NP-MRD: Showing NP-Card for Brevianamide-E-S-6 (NP0333405)

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Record Information

Version

1.0

Created at

2024-06-10 23:00:26 UTC

Updated at

2024-06-12 00:06:08 UTC

NP-MRD ID

NP0333405

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Brevianamide-E-S-6

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02232301352D          

 29 33  0  0  1  0            999 V2000
    4.7161   -5.1926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8306   -4.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1802   -3.8679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2946   -3.0509    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5530   -2.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9802   -3.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3678   -4.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0594   -2.7415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7098   -3.2491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5222   -3.1055    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1345   -2.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4063   -2.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8628   -1.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7469   -1.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1837   -0.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0950   -2.5118    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8367   -2.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6014   -2.5637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2518   -3.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1374   -3.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3726   -4.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7222   -3.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9098   -3.8337    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2975   -4.5620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3370   -4.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5953   -4.0662    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5669   -4.8907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2668   -5.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1739   -1.9245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 23 22  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 26 25  1  0  0  0  0
 26  9  1  0  0  0  0
 26  2  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
  8 29  2  0  0  0  0
M  END


  Mrv2104 02232301352D          

 29 33  0  0  1  0            999 V2000
    4.7161   -5.1926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8306   -4.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1802   -3.8679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2946   -3.0509    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5530   -2.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9802   -3.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3678   -4.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0594   -2.7415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7098   -3.2491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5222   -3.1055    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1345   -2.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4063   -2.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8628   -1.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7469   -1.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1837   -0.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0950   -2.5118    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8367   -2.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6014   -2.5637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2518   -3.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1374   -3.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3726   -4.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7222   -3.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9098   -3.8337    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2975   -4.5620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3370   -4.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5953   -4.0662    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5669   -4.8907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2668   -5.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1739   -1.9245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 23 22  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 26 25  1  0  0  0  0
 26  9  1  0  0  0  0
 26  2  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
  8 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333405

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@]12C[C@@]3(O)C4=CC=CC=C4N[C@]3(N1C(=O)[C@@H]1CCCN1C2=O)C(C)(C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C22H27N3O4/c1-5-19(2,3)22-20(28,14-9-6-7-10-15(14)23-22)13-21(29-4)18(27)24-12-8-11-16(24)17(26)25(21)22/h5-7,9-10,16,23,28H,1,8,11-13H2,2-4H3/t16-,20+,21+,22-/m0/s1

> <INCHI_KEY>
VWGLXPXJGZFKNY-ZJQURUERSA-N

> <FORMULA>
C22H27N3O4

> <MOLECULAR_WEIGHT>
397.475

> <EXACT_MASS>
397.200156361

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
41.51482907826744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,10R,12R)-12-hydroxy-10-methoxy-1-(2-methylbut-3-en-2-yl)-2,8,19-triazapentacyclo[10.7.0.0^{2,10}.0^{4,8}.0^{13,18}]nonadeca-13,15,17-triene-3,9-dione

> <JCHEM_LOGP>
2.4131353693333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.39167171077837

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.335367237702783

> <JCHEM_PKA_STRONGEST_BASIC>
0.7655606263529213

> <JCHEM_POLAR_SURFACE_AREA>
82.11000000000001

> <JCHEM_REFRACTIVITY>
107.5305

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,10R,12R)-12-hydroxy-10-methoxy-1-(2-methylbut-3-en-2-yl)-2,8,19-triazapentacyclo[10.7.0.0^{2,10}.0^{4,8}.0^{13,18}]nonadeca-13,15,17-triene-3,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-23         0                                  
HETATM    1  O   UNK     0       8.803  -9.693   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.017  -8.168   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       7.803  -7.220   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.017  -5.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.632  -5.021   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.563  -6.129   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.287  -7.488   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.444  -5.117   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      10.658  -6.065   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      12.175  -5.797   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.451  -4.438   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.092  -5.161   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.810  -3.714   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.727  -3.078   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.543  -1.772   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      13.244  -4.689   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      14.628  -5.363   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.056  -4.785   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.270  -5.733   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.056  -7.258   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.629  -7.836   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.415  -6.888   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.898  -7.156   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.622  -8.516   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      11.829  -8.265   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.445  -7.590   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.392  -9.129   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      11.698  -9.945   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.658  -3.592   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    3                                                       
CONECT    8    4    9   29                                                  
CONECT    9    8   10   26                                                  
CONECT   10    9   11   16   23                                             
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15                                                       
CONECT   15   14                                                            
CONECT   16   10   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17   23                                                  
CONECT   23   22   10   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25    9    2   27                                             
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29    8                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₇N₃O₄

Average Mass

397.4750 Da

Monoisotopic Mass

397.20016 Da

IUPAC Name

(1S,4S,10R,12R)-12-hydroxy-10-methoxy-1-(2-methylbut-3-en-2-yl)-2,8,19-triazapentacyclo[10.7.0.0^{2,10}.0^{4,8}.0^{13,18}]nonadeca-13,15,17-triene-3,9-dione

Traditional Name

(1S,4S,10R,12R)-12-hydroxy-10-methoxy-1-(2-methylbut-3-en-2-yl)-2,8,19-triazapentacyclo[10.7.0.0^{2,10}.0^{4,8}.0^{13,18}]nonadeca-13,15,17-triene-3,9-dione

CAS Registry Number

Not Available

SMILES

CO[C@@]12C[C@@]3(O)C4=CC=CC=C4N[C@]3(N1C(=O)[C@@H]1CCCN1C2=O)C(C)(C)C=C

InChI Identifier

InChI=1S/C22H27N3O4/c1-5-19(2,3)22-20(28,14-9-6-7-10-15(14)23-22)13-21(29-4)18(27)24-12-8-11-16(24)17(26)25(21)22/h5-7,9-10,16,23,28H,1,8,11-13H2,2-4H3/t16-,20+,21+,22-/m0/s1

InChI Key

VWGLXPXJGZFKNY-ZJQURUERSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	quan.khong@nih.gov	National Cancer Institute at Frederick	Quan T. Khong	2024-06-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C3D6O, experimental)	quan.khong@nih.gov	National Cancer Institute at Frederick	Quan T. Khong	2024-06-10	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	quan.khong@nih.gov	National Cancer Institute at Frederick	Quan T. Khong	2024-06-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C3D6O, experimental)	quan.khong@nih.gov	National Cancer Institute at Frederick	Quan T. Khong	2024-06-10	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	quan.khong@nih.gov	National Cancer Institute at Frederick	Quan T. Khong	2024-06-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C3D6O, experimental)	quan.khong@nih.gov	National Cancer Institute at Frederick	Quan T. Khong	2024-06-10	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	quan.khong@nih.gov	National Cancer Institute at Frederick	Quan T. Khong	2024-06-10	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C3D6O, experimental)	quan.khong@nih.gov	National Cancer Institute at Frederick	Quan T. Khong	2024-06-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C3D6O, experimental)	quan.khong@nih.gov	National Cancer Institute at Frederick	Quan T. Khong	2024-06-10	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.314502325, C3D6O, simulated)	quan.khong@nih.gov	National Cancer Institute at Frederick	Quan T. Khong	2024-06-10	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
sp.		Not Available

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	2.41	ChemAxon
pKa (Strongest Acidic)	12.34	ChemAxon
pKa (Strongest Basic)	0.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	82.11 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	107.53 m³·mol⁻¹	ChemAxon
Polarizability	41.51 Å³	ChemAxon
Number of Rings	5	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

Not Available

References

General References

Not Available

Showing NP-Card for Brevianamide-E-S-6 (NP0333405)

MOL for NP0333405 (Brevianamide-E-S-6)

3D MOL for NP0333405 (Brevianamide-E-S-6)

3D SDF for NP0333405 (Brevianamide-E-S-6)

3D-SDF for NP0333405 (Brevianamide-E-S-6)

PDB for NP0333405 (Brevianamide-E-S-6)

3D PDB for NP0333405 (Brevianamide-E-S-6)

SMILES for NP0333405 (Brevianamide-E-S-6)

INCHI for NP0333405 (Brevianamide-E-S-6)

Structure for NP0333405 (Brevianamide-E-S-6)

3D Structure for NP0333405 (Brevianamide-E-S-6)