NP-MRD: Showing NP-Card for brachystemidine a (NP0313534)

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Record Information

Version

2.0

Created at

2022-09-11 11:09:25 UTC

Updated at

2022-09-11 11:09:25 UTC

NP-MRD ID

NP0313534

Secondary Accession Numbers

None

Natural Product Identification

Common Name

brachystemidine a

Description

Brachystemidine A belongs to the class of organic compounds known as pyrrole carboxylic acids and derivatives. These are heterocyclic compounds containing a pyrrole ring bearing a carboxyl group (or a derivative thereof). brachystemidine a is found in Brachystemma calycinum. Based on a literature review very few articles have been published on Brachystemidine A.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
   -1.7796   -1.7712   -0.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3655   -0.8838    0.4913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2526   -0.0917   -0.1937 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6735   -0.2374    0.3235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3450    1.0314   -0.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2123    1.9859   -0.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3615    3.2108   -0.6234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9820    1.3131   -0.0851 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7185    1.9424    0.2066 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6788    1.6225   -0.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5066    1.5992   -0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8412    1.3376   -0.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4641    0.2053   -0.1265 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7371   -0.1915   -0.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2768    0.5028   -1.4242 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4260   -1.3280    0.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6880   -1.7407   -0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0555   -2.8440    0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9673   -3.0893    1.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0175   -2.1546    1.0248 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1922    1.9140    1.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1444    1.5154    1.3766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2469   -1.1953   -1.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0184   -2.4058    0.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5435   -2.3892   -0.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2857   -0.3444   -1.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7085   -0.3363    1.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2015   -1.0848   -0.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9924    1.3934    0.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8978    0.8788   -1.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8156    3.0432    0.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8030    1.4301   -1.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8952    1.2447   -1.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5088    2.2041   -0.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3365   -1.3018   -1.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9789   -3.3829    0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9353   -3.8943    2.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1117   -2.1086    1.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2282    3.0179    1.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8601    1.3830    1.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 22  1  0
 22 21  1  0
 21 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 11 10  2  0
  8  3  1  0
 10  9  1  0
 20 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  6
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  9 31  1  1
 21 39  1  0
 21 40  1  0
 12 33  1  0
 12 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 10 32  1  0
M  END


  Mrv1652309112213092D          

 22 24  0  0  1  0            999 V2000
    5.8006   -2.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0861   -2.4425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0861   -3.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7535   -3.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4986   -4.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6736   -4.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1887   -5.2045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4187   -3.7524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6340   -3.4975    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9666   -3.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2992   -3.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5145   -3.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014   -3.2004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1168   -3.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0547   -4.2623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4963   -2.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3032   -3.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7157   -2.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1637   -1.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100   -2.0828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5541   -2.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3791   -2.7129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  3  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 16 20  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
  9 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0313534

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1CCC(=O)N1[C@H]1OCC(COC(=O)C2=CC=CN2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H18N2O5/c1-20-13-5-4-12(18)17(13)14-7-10(8-21-14)9-22-15(19)11-3-2-6-16-11/h2-3,6-7,13-14,16H,4-5,8-9H2,1H3/t13?,14-/m0/s1

> <INCHI_KEY>
BPMLAWBYBLOCCU-KZUDCZAMSA-N

> <FORMULA>
C15H18N2O5

> <MOLECULAR_WEIGHT>
306.318

> <EXACT_MASS>
306.121571688

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
31.47747487736249

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(5S)-5-(2-methoxy-5-oxopyrrolidin-1-yl)-2,5-dihydrofuran-3-yl]methyl 1H-pyrrole-2-carboxylate

> <JCHEM_LOGP>
0.7866363553333331

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.638779104006694

> <JCHEM_PKA_STRONGEST_BASIC>
-2.472402585491164

> <JCHEM_POLAR_SURFACE_AREA>
80.86

> <JCHEM_REFRACTIVITY>
77.69180000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(5S)-5-(2-methoxy-5-oxopyrrolidin-1-yl)-2,5-dihydrofuran-3-yl]methyl 1H-pyrrole-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      10.828  -3.789   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.494  -4.559   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.494  -6.099   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.740  -7.005   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.264  -8.469   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.724  -8.469   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.819  -9.715   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       8.248  -7.005   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       6.784  -6.529   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.538  -7.434   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.292  -6.529   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.827  -7.005   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.683  -5.974   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.218  -6.450   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.102  -7.956   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.926  -5.420   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.433  -5.740   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.203  -4.406   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.172  -3.262   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      -0.765  -3.888   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       4.768  -5.064   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.308  -5.064   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    3    9                                                  
CONECT    9    8   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16                                                       
CONECT   21   11   22                                                       
CONECT   22   21    9                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈N₂O₅

Average Mass

306.3180 Da

Monoisotopic Mass

306.12157 Da

IUPAC Name

[(5S)-5-(2-methoxy-5-oxopyrrolidin-1-yl)-2,5-dihydrofuran-3-yl]methyl 1H-pyrrole-2-carboxylate

Traditional Name

[(5S)-5-(2-methoxy-5-oxopyrrolidin-1-yl)-2,5-dihydrofuran-3-yl]methyl 1H-pyrrole-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC1CCC(=O)N1[C@H]1OCC(COC(=O)C2=CC=CN2)=C1

InChI Identifier

InChI=1S/C15H18N2O5/c1-20-13-5-4-12(18)17(13)14-7-10(8-21-14)9-22-15(19)11-3-2-6-16-11/h2-3,6-7,13-14,16H,4-5,8-9H2,1H3/t13?,14-/m0/s1

InChI Key

BPMLAWBYBLOCCU-KZUDCZAMSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Brachystemma calycinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrole carboxylic acids and derivatives. These are heterocyclic compounds containing a pyrrole ring bearing a carboxyl group (or a derivative thereof).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrroles

Sub Class

Pyrrole carboxylic acids and derivatives

Direct Parent

Pyrrole carboxylic acids and derivatives

Alternative Parents

Substituents

Pyrrole-2-carboxylic acid or derivatives
Pyrrolidone
2-pyrrolidone
Substituted pyrrole
N-alkylpyrrolidine
Dihydrofuran
Pyrrolidine
Heteroaromatic compound
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Lactam
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Azacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrroles (CHEBI:69771 )

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	0.79	ChemAxon
pKa (Strongest Acidic)	12.64	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.86 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	77.69 m³·mol⁻¹	ChemAxon
Polarizability	31.48 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00045694

Chemspider ID

9067381

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10892118

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for brachystemidine a (NP0313534)

MOL for NP0313534 (brachystemidine a)

3D MOL for NP0313534 (brachystemidine a)

3D SDF for NP0313534 (brachystemidine a)

3D-SDF for NP0313534 (brachystemidine a)

PDB for NP0313534 (brachystemidine a)

3D PDB for NP0313534 (brachystemidine a)

SMILES for NP0313534 (brachystemidine a)

INCHI for NP0313534 (brachystemidine a)

Structure for NP0313534 (brachystemidine a)

3D Structure for NP0313534 (brachystemidine a)