NP-MRD: Showing NP-Card for elenolic acid (NP0227036)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 06:15:11 UTC

Updated at

2022-09-06 06:15:11 UTC

NP-MRD ID

NP0227036

Secondary Accession Numbers

None

Natural Product Identification

Common Name

elenolic acid

Description

2-[(2S,3S,4S)-3-formyl-5-(methoxycarbonyl)-2-methyl-3,4-dihydro-2H-pyran-4-yl]acetic acid belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. elenolic acid is found in Olea europaea. 2-[(2S,3S,4S)-3-formyl-5-(methoxycarbonyl)-2-methyl-3,4-dihydro-2H-pyran-4-yl]acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
    4.4652   -0.9421    0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3323   -0.2089   -0.1778 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0442   -0.5933    0.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9522   -1.6218    0.8809 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8653    0.1292   -0.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0131    1.2444   -1.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865    1.8523   -1.3414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0663    2.1751   -0.2571 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3828    2.6366   -0.8429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2593    0.9900    0.6811 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6696    0.6791    0.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2983    1.2980    1.7478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5335   -0.1979    0.0465 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8080   -1.5007    0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3875   -2.6447   -0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0795   -2.5184   -1.3204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4974   -3.9446    0.3213 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3147   -1.2189    1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5818   -1.8309   -0.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3832   -0.3022    0.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9977    1.5644   -1.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6896    3.0092    0.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1170    3.4047   -1.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9653    1.8488   -1.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9527    3.2044   -0.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7525    1.1751    1.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1809   -0.0937    0.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0312   -0.2529   -0.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2545   -1.5701    1.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9006   -1.6092    0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0956   -4.1610    1.1101 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 17  1  0
 15 16  2  0
 13  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  8 22  1  1
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  1
 11 27  1  0
 13 28  1  6
 14 29  1  0
 14 30  1  0
 17 31  1  0
M  END

169607
  Mrv0541 02271202152D          

 17 17  0  0  1  0            999 V2000
    3.7935   -2.1735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.9360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.9360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.7306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.3015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5560    1.0161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.5235    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0790   -0.9360    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0790   -1.7610    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5080   -0.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810    1.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 13  1  0  0  0  0
  2 14  2  0  0  0  0
  3 15  1  0  0  0  0
  3 17  1  0  0  0  0
  4 16  1  0  0  0  0
  5 15  2  0  0  0  0
  6 16  2  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  7 11  1  6  0  0  0
  8  9  1  0  0  0  0
  8 14  1  1  0  0  0
  9 12  1  1  0  0  0
 10 13  2  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0227036

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](C)[C@@H](C=O)[C@@H]1CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H14O6/c1-6-8(4-12)7(3-10(13)14)9(5-17-6)11(15)16-2/h4-8H,3H2,1-2H3,(H,13,14)/t6-,7-,8+/m0/s1

> <INCHI_KEY>
MQFAJBBHEYTHKF-BIIVOSGPSA-N

> <FORMULA>
C11H14O6

> <MOLECULAR_WEIGHT>
242.2253

> <EXACT_MASS>
242.07903818

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
22.963534182800302

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2S,3S,4S)-3-formyl-5-(methoxycarbonyl)-2-methyl-3,4-dihydro-2H-pyran-4-yl]acetic acid

> <ALOGPS_LOGP>
0.97

> <JCHEM_LOGP>
-0.15086738633333308

> <ALOGPS_LOGS>
-1.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.221015409621947

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.0542419932121465

> <JCHEM_PKA_STRONGEST_BASIC>
-4.7920131863567725

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
56.41020000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
elenolic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 169607                                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  O   UNK     0       7.081  -4.057   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.080  -1.747   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      11.082  -1.747   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.081   3.230   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       9.748   0.563   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       4.771   1.897   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.081  -0.977   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.747  -1.747   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.747  -3.287   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415  -1.747   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   0.563   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -4.057   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415  -3.287   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -0.977   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.748  -0.977   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.311   1.897   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.416  -0.977   0.000  0.00  0.00           C+0
CONECT    1    9   13                                                       
CONECT    2   14                                                            
CONECT    3   15   17                                                       
CONECT    4   16                                                            
CONECT    5   15                                                            
CONECT    6   16                                                            
CONECT    7    8   10   11                                                  
CONECT    8    7    9   14                                                  
CONECT    9    1    8   12                                                  
CONECT   10    7   13   15                                                  
CONECT   11    7   16                                                       
CONECT   12    9                                                            
CONECT   13    1   10                                                       
CONECT   14    2    8                                                       
CONECT   15    3    5   10                                                  
CONECT   16    4    6   11                                                  
CONECT   17    3                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
2-[(2S,3S,4S)-3-Formyl-5-(methoxycarbonyl)-2-methyl-3,4-dihydro-2H-pyran-4-yl]acetate	Generator
Calcium elenolate	MeSH
Elenolic acid ca salt, (2S-(2alpha,3alpha,4beta))-isomer	MeSH
Elenolic acid, calcium (2:1) salt, (2S-(2alpha,3alpha,4beta))-isomer	MeSH
Elenolate	Generator

Chemical Formula

C₁₁H₁₄O₆

Average Mass

242.2253 Da

Monoisotopic Mass

242.07904 Da

IUPAC Name

2-[(2S,3S,4S)-3-formyl-5-(methoxycarbonyl)-2-methyl-3,4-dihydro-2H-pyran-4-yl]acetic acid

Traditional Name

elenolic acid

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](C)[C@@H](C=O)[C@@H]1CC(O)=O

InChI Identifier

InChI=1S/C11H14O6/c1-6-8(4-12)7(3-10(13)14)9(5-17-6)11(15)16-2/h4-8H,3H2,1-2H3,(H,13,14)/t6-,7-,8+/m0/s1

InChI Key

MQFAJBBHEYTHKF-BIIVOSGPSA-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
Olea europaea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Carboxylic acid ester
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxide
Aldehyde
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	0.97	ALOGPS
logP	-0.15	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	4.05	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	56.41 m³·mol⁻¹	ChemAxon
Polarizability	22.96 Å³	ChemAxon
Number of Rings	1	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

169607

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for elenolic acid (NP0227036)

MOL for NP0227036 (elenolic acid)

3D MOL for NP0227036 (elenolic acid)

3D SDF for NP0227036 (elenolic acid)

3D-SDF for NP0227036 (elenolic acid)

PDB for NP0227036 (elenolic acid)

3D PDB for NP0227036 (elenolic acid)

SMILES for NP0227036 (elenolic acid)

INCHI for NP0227036 (elenolic acid)

Structure for NP0227036 (elenolic acid)

3D Structure for NP0227036 (elenolic acid)