NP-MRD: Showing NP-Card for Ginkgoic acid (NP0047780)

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Record Information

Version

2.0

Created at

2022-03-17 20:45:50 UTC

Updated at

2022-03-17 20:45:50 UTC

NP-MRD ID

NP0047780

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ginkgoic acid

Description

Ginkgoic acid, also known as ginkgoate or (8E)-anacardate, belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids. Ginkgoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Ginkgoic acid has been detected, but not quantified in, several different foods, such as cashew nuts, fats and oils, ginkgo nuts, and nuts. Ginkgoic acid is found in Amphipterygium adstringens, Brucea javanica, Knema laurina, Myrcia multiflora and Ozoroa insignis. This could make ginkgoic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307252D          

 25 25  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -1.6500    0.0000 O   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  2  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  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  2  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  2  0  0  0  0
 21 19  2  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 20  1  0  0  0  0
 24 22  2  0  0  0  0
 25 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047780

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC\C=C\CCCCCCCC1=C(C(O)=O)C(O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h7-8,15,17-18,23H,2-6,9-14,16H2,1H3,(H,24,25)/b8-7+

> <INCHI_KEY>
YXHVCZZLWZYHSA-BQYQJAHWSA-N

> <FORMULA>
C22H34O3

> <MOLECULAR_WEIGHT>
346.5036

> <EXACT_MASS>
346.250794954

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
43.120529525474986

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-6-[(8E)-pentadec-8-en-1-yl]benzoic acid

> <ALOGPS_LOGP>
7.76

> <JCHEM_LOGP>
8.352724445

> <ALOGPS_LOGS>
-6.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.364273313389209

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.640733551078049

> <JCHEM_PKA_STRONGEST_BASIC>
-6.287065354678508

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
105.86689999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.89e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-6-[(8E)-pentadec-8-en-1-yl]benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.671  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.004  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.338  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.672  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.006  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.005  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.673  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.006  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.339  -1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.673  -3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      21.339  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.005  -3.850   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      22.673  -5.390   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      20.005  -5.390   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      18.672  -3.080   0.000  0.00  0.00           O+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                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   16                                                       
CONECT   15   17   18                                                       
CONECT   16   14   19                                                       
CONECT   17   15   19                                                       
CONECT   18   15   20                                                       
CONECT   19   16   17   21                                                  
CONECT   20   18   21   23                                                  
CONECT   21   19   20   22                                                  
CONECT   22   21   24   25                                                  
CONECT   23   20                                                            
CONECT   24   22                                                            
CONECT   25   22                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

View in JSmol

Synonyms

Value	Source
Ginkgoate	Generator
6-(8'e-Pentadecaenyl)salicylic acid	HMDB
(8E)-Anacardic acid	HMDB
6-(8'e-Pentadecaenyl)salicylate	HMDB
(8E)-Anacardate	HMDB
(Z)-2-Hydroxy-6-(8-pentadecenyl)benzoic acid	HMDB
2-Hydroxy-6-(8-pentadecenyl)-(Z)-benzoic acid	HMDB
2-Hydroxy-6-(8-pentadecenyl)benzoic acid, 9ci	HMDB
6-(8-Pentadecenyl)salicylic acid	HMDB
Ginkgolic acid	HMDB
2-Hydroxy-6-[(8E)-pentadec-8-en-1-yl]benzoate	Generator

Chemical Formula

C₂₂H₃₄O₃

Average Mass

346.5036 Da

Monoisotopic Mass

346.25079 Da

IUPAC Name

2-hydroxy-6-[(8E)-pentadec-8-en-1-yl]benzoic acid

Traditional Name

2-hydroxy-6-[(8E)-pentadec-8-en-1-yl]benzoic acid

CAS Registry Number

22910-60-7

SMILES

CCCCCC\C=C\CCCCCCCC1=C(C(O)=O)C(O)=CC=C1

InChI Identifier

InChI=1S/C22H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h7-8,15,17-18,23H,2-6,9-14,16H2,1H3,(H,24,25)/b8-7+

InChI Key

YXHVCZZLWZYHSA-BQYQJAHWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amphipterygium adstringens	LOTUS Database	35616633
Anacardium occidentale	FooDB	KNAPSACK
Brucea javanica	LOTUS Database	35616633
Ginkgo biloba	FooDB	KNAPSACK
Knema laurina	LOTUS Database	35616633
Myrcia multiflora	LOTUS Database	35616633
Ozoroa insignis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Salicylic acids

Alternative Parents

Substituents

Salicylic acid
Benzoic acid
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	7.76	ALOGPS
logP	8.35	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	2.64	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	105.87 m³·mol⁻¹	ChemAxon
Polarizability	43.12 Å³	ChemAxon
Number of Rings	1	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

HMDB0033897

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5317600

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ginkgoic acid (NP0047780)

MOL for NP0047780 (Ginkgoic acid)

3D MOL for NP0047780 (Ginkgoic acid)

3D SDF for NP0047780 (Ginkgoic acid)

3D-SDF for NP0047780 (Ginkgoic acid)

PDB for NP0047780 (Ginkgoic acid)

3D PDB for NP0047780 (Ginkgoic acid)

SMILES for NP0047780 (Ginkgoic acid)

INCHI for NP0047780 (Ginkgoic acid)

Structure for NP0047780 (Ginkgoic acid)

3D Structure for NP0047780 (Ginkgoic acid)