NP-MRD: Showing NP-Card for 14-(acetyloxy)-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetate (NP0239570)

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Record Information

Version

2.0

Created at

2022-09-06 23:11:56 UTC

Updated at

2022-09-06 23:11:56 UTC

NP-MRD ID

NP0239570

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-(acetyloxy)-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetate

Description

14-(acetyloxy)-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetate is found in Tolypothrix nodosa. 14-(Acetyloxy)-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]Tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161513252D          

 38 42  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004161513252D          

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  7 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 13 34  2  0  0  0  0
 34 35  1  0  0  0  0
 11 35  2  0  0  0  0
 35 36  1  0  0  0  0
  9 37  1  0  0  0  0
  5 37  1  0  0  0  0
 37 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0239570

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1(C)C(=O)C2=N\C\1=C/C1=CC(C)=C(N1)\C=C1/N=C(/C=C3\N/C(/C=C3C)=C\2)C(C)(OC(C)=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H26N4O6/c1-13-8-18-10-23-27(5,37-15(3)33)25(35)21(31-23)9-17-7-14(2)20(29-17)12-24-28(6,38-16(4)34)26(36)22(32-24)11-19(13)30-18/h7-12,29-30H,1-6H3/b17-9-,18-10-,19-11-,20-12-,21-9-,22-11-,23-10-,24-12-

> <INCHI_KEY>
HFZVYGBRGMEKNE-RKIHEKEDSA-N

> <FORMULA>
C28H26N4O6

> <MOLECULAR_WEIGHT>
514.538

> <EXACT_MASS>
514.185234573

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
55.72183134361408

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-(acetyloxy)-4,9,14,20-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetate

> <ALOGPS_LOGP>
3.30

> <JCHEM_LOGP>
4.150414414

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.88660000518789

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.267424362017856

> <JCHEM_PKA_STRONGEST_BASIC>
0.39164215864960916

> <JCHEM_POLAR_SURFACE_AREA>
144.1

> <JCHEM_REFRACTIVITY>
135.54999999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.56e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-(acetyloxy)-4,9,14,20-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -1.694  -7.781   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.563  -6.509   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.099  -6.627   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.897  -5.121   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.766  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.947  -4.838   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.352  -3.072   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -1.583  -1.653   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -3.115  -1.393   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.837  -0.088   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.139   1.339   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -1.666   1.625   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -1.351   3.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.009   3.826   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.327   3.127   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       1.613   1.599   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       3.036   1.393   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.813   0.033   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.114  -1.284   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       1.587  -1.626   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       1.326  -3.104   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.021  -3.826   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.808  -3.801   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.837  -2.754   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.080  -5.317   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.789   2.821   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.310   3.057   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.741   3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.691   5.062   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.199   5.291   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.176   6.482   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.633   7.923   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.695   6.231   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.723   3.748   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.807   2.645   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -5.329   2.878   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.814  -2.821   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -5.332  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   37                                             
CONECT    6    5                                                            
CONECT    7    5    8   22                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   37                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   35                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   34                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21    7                                                       
CONECT   23   21   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23                                                            
CONECT   26   17   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   15   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   13   35                                                       
CONECT   35   34   11   36                                                  
CONECT   36   35                                                            
CONECT   37    9    5   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
14-(Acetyloxy)-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1,.1,.1,]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetic acid	Generator
14-(Acetyloxy)-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetic acid	Generator

Chemical Formula

C₂₈H₂₆N₄O₆

Average Mass

514.5380 Da

Monoisotopic Mass

514.18523 Da

IUPAC Name

14-(acetyloxy)-4,9,14,20-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetate

Traditional Name

14-(acetyloxy)-4,9,14,20-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1(C)C(=O)C2=N\C\1=C/C1=CC(C)=C(N1)\C=C1/N=C(/C=C3\N/C(/C=C3C)=C\2)C(C)(OC(C)=O)C1=O

InChI Identifier

InChI=1S/C28H26N4O6/c1-13-8-18-10-23-27(5,37-15(3)33)25(35)21(31-23)9-17-7-14(2)20(29-17)12-24-28(6,38-16(4)34)26(36)22(32-24)11-19(13)30-18/h7-12,29-30H,1-6H3/b17-9-,18-10-,19-11-,20-12-,21-9-,22-11-,23-10-,24-12-

InChI Key

HFZVYGBRGMEKNE-RKIHEKEDSA-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
Tolypothrix nodosa	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	3.3	ALOGPS
logP	4.15	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	15.27	ChemAxon
pKa (Strongest Basic)	0.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	144.1 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	135.55 m³·mol⁻¹	ChemAxon
Polarizability	55.72 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

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 14-(acetyloxy)-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetate (NP0239570)

MOL for NP0239570 (14-(acetyloxy)-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetate)

3D MOL for NP0239570 (14-(acetyloxy)-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetate)

3D SDF for NP0239570 (14-(acetyloxy)-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetate)

3D-SDF for NP0239570 (14-(acetyloxy)-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetate)

PDB for NP0239570 (14-(acetyloxy)-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetate)

3D PDB for NP0239570 (14-(acetyloxy)-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetate)

SMILES for NP0239570 (14-(acetyloxy)-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetate)

INCHI for NP0239570 (14-(acetyloxy)-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetate)

Structure for NP0239570 (14-(acetyloxy)-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetate)

3D Structure for NP0239570 (14-(acetyloxy)-4,10,14,19-tetramethyl-5,15-dioxo-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,16(22),17,19-nonaen-4-yl acetate)