NP-MRD: Showing NP-Card for Coronaric acid (NP0046109)

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Record Information

Version

2.0

Created at

2022-03-17 19:48:32 UTC

Updated at

2022-03-17 19:48:32 UTC

NP-MRD ID

NP0046109

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Coronaric acid

Description

Coronaric acid, also known as coronarate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Coronaric acid is found in Acacia mearnsii, Acacia pubescens and Pseudo-nitzschia multistriata. Coronaric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

  Mrv1652305221920062D          

 23 23  0  0  0  0            999 V2000
   -4.8908   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1763   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4618   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9533    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184   -1.0164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -3.0789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 15  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 21 16  1  0  0  0  0
 21 17  1  0  0  0  0
 22  7  1  0  0  0  0
 23 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046109

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(CCCCC)=C(\[H])CC1OC1CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O3/c1-2-3-4-5-7-10-13-16-17(21-16)14-11-8-6-9-12-15-18(19)20/h7,10,16-17H,2-6,8-9,11-15H2,1H3,(H,19,20)/b10-7+

> <INCHI_KEY>
FBUKMFOXMZRGRB-JXMROGBWSA-N

> <FORMULA>
C18H32O3

> <MOLECULAR_WEIGHT>
296.4449

> <EXACT_MASS>
296.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.68422089904108

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-{3-[(2E)-oct-2-en-1-yl]oxiran-2-yl}octanoic acid

> <ALOGPS_LOGP>
6.35

> <JCHEM_LOGP>
5.483879889333333

> <ALOGPS_LOGS>
-5.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.615325352098631

> <JCHEM_PKA_STRONGEST_BASIC>
-4.204825765954202

> <JCHEM_POLAR_SURFACE_AREA>
49.83

> <JCHEM_REFRACTIVITY>
86.92309999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.02e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-{3-[(2E)-oct-2-en-1-yl]oxiran-2-yl}octanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0      -9.129  -4.207   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.796  -3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.462  -4.207   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.128  -3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.795  -4.207   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.311  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.461  -3.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.977   0.206   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.645   0.206   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.127  -4.207   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.978  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.206  -3.437   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.310   0.206   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.312   0.206   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.206  -1.897   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.976  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.646  -0.564   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.979   0.206   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      11.646  -2.104   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.564  -0.564   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0      -2.461  -1.897   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      -1.127  -5.747   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    7                                                       
CONECT    6    8    9                                                       
CONECT    7    5   10   22                                                  
CONECT    8    6   11                                                       
CONECT    9    6   12                                                       
CONECT   10    7   13   23                                                  
CONECT   11    8   14                                                       
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   17                                                       
CONECT   15   12   18                                                       
CONECT   16   13   17   21                                                  
CONECT   17   14   16   21                                                  
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   17                                                       
CONECT   22    7                                                            
CONECT   23   10                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

View in JSmol

Synonyms

Value	Source
Coronarate	Generator
9,10-Epoxy-12-octadecenoate	MeSH
9,10-Epoxy-12-octadecenoic acid, (2alpha,3alpha(Z))-isomer	MeSH

Chemical Formula

C₁₈H₃₂O₃

Average Mass

296.4449 Da

Monoisotopic Mass

296.23514 Da

IUPAC Name

8-{3-[(2E)-oct-2-en-1-yl]oxiran-2-yl}octanoic acid

Traditional Name

8-{3-[(2E)-oct-2-en-1-yl]oxiran-2-yl}octanoic acid

CAS Registry Number

16833-56-0

SMILES

[H]\C(CCCCC)=C(\[H])CC1OC1CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H32O3/c1-2-3-4-5-7-10-13-16-17(21-16)14-11-8-6-9-12-15-18(19)20/h7,10,16-17H,2-6,8-9,11-15H2,1H3,(H,19,20)/b10-7+

InChI Key

FBUKMFOXMZRGRB-JXMROGBWSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Acacia mearnsii	LOTUS Database	35616633
Acacia pubescens	LOTUS Database	35616633
Chrysanthemum coronarium	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Oryza sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pseudo-nitzschia multistriata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Epoxy fatty acid
Heterocyclic fatty acid
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxide
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Other Octadecanoids (LMFA02000280 )

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	6.35	ALOGPS
logP	5.48	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.83 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	86.92 m³·mol⁻¹	ChemAxon
Polarizability	37.68 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

FDB003107

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Coronaric acid

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 Coronaric acid (NP0046109)

MOL for NP0046109 (Coronaric acid)

3D MOL for NP0046109 (Coronaric acid)

3D SDF for NP0046109 (Coronaric acid)

3D-SDF for NP0046109 (Coronaric acid)

PDB for NP0046109 (Coronaric acid)

3D PDB for NP0046109 (Coronaric acid)

SMILES for NP0046109 (Coronaric acid)

INCHI for NP0046109 (Coronaric acid)

Structure for NP0046109 (Coronaric acid)

3D Structure for NP0046109 (Coronaric acid)