NP-MRD: Showing NP-Card for Bagremycin A (NP0003937)

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Record Information

Version

2.0

Created at

2020-12-09 01:28:40 UTC

Updated at

2021-07-15 16:47:47 UTC

NP-MRD ID

NP0003937

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bagremycin A

Provided By

NPAtlas

Description

Bagremycin A is found in Streptomyces. Bagremycin A was first documented in 2001 (PMID: 11714229). Based on a literature review very few articles have been published on 4-ethenylphenyl 3-amino-4-hydroxybenzoate (PMID: 30526412) (PMID: 26946375) (PMID: 25801967) (PMID: 22065278).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117513D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242117513D          

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M  END
> <DATABASE_ID>
NP0003937

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1N([H])[H])C(=O)OC1=C([H])C([H])=C(C([H])=C([H])[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H13NO3/c1-2-10-3-6-12(7-4-10)19-15(18)11-5-8-14(17)13(16)9-11/h2-9,17H,1,16H2

> <INCHI_KEY>
RWDKQKLCXJVELF-UHFFFAOYSA-N

> <FORMULA>
C15H13NO3

> <MOLECULAR_WEIGHT>
255.273

> <EXACT_MASS>
255.089543283

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
27.44660335391137

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-ethenylphenyl 3-amino-4-hydroxybenzoate

> <ALOGPS_LOGP>
3.57

> <JCHEM_LOGP>
3.238892021

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.25079738665824

> <JCHEM_PKA_STRONGEST_BASIC>
2.8964136723425677

> <JCHEM_POLAR_SURFACE_AREA>
72.55

> <JCHEM_REFRACTIVITY>
74.22850000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-ethenylphenyl 3-amino-4-hydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
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  1 20  1  0
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  2 22  1  0
  4 23  1  0
  5 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 16 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       6.474   0.858   0.028  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.686  -0.018  -0.530  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.235   0.076  -0.514  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.571   1.105   0.098  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.172   1.186   0.108  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.441   0.222  -0.503  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.044   0.218  -0.546  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.696  -0.408   0.450  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.036  -0.956   1.368  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.160  -0.428   0.432  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.868  -1.056   1.432  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.258  -1.073   1.410  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.971  -0.458   0.380  0.00  0.00           C+0
HETATM   14  O   UNK     0      -6.348  -0.465   0.343  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.256   0.164  -0.610  0.00  0.00           C+0
HETATM   16  N   UNK     0      -4.991   0.790  -1.658  0.00  0.00           N+0
HETATM   17  C   UNK     0      -2.892   0.169  -0.569  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.083  -0.832  -1.132  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.450  -0.897  -1.133  0.00  0.00           C+0
HETATM   20  H   UNK     0       7.564   0.774   0.008  0.00  0.00           H+0
HETATM   21  H   UNK     0       6.090   1.707   0.537  0.00  0.00           H+0
HETATM   22  H   UNK     0       6.184  -0.855  -1.029  0.00  0.00           H+0
HETATM   23  H   UNK     0       4.133   1.883   0.591  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.700   2.017   0.604  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.297  -1.532   2.229  0.00  0.00           H+0
HETATM   26  H   UNK     0      -4.803  -1.558   2.183  0.00  0.00           H+0
HETATM   27  H   UNK     0      -6.831  -0.019  -0.403  0.00  0.00           H+0
HETATM   28  H   UNK     0      -5.026   0.363  -2.609  0.00  0.00           H+0
HETATM   29  H   UNK     0      -5.502   1.670  -1.503  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.353   0.666  -1.362  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.497  -1.608  -1.624  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.963  -1.704  -1.613  0.00  0.00           H+0
CONECT    1    2   20   21                                                  
CONECT    2    1    3   22                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6   24                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   17                                                  
CONECT   11   10   12   25                                                  
CONECT   12   11   13   26                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13   27                                                       
CONECT   15   13   16   17                                                  
CONECT   16   15   28   29                                                  
CONECT   17   15   10   30                                                  
CONECT   18    6   19   31                                                  
CONECT   19   18    3   32                                                  
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    2                                                            
CONECT   23    4                                                            
CONECT   24    5                                                            
CONECT   25   11                                                            
CONECT   26   12                                                            
CONECT   27   14                                                            
CONECT   28   16                                                            
CONECT   29   16                                                            
CONECT   30   17                                                            
CONECT   31   18                                                            
CONECT   32   19                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

RDKit          3D

32 33  0  0  0  0  0  0  0  0999 V2000
    6.4740    0.8576    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6865   -0.0179   -0.5302 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2353    0.0758   -0.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5708    1.1052    0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1716    1.1859    0.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4413    0.2223   -0.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0437    0.2179   -0.5456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6961   -0.4077    0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0356   -0.9558    1.3684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1603   -0.4284    0.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8682   -1.0560    1.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2583   -1.0726    1.4097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9709   -0.4576    0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3482   -0.4649    0.3431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2557    0.1639   -0.6098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9913    0.7896   -1.6578 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8916    0.1686   -0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0828   -0.8323   -1.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4504   -0.8970   -1.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5636    0.7743    0.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0904    1.7070    0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1840   -0.8553   -1.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1329    1.8826    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7005    2.0170    0.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2973   -1.5315    2.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8026   -1.5579    2.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8311   -0.0188   -0.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0259    0.3628   -2.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5016    1.6700   -1.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3525    0.6657   -1.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4966   -1.6084   -1.6239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9627   -1.7041   -1.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
  6 18  1  0
 18 19  2  0
 19  3  1  0
 17 10  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  4 23  1  0
  5 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 16 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
4-Ethenylphenyl 3-amino-4-hydroxybenzoic acid	Generator

Chemical Formula

C₁₅H₁₃NO₃

Average Mass

255.2730 Da

Monoisotopic Mass

255.08954 Da

IUPAC Name

4-ethenylphenyl 3-amino-4-hydroxybenzoate

Traditional Name

4-ethenylphenyl 3-amino-4-hydroxybenzoate

CAS Registry Number

Not Available

SMILES

NC1=C(O)C=CC(=C1)C(=O)OC1=CC=C(C=C)C=C1

InChI Identifier

InChI=1S/C15H13NO3/c1-2-10-3-6-12(7-4-10)19-15(18)11-5-8-14(17)13(16)9-11/h2-9,17H,1,16H2

InChI Key

RWDKQKLCXJVELF-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces	NPAtlas	11714229

Species Where Detected

Species Name	Source	Reference
Streptomyces sp. Tu 4128	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Depsides and depsidones

Sub Class

Not Available

Direct Parent

Depsides and depsidones

Alternative Parents

Substituents

Depside backbone
P-hydroxybenzoic acid ester
Aminobenzoic acid or derivatives
Benzoate ester
Phenol ester
Benzoic acid or derivatives
Phenoxy compound
O-aminophenol
Aniline or substituted anilines
Styrene
Aminophenol
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Amine
Primary amine
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	3.57	ALOGPS
logP	3.24	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.25	ChemAxon
pKa (Strongest Basic)	2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	72.55 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.23 m³·mol⁻¹	ChemAxon
Polarizability	27.45 Å³	ChemAxon
Number of Rings	2	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

NPAtlas ID

NPA019088

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00015972

Chemspider ID

8597909

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10422480

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bertasso M, Holzenkampfer M, Zeeck A, Dall'Antonia F, Fiedler HP: Bagremycin A and B, novel antibiotics from streptomyces sp. Tu 4128. J Antibiot (Tokyo). 2001 Sep;54(9):730-6. doi: 10.7164/antibiotics.54.730. [PubMed:11714229 ]
Ye J, Zhu Y, Hou B, Wu H, Zhang H: Characterization of the bagremycin biosynthetic gene cluster in Streptomyces sp. Tu 4128. Biosci Biotechnol Biochem. 2019 Mar;83(3):482-489. doi: 10.1080/09168451.2018.1553605. Epub 2018 Dec 10. [PubMed:30526412 ]
Tanvir R, Sajid I, Hasnain S, Kulik A, Grond S: Rare actinomycetes Nocardia caishijiensis and Pseudonocardia carboxydivorans as endophytes, their bioactivity and metabolites evaluation. Microbiol Res. 2016 Apr;185:22-35. doi: 10.1016/j.micres.2016.01.003. Epub 2016 Jan 23. [PubMed:26946375 ]
Liu F, Xu D, Zhang Y, Zhu Y, Ye J, Zhang H: Identification of BagI as a positive transcriptional regulator of bagremycin biosynthesis in engineered Streptomyces sp. Tu 4128. Microbiol Res. 2015 Apr;173:18-24. doi: 10.1016/j.micres.2015.01.011. Epub 2015 Feb 7. [PubMed:25801967 ]
Zhu Y, Liao S, Ye J, Zhang H: Cloning and characterization of a novel tyrosine ammonia lyase-encoding gene involved in bagremycins biosynthesis in Streptomyces sp. Biotechnol Lett. 2012 Feb;34(2):269-74. doi: 10.1007/s10529-011-0755-9. Epub 2011 Nov 8. [PubMed:22065278 ]

Showing NP-Card for Bagremycin A (NP0003937)

MOL for NP0003937 (Bagremycin A)

3D MOL for NP0003937 (Bagremycin A)

3D SDF for NP0003937 (Bagremycin A)

3D-SDF for NP0003937 (Bagremycin A)

PDB for NP0003937 (Bagremycin A)

3D PDB for NP0003937 (Bagremycin A)

SMILES for NP0003937 (Bagremycin A)

INCHI for NP0003937 (Bagremycin A)

Structure for NP0003937 (Bagremycin A)

3D Structure for NP0003937 (Bagremycin A)