MiMeDB: Showing metabocard for 9Î¾-O-2(2,3-dimethylbut-3-enyl)brevianamide Q (MMDBc0017931)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 08:13:38 UTC

Update Date

2022-08-31 06:43:14 UTC

Metabolite ID

MMDBc0017931

Metabolite Identification

Common Name

9Î¾-O-2(2,3-dimethylbut-3-enyl)brevianamide Q

Description

9xi-O-2(2,3-dimethylbut-3-enyl)brevianamide Q belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Based on a literature review very few articles have been published on 9xi-O-2(2,3-dimethylbut-3-enyl)brevianamide Q.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152110132D          

 33 36  0  0  0  0            999 V2000
    7.3037    3.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8846   -2.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3034   -1.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5406    2.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1545    1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3890   -0.4024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0601   -1.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5191    2.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2115   -1.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0185   -1.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9565   -0.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5705   -0.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9709   -1.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5086    0.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3155   -0.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760    1.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3475    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7245   -1.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7280    0.5475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4782   -0.8205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  2  0  0  0  0
 10  9  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 11  1  0  0  0  0
 17  2  2  0  0  0  0
 17  3  1  0  0  0  0
 18 12  2  0  0  0  0
 16 19  1  4  0  0  0
 19 18  1  0  0  0  0
 20 13  2  0  0  0  0
 20 18  1  0  0  0  0
 21 16  2  0  0  0  0
 22 19  2  0  0  0  0
 23 21  1  0  0  0  0
 25  4  1  0  0  0  0
 25  5  1  0  0  0  0
 25  8  1  0  0  0  0
 25 22  1  0  0  0  0
 26  6  1  0  0  0  0
 26  7  1  0  0  0  0
 26 17  1  0  0  0  0
 27 14  1  0  0  0  0
 27 24  1  0  0  0  0
 28 20  1  0  0  0  0
 28 22  1  0  0  0  0
 29 21  1  0  0  0  0
 29 24  2  0  0  0  0
 30 15  1  0  0  0  0
 30 23  1  0  0  0  0
 30 27  1  0  0  0  0
 31 23  2  0  0  0  0
 32 24  1  0  0  0  0
 33 26  1  0  0  0  0
 33 27  1  0  0  0  0
M  END


  Mrv1652305152110132D          

 33 36  0  0  0  0            999 V2000
    7.3037    3.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8846   -2.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3034   -1.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5406    2.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1545    1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3890   -0.4024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0601   -1.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5191    2.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2115   -1.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0185   -1.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9565   -0.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5705   -0.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9709   -1.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5086    0.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3155   -0.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760    1.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3475    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7245   -1.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7280    0.5475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4782   -0.8205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  2  0  0  0  0
 10  9  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 11  1  0  0  0  0
 17  2  2  0  0  0  0
 17  3  1  0  0  0  0
 18 12  2  0  0  0  0
 16 19  1  4  0  0  0
 19 18  1  0  0  0  0
 20 13  2  0  0  0  0
 20 18  1  0  0  0  0
 21 16  2  0  0  0  0
 22 19  2  0  0  0  0
 23 21  1  0  0  0  0
 25  4  1  0  0  0  0
 25  5  1  0  0  0  0
 25  8  1  0  0  0  0
 25 22  1  0  0  0  0
 26  6  1  0  0  0  0
 26  7  1  0  0  0  0
 26 17  1  0  0  0  0
 27 14  1  0  0  0  0
 27 24  1  0  0  0  0
 28 20  1  0  0  0  0
 28 22  1  0  0  0  0
 29 21  1  0  0  0  0
 29 24  2  0  0  0  0
 30 15  1  0  0  0  0
 30 23  1  0  0  0  0
 30 27  1  0  0  0  0
 31 23  2  0  0  0  0
 32 24  1  0  0  0  0
 33 26  1  0  0  0  0
 33 27  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0017931

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=C)C(C)(C)OC12CCCN1C(=O)C(=CC1=C(NC3=CC=CC=C13)C(C)(C)C=C)N=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C27H33N3O3/c1-8-25(4,5)22-19(18-12-9-10-13-20(18)28-22)16-21-23(31)30-15-11-14-27(30,24(32)29-21)33-26(6,7)17(2)3/h8-10,12-13,16,28H,1-2,11,14-15H2,3-7H3,(H,29,32)

> <INCHI_KEY>
FRBBRXZVWXUWHM-UHFFFAOYSA-N

> <FORMULA>
C27H33N3O3

> <MOLECULAR_WEIGHT>
447.579

> <EXACT_MASS>
447.252191935

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
50.01345238493559

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8a-[(2,3-dimethylbut-3-en-2-yl)oxy]-1-hydroxy-3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene}-3H,4H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one

> <ALOGPS_LOGP>
4.62

> <JCHEM_LOGP>
5.331283759999999

> <ALOGPS_LOGS>
-6.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.93101813046817

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7146591645158296

> <JCHEM_PKA_STRONGEST_BASIC>
0.4830467702047249

> <JCHEM_POLAR_SURFACE_AREA>
77.92

> <JCHEM_REFRACTIVITY>
132.1738

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.48e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8a-[(2,3-dimethylbut-3-en-2-yl)oxy]-1-hydroxy-3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene}-6H,7H,8H-pyrrolo[1,2-a]pyrazin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      13.634   5.655   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.651  -4.316   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.566  -1.879   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.342   3.993   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.355   3.353   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.593  -0.751   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.846  -3.565   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.169   5.179   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.728  -2.601   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.234  -2.921   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.252  -1.136   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.265  -1.776   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.812  -2.784   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.283   0.008   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.122   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.789  -0.312   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.529   2.166   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.849   3.673   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.219  -2.158   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      12.559   1.022   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0       7.454   0.000   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0       4.787   1.540   0.000  0.00  0.00           N+0
HETATM   31  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       4.626  -1.532   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   17                                                            
CONECT    3   17                                                            
CONECT    4   25                                                            
CONECT    5   25                                                            
CONECT    6   26                                                            
CONECT    7   26                                                            
CONECT    8    1   25                                                       
CONECT    9   10   12                                                       
CONECT   10    9   13                                                       
CONECT   11   14   15                                                       
CONECT   12    9   18                                                       
CONECT   13   10   20                                                       
CONECT   14   11   27                                                       
CONECT   15   11   30                                                       
CONECT   16   19   21                                                       
CONECT   17    2    3   26                                                  
CONECT   18   12   19   20                                                  
CONECT   19   16   18   22                                                  
CONECT   20   13   18   28                                                  
CONECT   21   16   23   29                                                  
CONECT   22   19   25   28                                                  
CONECT   23   21   30   31                                                  
CONECT   24   27   29   32                                                  
CONECT   25    4    5    8   22                                             
CONECT   26    6    7   17   33                                             
CONECT   27   14   24   30   33                                             
CONECT   28   20   22                                                       
CONECT   29   21   24                                                       
CONECT   30   15   23   27                                                  
CONECT   31   23                                                            
CONECT   32   24                                                            
CONECT   33   26   27                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

Synonyms

Not Available

Molecular Formula

C₂₇H₃₃N₃O₃

Average Mass

447.579

Monoisotopic Mass

447.252191935

IUPAC Name

8a-[(2,3-dimethylbut-3-en-2-yl)oxy]-1-hydroxy-3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene}-3H,4H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one

Traditional Name

8a-[(2,3-dimethylbut-3-en-2-yl)oxy]-1-hydroxy-3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene}-6H,7H,8H-pyrrolo[1,2-a]pyrazin-4-one

CAS Registry Number

Not Available

SMILES

CC(=C)C(C)(C)OC12CCCN1C(=O)C(=CC1=C(NC3=CC=CC=C13)C(C)(C)C=C)N=C2O

InChI Identifier

InChI=1S/C27H33N3O3/c1-8-25(4,5)22-19(18-12-9-10-13-20(18)28-22)16-21-23(31)30-15-11-14-27(30,24(32)29-21)33-26(6,7)17(2)3/h8-10,12-13,16,28H,1-2,11,14-15H2,3-7H3,(H,29,32)

InChI Key

FRBBRXZVWXUWHM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Indole or derivatives
Indole
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Cyclic carboximidic acid
Tertiary carboxylic acid amide
Pyrrolidine
Pyrrole
Lactam
Carboxamide group
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00035 g/L	ALOGPS
logP	4.62	ALOGPS
logP	5.33	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	2.71	ChemAxon
pKa (Strongest Basic)	0.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	77.92 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	132.17 m³·mol⁻¹	ChemAxon
Polarizability	50.01 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78435738

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139588057

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for 9Î¾-O-2(2,3-dimethylbut-3-enyl)brevianamide Q (MMDBc0017931)

MOL for #<Metabolite:0x00007f923c8cc438>

3D MOL for #<Metabolite:0x00007f923c8cc438>

3D SDF for #<Metabolite:0x00007f923c8cc438>

3D-SDF for #<Metabolite:0x00007f923c8cc438>

PDB for #<Metabolite:0x00007f923c8cc438>

3D PDB for #<Metabolite:0x00007f923c8cc438>

SMILES for #<Metabolite:0x00007f923c8cc438>

INCHI for #<Metabolite:0x00007f923c8cc438>

Structure for #<Metabolite:0x00007f923c8cc438>

3D Structure for #<Metabolite:0x00007f923c8cc438>