NP-MRD: Showing NP-Card for n-[5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-3-phenylprop-2-enimidic acid (NP0222330)

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Record Information

Version

2.0

Created at

2022-09-06 00:08:17 UTC

Updated at

2022-09-06 00:08:17 UTC

NP-MRD ID

NP0222330

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-3-phenylprop-2-enimidic acid

Description

N-[7-(butan-2-yl)-5,8-dihydroxy-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]Hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-3-phenylprop-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. n-[5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-3-phenylprop-2-enimidic acid is found in Scutia buxifolia. N-[7-(butan-2-yl)-5,8-dihydroxy-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]Hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-3-phenylprop-2-enimidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251512362D          

 39 42  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004251512362D          

 39 42  0  0  0  0            999 V2000
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    4.7971   -1.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7328   -2.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9883   -2.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3082   -2.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3725   -1.7092    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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  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
 13 11  1  4  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
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 26  1  4  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 32  1  0  0  0  0
 32 33  2  0  0  0  0
 23 33  1  0  0  0  0
 21 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
 34 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222330

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C1NC(=O)C(NC(=O)C=CC2=CC=CC=C2)C(OC2=CC=C(C=C2)C=CNC1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H33N3O4/c1-3-22(2)28-31(37)33-21-20-24-14-17-26(18-15-24)39-30(25-12-8-5-9-13-25)29(32(38)35-28)34-27(36)19-16-23-10-6-4-7-11-23/h4-22,28-30H,3H2,1-2H3,(H,33,37)(H,34,36)(H,35,38)

> <INCHI_KEY>
IEOKZWRWGLHTGX-UHFFFAOYSA-N

> <FORMULA>
C32H33N3O4

> <MOLECULAR_WEIGHT>
523.633

> <EXACT_MASS>
523.247106555

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
56.20835979975338

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.27

> <JCHEM_LOGP>
5.017894994666666

> <ALOGPS_LOGS>
-6.17

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.791532586780058

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.152303829631878

> <JCHEM_PKA_STRONGEST_BASIC>
-0.723728073595736

> <JCHEM_POLAR_SURFACE_AREA>
96.53

> <JCHEM_REFRACTIVITY>
151.45929999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.53e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      15.629   2.074   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.100   1.887   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.174   3.118   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.777   4.535   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.645   2.931   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      11.479   1.385   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      10.666   0.061   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.769  -1.014   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.361  -0.786   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       9.894  -2.231   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      11.412  -2.492   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.397  -1.308   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.945  -3.937   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.463  -4.197   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.996  -5.642   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.514  -5.902   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.047  -7.347   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.063  -8.531   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.545  -8.271   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.012  -6.826   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.805  -0.991   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.288  -0.544   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.291   0.733   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.088   1.752   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.364   3.274   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.782   3.941   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.843   5.163   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.303   5.825   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       9.888   5.511   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      11.097   4.432   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.371   5.296   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.924   2.914   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.701   1.394   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.685  -2.527   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.955  -3.398   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.835  -4.934   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.445  -5.597   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.175  -4.726   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.295  -3.191   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   30                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21    9   22   34                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   33                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    5   31                                                  
CONECT   31   30                                                            
CONECT   32   26   33                                                       
CONECT   33   32   23                                                       
CONECT   34   21   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   34                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₃₂H₃₃N₃O₄

Average Mass

523.6330 Da

Monoisotopic Mass

523.24711 Da

IUPAC Name

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

Traditional Name

N-[5,8-dioxo-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraen-4-yl]-3-phenylprop-2-enamide

CAS Registry Number

Not Available

SMILES

CCC(C)C1NC(=O)C(NC(=O)C=CC2=CC=CC=C2)C(OC2=CC=C(C=C2)C=CNC1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C32H33N3O4/c1-3-22(2)28-31(37)33-21-20-24-14-17-26(18-15-24)39-30(25-12-8-5-9-13-25)29(32(38)35-28)34-27(36)19-16-23-10-6-4-7-11-23/h4-22,28-30H,3H2,1-2H3,(H,33,37)(H,34,36)(H,35,38)

InChI Key

IEOKZWRWGLHTGX-UHFFFAOYSA-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
Scutia buxifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides 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

Alpha-dipeptide
Cyclic alpha peptide
Macrolactam
N-acyl-alpha amino acid or derivatives
Cinnamic acid amide
Cinnamic acid or derivatives
Alpha-amino acid or derivatives
Styrene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Lactam
Secondary carboxylic acid amide
Oxacycle
Azacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
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	4.27	ALOGPS
logP	5.02	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	11.15	ChemAxon
pKa (Strongest Basic)	-0.72	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	151.46 m³·mol⁻¹	ChemAxon
Polarizability	56.21 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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 n-[5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-3-phenylprop-2-enimidic acid (NP0222330)

MOL for NP0222330 (n-[5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-3-phenylprop-2-enimidic acid)

3D MOL for NP0222330 (n-[5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-3-phenylprop-2-enimidic acid)

3D SDF for NP0222330 (n-[5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-3-phenylprop-2-enimidic acid)

3D-SDF for NP0222330 (n-[5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-3-phenylprop-2-enimidic acid)

PDB for NP0222330 (n-[5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-3-phenylprop-2-enimidic acid)

3D PDB for NP0222330 (n-[5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-3-phenylprop-2-enimidic acid)

SMILES for NP0222330 (n-[5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-3-phenylprop-2-enimidic acid)

INCHI for NP0222330 (n-[5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-3-phenylprop-2-enimidic acid)

Structure for NP0222330 (n-[5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-3-phenylprop-2-enimidic acid)

3D Structure for NP0222330 (n-[5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-3-phenylprop-2-enimidic acid)