NP-MRD: Showing NP-Card for Grasshopper ketone (NP0342021)

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Record Information

Version

2.0

Created at

2024-12-04 23:46:34 UTC

Updated at

2026-01-07 06:35:14 UTC

NP-MRD ID

NP0342021

Natural Product DOI

https://doi.org/10.57994/3516

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Grasshopper ketone

Description

3,5-Dihydroxy-6,7-megastigmadien-9-one belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 3,5-Dihydroxy-6,7-megastigmadien-9-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241214382D          

 16 16  0  0  0  0            999 V2000
   -1.0726   -0.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012   -0.9591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0726    0.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6020    1.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5419    1.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4550   -0.4036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0711    1.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574    0.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3576    0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3576   -0.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0758   -1.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5012    1.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.1341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  2  0  0  0  0
  9 14  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0342021

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C=C=C1C(C)(C)CC(O)CC1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O3/c1-9(14)5-6-11-12(2,3)7-10(15)8-13(11,4)16/h5,10,15-16H,7-8H2,1-4H3

> <INCHI_KEY>
QMXLZUOHZGYGDY-UHFFFAOYSA-N

> <FORMULA>
C13H20O3

> <MOLECULAR_WEIGHT>
224.2961

> <EXACT_MASS>
224.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.657716497461777

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene)but-3-en-2-one

> <ALOGPS_LOGP>
1.55

> <JCHEM_LOGP>
0.7767904559999997

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.263725075318526

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.007504388621555

> <JCHEM_PKA_STRONGEST_BASIC>
-2.743137723333313

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
63.883799999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene)but-3-en-2-one

> <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  C   UNK     0      -2.002  -1.790   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.334  -1.020   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.669  -1.790   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -3.334   0.520   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.002   1.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.990   2.468   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.012   2.468   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.849  -0.753   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.999   2.060   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.667   1.290   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.668   0.520   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.668  -1.020   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.141  -2.468   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.334   1.290   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.669   2.060   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.334  -0.250   0.000  0.00  0.00           O+0
CONECT    1    2   12                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   11                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8   12                                                            
CONECT    9   10   14                                                       
CONECT   10    9   11                                                       
CONECT   11    5   10   12                                                  
CONECT   12    1    8   11   13                                             
CONECT   13   12                                                            
CONECT   14    9   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₂₀O₃

Average Mass

224.2961 Da

Monoisotopic Mass

224.14124 Da

IUPAC Name

4-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene)but-3-en-2-one

Traditional Name

4-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene)but-3-en-2-one

CAS Registry Number

Not Available

SMILES

CC(=O)C=C=C1C(C)(C)CC(O)CC1(C)O

InChI Identifier

InChI=1S/C13H20O3/c1-9(14)5-6-11-12(2,3)7-10(15)8-13(11,4)16/h5,10,15-16H,7-8H2,1-4H3

InChI Key

QMXLZUOHZGYGDY-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	[email protected]	University of Mississippi	Sophie Fadime Aydogan	2024-12-04	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	[email protected]	University of Mississippi	Sophie Fadime Aydogan	2024-12-04	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	[email protected]	University of Mississippi	Sophie Fadime Aydogan	2024-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	[email protected]	University of Mississippi	Sophie Fadime Aydogan	2024-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	[email protected]	University of Mississippi	Sophie Fadime Aydogan	2024-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	[email protected]	University of Mississippi	Sophie Fadime Aydogan	2024-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CD3OD, experimental)	[email protected]	University of Mississippi	Sophie Fadime Aydogan	2024-12-04	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dalbergiella welwitschii		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Megastigmane sesquiterpenoid
Sesquiterpenoid
Tertiary alcohol
Enone
Cyclic alcohol
Acryloyl-group
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

a 9-apo-carotenone (CPD-7201 )

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	1.55	ALOGPS
logP	0.78	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	14.01	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	63.88 m³·mol⁻¹	ChemAxon
Polarizability	24.66 Å³	ChemAxon
Number of Rings	1	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013523

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10220146

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Grasshopper ketone (NP0342021)

MOL for NP0342021 (Grasshopper ketone)

3D MOL for NP0342021 (Grasshopper ketone)

3D SDF for NP0342021 (Grasshopper ketone)

3D-SDF for NP0342021 (Grasshopper ketone)

PDB for NP0342021 (Grasshopper ketone)

3D PDB for NP0342021 (Grasshopper ketone)

SMILES for NP0342021 (Grasshopper ketone)

INCHI for NP0342021 (Grasshopper ketone)

Structure for NP0342021 (Grasshopper ketone)

3D Structure for NP0342021 (Grasshopper ketone)