NP-MRD: Showing NP-Card for (2e)-n-{4-[(3-aminopropyl)amino]butyl}-3-(4-hydroxyphenyl)-n-[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]prop-2-enamide (NP0183591)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 22:31:40 UTC

Updated at

2022-09-03 22:31:40 UTC

NP-MRD ID

NP0183591

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-n-{4-[(3-aminopropyl)amino]butyl}-3-(4-hydroxyphenyl)-n-[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]prop-2-enamide

Description

Di-p-coumaroylspermidine belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. (2e)-n-{4-[(3-aminopropyl)amino]butyl}-3-(4-hydroxyphenyl)-n-[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]prop-2-enamide is found in Arum maculatum. (2e)-n-{4-[(3-aminopropyl)amino]butyl}-3-(4-hydroxyphenyl)-n-[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]prop-2-enamide was first documented in 2022 (PMID: 35057613). Based on a literature review very few articles have been published on di-p-coumaroylspermidine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042200312D          

 32 33  0  0  0  0            999 V2000
    3.6142    0.8943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4068    0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7939    1.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3884    1.5807    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1810    1.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7755    1.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5682    1.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1626    2.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9553    2.0383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5497    2.6104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3516    3.4112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3424    2.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9368    2.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7295    2.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3240    3.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1166    3.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3148    2.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1074    2.0383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7203    1.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9276    1.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1534    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9461    1.0087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5589    0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7571   -0.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1626   -0.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3608   -1.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7663   -2.0803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9737   -1.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3792   -2.4235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7755   -1.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3700   -0.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 26 32  1  0  0  0  0
M  END

     RDKit          3D

 63 64  0  0  0  0  0  0  0  0999 V2000
    3.0464   -3.4977    2.0451 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1450   -3.4864    1.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1070   -2.3641    0.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1270   -1.0010    0.7739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0281   -0.7442    1.6495 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7640   -0.6349    0.9935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6574    0.5975    0.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3164    0.6893   -0.5610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8251    0.7524    0.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1150    0.8403   -0.2330 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8561   -0.3583   -0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9848   -0.2187   -1.0729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2971   -1.6647   -0.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0240   -2.7336   -0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5531   -4.0769   -0.3755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3699   -5.1668   -0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9319   -6.4321   -0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7070   -6.7292    0.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3002   -8.0403    0.2454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9218   -5.6586    0.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3349   -4.3388    0.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7134    2.0473   -0.6032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9280    1.9187   -1.1100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3009    3.4143   -0.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1923    3.9779   -0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9140    5.4180   -0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3227    5.8549    0.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6745    7.1978    0.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2128    8.1619   -0.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1626    9.4976   -0.0969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4371    7.7393   -0.5813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7794    6.3763   -0.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1133   -2.8107    2.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1147   -3.4835    1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0753   -4.4384    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0857   -3.4919    1.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1924   -2.4812   -0.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9734   -2.4158   -0.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0580   -0.9753    1.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2879   -0.2282    0.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2051   -0.0811    2.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6069   -1.5154    0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9821   -0.6563    1.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4699    0.5738   -0.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7986    1.5310    0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2117   -0.2048   -1.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3636    1.5688   -1.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8216   -0.2535    0.9353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6871    1.4768    1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3272   -1.8317    0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0142   -2.5451   -1.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3266   -4.9232   -1.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5754   -7.2576   -0.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7945   -8.4972   -0.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0441   -5.8518    0.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6403   -3.5636    0.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0476    4.1777   -0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4130    3.3316    0.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0513    5.1243    0.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6418    7.5382    0.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3883   10.2700   -0.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1389    8.4878   -0.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7537    6.0889   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 10 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
 21 15  1  0
 32 26  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
  7 44  1  0
  7 45  1  0
  8 46  1  0
  8 47  1  0
  9 48  1  0
  9 49  1  0
 13 50  1  0
 14 51  1  0
 16 52  1  0
 17 53  1  0
 19 54  1  0
 20 55  1  0
 21 56  1  0
 24 57  1  0
 25 58  1  0
 27 59  1  0
 28 60  1  0
 30 61  1  0
 31 62  1  0
 32 63  1  0
M  END


  Mrv1652309042200312D          

 32 33  0  0  0  0            999 V2000
    3.6142    0.8943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4068    0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7939    1.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3884    1.5807    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1810    1.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7755    1.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5682    1.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1626    2.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9553    2.0383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5497    2.6104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3516    3.4112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3424    2.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9368    2.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7295    2.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3240    3.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1166    3.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3148    2.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1074    2.0383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7203    1.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9276    1.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1534    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9461    1.0087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5589    0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7571   -0.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1626   -0.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3608   -1.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7663   -2.0803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9737   -1.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3792   -2.4235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7755   -1.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3700   -0.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 26 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0183591

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCCNCCCCN(C(=O)\C=C\C1=CC=C(O)C=C1)C(=O)\C=C\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H31N3O4/c26-16-3-18-27-17-1-2-19-28(24(31)14-8-20-4-10-22(29)11-5-20)25(32)15-9-21-6-12-23(30)13-7-21/h4-15,27,29-30H,1-3,16-19,26H2/b14-8+,15-9+

> <INCHI_KEY>
ILMNZNQVJUUAQO-VOMDNODZSA-N

> <FORMULA>
C25H31N3O4

> <MOLECULAR_WEIGHT>
437.54

> <EXACT_MASS>
437.23145649

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
50.34870074465063

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-N-{4-[(3-aminopropyl)amino]butyl}-3-(4-hydroxyphenyl)-N-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]prop-2-enamide

> <JCHEM_LOGP>
1.4856592302774458

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
9.65296323608684

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.116728479446062

> <JCHEM_PKA_STRONGEST_BASIC>
10.392777544563472

> <JCHEM_POLAR_SURFACE_AREA>
115.89

> <JCHEM_REFRACTIVITY>
128.7723

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-N-{4-[(3-aminopropyl)amino]butyl}-3-(4-hydroxyphenyl)-N-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]prop-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  N   UNK     0       6.746   1.669   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       8.226   1.242   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.815   1.883   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      11.925   2.951   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      13.405   2.524   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.514   3.591   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.994   3.164   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.104   4.232   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      18.583   3.805   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      19.693   4.873   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      19.323   6.368   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      21.172   4.446   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.282   5.513   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.762   5.086   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.871   6.154   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.351   5.727   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.721   4.232   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      28.200   3.805   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      25.611   3.164   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.132   3.591   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.953   2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      20.433   1.883   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      17.843   1.242   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.213  -0.253   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.104  -1.321   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.473  -2.815   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.364  -3.883   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.884  -3.456   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      13.775  -4.524   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      14.514  -1.961   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.624  -0.893   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   22                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   15                                                       
CONECT   22   10   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   26                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₁N₃O₄

Average Mass

437.5400 Da

Monoisotopic Mass

437.23146 Da

IUPAC Name

(2E)-N-{4-[(3-aminopropyl)amino]butyl}-3-(4-hydroxyphenyl)-N-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]prop-2-enamide

Traditional Name

(2E)-N-{4-[(3-aminopropyl)amino]butyl}-3-(4-hydroxyphenyl)-N-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]prop-2-enamide

CAS Registry Number

Not Available

SMILES

NCCCNCCCCN(C(=O)\C=C\C1=CC=C(O)C=C1)C(=O)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C25H31N3O4/c26-16-3-18-27-17-1-2-19-28(24(31)14-8-20-4-10-22(29)11-5-20)25(32)15-9-21-6-12-23(30)13-7-21/h4-15,27,29-30H,1-3,16-19,26H2/b14-8+,15-9+

InChI Key

ILMNZNQVJUUAQO-VOMDNODZSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arum maculatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Carboxylic acid imide, n-substituted
Monocyclic benzene moiety
Dicarboximide
Carboxylic acid imide
Amino acid or derivatives
Secondary amine
Secondary aliphatic amine
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
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	1.49	ChemAxon
pKa (Strongest Acidic)	9.12	ChemAxon
pKa (Strongest Basic)	10.39	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.89 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	128.77 m³·mol⁻¹	ChemAxon
Polarizability	50.35 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129664297

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Miyata R, Hoshino S, Ahn MR, Kumazawa S: Chemical Profiles of Korean Bee Pollens and Their Catechol-O-methyltransferase Inhibitory Activities. J Agric Food Chem. 2022 Feb 2;70(4):1174-1181. doi: 10.1021/acs.jafc.1c07778. Epub 2022 Jan 21. [PubMed:35057613 ]
LOTUS database [Link]

Showing NP-Card for (2e)-n-{4-[(3-aminopropyl)amino]butyl}-3-(4-hydroxyphenyl)-n-[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]prop-2-enamide (NP0183591)

MOL for NP0183591 ((2e)-n-{4-[(3-aminopropyl)amino]butyl}-3-(4-hydroxyphenyl)-n-[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]prop-2-enamide)

3D MOL for NP0183591 ((2e)-n-{4-[(3-aminopropyl)amino]butyl}-3-(4-hydroxyphenyl)-n-[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]prop-2-enamide)

3D SDF for NP0183591 ((2e)-n-{4-[(3-aminopropyl)amino]butyl}-3-(4-hydroxyphenyl)-n-[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]prop-2-enamide)

3D-SDF for NP0183591 ((2e)-n-{4-[(3-aminopropyl)amino]butyl}-3-(4-hydroxyphenyl)-n-[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]prop-2-enamide)

PDB for NP0183591 ((2e)-n-{4-[(3-aminopropyl)amino]butyl}-3-(4-hydroxyphenyl)-n-[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]prop-2-enamide)

3D PDB for NP0183591 ((2e)-n-{4-[(3-aminopropyl)amino]butyl}-3-(4-hydroxyphenyl)-n-[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]prop-2-enamide)

SMILES for NP0183591 ((2e)-n-{4-[(3-aminopropyl)amino]butyl}-3-(4-hydroxyphenyl)-n-[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]prop-2-enamide)

INCHI for NP0183591 ((2e)-n-{4-[(3-aminopropyl)amino]butyl}-3-(4-hydroxyphenyl)-n-[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]prop-2-enamide)

Structure for NP0183591 ((2e)-n-{4-[(3-aminopropyl)amino]butyl}-3-(4-hydroxyphenyl)-n-[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]prop-2-enamide)

3D Structure for NP0183591 ((2e)-n-{4-[(3-aminopropyl)amino]butyl}-3-(4-hydroxyphenyl)-n-[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]prop-2-enamide)