MiMeDB: Showing metabocard for Bezerramycin B (MMDBc0018530)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 08:42:07 UTC

Update Date

2025-10-07 16:06:50 UTC

Metabolite ID

MMDBc0018530

Metabolite Identification

Common Name

Bezerramycin B

Description

Bezerramycin B is a polyketide compound belonging to the class of natural products. There is limited literature available on this metabolite, indicating that further research may be needed to fully understand its properties and potential applications.

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251511172D          

 24 26  0  0  0  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  6 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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0018530

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=O)NC1=C(C(O)=O)C2=NC3=CC(CO)=CC=C3OC2=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12N2O6/c1-7(20)17-14-10(21)5-12-15(13(14)16(22)23)18-9-4-8(6-19)2-3-11(9)24-12/h2-5,19H,6H2,1H3,(H,17,20)(H,22,23)

> <INCHI_KEY>
PVALJFNMUZXLJQ-UHFFFAOYSA-N

> <FORMULA>
C16H12N2O6

> <MOLECULAR_WEIGHT>
328.28

> <EXACT_MASS>
328.069536114

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
32.063049971697815

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-acetamido-8-(hydroxymethyl)-3-oxo-3H-phenoxazine-1-carboxylic acid

> <ALOGPS_LOGP>
0.61

> <JCHEM_LOGP>
-0.16751061499999995

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.803247438701074

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.867161933428644

> <JCHEM_PKA_STRONGEST_BASIC>
-2.858928576365609

> <JCHEM_POLAR_SURFACE_AREA>
125.29000000000002

> <JCHEM_REFRACTIVITY>
85.90259999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-acetamido-8-(hydroxymethyl)-3-oxophenoxazine-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.334  -5.390   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   23                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6   11   21                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   12   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   10   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22    5   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

Synonyms

Value	Source
2-[(1-Hydroxyethylidene)amino]-8-(hydroxymethyl)-3-oxo-3H-phenoxazine-1-carboxylate	Generator

Molecular Formula

C₁₆H₁₂N₂O₆

Average Mass

328.28

Monoisotopic Mass

328.069536114

IUPAC Name

2-acetamido-8-(hydroxymethyl)-3-oxo-3H-phenoxazine-1-carboxylic acid

Traditional Name

2-acetamido-8-(hydroxymethyl)-3-oxophenoxazine-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(=O)NC1=C(C(O)=O)C2=NC3=CC(CO)=CC=C3OC2=CC1=O

InChI Identifier

InChI=1S/C16H12N2O6/c1-7(20)17-14-10(21)5-12-15(13(14)16(22)23)18-9-4-8(6-19)2-3-11(9)24-12/h2-5,19H,6H2,1H3,(H,17,20)(H,22,23)

InChI Key

PVALJFNMUZXLJQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenoxazines. These are polycyclic aromatic compounds containing a phenoxazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a 1,4-oxazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazines

Sub Class

Phenoxazines

Direct Parent

Phenoxazines

Alternative Parents

Substituents

Phenoxazine
N-acetylarylamine
N-arylamide
Benzenoid
Heteroaromatic compound
Acetamide
Vinylogous amide
Carboxamide group
Secondary carboxylic acid amide
Cyclic ketone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Azacycle
Organic oxide
Primary alcohol
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Aromatic alcohol
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
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	0.13 g/L	ALOGPS
logP	0.61	ALOGPS
logP	-0.17	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	125.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	85.9 m³·mol⁻¹	ChemAxon
Polarizability	32.06 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

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	210.3
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	114.4
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	281.3
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	469.3
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	310.0
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	235.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	1451.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	143.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	531.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	205.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	203.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	165.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	98.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	225.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	483.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	80.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	243.2
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1285.9
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	724.9

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Bezerramycin B_TMS_1	CC(=O)NC1=C(C(=O)O[Si](C)(C)C)C2=NC3=CC(CO)=CC=C3OC2=CC1=O	standard non polar	2025-10-23	2478.85
Gas Chromatography	Bezerramycin B_TMS_2	CC(=O)NC1=C(C(=O)O)C2=NC3=CC(CO[Si](C)(C)C)=CC=C3OC2=CC1=O	standard non polar	2025-10-23	2307.59
Gas Chromatography	Bezerramycin B_TMS_3	CC(=O)N(C1=C(C(=O)O)C2=NC3=CC(CO)=CC=C3OC2=CC1=O)[Si](C)(C)C	standard non polar	2025-10-23	3071.46
Gas Chromatography	Bezerramycin B_TMS_4	CC(=O)NC1=C(C(=O)O[Si](C)(C)C)C2=NC3=CC(CO[Si](C)(C)C)=CC=C3OC2=CC1=O	standard non polar	2025-10-23	1165.15
Gas Chromatography	Bezerramycin B_TMS_5	CC(=O)N(C1=C(C(=O)O[Si](C)(C)C)C2=NC3=CC(CO)=CC=C3OC2=CC1=O)[Si](C)(C)C	standard non polar	2025-10-23	2000.29
Gas Chromatography	Bezerramycin B_TMS_6	CC(=O)N(C1=C(C(=O)O)C2=NC3=CC(CO[Si](C)(C)C)=CC=C3OC2=CC1=O)[Si](C)(C)C	standard non polar	2025-10-23	476.657
Gas Chromatography	Bezerramycin B_TMS_7	CC(=O)N(C1=C(C(=O)O[Si](C)(C)C)C2=NC3=CC(CO[Si](C)(C)C)=CC=C3OC2=CC1=O)[Si](C)(C)C	standard non polar	2025-10-23	2254.07
Gas Chromatography	Bezerramycin B_TMS_1	CC(=O)NC1=C(C(=O)O[Si](C)(C)C)C2=NC3=CC(CO)=CC=C3OC2=CC1=O	standard polar	2025-10-23	2771.82
Gas Chromatography	Bezerramycin B_TMS_2	CC(=O)NC1=C(C(=O)O)C2=NC3=CC(CO[Si](C)(C)C)=CC=C3OC2=CC1=O	standard polar	2025-10-23	1856.12
Gas Chromatography	Bezerramycin B_TMS_3	CC(=O)N(C1=C(C(=O)O)C2=NC3=CC(CO)=CC=C3OC2=CC1=O)[Si](C)(C)C	standard polar	2025-10-23	2251.3
Gas Chromatography	Bezerramycin B_TMS_4	CC(=O)NC1=C(C(=O)O[Si](C)(C)C)C2=NC3=CC(CO[Si](C)(C)C)=CC=C3OC2=CC1=O	standard polar	2025-10-23	1965.01
Gas Chromatography	Bezerramycin B_TMS_5	CC(=O)N(C1=C(C(=O)O[Si](C)(C)C)C2=NC3=CC(CO)=CC=C3OC2=CC1=O)[Si](C)(C)C	standard polar	2025-10-23	1763.74
Gas Chromatography	Bezerramycin B_TMS_6	CC(=O)N(C1=C(C(=O)O)C2=NC3=CC(CO[Si](C)(C)C)=CC=C3OC2=CC1=O)[Si](C)(C)C	standard polar	2025-10-23	2432.44
Gas Chromatography	Bezerramycin B_TMS_7	CC(=O)N(C1=C(C(=O)O[Si](C)(C)C)C2=NC3=CC(CO[Si](C)(C)C)=CC=C3OC2=CC1=O)[Si](C)(C)C	standard polar	2025-10-23	1682.05

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated 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
Bacteria/Eubacteria	Actinobacteria	1		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

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

46183339

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

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 Bezerramycin B (MMDBc0018530)

MOL for #<Metabolite:0x00007f9aa5a12420>

3D MOL for #<Metabolite:0x00007f9aa5a12420>

3D SDF for #<Metabolite:0x00007f9aa5a12420>

3D-SDF for #<Metabolite:0x00007f9aa5a12420>

PDB for #<Metabolite:0x00007f9aa5a12420>

3D PDB for #<Metabolite:0x00007f9aa5a12420>

SMILES for #<Metabolite:0x00007f9aa5a12420>

INCHI for #<Metabolite:0x00007f9aa5a12420>

Structure for #<Metabolite:0x00007f9aa5a12420>

3D Structure for #<Metabolite:0x00007f9aa5a12420>