NP-MRD: Showing NP-Card for (2e)-n-[(3s,4s,7r,10e)-7-benzyl-5,8-dihydroxy-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methylpent-2-enimidic acid (NP0172413)

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Record Information

Version

2.0

Created at

2022-09-03 09:20:02 UTC

Updated at

2024-09-12 20:46:36 UTC

NP-MRD ID

NP0172413

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-n-[(3s,4s,7r,10e)-7-benzyl-5,8-dihydroxy-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methylpent-2-enimidic acid

Description

(2E)-n-[(3s,4s,7r,10e)-7-benzyl-5,8-dihydroxy-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]Hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methylpent-2-enimidic acid belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone. (2e)-n-[(3s,4s,7r,10e)-7-benzyl-5,8-dihydroxy-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methylpent-2-enimidic acid is found in Discaria americana. Based on a literature review very few articles have been published on (2e)-n-[(3s,4s,7r,10e)-7-benzyl-5,8-dihydroxy-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]Hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methylpent-2-enimidic acid.

Structure

MOL SDF PDB SMILES InChI

NP0172413
  Mrv2104 05272323183D          

 72 75  0  0  0  0            999 V2000
    5.6670    3.0495    0.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3192    3.3025    1.2177 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5073    3.3749    2.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3091    2.2838    0.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6548    1.3799    1.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6346    0.4479    0.9456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6959    0.0825    1.6440 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    0.0031   -0.3302 N   0  0  2  0  0  0  0  0  0  0  0  0
    1.0396   -1.0711   -0.9431 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3494   -0.4753   -1.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6527   -0.2554   -2.4852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1980   -0.1378   -0.2765 N   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4008    0.6903   -0.4957 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0524    2.1812   -0.4062 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1821    3.0538   -0.9000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3113    4.6209   -1.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4416    0.3109    0.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4697   -0.5048    0.0946 N   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3328   -1.8529    0.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5680   -2.7782   -0.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7347   -3.3392   -2.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7040   -3.5419   -1.0439 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9997   -2.4202   -0.1576 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.7815   -3.0282    2.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8638   -3.3421    1.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5598    3.5895    3.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2068    4.1761    2.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7619    0.1601   -0.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5262   -1.2648   -1.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8118   -0.1323    0.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7988    0.4524   -1.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1573    2.3984   -1.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7882    2.4618    0.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6130    2.9104   -2.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4891    4.3009   -3.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1336    5.2332   -2.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8982    4.7707    0.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0297    3.3875    1.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7633   -0.3077   -0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6576   -2.0456    1.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1918   -2.5601   -1.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2735   -2.8682   -2.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8475   -3.1141   -3.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6877   -4.6984    0.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1375   -4.4866    1.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2677   -2.3547    0.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047   -2.4946    2.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9059   -3.0023    3.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8313   -3.5680    2.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5437   -3.6341   -0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3485   -3.1340   -1.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 33  9  1  0  0  0  0
 39 34  1  0  0  0  0
 20 15  1  0  0  0  0
 31 26  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
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  2 43  1  0  0  0  0
  3 44  1  0  0  0  0
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  5 48  1  0  0  0  0
  8 49  1  0  0  0  0
  9 50  1  6  0  0  0
 12 51  1  0  0  0  0
 13 52  1  6  0  0  0
 14 53  1  0  0  0  0
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 16 55  1  0  0  0  0
 17 56  1  0  0  0  0
 18 57  1  0  0  0  0
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 23 60  1  0  0  0  0
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 27 63  1  0  0  0  0
 28 64  1  0  0  0  0
 30 65  1  0  0  0  0
 31 66  1  0  0  0  0
 33 67  1  1  0  0  0
 35 68  1  0  0  0  0
 36 69  1  0  0  0  0
 37 70  1  0  0  0  0
 38 71  1  0  0  0  0
 39 72  1  0  0  0  0
M  END

NP0172413
  Mrv2104 05272323183D          

 72 75  0  0  0  0            999 V2000
    5.6670    3.0495    0.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3192    3.3025    1.2177 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5073    3.3749    2.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3091    2.2838    0.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6548    1.3799    1.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6346    0.4479    0.9456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6959    0.0825    1.6440 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    0.0031   -0.3302 N   0  0  2  0  0  0  0  0  0  0  0  0
    1.0396   -1.0711   -0.9431 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3494   -0.4753   -1.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6527   -0.2554   -2.4852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1980   -0.1378   -0.2765 N   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4008    0.6903   -0.4957 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0524    2.1812   -0.4062 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1821    3.0538   -0.9000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3275    3.3141   -2.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3862    4.0972   -2.7300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3113    4.6209   -1.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1773    4.3631   -0.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1183    3.5825   -0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4416    0.3109    0.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2593    0.5135    1.7835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4697   -0.5048    0.0946 N   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3328   -1.8529    0.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
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  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  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  0  0  0  0
 13 14  1  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
 19 20  2  0  0  0  0
 13 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 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
 30 31  2  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 33  9  1  0  0  0  0
 39 34  1  0  0  0  0
 20 15  1  0  0  0  0
 31 26  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
  1 42  1  0  0  0  0
  2 43  1  0  0  0  0
  3 44  1  0  0  0  0
  3 45  1  0  0  0  0
  3 46  1  0  0  0  0
  4 47  1  0  0  0  0
  5 48  1  0  0  0  0
  8 49  1  0  0  0  0
  9 50  1  6  0  0  0
 12 51  1  0  0  0  0
 13 52  1  6  0  0  0
 14 53  1  0  0  0  0
 14 54  1  0  0  0  0
 16 55  1  0  0  0  0
 17 56  1  0  0  0  0
 18 57  1  0  0  0  0
 19 58  1  0  0  0  0
 20 59  1  0  0  0  0
 23 60  1  0  0  0  0
 24 61  1  0  0  0  0
 25 62  1  0  0  0  0
 27 63  1  0  0  0  0
 28 64  1  0  0  0  0
 30 65  1  0  0  0  0
 31 66  1  0  0  0  0
 33 67  1  1  0  0  0
 35 68  1  0  0  0  0
 36 69  1  0  0  0  0
 37 70  1  0  0  0  0
 38 71  1  0  0  0  0
 39 72  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0172413

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N(C(=O)C(\[H])=C(/[H])C([H])(C([H])([H])[H])C([H])([H])[H])[C@]1([H])C(=O)N([H])[C@@]([H])(C(=O)N([H])\C([H])=C([H])\C2=C([H])C([H])=C(O[C@@]1([H])C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])=C2[H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1/C32H33N3O4/c1-22(2)13-18-28(36)35-29-30(25-11-7-4-8-12-25)39-26-16-14-23(15-17-26)19-20-33-31(37)27(34-32(29)38)21-24-9-5-3-6-10-24/h3-20,22,27,29-30H,21H2,1-2H3,(H,33,37)(H,34,38)(H,35,36)/b18-13+,20-19+/t27-,29+,30+/s2

> <INCHI_KEY>
NXIUUPIVEHYUQL-MNTCWZLVNA-N

> <FORMULA>
C32H33N3O4

> <MOLECULAR_WEIGHT>
523.633

> <EXACT_MASS>
523.247106555

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
56.16716627235549

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-N-[(3S,4S,7R,10E)-7-benzyl-5,8-dioxo-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraen-4-yl]-4-methylpent-2-enamide

> <JCHEM_LOGP>
4.8572412646666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.84242376072224

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.17883024308841

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4237011271479554

> <JCHEM_POLAR_SURFACE_AREA>
96.53000000000002

> <JCHEM_REFRACTIVITY>
151.53629999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-N-[(3S,4S,7R,10E)-7-benzyl-5,8-dioxo-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraen-4-yl]-4-methylpent-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: NP0172413                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0       5.667   3.050   0.538  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.319   3.303   1.218  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.507   3.375   2.735  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.309   2.284   0.733  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.655   1.380   1.482  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.635   0.448   0.946  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.696   0.083   1.644  0.00  0.00           O+0
HETATM    8  N   UNK     0       1.847   0.003  -0.330  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.040  -1.071  -0.943  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.349  -0.475  -1.309  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.653  -0.255  -2.485  0.00  0.00           O+0
HETATM   12  N   UNK     0      -1.198  -0.138  -0.277  0.00  0.00           N+0
HETATM   13  C   UNK     0      -2.401   0.690  -0.496  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.052   2.181  -0.406  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.182   3.054  -0.900  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.328   3.314  -2.269  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.386   4.097  -2.730  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.311   4.621  -1.828  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.177   4.363  -0.465  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.118   3.583  -0.002  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.442   0.311   0.583  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.259   0.514   1.784  0.00  0.00           O+0
HETATM   23  N   UNK     0      -4.470  -0.505   0.095  0.00  0.00           N+0
HETATM   24  C   UNK     0      -4.333  -1.853   0.378  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.568  -2.778  -0.570  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.365  -3.598  -0.847  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.735  -3.339  -2.076  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.355  -3.458  -2.180  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.634  -3.822  -1.052  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.269  -4.341   0.075  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.655  -4.240   0.177  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.704  -3.542  -1.044  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.000  -2.420  -0.158  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.361  -2.765   0.449  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.537  -2.744   1.842  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.781  -3.028   2.405  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.864  -3.342   1.586  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.702  -3.376   0.203  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.460  -3.090  -0.364  0.00  0.00           C+0
HETATM   40  H   UNK     0       6.085   2.079   0.830  0.00  0.00           H+0
HETATM   41  H   UNK     0       5.569   3.059  -0.553  0.00  0.00           H+0
HETATM   42  H   UNK     0       6.391   3.825   0.812  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.957   4.285   0.889  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.909   2.439   3.139  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.560   3.590   3.242  0.00  0.00           H+0
HETATM   46  H   UNK     0       5.207   4.176   2.997  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.091   2.349  -0.333  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.778   1.318   2.557  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.762   0.160  -0.730  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.526  -1.265  -1.910  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.812  -0.132   0.672  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.799   0.452  -1.490  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.157   2.398  -1.004  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.788   2.462   0.622  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.613   2.910  -2.985  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.489   4.301  -3.793  0.00  0.00           H+0
HETATM   57  H   UNK     0      -6.134   5.233  -2.187  0.00  0.00           H+0
HETATM   58  H   UNK     0      -5.898   4.771   0.239  0.00  0.00           H+0
HETATM   59  H   UNK     0      -4.030   3.388   1.067  0.00  0.00           H+0
HETATM   60  H   UNK     0      -4.763  -0.308  -0.857  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.658  -2.046   1.214  0.00  0.00           H+0
HETATM   62  H   UNK     0      -5.192  -2.560  -1.433  0.00  0.00           H+0
HETATM   63  H   UNK     0      -3.273  -2.868  -2.895  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.848  -3.114  -3.077  0.00  0.00           H+0
HETATM   65  H   UNK     0      -0.688  -4.698   0.920  0.00  0.00           H+0
HETATM   66  H   UNK     0      -3.138  -4.487   1.119  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.268  -2.355   0.658  0.00  0.00           H+0
HETATM   68  H   UNK     0       1.705  -2.495   2.499  0.00  0.00           H+0
HETATM   69  H   UNK     0       3.906  -3.002   3.484  0.00  0.00           H+0
HETATM   70  H   UNK     0       5.831  -3.568   2.027  0.00  0.00           H+0
HETATM   71  H   UNK     0       5.544  -3.634  -0.436  0.00  0.00           H+0
HETATM   72  H   UNK     0       3.349  -3.134  -1.446  0.00  0.00           H+0
CONECT    1    2   40   41   42                                             
CONECT    2    1    3    4   43                                             
CONECT    3    2   44   45   46                                             
CONECT    4    2    5   47                                                  
CONECT    5    4    6   48                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   49                                                  
CONECT    9    8   10   33   50                                             
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   51                                                  
CONECT   13   12   14   21   52                                             
CONECT   14   13   15   53   54                                             
CONECT   15   14   16   20                                                  
CONECT   16   15   17   55                                                  
CONECT   17   16   18   56                                                  
CONECT   18   17   19   57                                                  
CONECT   19   18   20   58                                                  
CONECT   20   19   15   59                                                  
CONECT   21   13   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   60                                                  
CONECT   24   23   25   61                                                  
CONECT   25   24   26   62                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28   63                                                  
CONECT   28   27   29   64                                                  
CONECT   29   28   30   32                                                  
CONECT   30   29   31   65                                                  
CONECT   31   30   26   66                                                  
CONECT   32   29   33                                                       
CONECT   33   32   34    9   67                                             
CONECT   34   33   35   39                                                  
CONECT   35   34   36   68                                                  
CONECT   36   35   37   69                                                  
CONECT   37   36   38   70                                                  
CONECT   38   37   39   71                                                  
CONECT   39   38   34   72                                                  
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    2                                                            
CONECT   44    3                                                            
CONECT   45    3                                                            
CONECT   46    3                                                            
CONECT   47    4                                                            
CONECT   48    5                                                            
CONECT   49    8                                                            
CONECT   50    9                                                            
CONECT   51   12                                                            
CONECT   52   13                                                            
CONECT   53   14                                                            
CONECT   54   14                                                            
CONECT   55   16                                                            
CONECT   56   17                                                            
CONECT   57   18                                                            
CONECT   58   19                                                            
CONECT   59   20                                                            
CONECT   60   23                                                            
CONECT   61   24                                                            
CONECT   62   25                                                            
CONECT   63   27                                                            
CONECT   64   28                                                            
CONECT   65   30                                                            
CONECT   66   31                                                            
CONECT   67   33                                                            
CONECT   68   35                                                            
CONECT   69   36                                                            
CONECT   70   37                                                            
CONECT   71   38                                                            
CONECT   72   39                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  150    0
END

View in JSmol

Synonyms

Value	Source
(2E)-N-[(3S,4S,7R,10E)-7-Benzyl-5,8-dihydroxy-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methylpent-2-enimidate	Generator

Chemical Formula

C₃₂H₃₃N₃O₄

Average Mass

523.6330 Da

Monoisotopic Mass

523.24711 Da

IUPAC Name

(2E)-N-[(3S,4S,7R,10E)-7-benzyl-5,8-dioxo-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraen-4-yl]-4-methylpent-2-enamide

Traditional Name

(2E)-N-[(3S,4S,7R,10E)-7-benzyl-5,8-dioxo-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraen-4-yl]-4-methylpent-2-enamide

CAS Registry Number

Not Available

SMILES

[H]N(C(=O)C(\[H])=C(/[H])C([H])(C([H])([H])[H])C([H])([H])[H])[C@]1([H])C(=O)N([H])[C@@]([H])(C(=O)N([H])\C([H])=C([H])\C2=C([H])C([H])=C(O[C@@]1([H])C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])=C2[H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H]

InChI Identifier

InChI=1/C32H33N3O4/c1-22(2)13-18-28(36)35-29-30(25-11-7-4-8-12-25)39-26-16-14-23(15-17-26)19-20-33-31(37)27(34-32(29)38)21-24-9-5-3-6-10-24/h3-20,22,27,29-30H,21H2,1-2H3,(H,33,37)(H,34,38)(H,35,36)/b18-13+,20-19+/t27-,29+,30+/s2

InChI Key

NXIUUPIVEHYUQL-MNTCWZLVNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Discaria americana	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as cyclic peptides. These are compounds containing a cyclic moiety bearing a peptide backbone.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cyclic peptides

Alternative Parents

Substituents

Cyclic alpha peptide
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Cyclic carboximidic acid
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Ether
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.86	ChemAxon
pKa (Strongest Acidic)	11.18	ChemAxon
pKa (Strongest Basic)	-0.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	151.54 m³·mol⁻¹	ChemAxon
Polarizability	56.17 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-n-[(3s,4s,7r,10e)-7-benzyl-5,8-dihydroxy-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methylpent-2-enimidic acid (NP0172413)

MOL for NP0172413 ((2e)-n-[(3s,4s,7r,10e)-7-benzyl-5,8-dihydroxy-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methylpent-2-enimidic acid)

3D MOL for NP0172413 ((2e)-n-[(3s,4s,7r,10e)-7-benzyl-5,8-dihydroxy-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methylpent-2-enimidic acid)

3D SDF for NP0172413 ((2e)-n-[(3s,4s,7r,10e)-7-benzyl-5,8-dihydroxy-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methylpent-2-enimidic acid)

3D-SDF for NP0172413 ((2e)-n-[(3s,4s,7r,10e)-7-benzyl-5,8-dihydroxy-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methylpent-2-enimidic acid)

PDB for NP0172413 ((2e)-n-[(3s,4s,7r,10e)-7-benzyl-5,8-dihydroxy-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methylpent-2-enimidic acid)

3D PDB for NP0172413 ((2e)-n-[(3s,4s,7r,10e)-7-benzyl-5,8-dihydroxy-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methylpent-2-enimidic acid)

SMILES for NP0172413 ((2e)-n-[(3s,4s,7r,10e)-7-benzyl-5,8-dihydroxy-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methylpent-2-enimidic acid)

INCHI for NP0172413 ((2e)-n-[(3s,4s,7r,10e)-7-benzyl-5,8-dihydroxy-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methylpent-2-enimidic acid)

Structure for NP0172413 ((2e)-n-[(3s,4s,7r,10e)-7-benzyl-5,8-dihydroxy-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methylpent-2-enimidic acid)

3D Structure for NP0172413 ((2e)-n-[(3s,4s,7r,10e)-7-benzyl-5,8-dihydroxy-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methylpent-2-enimidic acid)