NP-MRD: Showing NP-Card for Aurantiamide acetate (NP0331160)

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Record Information

Version

2.0

Created at

2022-11-21 17:39:55 UTC

Updated at

2024-09-03 04:16:59 UTC

NP-MRD ID

NP0331160

Natural Product DOI

https://doi.org/10.57994/0878

Secondary Accession Numbers

NP0248720

Natural Product Identification

Common Name

Aurantiamide acetate

Description

N-[1-(acetyloxy)-3-phenylpropan-2-yl]-2-{[hydroxy(phenyl)methylidene]amino}-3-phenylpropanimidic acid belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-[1-(acetyloxy)-3-phenylpropan-2-yl]-2-{[hydroxy(phenyl)methylidene]amino}-3-phenylpropanimidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171512302D          

 33 35  0  0  0  0            999 V2000
    4.1763   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -2.9980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -2.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -2.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638   -1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763   -2.2836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -2.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763   -0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -0.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -0.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -2.9980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6013   -5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888   -5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513   -5.1414    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 17 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
M  END

     RDKit          3D

 61 63  0  0  0  0  0  0  0  0999 V2000
   -3.5298    3.7521   -0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9651    2.4928    0.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9376    2.6075    1.2054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5086    1.2848    0.3361 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2268    0.0094    0.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9609   -0.5569    0.3122 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9570   -2.0532    0.7620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1000   -2.7388    0.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9670   -3.2613   -1.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9834   -3.9345   -1.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1953   -4.1212   -1.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3576   -3.6162    0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3269   -2.9482    0.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7187    0.0285    0.6830 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4044    0.1356   -0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2729   -0.3009   -1.3585 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6794    0.7072    0.2313 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0623    2.0440   -0.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2406    3.1962    0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3967    3.8925    1.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    5.0329    1.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2636    5.4927    0.5493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4345    4.8098   -0.6335 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3192    3.6751   -0.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484   -0.1934   -0.3361 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5816   -0.9175    0.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4267   -0.8070    1.7879 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6089   -1.7831   -0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4466   -2.4297    0.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4272   -3.2552    0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6112   -3.4655   -0.9280 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7845   -2.8263   -1.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7668   -1.9717   -1.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2121    3.7183   -1.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6277    3.7630   -0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1540    4.6405    0.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3674   -0.0931    1.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1212   -0.6134    0.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8983   -0.6839   -0.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0747   -2.1056    1.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9822   -2.4591    0.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9993   -3.1015   -1.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8569   -4.3290   -2.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0119   -4.6475   -1.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3234   -3.7770    0.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4820   -2.5650    1.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5893    0.3901    1.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7465    0.6285    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2298    1.9490   -1.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1348    2.2348    0.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1139    3.5353    1.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7626    5.5908    2.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8553    6.3783    0.7299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1593    5.1783   -1.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1615    3.1679   -1.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7863   -0.2072   -1.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2951   -2.2583    1.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0616   -3.7424    1.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4028   -4.1286   -1.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8946   -2.9636   -2.8799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1271   -1.4800   -2.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
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 11 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  1  0
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 17 18  1  0
 18 19  1  0
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 22 23  1  0
 23 24  2  0
 17 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
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 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 13  8  1  0
 24 19  1  0
 33 28  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  6
  7 40  1  0
  7 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 14 47  1  0
 17 48  1  1
 18 49  1  0
 18 50  1  0
 20 51  1  0
 21 52  1  0
 22 53  1  0
 23 54  1  0
 24 55  1  0
 25 56  1  0
 29 57  1  0
 30 58  1  0
 31 59  1  0
 32 60  1  0
 33 61  1  0
M  END


  Mrv1533004171512302D          

 33 35  0  0  0  0            999 V2000
    4.1763   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -2.9980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -2.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -2.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638   -1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763   -2.2836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -2.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763   -0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -0.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -0.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -2.9980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6013   -5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888   -5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513   -5.1414    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 17 25  1  0  0  0  0
 25 26  1  0  0  0  0
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 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
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 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331160

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC(CC1=CC=CC=C1)NC(=O)C(CC1=CC=CC=C1)NC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H28N2O4/c1-20(30)33-19-24(17-21-11-5-2-6-12-21)28-27(32)25(18-22-13-7-3-8-14-22)29-26(31)23-15-9-4-10-16-23/h2-16,24-25H,17-19H2,1H3,(H,28,32)(H,29,31)

> <INCHI_KEY>
VZPAURMDJZOGHU-UHFFFAOYSA-N

> <FORMULA>
C27H28N2O4

> <MOLECULAR_WEIGHT>
444.531

> <EXACT_MASS>
444.20490739

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
47.48753204821401

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-phenyl-2-[3-phenyl-2-(phenylformamido)propanamido]propyl acetate

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
3.9912943369999994

> <ALOGPS_LOGS>
-6.03

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.169641981013303

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.820533081744856

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2995821608649534

> <JCHEM_POLAR_SURFACE_AREA>
84.5

> <JCHEM_REFRACTIVITY>
126.43110000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.13e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-phenyl-2-[3-phenyl-2-(phenylformamido)propanamido]propyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       7.796  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.106  -8.264   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.106  -5.596   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.646  -5.596   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.416  -4.263   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.646  -2.929   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.106  -2.929   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -4.263   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.796  -4.263   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.026  -2.929   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.796  -1.595   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -1.595   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      13.956  -4.263   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      14.726  -5.596   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.956  -6.930   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      16.266  -5.596   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.036  -4.263   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.266  -2.929   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.726  -2.929   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.956  -1.595   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.726  -0.262   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.266  -0.262   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.036  -1.595   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      17.036  -6.930   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      18.576  -6.930   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      19.346  -5.596   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      19.346  -8.264   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      20.886  -8.264   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      21.656  -9.597   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      20.886 -10.931   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      19.346 -10.931   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.576  -9.597   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    6   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   25                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
CONECT   25   17   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
N-[1-(Acetyloxy)-3-phenylpropan-2-yl]-2-{[hydroxy(phenyl)methylidene]amino}-3-phenylpropanimidate	Generator
Lyciumamide	MeSH
Aurantiamide acetate	MeSH
N-Benzoylphenylalanylphenylalinol acetate	MeSH
N-Benzoyl-1-phenylalanyl-1-phenylalaninol acetate	MeSH
N-Benzoyl-phe-phe-ol-acetate	MeSH

Chemical Formula

C₂₇H₂₈N₂O₄

Average Mass

444.5310 Da

Monoisotopic Mass

444.20491 Da

IUPAC Name

3-phenyl-2-[3-phenyl-2-(phenylformamido)propanamido]propyl acetate

Traditional Name

3-phenyl-2-[3-phenyl-2-(phenylformamido)propanamido]propyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC(CC1=CC=CC=C1)NC(=O)C(CC1=CC=CC=C1)NC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C27H28N2O4/c1-20(30)33-19-24(17-21-11-5-2-6-12-21)28-27(32)25(18-22-13-7-3-8-14-22)29-26(31)23-15-9-4-10-16-23/h2-16,24-25H,17-19H2,1H3,(H,28,32)(H,29,31)

InChI Key

VZPAURMDJZOGHU-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	hxkuang@hljucm.net	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-09-08	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-09-08	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, simulated)	Not Available	Not Available	Not Available	2024-05-11	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Datura metel		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
Hippuric acid or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Amphetamine or derivatives
Benzamide
Benzoic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Benzenoid
Carboxylic acid ester
Carboxamide group
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	3.54	ALOGPS
logP	3.99	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	13.82	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	84.5 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	126.43 m³·mol⁻¹	ChemAxon
Polarizability	47.49 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

9832120

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Aurantiamide acetate (NP0331160)

MOL for NP0331160 (Aurantiamide acetate)

3D MOL for NP0331160 (Aurantiamide acetate)

3D SDF for NP0331160 (Aurantiamide acetate)

3D-SDF for NP0331160 (Aurantiamide acetate)

PDB for NP0331160 (Aurantiamide acetate)

3D PDB for NP0331160 (Aurantiamide acetate)

SMILES for NP0331160 (Aurantiamide acetate)

INCHI for NP0331160 (Aurantiamide acetate)

Structure for NP0331160 (Aurantiamide acetate)

3D Structure for NP0331160 (Aurantiamide acetate)