NP-MRD: Showing NP-Card for alpha-Eleostearic acid (NP0047885)

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Record Information

Version

2.0

Created at

2022-03-17 20:47:33 UTC

Updated at

2022-03-17 20:47:33 UTC

NP-MRD ID

NP0047885

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-Eleostearic acid

Description

Alpha-Eleostearic acid, also known as 9t,11C,13t-CLN or a-eleostearate, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Alpha-Eleostearic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, alpha-Eleostearic acid is found, on average, in the highest concentration within bitter gourds. Alpha-Eleostearic acid has also been detected, but not quantified in, fruits. This could make alpha-eleostearic acid a potential biomarker for the consumption of these foods. alpha-Eleostearic acid is found in Aleurites cordata, Centranthus macrosiphon , Pleurocybella porrigens , Punica granatum , Trichosanthes cucumeroides , Trichosanthes kirilowii, Trichosanthes ovigera, Trichosanthes rosthornii and Trichosanthes tricuspidata. A 9,11,13-octadecatrienoic acid having its double bonds in trans, cis and trans configurations, respectively.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241217352D          

 20 19  0  0  0  0            999 V2000
    2.5159    2.1034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734    1.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734    0.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    0.3709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734   -0.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734   -1.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -2.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709   -1.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709   -2.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133   -1.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734   -2.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5159   -1.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5159   -0.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734   -0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734    0.3709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133    0.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709    0.3709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709   -0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    2.1034    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
  2 20  2  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  7  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  2  0  0  0  0
 11 12  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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047885

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC\C=C\C=C/C=C/CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h5-10H,2-4,11-17H2,1H3,(H,19,20)/b6-5+,8-7-,10-9+

> <INCHI_KEY>
CUXYLFPMQMFGPL-MRZTUZPCSA-N

> <FORMULA>
C18H30O2

> <MOLECULAR_WEIGHT>
278.4296

> <EXACT_MASS>
278.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
35.911822169017995

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9E,11Z,13E)-octadeca-9,11,13-trienoic acid

> <ALOGPS_LOGP>
6.65

> <JCHEM_LOGP>
6.059955137666666

> <ALOGPS_LOGS>
-6.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167283903808

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
89.63539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.42e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9t,11c,13t-linolenic 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  O   UNK     0       4.696   3.926   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.310   3.156   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.310   1.462   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.078   0.692   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.078  -0.846   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.310  -1.616   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.310  -3.156   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.078  -3.926   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.692  -3.156   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.692  -3.926   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.078  -3.156   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.310  -3.926   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.696  -3.156   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.696  -1.616   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.310  -0.846   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.310   0.692   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.078   1.462   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.692   0.692   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.692  -0.846   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.078   3.926   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20    2                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol

Synonyms

Value	Source
(9E,11Z,13E)-9,11,13-Octadecatrienoic acid	ChEBI
(e,Z,e)-9,11,13-Octadecatrienoic acid	ChEBI
9-trans,11-cis,13-trans-Octadecatrienoic acid	ChEBI
9t,11C,13t-CLN	ChEBI
9t,11C,13t-CLnA	ChEBI
9t,11C,13t-Conjugated linolenic acid	ChEBI
9t,11C,13t-Linolenic acid	ChEBI
9trans,11-cis,13trans-Octadecatrienoic acid	ChEBI
C18:3 N-5 trans, 7 cis, 9 trans	ChEBI
Octadeca-9t,11C,13t-trienoic acid	ChEBI
Octadeca-9t,11C,13t-triensaeure	ChEBI
t9,C11,t13-CLN	ChEBI
t9,C11,t13-CLnA	ChEBI
t9,C11,t13-Conjugated linolenic acid	ChEBI
t9,C11,t13-Linolenic acid	ChEBI
(9E,11Z,13E)-9,11,13-Octadecatrienoate	Generator
(e,Z,e)-9,11,13-Octadecatrienoate	Generator
9-trans,11-cis,13-trans-Octadecatrienoate	Generator
9t,11C,13t-Conjugated linolenate	Generator
9t,11C,13t-Linolenate	Generator
9trans,11-cis,13trans-Octadecatrienoate	Generator
Octadeca-9t,11C,13t-trienoate	Generator
t9,C11,t13-Conjugated linolenate	Generator
t9,C11,t13-Linolenate	Generator
a-Eleostearate	Generator
a-Eleostearic acid	Generator
alpha-Eleostearate	Generator
Α-eleostearate	Generator
Α-eleostearic acid	Generator
Punicate	Generator, HMDB
(9Z,11E,13Z)-Octadeca-9,11,13-trienoic acid	HMDB
cis-9,trans-11,cis-13-Octadecatrienoic acid	HMDB
Eleostearic acid	HMDB
Punicinic acid	HMDB
Trichosanic acid	HMDB
9E,11Z,13E-Octadecatrienoate	Generator
9,11,13-CLN	MeSH
9C,11t,13t-CLN	MeSH
Eleostearic acid, (e,Z,e)-isomer	MeSH
9,11,13-Octadecatrienoic acid	MeSH
9cis,11trans,13trans-Conjugated linolenic acid	MeSH
Eleostearic acid, (e,e,e)-isomer	MeSH
9,11,13-Conjugated linolenic acid	MeSH
Eleostearic acid, (Z,e,e)-isomer	MeSH
Eleostearic acid, (Z,Z,e)-isomer	MeSH

Chemical Formula

C₁₈H₃₀O₂

Average Mass

278.4296 Da

Monoisotopic Mass

278.22458 Da

IUPAC Name

(9E,11Z,13E)-octadeca-9,11,13-trienoic acid

Traditional Name

9t,11c,13t-linolenic acid

CAS Registry Number

544-72-9

SMILES

CCCC\C=C\C=C/C=C/CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h5-10H,2-4,11-17H2,1H3,(H,19,20)/b6-5+,8-7-,10-9+

InChI Key

CUXYLFPMQMFGPL-MRZTUZPCSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aleurites cordata	Plant	KNApSAcK
Centranthus macrosiphon	Plant	KNApSAcK
Momordica charantia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pleurocybella porrigens	Fungi	KNApSAcK
Punica granatum	Plant	KNApSAcK
Trichosanthes cucumeroides	Plant	KNApSAcK
Trichosanthes kirilowii	LOTUS Database	35616633
Trichosanthes ovigera	LOTUS Database	35616633
Trichosanthes rosthornii	LOTUS Database	35616633
Trichosanthes tricuspidata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
Fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

9,11,13-octadecatrienoic acid (CHEBI:38383 )

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	6.65	ALOGPS
logP	6.06	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	89.64 m³·mol⁻¹	ChemAxon
Polarizability	35.91 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030963

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012466

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alpha-Eleostearic acid

METLIN ID

Not Available

PubChem Compound

12309425

PDB ID

Not Available

ChEBI ID

38383

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for alpha-Eleostearic acid (NP0047885)

MOL for NP0047885 (alpha-Eleostearic acid)

3D MOL for NP0047885 (alpha-Eleostearic acid)

3D SDF for NP0047885 (alpha-Eleostearic acid)

3D-SDF for NP0047885 (alpha-Eleostearic acid)

PDB for NP0047885 (alpha-Eleostearic acid)

3D PDB for NP0047885 (alpha-Eleostearic acid)

SMILES for NP0047885 (alpha-Eleostearic acid)

INCHI for NP0047885 (alpha-Eleostearic acid)

Structure for NP0047885 (alpha-Eleostearic acid)

3D Structure for NP0047885 (alpha-Eleostearic acid)