NP-MRD: Showing NP-Card for 25,28-dimethoxy-2-oxa-11,15,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3(29),4,6,8,10,20,22,24,27-decaene-4,10,21-triol (NP0315318)

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Record Information

Version

2.0

Created at

2022-09-11 13:53:30 UTC

Updated at

2022-09-11 13:53:30 UTC

NP-MRD ID

NP0315318

Secondary Accession Numbers

None

Natural Product Identification

Common Name

25,28-dimethoxy-2-oxa-11,15,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3(29),4,6,8,10,20,22,24,27-decaene-4,10,21-triol

Description

25,28-Dimethoxy-2-oxa-11,15,20-triazatricyclo[22.2.2.1³,⁷]Nonacosa-1(26),3,5,7(29),8,10,20,22,24,27-decaene-4,10,21-triol belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides. 25,28-dimethoxy-2-oxa-11,15,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3(29),4,6,8,10,20,22,24,27-decaene-4,10,21-triol is found in Capparis decidua. 25,28-Dimethoxy-2-oxa-11,15,20-triazatricyclo[22.2.2.1³,⁷]Nonacosa-1(26),3,5,7(29),8,10,20,22,24,27-decaene-4,10,21-triol is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171523002D          

 36 38  0  0  0  0            999 V2000
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    3.6640   -1.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5269   -0.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0392   -1.6008    0.0000 C   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


  Mrv1533004171523002D          

 36 38  0  0  0  0            999 V2000
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 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 26 24  1  4  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
  3 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
  5 32  2  0  0  0  0
  9 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
  7 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0315318

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=CC(OC)=C1C=CC(=O)NCCCCNCCCNC(=O)C=CC1=CC=C(O)C(O2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H33N3O6/c1-34-23-17-20-18-24(35-2)21(23)8-11-27(33)29-14-4-3-12-28-13-5-15-30-26(32)10-7-19-6-9-22(31)25(16-19)36-20/h6-11,16-18,28,31H,3-5,12-15H2,1-2H3,(H,29,33)(H,30,32)

> <INCHI_KEY>
NUYJJSYIZAZKPD-UHFFFAOYSA-N

> <FORMULA>
C27H33N3O6

> <MOLECULAR_WEIGHT>
495.576

> <EXACT_MASS>
495.236935795

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.20466212129634

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-25,28-dimethoxy-2-oxa-11,15,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3(29),4,6,8,22,24,27-octaene-10,21-dione

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
0.9762625775913566

> <ALOGPS_LOGS>
-5.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.112182555812414

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.363449168641292

> <JCHEM_PKA_STRONGEST_BASIC>
10.187956842263064

> <JCHEM_POLAR_SURFACE_AREA>
118.15

> <JCHEM_REFRACTIVITY>
139.77849999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.37e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-25,28-dimethoxy-2-oxa-11,15,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3(29),4,6,8,22,24,27-octaene-10,21-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       1.352  -7.171   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.615  -6.290   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.483  -4.756   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.772  -3.892   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.674  -2.323   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.224  -1.803   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.839  -1.968   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.450  -1.743   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.406  -2.988   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.733  -3.985   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.445  -5.453   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.706  -7.085   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      13.245  -7.048   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0      11.531  -8.675   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      10.962 -10.139   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.026 -11.397   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.766 -12.373   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       7.309 -12.967   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       5.764 -13.155   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.226 -12.938   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.798 -12.333   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.566 -11.370   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       0.622 -10.103   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       0.034  -8.629   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.461  -9.000   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.139  -7.015   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.129  -5.449   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.047  -4.116   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.986  -2.515   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.391  -1.825   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.483  -0.288   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.294  -1.613   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.724  -4.407   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.209  -4.659   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.272  -3.448   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.749  -3.672   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   35                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   33                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    3   29                                                  
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29    5                                                       
CONECT   33    9   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34    7   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₃N₃O₆

Average Mass

495.5760 Da

Monoisotopic Mass

495.23694 Da

IUPAC Name

4-hydroxy-25,28-dimethoxy-2-oxa-11,15,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3(29),4,6,8,22,24,27-octaene-10,21-dione

Traditional Name

4-hydroxy-25,28-dimethoxy-2-oxa-11,15,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3(29),4,6,8,22,24,27-octaene-10,21-dione

CAS Registry Number

Not Available

SMILES

COC1=CC2=CC(OC)=C1C=CC(=O)NCCCCNCCCNC(=O)C=CC1=CC=C(O)C(O2)=C1

InChI Identifier

InChI=1S/C27H33N3O6/c1-34-23-17-20-18-24(35-2)21(23)8-11-27(33)29-14-4-3-12-28-13-5-15-30-26(32)10-7-19-6-9-22(31)25(16-19)36-20/h6-11,16-18,28,31H,3-5,12-15H2,1-2H3,(H,29,33)(H,30,32)

InChI Key

NUYJJSYIZAZKPD-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
Capparis decidua	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolactams

Sub Class

Not Available

Direct Parent

Macrolactams

Alternative Parents

Substituents

Macrolactam
Diaryl ether
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Amino acid or derivatives
Carboxamide group
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Secondary aliphatic amine
Ether
Oxacycle
Azacycle
Secondary amine
Organoheterocyclic compound
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic oxide
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	2.62	ALOGPS
logP	0.98	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	8.36	ChemAxon
pKa (Strongest Basic)	10.19	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	118.15 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	139.78 m³·mol⁻¹	ChemAxon
Polarizability	52.2 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	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

595432

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 25,28-dimethoxy-2-oxa-11,15,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3(29),4,6,8,10,20,22,24,27-decaene-4,10,21-triol (NP0315318)

MOL for NP0315318 (25,28-dimethoxy-2-oxa-11,15,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3(29),4,6,8,10,20,22,24,27-decaene-4,10,21-triol)

3D MOL for NP0315318 (25,28-dimethoxy-2-oxa-11,15,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3(29),4,6,8,10,20,22,24,27-decaene-4,10,21-triol)

3D SDF for NP0315318 (25,28-dimethoxy-2-oxa-11,15,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3(29),4,6,8,10,20,22,24,27-decaene-4,10,21-triol)

3D-SDF for NP0315318 (25,28-dimethoxy-2-oxa-11,15,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3(29),4,6,8,10,20,22,24,27-decaene-4,10,21-triol)

PDB for NP0315318 (25,28-dimethoxy-2-oxa-11,15,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3(29),4,6,8,10,20,22,24,27-decaene-4,10,21-triol)

3D PDB for NP0315318 (25,28-dimethoxy-2-oxa-11,15,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3(29),4,6,8,10,20,22,24,27-decaene-4,10,21-triol)

SMILES for NP0315318 (25,28-dimethoxy-2-oxa-11,15,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3(29),4,6,8,10,20,22,24,27-decaene-4,10,21-triol)

INCHI for NP0315318 (25,28-dimethoxy-2-oxa-11,15,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3(29),4,6,8,10,20,22,24,27-decaene-4,10,21-triol)

Structure for NP0315318 (25,28-dimethoxy-2-oxa-11,15,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3(29),4,6,8,10,20,22,24,27-decaene-4,10,21-triol)

3D Structure for NP0315318 (25,28-dimethoxy-2-oxa-11,15,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3(29),4,6,8,10,20,22,24,27-decaene-4,10,21-triol)