Showing NP-Card for Gadoleic acid (NP0046242)

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Record Information
Version2.0
Created at2022-03-17 19:54:52 UTC
Updated at2022-03-17 19:54:53 UTC
NP-MRD IDNP0046242
Secondary Accession NumbersNone
Natural Product Identification
Common NameGadoleic acid
DescriptionGadoleic acid, also known as 9C-eicosensaeure or C20:1C, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Gadoleic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Gadoleic acid is found, on average, in the highest concentration within a few different foods, such as other fish products, lumpsuckers, and white mustards and in a lower concentration in garfish, lards, and buttermilks. Gadoleic acid has also been detected, but not quantified in, several different foods, such as sweet oranges, tea, rices, thistles, and lemons. This could make gadoleic acid a potential biomarker for the consumption of these foods. Gadoleic acid is found in Chlamydomonas reinhardtii. An icosenoic acid having a cis- double bond at position 9.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0046242 (Gadoleic acid)

  Mrv1652306301800182D          

 24 23  0  0  0  0            999 V2000
    4.2355   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092   -1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092   -0.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237   -0.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237    0.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381    0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381    1.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9526    2.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9526    2.9171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6671    1.6796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802   -4.0954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092   -3.2704    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
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  2  0  0  0  0
 22 20  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  1  0  0  0  0
M  END
Download

3D MOL for NP0046242 (Gadoleic acid)

Download
3D SDF for NP0046242 (Gadoleic acid)
  Mrv1652306301800182D          

 24 23  0  0  0  0            999 V2000
    4.2355   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092   -1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092   -0.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237   -0.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237    0.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381    0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381    1.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9526    2.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9526    2.9171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6671    1.6796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802   -4.0954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092   -3.2704    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
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  2  0  0  0  0
 22 20  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046242

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(CCCCCCCCCC)=C(/[H])CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h11-12H,2-10,13-19H2,1H3,(H,21,22)/b12-11-

> <INCHI_KEY>
LQJBNNIYVWPHFW-QXMHVHEDSA-N

> <FORMULA>
C20H38O2

> <MOLECULAR_WEIGHT>
310.522

> <EXACT_MASS>
310.287180464

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
41.32220070505214

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9Z)-icos-9-enoic acid

> <ALOGPS_LOGP>
8.41

> <JCHEM_LOGP>
7.672935781000001

> <ALOGPS_LOGS>
-6.80

> <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>
96.60419999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.92e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gadoleic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0046242 (Gadoleic acid)
Download
PDB for NP0046242 (Gadoleic acid)
HEADER    PROTEIN                                 30-JUN-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-18         0                                  
HETATM    1  C   UNK     0       7.906  -6.105   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.240  -5.335   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.574  -6.105   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.907  -5.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.241  -6.105   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.575  -5.335   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.908  -6.105   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.242  -5.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.576  -6.105   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.909  -5.335   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.243  -6.105   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.577  -5.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.577  -3.795   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.910  -3.025   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.910  -1.485   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.244  -0.715   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.244   0.825   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.578   1.595   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.578   3.135   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.912   3.905   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      27.912   5.445   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      29.245   3.135   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0      21.243  -7.645   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      23.910  -6.105   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    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   23                                                  
CONECT   12   11   13   24                                                  
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   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   11                                                            
CONECT   24   12                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

Download
3D PDB for NP0046242 (Gadoleic acid)
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SMILES for NP0046242 (Gadoleic acid)
[H]\C(CCCCCCCCCC)=C(/[H])CCCCCCCC(O)=O
Download
INCHI for NP0046242 (Gadoleic acid)
InChI=1S/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h11-12H,2-10,13-19H2,1H3,(H,21,22)/b12-11-
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Synonyms
Chemical FormulaC20H38O2
Average Mass310.5220 Da
Monoisotopic Mass310.28718 Da
IUPAC Name(9Z)-icos-9-enoic acid
Traditional Namegadoleic acid
CAS Registry Number29204-02-2
SMILES
[H]\C(CCCCCCCCCC)=C(/[H])CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h11-12H,2-10,13-19H2,1H3,(H,21,22)/b12-11-
InChI KeyLQJBNNIYVWPHFW-QXMHVHEDSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acids and conjugates  
Direct ParentLong-chain fatty acids  
Alternative Parents
Substituents
  • Long-chain 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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.41ALOGPS
logP7.67ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity96.6 m³·mol⁻¹ChemAxon
Polarizability41.32 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0062436  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003771  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGadoleic acid  
METLIN IDNot Available
PubChem Compound5282767  
PDB IDNot Available
ChEBI ID32419  
Good Scents IDNot Available
References
General ReferencesNot Available