTIVITY>
82.56890000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(2Z)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-5H-pyrrol-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.2330   -0.0188   -5.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6989    0.9923   -4.3362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1163    1.0584   -3.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065    0.3227   -2.7054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5284    0.4503   -1.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6939   -0.3314   -0.9826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7415   -1.6723   -0.9287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5921   -2.5237   -1.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6176   -3.1259   -2.3796 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5427   -2.5978   -0.4113 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6837   -3.2319   -0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5227   -3.0811    0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8737   -2.4727    1.4061 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4821   -2.1692    0.9161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393   -1.6624    1.6171 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9261    1.3270   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2064    2.0554   -0.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7106    2.8764    0.1034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1274    2.8049    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022    1.9500   -2.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7916    2.6934   -2.5681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3497    3.9143   -3.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8574    0.0103   -6.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3352   -1.0148   -4.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7997    0.1752   -5.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4981   -0.3578   -3.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5571    0.2466   -0.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6326   -2.1974   -0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1071   -2.7143   -1.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5007   -4.2811   -1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5438   -3.4297    0.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2161   -2.2311    2.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3170    1.4259    0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3639    3.0249    1.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266    1.8096    0.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6110    3.5704   -0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2377    4.4911   -3.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651    4.5124   -2.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7707    3.7306   -4.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
 10 11  1  0
  5 16  2  0
 16 17  1  0
 17 20  2  0
  5  6  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  1  0
  3  4  2  0
 14 15  2  0
  6  7  2  0
  3  2  1  0
  2  1  1  0
  7  8  1  0
 20 21  1  0
  4  5  1  0
 21 22  1  0
  8 10  1  0
 17 18  1  0
 20  3  1  0
 18 19  1  0
  4 26  1  0
 16 33  1  0
  6 27  1  0
  7 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 22 37  1  0
 22 38  1  0
 22 39  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.233  -0.019  -5.221  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.699   0.992  -4.336  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.116   1.058  -3.096  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.006   0.323  -2.705  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.528   0.450  -1.410  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.694  -0.331  -0.983  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.741  -1.672  -0.929  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.592  -2.524  -1.308  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.618  -3.126  -2.380  0.00  0.00           O+0
HETATM   10  N   UNK     0       0.543  -2.598  -0.411  0.00  0.00           N+0
HETATM   11  C   UNK     0      -0.684  -3.232  -0.807  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.523  -3.081   0.410  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.874  -2.473   1.406  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.482  -2.169   0.916  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.339  -1.662   1.617  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.926   1.327  -0.504  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.206   2.055  -0.872  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.711   2.876   0.103  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.127   2.805   0.248  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.702   1.950  -2.179  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.792   2.693  -2.568  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.350   3.914  -3.163  0.00  0.00           C+0
HETATM   23  H   UNK     0      -0.857   0.010  -6.119  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.335  -1.015  -4.777  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.800   0.175  -5.529  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.498  -0.358  -3.395  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.557   0.247  -0.662  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.633  -2.197  -0.609  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.107  -2.714  -1.674  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.501  -4.281  -1.059  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.544  -3.430   0.470  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.216  -2.231   2.397  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.317   1.426   0.507  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.364   3.025   1.294  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.527   1.810   0.021  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.611   3.570  -0.365  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.238   4.491  -3.439  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.765   4.512  -2.456  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.771   3.731  -4.075  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    3    1                                                       
CONECT    3    4    2   20                                                  
CONECT    4    3    5   26                                                  
CONECT    5   16    6    4                                                  
CONECT    6    5    7   27                                                  
CONECT    7    6    8   28                                                  
CONECT    8    9    7   10                                                  
CONECT    9    8                                                            
CONECT   10   11   14    8                                                  
CONECT   11   10   12   29   30                                             
CONECT   12   11   13   31                                                  
CONECT   13   12   14   32                                                  
CONECT   14   13   10   15                                                  
CONECT   15   14                                                            
CONECT   16    5   17   33                                                  
CONECT   17   16   20   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   34   35   36                                             
CONECT   20   17   21    3                                                  
CONECT   21   20   22                                                       
CONECT   22   21   37   38   39                                             
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    4                                                            
CONECT   27    6                                                            
CONECT   28    7                                                            
CONECT   29   11                                                            
CONECT   30   11                                                            
CONECT   31   12                                                            
CONECT   32   13                                                            
CONECT   33   16                                                            
CONECT   34   19                                                            
CONECT   35   19                                                            
CONECT   36   19                                                            
CONECT   37   22                                                            
CONECT   38   22                                                            
CONECT   39   22                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   80    0
END

RDKit          3D

39 40  0  0  0  0  0  0  0  0999 V2000
   -0.2330   -0.0188   -5.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6989    0.9923   -4.3362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1163    1.0584   -3.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065    0.3227   -2.7054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5284    0.4503   -1.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6939   -0.3314   -0.9826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7415   -1.6723   -0.9287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5921   -2.5237   -1.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6176   -3.1259   -2.3796 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5427   -2.5978   -0.4113 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6837   -3.2319   -0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5227   -3.0811    0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8737   -2.4727    1.4061 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4821   -2.1692    0.9161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393   -1.6624    1.6171 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9261    1.3270   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2064    2.0554   -0.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7106    2.8764    0.1034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1274    2.8049    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022    1.9500   -2.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7916    2.6934   -2.5681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3497    3.9143   -3.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8574    0.0103   -6.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3352   -1.0148   -4.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7997    0.1752   -5.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4981   -0.3578   -3.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5571    0.2466   -0.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6326   -2.1974   -0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1071   -2.7143   -1.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5007   -4.2811   -1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5438   -3.4297    0.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2161   -2.2311    2.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3170    1.4259    0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3639    3.0249    1.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266    1.8096    0.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6110    3.5704   -0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2377    4.4911   -3.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651    4.5124   -2.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7707    3.7306   -4.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
 10 11  1  0
  5 16  2  0
 16 17  1  0
 17 20  2  0
  5  6  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  1  0
  3  4  2  0
 14 15  2  0
  6  7  2  0
  3  2  1  0
  2  1  1  0
  7  8  1  0
 20 21  1  0
  4  5  1  0
 21 22  1  0
  8 10  1  0
 17 18  1  0
 20  3  1  0
 18 19  1  0
  4 26  1  0
 16 33  1  0
  6 27  1  0
  7 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 22 37  1  0
 22 38  1  0
 22 39  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₁₆H₁₇NO₅

Average Mass

303.3140 Da

Monoisotopic Mass

303.11067 Da

IUPAC Name

1-[(2Z)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,5-dihydro-1H-pyrrol-2-one

Traditional Name

1-[(2Z)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-5H-pyrrol-2-one

CAS Registry Number

Not Available

SMILES

[H]\C(=C(/[H])C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H])C(=O)N1C(=O)C([H])=C([H])C1([H])[H]

InChI Identifier

InChI=1S/C16H17NO5/c1-20-12-9-11(10-13(21-2)16(12)22-3)6-7-15(19)17-8-4-5-14(17)18/h4-7,9-10H,8H2,1-3H3/b7-6-

InChI Key

RZTXFCPQEOFMDN-SREVYHEPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
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
Piper sarmentosum	JEOL database	Bokesch, H. R., et al, Chem. Pharm. Bull. 59, 1178 (2011)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Not Available

Direct Parent

Cinnamic acids and derivatives

Alternative Parents

Substituents

Cinnamic acid or derivatives
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Styrene
Alkyl aryl ether
Monocyclic benzene moiety
Carboxylic acid imide, n-substituted
Benzenoid
Carboxylic acid imide
Dicarboximide
Pyrroline
Ether
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
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	2.03	ALOGPS
logP	1.45	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	10.06	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	82.57 m³·mol⁻¹	ChemAxon
Polarizability	30.07 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

88296342

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53494929

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bokesch HR, Gardella RS, Rabe DC, Bottaro DP, Linehan WM, McMahon JB, McKee TC: A new hypoxia inducible factor-2 inhibitory pyrrolinone alkaloid from roots and stems of Piper sarmentosum. Chem Pharm Bull (Tokyo). 2011;59(9):1178-9. doi: 10.1248/cpb.59.1178. [PubMed:21881266 ]
Bokesch, H. R., et al. (2011). Bokesch, H. R., et al, Chem. Pharm. Bull. 59, 1178 (2011). Chem. Pharm. Bull..

Showing NP-Card for langkamide (NP0040702)

MOL for NP0040702 (langkamide)

3D MOL for NP0040702 (langkamide)

3D SDF for NP0040702 (langkamide)

3D-SDF for NP0040702 (langkamide)

PDB for NP0040702 (langkamide)

3D PDB for NP0040702 (langkamide)

SMILES for NP0040702 (langkamide)

INCHI for NP0040702 (langkamide)

Structure for NP0040702 (langkamide)

3D Structure for NP0040702 (langkamide)