NP-MRD: Showing NP-Card for Taraxinic acid (NP0048320)

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Record Information

Version

2.0

Created at

2022-03-17 20:54:35 UTC

Updated at

2022-03-17 20:54:35 UTC

NP-MRD ID

NP0048320

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Taraxinic acid

Description

Taraxinic acid, also known as taraxinate, belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Taraxinic acid is found in Perymenium discolor. Taraxinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241214262D          

 19 20  0  0  0  0            999 V2000
   -0.6463   -1.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0653   -1.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4679   -0.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2718    0.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2794    0.7148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9929    0.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7366    0.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0425   -0.1147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9430   -0.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4723   -1.4903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8747   -2.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8918   -0.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2781   -0.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3616   -1.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0425   -2.0149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8541    2.1190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0759    1.7977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3968    2.2524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6173   -1.9860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  2  0  0  0  0
  2  3  1  0  0  0  0
  2 19  1  0  0  0  0
  3  4  1  0  0  0  0
  3 13  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 17  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 19  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048320

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C\C2OC(=O)C(=C)C2CC\C(=C/CC1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O4/c1-9-4-3-5-11(14(16)17)6-7-12-10(2)15(18)19-13(12)8-9/h5,8,12-13H,2-4,6-7H2,1H3,(H,16,17)/b9-8-,11-5+

> <INCHI_KEY>
KZWCOWFKXMTBRH-IMDCMVKOSA-N

> <FORMULA>
C15H18O4

> <MOLECULAR_WEIGHT>
262.301

> <EXACT_MASS>
262.120509064

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.114242783108267

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylic acid

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
3.007859245666666

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.569612065092144

> <JCHEM_PKA_STRONGEST_BASIC>
-6.874751580755802

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
71.66359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.65e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-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      -1.206  -2.928   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.122  -2.563   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.873  -1.139   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.507   0.188   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.522   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.853   1.754   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.242   1.085   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.813  -0.214   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.627  -1.666   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.748  -2.782   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.499  -4.204   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.531  -0.408   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.386  -1.437   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.542  -3.040   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.813  -3.761   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -3.461   3.955   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.008   3.356   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.741   4.204   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.152  -3.707   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3   19                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    1    9   11                                                  
CONECT   11   10                                                            
CONECT   12   13                                                            
CONECT   13    3   12   14                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14                                                            
CONECT   16   17                                                            
CONECT   17    6   16   18                                                  
CONECT   18   17                                                            
CONECT   19    2   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
Taraxinate	Generator

Chemical Formula

C₁₅H₁₈O₄

Average Mass

262.3010 Da

Monoisotopic Mass

262.12051 Da

IUPAC Name

10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylic acid

Traditional Name

10-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylic acid

CAS Registry Number

Not Available

SMILES

C\C1=C\C2OC(=O)C(=C)C2CC\C(=C/CC1)C(O)=O

InChI Identifier

InChI=1S/C15H18O4/c1-9-4-3-5-11(14(16)17)6-7-12-10(2)15(18)19-13(12)8-9/h5,8,12-13H,2-4,6-7H2,1H3,(H,16,17)/b9-8-,11-5+

InChI Key

KZWCOWFKXMTBRH-IMDCMVKOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Perymenium discolor	Plant	KNApSAcK
Taraxacum officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.43	ALOGPS
logP	3.01	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.57	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.66 m³·mol⁻¹	ChemAxon
Polarizability	27.11 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014521

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Taraxinic acid (NP0048320)

MOL for NP0048320 (Taraxinic acid)

3D MOL for NP0048320 (Taraxinic acid)

3D SDF for NP0048320 (Taraxinic acid)

3D-SDF for NP0048320 (Taraxinic acid)

PDB for NP0048320 (Taraxinic acid)

3D PDB for NP0048320 (Taraxinic acid)

SMILES for NP0048320 (Taraxinic acid)

INCHI for NP0048320 (Taraxinic acid)

Structure for NP0048320 (Taraxinic acid)

3D Structure for NP0048320 (Taraxinic acid)