NP-MRD: Showing NP-Card for (8e,22e)-2-oxa-11,16,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3(29),4,6,8,10,20,22,24,27-decaene-4,10,21-triol (NP0305861)

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Record Information

Version

2.0

Created at

2022-09-10 21:59:53 UTC

Updated at

2022-09-10 21:59:54 UTC

NP-MRD ID

NP0305861

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(8e,22e)-2-oxa-11,16,20-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

Cadabicine belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. Cadabicine is a very strong basic compound (based on its pKa). Outside of the human body, cadabicine has been detected, but not quantified in, fruits. (8e,22e)-2-oxa-11,16,20-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 Cadaba farinosa. This could make cadabicine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1572004251623292D          

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M  END

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M  END


  Mrv1572004251623292D          

 36 38  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0305861

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C1=C([H])\C(O)=NCCCNCCCCN=C(O)\C([H])=C([H])/C2=CC(OC3=CC=C1C=C3)=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C25H29N3O4/c29-22-11-6-20-8-13-25(31)27-16-2-1-14-26-15-3-17-28-24(30)12-7-19-4-9-21(10-5-19)32-23(22)18-20/h4-13,18,26,29H,1-3,14-17H2,(H,27,31)(H,28,30)/b12-7-,13-8-

> <INCHI_KEY>
QBKGCCSZLPZTIE-AJDRMPRJSA-N

> <FORMULA>
C25H29N3O4

> <MOLECULAR_WEIGHT>
435.524

> <EXACT_MASS>
435.215806426

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
46.7856919613928

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(8E,22E)-2-oxa-11,16,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3,5,7(29),8,10,20,22,24,27-decaene-4,10,21-triol

> <ALOGPS_LOGP>
3.42

> <JCHEM_LOGP>
0.6495916320040968

> <ALOGPS_LOGS>
-5.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
6.199938695602964

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.744178704594425

> <JCHEM_PKA_STRONGEST_BASIC>
10.657632827344093

> <JCHEM_POLAR_SURFACE_AREA>
106.67000000000002

> <JCHEM_REFRACTIVITY>
127.89549999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.64e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8E,22E)-2-oxa-11,16,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3,5,7(29),8,10,20,22,24,27-decaene-4,10,21-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-16         0                                  
HETATM    1  C   UNK     0      12.538   6.478   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.090   5.856   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.327   4.941   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.506  -4.967   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.673  -2.449   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.428  -3.639   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.152  -2.397   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.735  -1.007   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.020  -5.462   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.197  -2.928   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.909  -5.114   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.821  -0.932   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.311   0.516   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.087   6.693   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.087   5.897   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.859   4.869   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.274   3.695   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.969  -2.806   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.884  -3.434   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.445  -2.440   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.803  -4.443   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.438  -5.411   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.537  -4.273   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      20.056   0.653   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.409   2.093   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      15.645   6.494   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0       8.939   3.575   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0      19.865   2.222   0.000  0.00  0.00           N+0
HETATM   29  O   UNK     0      10.901  -6.879   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      21.596   0.633   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       6.901   2.403   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      13.162  -4.357   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0      20.372  -3.337   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       7.297  -1.557   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      21.298  -1.369   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0       6.779   0.355   0.000  0.00  0.00           H+0
CONECT    1    2   14                                                       
CONECT    2    1   16                                                       
CONECT    3   15   17                                                       
CONECT    4    9   19                                                       
CONECT    5   10   19                                                       
CONECT    6   11   20                                                       
CONECT    7   12   19   33                                                  
CONECT    8   13   20   34                                                  
CONECT    9    4   21                                                       
CONECT   10    5   21                                                       
CONECT   11    6   22                                                       
CONECT   12    7   24   35                                                  
CONECT   13    8   25   36                                                  
CONECT   14    1   26                                                       
CONECT   15    3   26                                                       
CONECT   16    2   27                                                       
CONECT   17    3   28                                                       
CONECT   18   20   23                                                       
CONECT   19    4    5    7                                                  
CONECT   20    6    8   18                                                  
CONECT   21    9   10   32                                                  
CONECT   22   11   23   29                                                  
CONECT   23   18   22   32                                                  
CONECT   24   12   28   30                                                  
CONECT   25   13   27   31                                                  
CONECT   26   14   15                                                       
CONECT   27   16   25                                                       
CONECT   28   17   24                                                       
CONECT   29   22                                                            
CONECT   30   24                                                            
CONECT   31   25                                                            
CONECT   32   21   23                                                       
CONECT   33    7                                                            
CONECT   34    8                                                            
CONECT   35   12                                                            
CONECT   36   13                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₉N₃O₄

Average Mass

435.5240 Da

Monoisotopic Mass

435.21581 Da

IUPAC Name

(8E,22E)-2-oxa-11,16,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3,5,7(29),8,10,20,22,24,27-decaene-4,10,21-triol

Traditional Name

(8E,22E)-2-oxa-11,16,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3,5,7(29),8,10,20,22,24,27-decaene-4,10,21-triol

CAS Registry Number

Not Available

SMILES

[H]\C1=C([H])\C(O)=NCCCNCCCCN=C(O)\C([H])=C([H])/C2=CC(OC3=CC=C1C=C3)=C(O)C=C2

InChI Identifier

InChI=1S/C25H29N3O4/c29-22-11-6-20-8-13-25(31)27-16-2-1-14-26-15-3-17-28-24(30)12-7-19-4-9-21(10-5-19)32-23(22)18-20/h4-13,18,26,29H,1-3,14-17H2,(H,27,31)(H,28,30)/b12-7-,13-8-

InChI Key

QBKGCCSZLPZTIE-AJDRMPRJSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
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
Cadaba farinosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Diarylethers

Alternative Parents

Substituents

Diaryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Cyclic carboximidic acid
Secondary aliphatic amine
Polyol
Secondary amine
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organoheterocyclic compound
Oxacycle
Azacycle
Organic nitrogen compound
Organonitrogen compound
Hydrocarbon derivative
Amine
Organopnictogen 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	3.42	ALOGPS
logP	0.65	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	4.74	ChemAxon
pKa (Strongest Basic)	10.66	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.67 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	127.9 m³·mol⁻¹	ChemAxon
Polarizability	46.79 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033451

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011489

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 (8e,22e)-2-oxa-11,16,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3(29),4,6,8,10,20,22,24,27-decaene-4,10,21-triol (NP0305861)

MOL for NP0305861 ((8e,22e)-2-oxa-11,16,20-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 NP0305861 ((8e,22e)-2-oxa-11,16,20-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 NP0305861 ((8e,22e)-2-oxa-11,16,20-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 NP0305861 ((8e,22e)-2-oxa-11,16,20-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 NP0305861 ((8e,22e)-2-oxa-11,16,20-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 NP0305861 ((8e,22e)-2-oxa-11,16,20-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 NP0305861 ((8e,22e)-2-oxa-11,16,20-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 NP0305861 ((8e,22e)-2-oxa-11,16,20-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 NP0305861 ((8e,22e)-2-oxa-11,16,20-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 NP0305861 ((8e,22e)-2-oxa-11,16,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3(29),4,6,8,10,20,22,24,27-decaene-4,10,21-triol)