NP-MRD: Showing NP-Card for (+/-)-dihydroactinidiolide (NP0286007)

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Record Information

Version

2.0

Created at

2022-09-09 14:24:34 UTC

Updated at

2022-09-09 14:24:34 UTC

NP-MRD ID

NP0286007

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+/-)-dihydroactinidiolide

Description

Dihydroactinidiolide belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Dihydroactinidiolide is a pheromone for a variety of insects; for example, it is one of the three components of the pheromone for queen recognition of the workers of the red fire ant. Dihydroactinidiolide is an extremely weak basic (essentially neutral) compound (based on its pKa). Dihydroactinidiolide is a coumarin and musk tasting compound. Outside of the human body, Dihydroactinidiolide is found, on average, in the highest concentration within safflowers. Dihydroactinidiolide has also been detected, but not quantified in, fenugreeks and tea. This could make dihydroactinidiolide a potential biomarker for the consumption of these foods. Dihydroactinidiolide occurs naturally in black tea, fenugreek, fire ants, mangoes, and tobacco. It has a sweet, tea-like odor and is used as a fragrance. Dihydroactinidiolide is a volatile terpene. (+/-)-dihydroactinidiolide is found in Actinidia polygama, Cannabis sativa, Eleocharis coloradoensis, Tagetes lucida, Triticum aestivum and Vitis vinifera. It has also been prepared synthetically.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -1.5537   -0.9403   -0.9829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1191   -0.0927    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1536   -0.2337    1.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0943    1.3630   -0.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1516    1.8444   -0.8614 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4125    1.3620   -0.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4497   -0.1239   -0.1120 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4447   -0.7458   -1.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5459   -0.5863    0.5869 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1304   -1.2636    1.7374 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8505   -1.8322    2.6077 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6645   -1.1708    1.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2386   -0.5154    0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1942   -0.5910   -1.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6800   -0.8442   -1.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3740   -2.0245   -0.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1665   -0.3954    0.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8322   -1.1347    1.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0810    0.6200    1.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2557    1.9554    0.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9664    1.5375   -0.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1276    1.6750   -1.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1614    2.9707   -0.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292    1.7753    0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2881    1.7562   -0.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1217   -0.0623   -2.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5132   -0.9930   -1.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8909   -1.6938   -1.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0503   -1.6157    2.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  6
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
  2 13  1  0
 13 12  2  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
 13  7  1  0
  9  7  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  6 24  1  0
  6 25  1  0
  5 22  1  0
  5 23  1  0
  4 20  1  0
  4 21  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
 12 29  1  0
M  END

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       5.914   5.562   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.934   5.562   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.429   0.541   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.320   2.843   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4    5    6                                                       
CONECT    5    4   10                                                       
CONECT    6    4   11                                                       
CONECT    7    8    9                                                       
CONECT    8    7   10   11                                                  
CONECT    9    7   12   13                                                  
CONECT   10    1    2    5    8                                             
CONECT   11    3    6    8   13                                             
CONECT   12    9                                                            
CONECT   13    9   11                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol

Synonyms

Value	Source
2-Hydroxy-2,6,6-trimethylcyclohexylidene-1-acetic acid lactone	HMDB
4,4,7a-Trimethyl-5,6,7,7a-tetrahydro-4H-benzofuran-2-one	HMDB
4,5,7,7a-Tetrahydro-4,4,7a-trimethyl-2(6H)benzofuranone	HMDB
2-Hydroxy-2,6,6-trimethylcyclohexylideneacetic acid gamma-lactone	HMDB
(S)-5,6,7,7a-Tetrahydro-4,4,7a-trimethyl-2(4H)-benzofuranone	Generator
(S)-5,6,7,7Α-tetrahydro-4,4,7α-trimethyl-2(4H)-benzofuranone	Generator

Chemical Formula

C₁₁H₁₆O₂

Average Mass

180.2435 Da

Monoisotopic Mass

180.11503 Da

IUPAC Name

4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one

Traditional Name

dihydroactinidiolide

CAS Registry Number

Not Available

SMILES

CC12CCCC(C)(C)C1=CC(=O)O2

InChI Identifier

InChI=1S/C11H16O2/c1-10(2)5-4-6-11(3)8(10)7-9(12)13-11/h7H,4-6H2,1-3H3

InChI Key

IMKHDCBNRDRUEB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Actinidia polygama	LOTUS Database	35616633
Cannabis sativa	LOTUS Database	35616633
Eleocharis coloradoensis	LOTUS Database	35616633
Tagetes lucida	LOTUS Database	35616633
Triticum aestivum	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
2-furanone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	3.28	ALOGPS
logP	2.57	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	50.93 m³·mol⁻¹	ChemAxon
Polarizability	19.89 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0035240

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013900

KNApSAcK ID

Not Available

Chemspider ID

25323

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dihydroactinidiolide

METLIN ID

Not Available

PubChem Compound

27209

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (+/-)-dihydroactinidiolide (NP0286007)

MOL for NP0286007 ((+/-)-dihydroactinidiolide)

3D MOL for NP0286007 ((+/-)-dihydroactinidiolide)

3D SDF for NP0286007 ((+/-)-dihydroactinidiolide)

3D-SDF for NP0286007 ((+/-)-dihydroactinidiolide)

PDB for NP0286007 ((+/-)-dihydroactinidiolide)

3D PDB for NP0286007 ((+/-)-dihydroactinidiolide)

SMILES for NP0286007 ((+/-)-dihydroactinidiolide)

INCHI for NP0286007 ((+/-)-dihydroactinidiolide)

Structure for NP0286007 ((+/-)-dihydroactinidiolide)

3D Structure for NP0286007 ((+/-)-dihydroactinidiolide)