NP-MRD: Showing NP-Card for Geranyl acetoacetate (NP0337594)

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Record Information

Version

2.0

Created at

2024-09-11 11:32:07 UTC

Updated at

2024-09-11 11:32:08 UTC

NP-MRD ID

NP0337594

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Geranyl acetoacetate

Description

Geranyl acetoacetate, also known as fema 2510 or geranyl 3-oxobutanoate, belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Geranyl acetoacetate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Geranyl acetoacetate is a sweet, apple skin, and fermented tasting compound. Outside of the human body,.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310192D          

 17 16  0  0  0  0            999 V2000
   -3.2704   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    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
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  6  2  0  0  0  0
 12  3  1  0  0  0  0
 12  7  1  0  0  0  0
 12  8  2  0  0  0  0
 13  4  1  0  0  0  0
 13 10  1  0  0  0  0
 14 10  1  0  0  0  0
 15 13  2  0  0  0  0
 16 14  2  0  0  0  0
 17  9  1  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337594

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)CC(=O)OC\C=C(\C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C14H22O3/c1-11(2)6-5-7-12(3)8-9-17-14(16)10-13(4)15/h6,8H,5,7,9-10H2,1-4H3/b12-8-

> <INCHI_KEY>
RYILZWKGLGVPOC-WQLSENKSSA-N

> <FORMULA>
C14H22O3

> <MOLECULAR_WEIGHT>
238.3227

> <EXACT_MASS>
238.15689457

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.24669036674354

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3,7-dimethylocta-2,6-dien-1-yl 3-oxobutanoate

> <ALOGPS_LOGP>
3.70

> <JCHEM_LOGP>
3.165362674999999

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.392428162495866

> <JCHEM_PKA_STRONGEST_BASIC>
-6.967411446340511

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
70.22879999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3,7-dimethylocta-2,6-dien-1-yl 3-oxobutanoate

> <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      -6.105  -7.494   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.438  -5.184   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.771  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.898  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.771  -3.644   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.771  -5.184   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.437  -2.874   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.231  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.105  -5.954   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.437  -1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.565  -1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.897  -1.334   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.565  -2.874   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.897  -2.874   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.564  -0.564   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   13                                                            
CONECT    5    6    7                                                       
CONECT    6    5   11                                                       
CONECT    7    5   12                                                       
CONECT    8    9   12                                                       
CONECT    9    8   17                                                       
CONECT   10   13   14                                                       
CONECT   11    1    2    6                                                  
CONECT   12    3    7    8                                                  
CONECT   13    4   10   15                                                  
CONECT   14   10   16   17                                                  
CONECT   15   13                                                            
CONECT   16   14                                                            
CONECT   17    9   14                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

View in JSmol

Synonyms

Value	Source
Geranyl acetoacetic acid	Generator
(e)-3,7-Dimethyl-2,6-octadienyl 3-oxobutanoate	HMDB
(e)-3,7-Dimethyl-2,6-octadienyl acetoacetate	HMDB
3,7-Dimethyl-2,6-octadienyl ester(e)-acetoacetic acid	HMDB
Acetoacetic acid, 3,7-dimethyl-2,6-octadienyl ester	HMDB
FEMA 2510	HMDB
Geranyl 3-oxobutanoate	HMDB
Geranyl beta-ketobutyrate	HMDB
trans-3,7-Dimethyl-2,6-octadien-1-yl 3-oxobutanoate	HMDB
trans-3,7-Dimethyl-2,6-octadien-1-yl acetoacetate	HMDB

Chemical Formula

C₁₄H₂₂O₃

Average Mass

238.3227 Da

Monoisotopic Mass

238.15689 Da

IUPAC Name

(2Z)-3,7-dimethylocta-2,6-dien-1-yl 3-oxobutanoate

Traditional Name

(2Z)-3,7-dimethylocta-2,6-dien-1-yl 3-oxobutanoate

CAS Registry Number

Not Available

SMILES

CC(=O)CC(=O)OC\C=C(\C)CCC=C(C)C

InChI Identifier

InChI=1S/C14H22O3/c1-11(2)6-5-7-12(3)8-9-17-14(16)10-13(4)15/h6,8H,5,7,9-10H2,1-4H3/b12-8-

InChI Key

RYILZWKGLGVPOC-WQLSENKSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohol esters

Direct Parent

Fatty alcohol esters

Alternative Parents

Substituents

Fatty alcohol ester
Acyclic monoterpenoid
Monoterpenoid
Beta-keto acid
Fatty acid ester
1,3-dicarbonyl compound
Keto acid
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	3.7	ALOGPS
logP	3.17	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	10.39	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	70.23 m³·mol⁻¹	ChemAxon
Polarizability	27.25 Å³	ChemAxon
Number of Rings	0	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

HMDB0038256

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017550

KNApSAcK ID

Not Available

Chemspider ID

30777244

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54611954

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Geranyl acetoacetate (NP0337594)

MOL for NP0337594 (Geranyl acetoacetate)

3D MOL for NP0337594 (Geranyl acetoacetate)

3D SDF for NP0337594 (Geranyl acetoacetate)

3D-SDF for NP0337594 (Geranyl acetoacetate)

PDB for NP0337594 (Geranyl acetoacetate)

3D PDB for NP0337594 (Geranyl acetoacetate)

SMILES for NP0337594 (Geranyl acetoacetate)

INCHI for NP0337594 (Geranyl acetoacetate)

Structure for NP0337594 (Geranyl acetoacetate)

3D Structure for NP0337594 (Geranyl acetoacetate)