MiMeDB: Showing metabocard for Aqabamycin E1 (MMDBc0006408)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 23:37:56 UTC

Update Date

2022-08-31 06:25:17 UTC

Metabolite ID

MMDBc0006408

Metabolite Identification

Common Name

Aqabamycin E1

Description

Aqabamycin E1 belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond. Aqabamycin E1 is a strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152101372D          

 24 26  0  0  0  0            999 V2000
    1.6991    2.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0860    3.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5275    1.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3014    2.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429    1.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1298    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    3.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6548    1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9897    1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347    1.0206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4248    0.3532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512    4.7652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    5.5902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7743    2.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7604   -0.4005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512    5.5902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4656    4.3527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  6  2  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  2  0  0  0  0
 11  8  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  2  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 14 13  1  0  0  0  0
 15 13  2  0  0  0  0
 16 14  2  0  0  0  0
 17 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 15  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 16  1  0  0  0  0
 22 18  2  0  0  0  0
 23 19  2  0  0  0  0
 24 19  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0006408

> <DATABASE_NAME>
MIME

> <SMILES>
OC1=C(C(=C(N1)N=O)C1=CC=CC=C1)C1=CC(=C(O)C=C1)N(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H11N3O5/c20-12-7-6-10(8-11(12)19(23)24)14-13(9-4-2-1-3-5-9)15(18-22)17-16(14)21/h1-8,17,20-21H

> <INCHI_KEY>
USHVEFFKMOOCLY-UHFFFAOYSA-N

> <FORMULA>
C16H11N3O5

> <MOLECULAR_WEIGHT>
325.28

> <EXACT_MASS>
325.069870466

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
30.658672014663942

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4-hydroxy-3-nitrophenyl)-5-nitroso-4-phenyl-1H-pyrrol-2-ol

> <ALOGPS_LOGP>
3.69

> <JCHEM_LOGP>
3.9367242796666666

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.517627498847356

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.01015391514708

> <JCHEM_PKA_STRONGEST_BASIC>
3.56924245648579

> <JCHEM_POLAR_SURFACE_AREA>
131.5

> <JCHEM_REFRACTIVITY>
86.4557

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.09e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(4-hydroxy-3-nitrophenyl)-5-nitroso-4-phenyl-1H-pyrrol-2-ol

> <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       3.172   4.797   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.027   5.828   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.851   3.291   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.563   5.352   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.387   2.815   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.134   6.585   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.134   8.125   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.802   6.585   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.242   3.846   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.468   5.815   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.802   8.125   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.468   8.895   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.222   3.370   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.468   4.275   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.698   1.905   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.714   3.370   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -3.238   1.905   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      -0.793   0.659   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0      -5.136   8.895   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      -2.468  10.435   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -5.179   3.846   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.419  -0.748   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -5.136  10.435   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -6.469   8.125   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    9                                                       
CONECT    5    3    9                                                       
CONECT    6    7   10                                                       
CONECT    7    6   12                                                       
CONECT    8   10   11                                                       
CONECT    9    4    5   13                                                  
CONECT   10    6    8   14                                                  
CONECT   11    8   12   19                                                  
CONECT   12    7   11   20                                                  
CONECT   13    9   14   15                                                  
CONECT   14   10   13   16                                                  
CONECT   15   13   17   18                                                  
CONECT   16   14   17   21                                                  
CONECT   17   15   16                                                       
CONECT   18   15   22                                                       
CONECT   19   11   23   24                                                  
CONECT   20   12                                                            
CONECT   21   16                                                            
CONECT   22   18                                                            
CONECT   23   19                                                            
CONECT   24   19                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

Synonyms

Not Available

Molecular Formula

C₁₆H₁₁N₃O₅

Average Mass

325.28

Monoisotopic Mass

325.069870466

IUPAC Name

3-(4-hydroxy-3-nitrophenyl)-5-nitroso-4-phenyl-1H-pyrrol-2-ol

Traditional Name

3-(4-hydroxy-3-nitrophenyl)-5-nitroso-4-phenyl-1H-pyrrol-2-ol

CAS Registry Number

Not Available

SMILES

OC1=C(C(=C(N1)N=O)C1=CC=CC=C1)C1=CC(=C(O)C=C1)N(=O)=O

InChI Identifier

InChI=1S/C16H11N3O5/c20-12-7-6-10(8-11(12)19(23)24)14-13(9-4-2-1-3-5-9)15(18-22)17-16(14)21/h1-8,17,20-21H

InChI Key

USHVEFFKMOOCLY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrroles

Sub Class

Substituted pyrroles

Direct Parent

Phenylpyrroles

Alternative Parents

Substituents

3-phenylpyrrole
Nitrophenol
Nitrobenzene
Nitroaromatic compound
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Organic nitro compound
C-nitro compound
Organic nitroso compound
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxoazanium
C-nitroso compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	3.69	ALOGPS
logP	3.94	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	6.01	ChemAxon
pKa (Strongest Basic)	3.57	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	131.5 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	86.46 m³·mol⁻¹	ChemAxon
Polarizability	30.66 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

Not Available

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
Bacteria	Proteobacteria	1		Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	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

78434739

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

136756036

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 Aqabamycin E1 (MMDBc0006408)

MOL for #<Metabolite:0x0000559d020ad0d0>

3D MOL for #<Metabolite:0x0000559d020ad0d0>

3D SDF for #<Metabolite:0x0000559d020ad0d0>

3D-SDF for #<Metabolite:0x0000559d020ad0d0>

PDB for #<Metabolite:0x0000559d020ad0d0>

3D PDB for #<Metabolite:0x0000559d020ad0d0>

SMILES for #<Metabolite:0x0000559d020ad0d0>

INCHI for #<Metabolite:0x0000559d020ad0d0>

Structure for #<Metabolite:0x0000559d020ad0d0>

3D Structure for #<Metabolite:0x0000559d020ad0d0>