NP-MRD: Showing NP-Card for methyl brevifolincarboxylate (NP0269874)

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Record Information

Version

2.0

Created at

2022-09-08 15:29:53 UTC

Updated at

2022-09-08 15:29:53 UTC

NP-MRD ID

NP0269874

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl brevifolincarboxylate

Description

Methyl brevifolincarboxylate belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1. Methyl brevifolincarboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa). methyl brevifolincarboxylate is found in Euphorbia maculata, Macaranga tanarius and Phyllanthus niruri. methyl brevifolincarboxylate was first documented in 2006 (PMID: 16394535). Isolated from Phyllanthus urinaria and Phyllanthus niruri, it exhibits vasorelaxant activity (PMID: 17268086) (PMID: 18187278) (PMID: 18557426) (PMID: 20433066).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -3.4908   -0.0018    2.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7446   -0.4794    1.2627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5202   -1.0927    1.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1243   -1.1970    2.6922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6650   -1.6264    0.4322 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5925   -2.5332   -0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1844   -1.5665   -1.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3386   -1.6663   -1.8199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1491   -0.5816   -1.6190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0128    0.2354   -2.6337 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0102    1.0826   -2.6996 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1458    1.8687   -3.6706 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9397    1.0960   -1.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0149    1.9577   -1.7134 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9592    1.9944   -0.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0422    2.8660   -0.7550 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8533    1.1389    0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8318    1.2224    1.3565 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7764    0.2832    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6135   -0.5760    1.4543 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8225    0.2472   -0.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2601   -0.6218   -0.5664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2250   -0.7795    2.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9838    0.9587    2.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8177    0.1799    3.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1141   -2.2550    0.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0127   -3.3168   -0.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3733   -2.9933    0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0926    2.6161   -2.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2139    3.5118   -1.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8031    0.6331    2.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2617   -0.6048    2.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 22  2  0
 22 21  1  0
 21 19  2  0
 19 20  1  0
 19 17  1  0
 17 18  1  0
 17 15  2  0
 15 16  1  0
 15 14  1  0
 14 13  2  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 22  5  1  0
 13 21  1  0
 10  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  1
  6 27  1  0
  6 28  1  0
 20 32  1  0
 18 31  1  0
 16 30  1  0
 14 29  1  0
M  END


  Mrv1533004171514332D          

 22 24  0  0  0  0            999 V2000
    3.0986   -2.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2952   -1.6412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996   -1.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9074   -1.3006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995    0.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2295    1.3982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4944   -1.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547   -0.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347    0.4640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1937    2.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083    1.7892    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  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
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  9 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0269874

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1CC(=O)C2=C1C1=C(O)C(O)=C(O)C=C1C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O8/c1-21-13(19)5-3-7(16)12-9(5)8-4(14(20)22-12)2-6(15)10(17)11(8)18/h2,5,15,17-18H,3H2,1H3

> <INCHI_KEY>
JNWDNAASYHRXMG-UHFFFAOYSA-N

> <FORMULA>
C14H10O8

> <MOLECULAR_WEIGHT>
306.226

> <EXACT_MASS>
306.037567282

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
27.378886954063464

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 7,8,9-trihydroxy-3,5-dioxo-1H,2H,3H,5H-cyclopenta[c]isochromene-1-carboxylate

> <ALOGPS_LOGP>
1.39

> <JCHEM_LOGP>
0.5602208416666665

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.992122987162253

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.64773397815162

> <JCHEM_PKA_STRONGEST_BASIC>
-6.73223791026095

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
71.79979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.01e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 7,8,9-trihydroxy-3,5-dioxo-1H,2H-cyclopenta[c]isochromene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       5.784  -4.559   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.151  -3.064   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.039  -1.998   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.561  -2.428   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.406  -0.502   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.832   0.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.719   1.616   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.895   2.610   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.223   1.983   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.412   0.674   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.873   0.722   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.062  -0.587   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.790  -1.944   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.522  -0.539   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.289  -1.848   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.206   0.818   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.745   0.866   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.606   2.127   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.145   2.079   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.956   3.388   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.228   4.745   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.495   3.340   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   22                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   11   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    9                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
Methyl brevifolincarboxylic acid	Generator

Chemical Formula

C₁₄H₁₀O₈

Average Mass

306.2260 Da

Monoisotopic Mass

306.03757 Da

IUPAC Name

methyl 7,8,9-trihydroxy-3,5-dioxo-1H,2H,3H,5H-cyclopenta[c]isochromene-1-carboxylate

Traditional Name

methyl 7,8,9-trihydroxy-3,5-dioxo-1H,2H-cyclopenta[c]isochromene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1CC(=O)C2=C1C1=C(O)C(O)=C(O)C=C1C(=O)O2

InChI Identifier

InChI=1S/C14H10O8/c1-21-13(19)5-3-7(16)12-9(5)8-4(14(20)22-12)2-6(15)10(17)11(8)18/h2,5,15,17-18H,3H2,1H3

InChI Key

JNWDNAASYHRXMG-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, 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
Euphorbia maculata	LOTUS Database	35616633
Macaranga tanarius	LOTUS Database	35616633
Phyllanthus niruri	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isocoumarins and derivatives

Sub Class

Not Available

Direct Parent

Isocoumarins and derivatives

Alternative Parents

Substituents

Isocoumarin
Benzopyran
2-benzopyran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Methyl ester
Carboxylic acid ester
Ketone
Lactone
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cyclic ketone (CHEBI:66711 )
organic heterotricyclic compound (CHEBI:66711 )
phenols (CHEBI:66711 )
delta-lactone (CHEBI:66711 )

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	1.39	ALOGPS
logP	0.56	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	6.65	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.8 m³·mol⁻¹	ChemAxon
Polarizability	27.38 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

5319518

PDB ID

Not Available

ChEBI ID

66711

Good Scents ID

Not Available

References

General References

Iizuka T, Moriyama H, Nagai M: Vasorelaxant effects of methyl brevifolincarboxylate from the leaves of Phyllanthus niruri. Biol Pharm Bull. 2006 Jan;29(1):177-9. doi: 10.1248/bpb.29.177. [PubMed:16394535 ]
Iizuka T, Nagai M, Taniguchi A, Moriyama H, Hoshi K: Inhibitory effects of methyl brevifolincarboxylate isolated from Phyllanthus niruri L. on platelet aggregation. Biol Pharm Bull. 2007 Feb;30(2):382-4. doi: 10.1248/bpb.30.382. [PubMed:17268086 ]
Fang SH, Rao YK, Tzeng YM: Anti-oxidant and inflammatory mediator's growth inhibitory effects of compounds isolated from Phyllanthus urinaria. J Ethnopharmacol. 2008 Mar 5;116(2):333-40. doi: 10.1016/j.jep.2007.11.040. Epub 2007 Dec 4. [PubMed:18187278 ]
Tomczyk M, Drozdowska D, Bielawska A, Bielawski K, Gudej J: Human DNA topoisomerase inhibitors from Potentilla argentea and their cytotoxic effect against MCF-7. Pharmazie. 2008 May;63(5):389-93. [PubMed:18557426 ]
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LOTUS database [Link]

Showing NP-Card for methyl brevifolincarboxylate (NP0269874)

MOL for NP0269874 (methyl brevifolincarboxylate)

3D MOL for NP0269874 (methyl brevifolincarboxylate)

3D SDF for NP0269874 (methyl brevifolincarboxylate)

3D-SDF for NP0269874 (methyl brevifolincarboxylate)

PDB for NP0269874 (methyl brevifolincarboxylate)

3D PDB for NP0269874 (methyl brevifolincarboxylate)

SMILES for NP0269874 (methyl brevifolincarboxylate)

INCHI for NP0269874 (methyl brevifolincarboxylate)

Structure for NP0269874 (methyl brevifolincarboxylate)

3D Structure for NP0269874 (methyl brevifolincarboxylate)