NP-MRD: Showing NP-Card for Brevianamide-E1 (NP0333403)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-06-10 22:45:15 UTC

Updated at

2024-09-16 20:04:30 UTC

NP-MRD ID

NP0333403

Natural Product DOI

https://doi.org/10.57994/2800

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Brevianamide-E1

Description

Brevianamide-E1 belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Based on a literature review very few articles have been published on Brevianamide-E1.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02232301202D          

 28 32  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
    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
  8 28  2  0  0  0  0
M  END


  Mrv2104 02232301202D          

 28 32  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
    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
  8 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333403

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(C=C)[C@@]12NC3=CC=CC=C3[C@]1(O)C[C@]1(O)N2C(=O)[C@@H]2CCCN2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H25N3O4/c1-4-18(2,3)21-19(27,13-8-5-6-9-14(13)22-21)12-20(28)17(26)23-11-7-10-15(23)16(25)24(20)21/h4-6,8-9,15,22,27-28H,1,7,10-12H2,2-3H3/t15-,19+,20+,21-/m0/s1

> <INCHI_KEY>
IYEHPANJJGMQFC-NOOVBMIQSA-N

> <FORMULA>
C21H25N3O4

> <MOLECULAR_WEIGHT>
383.448

> <EXACT_MASS>
383.184506297

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
39.57532040774794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,10R,12R)-10,12-dihydroxy-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>
1.7700088656666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.491209642858504

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.004370953804154

> <JCHEM_PKA_STRONGEST_BASIC>
0.7390521134036003

> <JCHEM_POLAR_SURFACE_AREA>
93.11000000000001

> <JCHEM_REFRACTIVITY>
102.77929999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,10R,12R)-10,12-dihydroxy-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  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   28                                                  
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                                                            
CONECT   28    8                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₅N₃O₄

Average Mass

383.4480 Da

Monoisotopic Mass

383.18451 Da

IUPAC Name

(1S,4S,10R,12R)-10,12-dihydroxy-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)-10,12-dihydroxy-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

CC(C)(C=C)[C@@]12NC3=CC=CC=C3[C@]1(O)C[C@]1(O)N2C(=O)[C@@H]2CCCN2C1=O

InChI Identifier

InChI=1S/C21H25N3O4/c1-4-18(2,3)21-19(27,13-8-5-6-9-14(13)22-21)12-20(28)17(26)23-11-7-10-15(23)16(25)24(20)21/h4-6,8-9,15,22,27-28H,1,7,10-12H2,2-3H3/t15-,19+,20+,21-/m0/s1

InChI Key

IYEHPANJJGMQFC-NOOVBMIQSA-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
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
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	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

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

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

Description

This compound belongs to the class of organic compounds known as pyrroloindoles. These are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Alpha-amino acid or derivatives
Dihydroindole
Indole
2,5-dioxopiperazine
Pyrrolidine-2-carboxamide
Pyrrolidine carboxylic acid or derivatives
N-acylpyrrolidine
Dioxopiperazine
N-alkylpiperazine
Secondary aliphatic/aromatic amine
Benzenoid
Piperazine
N-acyl-amine
1,4-diazinane
Tertiary carboxylic acid amide
Tertiary alcohol
Pyrrolidine
Pyrrole
Lactam
Carboxamide group
Amino acid or derivatives
Azacycle
Secondary amine
Secondary aliphatic amine
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
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	1.77	ChemAxon
pKa (Strongest Acidic)	11	ChemAxon
pKa (Strongest Basic)	0.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	93.11 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	102.78 m³·mol⁻¹	ChemAxon
Polarizability	39.58 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

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

Not Available

Showing NP-Card for Brevianamide-E1 (NP0333403)

MOL for NP0333403 (Brevianamide-E1)

3D MOL for NP0333403 (Brevianamide-E1)

3D SDF for NP0333403 (Brevianamide-E1)

3D-SDF for NP0333403 (Brevianamide-E1)

PDB for NP0333403 (Brevianamide-E1)

3D PDB for NP0333403 (Brevianamide-E1)

SMILES for NP0333403 (Brevianamide-E1)

INCHI for NP0333403 (Brevianamide-E1)

Structure for NP0333403 (Brevianamide-E1)

3D Structure for NP0333403 (Brevianamide-E1)