NP-MRD: Showing NP-Card for n-[5,8-dihydroxy-7-(2-methylpropyl)-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 (NP0224995)

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Record Information

Version

2.0

Created at

2022-09-06 03:35:13 UTC

Updated at

2022-09-06 03:35:13 UTC

NP-MRD ID

NP0224995

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[5,8-dihydroxy-7-(2-methylpropyl)-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

N-[5,8-dihydroxy-7-(2-methylpropyl)-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. n-[5,8-dihydroxy-7-(2-methylpropyl)-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. N-[5,8-dihydroxy-7-(2-methylpropyl)-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 an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191519152D          

 36 38  0  0  0  0            999 V2000
    7.2308    0.2519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5536    1.0111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3726    1.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1493    0.7420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7139    0.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3047   -0.5431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004191519152D          

 36 38  0  0  0  0            999 V2000
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 15 17  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 24 23  1  4  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  2  0  0  0  0
 20 30  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224995

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC1NC(=O)C(NC(=O)C=CC(C)C)C(OC2=CC=C(C=C2)C=CNC1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H35N3O4/c1-19(2)10-15-25(33)32-26-27(22-8-6-5-7-9-22)36-23-13-11-21(12-14-23)16-17-30-28(34)24(18-20(3)4)31-29(26)35/h5-17,19-20,24,26-27H,18H2,1-4H3,(H,30,34)(H,31,35)(H,32,33)

> <INCHI_KEY>
BCKFBSQASKVSKD-UHFFFAOYSA-N

> <FORMULA>
C29H35N3O4

> <MOLECULAR_WEIGHT>
489.616

> <EXACT_MASS>
489.262756619

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.80226057843416

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
4.4550250533333315

> <ALOGPS_LOGS>
-5.62

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.862593273123458

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.279301235671866

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4236986381760305

> <JCHEM_POLAR_SURFACE_AREA>
96.53

> <JCHEM_REFRACTIVITY>
140.59089999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      13.498   0.470   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      15.629   2.074   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.174   3.118   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      14.448  -3.013   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.966  -3.274   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.915  -1.568   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.805  -0.991   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.288  -0.544   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.291   0.733   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.088   1.752   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.364   3.274   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.782   3.941   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.843   5.163   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.303   5.825   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       9.888   5.511   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      11.097   4.432   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.371   5.296   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.924   2.914   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.701   1.394   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.685  -2.527   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.955  -3.398   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.835  -4.934   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.445  -5.597   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.175  -4.726   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.295  -3.191   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   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    9   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   30                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    5   28                                                  
CONECT   28   27                                                            
CONECT   29   23   30                                                       
CONECT   30   29   20                                                       
CONECT   31   18   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
N-[5,8-Dihydroxy-7-(2-methylpropyl)-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

C₂₉H₃₅N₃O₄

Average Mass

489.6160 Da

Monoisotopic Mass

489.26276 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(C)CC1NC(=O)C(NC(=O)C=CC(C)C)C(OC2=CC=C(C=C2)C=CNC1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C29H35N3O4/c1-19(2)10-15-25(33)32-26-27(22-8-6-5-7-9-22)36-23-13-11-21(12-14-23)16-17-30-28(34)24(18-20(3)4)31-29(26)35/h5-17,19-20,24,26-27H,18H2,1-4H3,(H,30,34)(H,31,35)(H,32,33)

InChI Key

BCKFBSQASKVSKD-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
Discaria americana	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

Cyclic alpha peptide
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Cyclic carboximidic acid
Carboximidic acid
Carboximidic acid derivative
Ether
Oxacycle
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen 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	3.56	ALOGPS
logP	4.46	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	11.28	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	140.59 m³·mol⁻¹	ChemAxon
Polarizability	52.8 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

85347342

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-7-(2-methylpropyl)-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 (NP0224995)

MOL for NP0224995 (n-[5,8-dihydroxy-7-(2-methylpropyl)-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 NP0224995 (n-[5,8-dihydroxy-7-(2-methylpropyl)-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 NP0224995 (n-[5,8-dihydroxy-7-(2-methylpropyl)-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 NP0224995 (n-[5,8-dihydroxy-7-(2-methylpropyl)-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 NP0224995 (n-[5,8-dihydroxy-7-(2-methylpropyl)-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 NP0224995 (n-[5,8-dihydroxy-7-(2-methylpropyl)-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 NP0224995 (n-[5,8-dihydroxy-7-(2-methylpropyl)-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 NP0224995 (n-[5,8-dihydroxy-7-(2-methylpropyl)-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 NP0224995 (n-[5,8-dihydroxy-7-(2-methylpropyl)-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 NP0224995 (n-[5,8-dihydroxy-7-(2-methylpropyl)-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)