NP-MRD: Showing NP-Card for Brevianamide-E-S-8 (NP0333407)

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Record Information

Version

1.0

Created at

2024-06-10 23:14:32 UTC

Updated at

2024-06-12 00:06:13 UTC

NP-MRD ID

NP0333407

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Brevianamide-E-S-8

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02232301492D          

 31 34  0  0  1  0            999 V2000
    4.3519   -2.7367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1748   -2.7942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5365   -3.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6362   -2.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2745   -1.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7359   -0.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3742    0.0567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7615    0.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5620    0.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7894    1.7778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2163    2.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4158    2.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1884    1.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469    1.0169    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1648    1.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6345    2.7107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469    2.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6464    0.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5617    0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9683   -0.3731    0.0000 O   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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 14 13  1  0  0  0  0
 14 15  1  1  0  0  0
 16 15  1  6  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  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
 21 25  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 16 26  1  0  0  0  0
 26 27  2  0  0  0  0
 20 28  2  0  0  0  0
 14 29  1  6  0  0  0
 14 30  1  0  0  0  0
  7 30  1  0  0  0  0
 30 31  2  0  0  0  0
M  END


  Mrv2104 02232301492D          

 31 34  0  0  1  0            999 V2000
    4.3519   -2.7367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1748   -2.7942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5365   -3.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6362   -2.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2745   -1.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7359   -0.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3742    0.0567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7615    0.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5620    0.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7894    1.7778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2163    2.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4158    2.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1884    1.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469    1.0169    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1648    1.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6345    2.7107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469    2.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6464    0.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5617    0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9683   -0.3731    0.0000 O   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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 14 13  1  0  0  0  0
 14 15  1  1  0  0  0
 16 15  1  6  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  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
 21 25  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 16 26  1  0  0  0  0
 26 27  2  0  0  0  0
 20 28  2  0  0  0  0
 14 29  1  6  0  0  0
 14 30  1  0  0  0  0
  7 30  1  0  0  0  0
 30 31  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333407

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@]1(C[C@]2(O)C(=O)N(CCC=C(C)C)C3=CC=CC=C23)NC(=O)[C@@H]2CCCN2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H29N3O5/c1-15(2)8-6-12-25-17-10-5-4-9-16(17)22(30,20(25)28)14-23(31-3)21(29)26-13-7-11-18(26)19(27)24-23/h4-5,8-10,18,30H,6-7,11-14H2,1-3H3,(H,24,27)/t18-,22+,23+/m0/s1

> <INCHI_KEY>
TZROKEARDBOUTL-CDNPAEQRSA-N

> <FORMULA>
C23H29N3O5

> <MOLECULAR_WEIGHT>
427.501

> <EXACT_MASS>
427.210721046

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
46.027756848236216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,8aS)-3-{[(3R)-3-hydroxy-1-(4-methylpent-3-en-1-yl)-2-oxo-2,3-dihydro-1H-indol-3-yl]methyl}-3-methoxy-octahydropyrrolo[1,2-a]pyrazine-1,4-dione

> <JCHEM_LOGP>
1.4940525066666672

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.753918003706998

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.965723991499042

> <JCHEM_PKA_STRONGEST_BASIC>
-4.17404341029356

> <JCHEM_POLAR_SURFACE_AREA>
99.18

> <JCHEM_REFRACTIVITY>
114.18859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,8aS)-3-{[(3R)-3-hydroxy-1-(4-methylpent-3-en-1-yl)-2-oxoindol-3-yl]methyl}-3-methoxy-tetrahydro-2H-pyrrolo[1,2-a]pyrazine-1,4-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  C   UNK     0       8.123  -5.108   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.660  -5.216   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.335  -6.600   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.521  -3.939   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.846  -2.555   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.707  -1.278   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      10.032   0.106   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      10.755   1.466   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.249   1.838   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.674   3.318   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.604   4.426   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.110   4.054   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.685   2.573   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.301   1.898   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.774   3.345   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.784   5.060   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.301   5.327   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       6.258   2.073   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       3.590   3.613   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       6.807   1.526   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.515   0.373   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.407  -0.697   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                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   30                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13   15   29   30                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   19   26                                             
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   21   24   26                                                  
CONECT   26   25   16   27                                                  
CONECT   27   26                                                            
CONECT   28   20                                                            
CONECT   29   14                                                            
CONECT   30   14    7   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₉N₃O₅

Average Mass

427.5010 Da

Monoisotopic Mass

427.21072 Da

IUPAC Name

(3R,8aS)-3-{[(3R)-3-hydroxy-1-(4-methylpent-3-en-1-yl)-2-oxo-2,3-dihydro-1H-indol-3-yl]methyl}-3-methoxy-octahydropyrrolo[1,2-a]pyrazine-1,4-dione

Traditional Name

(3R,8aS)-3-{[(3R)-3-hydroxy-1-(4-methylpent-3-en-1-yl)-2-oxoindol-3-yl]methyl}-3-methoxy-tetrahydro-2H-pyrrolo[1,2-a]pyrazine-1,4-dione

CAS Registry Number

Not Available

SMILES

CO[C@@]1(C[C@]2(O)C(=O)N(CCC=C(C)C)C3=CC=CC=C23)NC(=O)[C@@H]2CCCN2C1=O

InChI Identifier

InChI=1S/C23H29N3O5/c1-15(2)8-6-12-25-17-10-5-4-9-16(17)22(30,20(25)28)14-23(31-3)21(29)26-13-7-11-18(26)19(27)24-23/h4-5,8-10,18,30H,6-7,11-14H2,1-3H3,(H,24,27)/t18-,22+,23+/m0/s1

InChI Key

TZROKEARDBOUTL-CDNPAEQRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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
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
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
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
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	1.49	ChemAxon
pKa (Strongest Acidic)	9.97	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.18 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	114.19 m³·mol⁻¹	ChemAxon
Polarizability	46.03 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

Not Available

References

General References

Not Available

Showing NP-Card for Brevianamide-E-S-8 (NP0333407)

MOL for NP0333407 (Brevianamide-E-S-8)

3D MOL for NP0333407 (Brevianamide-E-S-8)

3D SDF for NP0333407 (Brevianamide-E-S-8)

3D-SDF for NP0333407 (Brevianamide-E-S-8)

PDB for NP0333407 (Brevianamide-E-S-8)

3D PDB for NP0333407 (Brevianamide-E-S-8)

SMILES for NP0333407 (Brevianamide-E-S-8)

INCHI for NP0333407 (Brevianamide-E-S-8)

Structure for NP0333407 (Brevianamide-E-S-8)

3D Structure for NP0333407 (Brevianamide-E-S-8)