NP-MRD: Showing NP-Card for Brevifolincarboxylic acid (NP0049156)

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Record Information

Version

2.0

Created at

2022-03-17 21:08:00 UTC

Updated at

2022-03-17 21:08:00 UTC

NP-MRD ID

NP0049156

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Brevifolincarboxylic acid

Description

Brevifolincarboxylic acid is found in Combretum indicum, Elaeagnus umbellata, Mallotus repandus, Melaleuca leucadendra, Pelargonium reniforme, Phyllanthus flexuosus, Phyllanthus niruri, Phyllanthus urinaria and Phyllanthus virgatus.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212592D          

 21 23  0  0  0  0            999 V2000
   -0.3051    0.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0195   -0.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0195   -1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3051   -1.4860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4094   -1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4094   -0.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4094    1.4015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3051    0.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1238    0.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1238    0.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8042    0.0064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2891   -0.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8042   -1.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0591    0.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0591   -2.1131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1239   -1.4860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8383    1.4015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4094    2.2265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8416    1.4015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7064    1.3695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7688    1.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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  9  1  0  0  0  0
  1  6  2  0  0  0  0
  8  1  1  0  0  0  0
  7  8  2  0  0  0  0
  9 10  2  0  0  0  0
  7 10  1  0  0  0  0
 13  3  1  0  0  0  0
  3  2  2  0  0  0  0
 11  2  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 13 15  2  0  0  0  0
  5 16  2  0  0  0  0
 10 17  1  0  0  0  0
  7 18  1  0  0  0  0
  8 19  1  0  0  0  0
 14 20  1  0  0  0  0
 14 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0049156

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1CC(=O)C2=C1C1=C(C=C(O)C(O)=C1O)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C13H8O8/c14-5-2-4-7(10(17)9(5)16)8-3(12(18)19)1-6(15)11(8)21-13(4)20/h2-3,14,16-17H,1H2,(H,18,19)

> <INCHI_KEY>
JFJWMFPFMLRLMI-UHFFFAOYSA-N

> <FORMULA>
C13H8O8

> <MOLECULAR_WEIGHT>
292.1978

> <EXACT_MASS>
292.021917232

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
25.29680585925856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.38

> <JCHEM_LOGP>
0.4143267856666668

> <ALOGPS_LOGS>
-1.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.685074288983295

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9120313762904333

> <JCHEM_PKA_STRONGEST_BASIC>
-6.732237543344348

> <JCHEM_POLAR_SURFACE_AREA>
141.36

> <JCHEM_REFRACTIVITY>
67.03070000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.96e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.570   0.306   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.903  -0.464   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.903  -2.004   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.570  -2.774   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.764  -2.004   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.764  -0.464   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.764   2.616   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.570   1.846   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.098   0.306   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.098   1.846   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.368   0.012   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.273  -1.234   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.368  -2.480   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.844   1.477   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.844  -3.944   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.098  -2.774   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.431   2.616   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.764   4.156   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.571   2.616   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -3.185   2.556   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -5.168   1.875   0.000  0.00  0.00           O+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3   11                                                  
CONECT    3    4   13    2                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    9    1                                                  
CONECT    7    8   10   18                                                  
CONECT    8    1    7   19                                                  
CONECT    9    6   10                                                       
CONECT   10    9    7   17                                                  
CONECT   11    2   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13    3   12   15                                                  
CONECT   14   11   20   21                                                  
CONECT   15   13                                                            
CONECT   16    5                                                            
CONECT   17   10                                                            
CONECT   18    7                                                            
CONECT   19    8                                                            
CONECT   20   14                                                            
CONECT   21   14                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
Brevifolincarboxylate	Generator

Chemical Formula

C₁₃H₈O₈

Average Mass

292.1978 Da

Monoisotopic Mass

292.02192 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

18490-95-4

SMILES

OC(=O)C1CC(=O)C2=C1C1=C(C=C(O)C(O)=C1O)C(=O)O2

InChI Identifier

InChI=1S/C13H8O8/c14-5-2-4-7(10(17)9(5)16)8-3(12(18)19)1-6(15)11(8)21-13(4)20/h2-3,14,16-17H,1H2,(H,18,19)

InChI Key

JFJWMFPFMLRLMI-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Combretum indicum	LOTUS Database	35616633
Elaeagnus umbellata	LOTUS Database	35616633
Mallotus repandus	LOTUS Database	35616633
Melaleuca leucadendra	LOTUS Database	35616633
Pelargonium reniforme	Plant	KNApSAcK
Phyllanthus flexuosus	LOTUS Database	35616633
Phyllanthus niruri	LOTUS Database	35616633
Phyllanthus urinaria	LOTUS Database	35616633
Phyllanthus virgatus	LOTUS Database	35616633
Punica granatum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Ketone
Lactone
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	1.38	ALOGPS
logP	0.41	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	2.91	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	141.36 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.03 m³·mol⁻¹	ChemAxon
Polarizability	25.3 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

FDB017920

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

9838995

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Brevifolincarboxylic acid (NP0049156)

MOL for NP0049156 (Brevifolincarboxylic acid)

3D MOL for NP0049156 (Brevifolincarboxylic acid)

3D SDF for NP0049156 (Brevifolincarboxylic acid)

3D-SDF for NP0049156 (Brevifolincarboxylic acid)

PDB for NP0049156 (Brevifolincarboxylic acid)

3D PDB for NP0049156 (Brevifolincarboxylic acid)

SMILES for NP0049156 (Brevifolincarboxylic acid)

INCHI for NP0049156 (Brevifolincarboxylic acid)

Structure for NP0049156 (Brevifolincarboxylic acid)

3D Structure for NP0049156 (Brevifolincarboxylic acid)