NP-MRD: Showing NP-Card for 1-[8,11-dihydroxy-10-(sec-butyl)-2-oxa-6,9,12-triazatricyclo[13.2.2.0³,⁷]nonadeca-1(17),8,11,13,15,18-hexaen-6-yl]-2-(methylamino)-3-phenylpropan-1-one (NP0185834)

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Record Information

Version

2.0

Created at

2022-09-04 01:25:03 UTC

Updated at

2022-09-04 01:25:04 UTC

NP-MRD ID

NP0185834

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[8,11-dihydroxy-10-(sec-butyl)-2-oxa-6,9,12-triazatricyclo[13.2.2.0³,⁷]nonadeca-1(17),8,11,13,15,18-hexaen-6-yl]-2-(methylamino)-3-phenylpropan-1-one

Description

1-[10-(Butan-2-yl)-8,11-dihydroxy-2-oxa-6,9,12-triazatricyclo[13.2.2.0³,⁷]Nonadeca-1(17),8,11,13,15,18-hexaen-6-yl]-2-(methylamino)-3-phenylpropan-1-one belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. 1-[8,11-dihydroxy-10-(sec-butyl)-2-oxa-6,9,12-triazatricyclo[13.2.2.0³,⁷]nonadeca-1(17),8,11,13,15,18-hexaen-6-yl]-2-(methylamino)-3-phenylpropan-1-one is found in Paliurus ramosissimus. 1-[10-(Butan-2-yl)-8,11-dihydroxy-2-oxa-6,9,12-triazatricyclo[13.2.2.0³,⁷]Nonadeca-1(17),8,11,13,15,18-hexaen-6-yl]-2-(methylamino)-3-phenylpropan-1-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171515432D          

 37 40  0  0  0  0            999 V2000
    5.0854    6.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4034    2.8469    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


  Mrv1533004171515432D          

 37 40  0  0  0  0            999 V2000
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    3.7412    1.4518    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  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  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
 18 23  1  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  0  0  0  0
 10 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 31 30  1  4  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  5 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 36  1  0  0  0  0
 36 37  2  0  0  0  0
 27 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0185834

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C1NC(=O)C2C(CCN2C(=O)C(CC2=CC=CC=C2)NC)OC2=CC=C(C=C2)C=CNC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H36N4O4/c1-4-19(2)25-27(34)31-16-14-20-10-12-22(13-11-20)37-24-15-17-33(26(24)28(35)32-25)29(36)23(30-3)18-21-8-6-5-7-9-21/h5-14,16,19,23-26,30H,4,15,17-18H2,1-3H3,(H,31,34)(H,32,35)

> <INCHI_KEY>
OLALXNPCMVWJPU-UHFFFAOYSA-N

> <FORMULA>
C29H36N4O4

> <MOLECULAR_WEIGHT>
504.631

> <EXACT_MASS>
504.273655655

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
54.48041318411681

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10-(butan-2-yl)-6-[2-(methylamino)-3-phenylpropanoyl]-2-oxa-6,9,12-triazatricyclo[13.2.2.0³,⁷]nonadeca-1(17),13,15,18-tetraene-8,11-dione

> <ALOGPS_LOGP>
2.47

> <JCHEM_LOGP>
2.7796419253333324

> <ALOGPS_LOGS>
-4.53

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.15943938942479

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.223597179095744

> <JCHEM_PKA_STRONGEST_BASIC>
8.371889190159873

> <JCHEM_POLAR_SURFACE_AREA>
99.77000000000001

> <JCHEM_REFRACTIVITY>
141.4708

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[2-(methylamino)-3-phenylpropanoyl]-10-(sec-butyl)-2-oxa-6,9,12-triazatricyclo[13.2.2.0³,⁷]nonadeca-1(17),13,15,18-tetraene-8,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       9.493  11.587   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.724  10.253   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.495   8.920   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.035   8.921   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.725   7.586   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       9.861   6.524   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      10.431   5.078   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.953   5.314   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.325   3.526   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.568   2.185   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.610   1.051   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.011   1.691   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      11.834   3.221   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      12.968   4.263   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.633   5.766   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.438   3.802   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.572   4.844   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.041   4.383   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.175   5.425   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.644   4.964   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.980   3.461   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.846   2.419   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.376   2.880   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      14.773   2.299   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      16.242   1.838   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.285   1.216   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.665   1.186   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.128   0.835   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.076   1.971   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.395   3.506   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.055   5.087   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.404   6.652   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       5.607   7.731   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       7.196   8.049   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.271   9.587   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.902   3.801   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.984   2.710   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   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   13                                                  
CONECT   10    9   11   26                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   16   25                                                       
CONECT   25   24                                                            
CONECT   26   10   27                                                       
CONECT   27   26   28   37                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   36                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    5   35                                                  
CONECT   35   34                                                            
CONECT   36   30   37                                                       
CONECT   37   36   27                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₆N₄O₄

Average Mass

504.6310 Da

Monoisotopic Mass

504.27366 Da

IUPAC Name

10-(butan-2-yl)-6-[2-(methylamino)-3-phenylpropanoyl]-2-oxa-6,9,12-triazatricyclo[13.2.2.0³,⁷]nonadeca-1(17),13,15,18-tetraene-8,11-dione

Traditional Name

6-[2-(methylamino)-3-phenylpropanoyl]-10-(sec-butyl)-2-oxa-6,9,12-triazatricyclo[13.2.2.0³,⁷]nonadeca-1(17),13,15,18-tetraene-8,11-dione

CAS Registry Number

Not Available

SMILES

CCC(C)C1NC(=O)C2C(CCN2C(=O)C(CC2=CC=CC=C2)NC)OC2=CC=C(C=C2)C=CNC1=O

InChI Identifier

InChI=1S/C29H36N4O4/c1-4-19(2)25-27(34)31-16-14-20-10-12-22(13-11-20)37-24-15-17-33(26(24)28(35)32-25)29(36)23(30-3)18-21-8-6-5-7-9-21/h5-14,16,19,23-26,30H,4,15,17-18H2,1-3H3,(H,31,34)(H,32,35)

InChI Key

OLALXNPCMVWJPU-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
Paliurus ramosissimus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Cyclic alpha peptide
Macrolactam
Alpha-amino acid amide
Alpha-amino acid or derivatives
Amphetamine or derivatives
N-acylpyrrolidine
Alkyl aryl ether
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Lactam
Secondary carboxylic acid amide
Secondary amine
Organoheterocyclic compound
Azacycle
Oxacycle
Ether
Secondary aliphatic amine
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Amine
Organopnictogen compound
Organic oxygen 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	2.47	ALOGPS
logP	2.78	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	11.22	ChemAxon
pKa (Strongest Basic)	8.37	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.77 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	141.47 m³·mol⁻¹	ChemAxon
Polarizability	54.48 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 1-[8,11-dihydroxy-10-(sec-butyl)-2-oxa-6,9,12-triazatricyclo[13.2.2.0³,⁷]nonadeca-1(17),8,11,13,15,18-hexaen-6-yl]-2-(methylamino)-3-phenylpropan-1-one (NP0185834)

MOL for NP0185834 (1-[8,11-dihydroxy-10-(sec-butyl)-2-oxa-6,9,12-triazatricyclo[13.2.2.0³,⁷]nonadeca-1(17),8,11,13,15,18-hexaen-6-yl]-2-(methylamino)-3-phenylpropan-1-one)

3D MOL for NP0185834 (1-[8,11-dihydroxy-10-(sec-butyl)-2-oxa-6,9,12-triazatricyclo[13.2.2.0³,⁷]nonadeca-1(17),8,11,13,15,18-hexaen-6-yl]-2-(methylamino)-3-phenylpropan-1-one)

3D SDF for NP0185834 (1-[8,11-dihydroxy-10-(sec-butyl)-2-oxa-6,9,12-triazatricyclo[13.2.2.0³,⁷]nonadeca-1(17),8,11,13,15,18-hexaen-6-yl]-2-(methylamino)-3-phenylpropan-1-one)

3D-SDF for NP0185834 (1-[8,11-dihydroxy-10-(sec-butyl)-2-oxa-6,9,12-triazatricyclo[13.2.2.0³,⁷]nonadeca-1(17),8,11,13,15,18-hexaen-6-yl]-2-(methylamino)-3-phenylpropan-1-one)

PDB for NP0185834 (1-[8,11-dihydroxy-10-(sec-butyl)-2-oxa-6,9,12-triazatricyclo[13.2.2.0³,⁷]nonadeca-1(17),8,11,13,15,18-hexaen-6-yl]-2-(methylamino)-3-phenylpropan-1-one)

3D PDB for NP0185834 (1-[8,11-dihydroxy-10-(sec-butyl)-2-oxa-6,9,12-triazatricyclo[13.2.2.0³,⁷]nonadeca-1(17),8,11,13,15,18-hexaen-6-yl]-2-(methylamino)-3-phenylpropan-1-one)

SMILES for NP0185834 (1-[8,11-dihydroxy-10-(sec-butyl)-2-oxa-6,9,12-triazatricyclo[13.2.2.0³,⁷]nonadeca-1(17),8,11,13,15,18-hexaen-6-yl]-2-(methylamino)-3-phenylpropan-1-one)

INCHI for NP0185834 (1-[8,11-dihydroxy-10-(sec-butyl)-2-oxa-6,9,12-triazatricyclo[13.2.2.0³,⁷]nonadeca-1(17),8,11,13,15,18-hexaen-6-yl]-2-(methylamino)-3-phenylpropan-1-one)

Structure for NP0185834 (1-[8,11-dihydroxy-10-(sec-butyl)-2-oxa-6,9,12-triazatricyclo[13.2.2.0³,⁷]nonadeca-1(17),8,11,13,15,18-hexaen-6-yl]-2-(methylamino)-3-phenylpropan-1-one)

3D Structure for NP0185834 (1-[8,11-dihydroxy-10-(sec-butyl)-2-oxa-6,9,12-triazatricyclo[13.2.2.0³,⁷]nonadeca-1(17),8,11,13,15,18-hexaen-6-yl]-2-(methylamino)-3-phenylpropan-1-one)