NP-MRD: Showing NP-Card for 9-Acetoxyfukinanolide (NP0048037)

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Record Information

Version

2.0

Created at

2022-03-17 20:50:04 UTC

Updated at

2022-03-17 20:50:04 UTC

NP-MRD ID

NP0048037

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-Acetoxyfukinanolide

Description

9-Acetoxyfukinanolide belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 9-Acetoxyfukinanolide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 9-Acetoxyfukinanolide has been detected, but not quantified in, giant butterburs and green vegetables. 9-Acetoxyfukinanolide is found in Petasites japonica. This could make 9-acetoxyfukinanolide a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307592D          

 21 23  0  0  0  0            999 V2000
    4.7432    4.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9425    3.9715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4576    2.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4576    3.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7432    1.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4896    2.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441    3.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7432    3.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2742    2.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0287    2.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441    2.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2742    3.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0287    3.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7592    2.7385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292    4.1905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4896    3.1510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4877    1.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4576    1.2741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1721    0.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8866    1.2741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1721    0.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  8  1  1  0  0  0  0
  8  4  1  0  0  0  0
  9  6  1  0  0  0  0
 10  5  1  0  0  0  0
 11 10  1  0  0  0  0
 13  2  1  0  0  0  0
 13  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  1  0  0  0  0
 14  7  1  0  0  0  0
 14  9  1  0  0  0  0
 14 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 12  2  0  0  0  0
 16  6  1  0  0  0  0
 16 12  1  0  0  0  0
  9 17  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048037

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCCC2C(OC(C)=O)C3(CC12C)C(=C)COC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O4/c1-10-6-5-7-13-14(21-12(3)18)17(9-16(10,13)4)11(2)8-20-15(17)19/h10,13-14H,2,5-9H2,1,3-4H3

> <INCHI_KEY>
ZZZDGYZKGIPSPD-UHFFFAOYSA-N

> <FORMULA>
C17H24O4

> <MOLECULAR_WEIGHT>
292.3701

> <EXACT_MASS>
292.167459256

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
31.49289531951589

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3a,4-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-1-yl acetate

> <ALOGPS_LOGP>
3.42

> <JCHEM_LOGP>
2.644027968333333

> <ALOGPS_LOGS>
-4.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.792377466308519

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
77.0662

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1H-spiro[indene-2,3'-oxolane]-3-yl acetate

> <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       8.854   8.192   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.359   7.413   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.188   4.342   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.188   5.882   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.854   3.572   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.781   4.342   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.056   6.358   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.854   6.652   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.245   3.866   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.520   4.342   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.056   3.866   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.245   6.358   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.520   5.882   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.151   5.112   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.721   7.822   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.781   5.882   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.644   2.378   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.454   2.378   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.788   1.608   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.122   2.378   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.788   0.068   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2   13                                                            
CONECT    3    4    5                                                       
CONECT    4    3    8                                                       
CONECT    5    3   10                                                       
CONECT    6    9   16                                                       
CONECT    7   13   14                                                       
CONECT    8    1    4   13                                                  
CONECT    9    6   14   17                                                  
CONECT   10    5   11   13                                                  
CONECT   11   10   14   18                                                  
CONECT   12   14   15   16                                                  
CONECT   13    2    7    8   10                                             
CONECT   14    7    9   11   12                                             
CONECT   15   12                                                            
CONECT   16    6   12                                                       
CONECT   17    9                                                            
CONECT   18   11   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
7,7a-Dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-3-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₄O₄

Average Mass

292.3701 Da

Monoisotopic Mass

292.16746 Da

IUPAC Name

3a,4-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-1-yl acetate

Traditional Name

7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1H-spiro[indene-2,3'-oxolane]-3-yl acetate

CAS Registry Number

35945-70-1

SMILES

CC1CCCC2C(OC(C)=O)C3(CC12C)C(=C)COC3=O

InChI Identifier

InChI=1S/C17H24O4/c1-10-6-5-7-13-14(21-12(3)18)17(9-16(10,13)4)11(2)8-20-15(17)19/h10,13-14H,2,5-9H2,1,3-4H3

InChI Key

ZZZDGYZKGIPSPD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Petasites japonica	Plant	KNApSAcK
Petasites japonicus	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
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	3.42	ALOGPS
logP	2.64	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.07 m³·mol⁻¹	ChemAxon
Polarizability	31.49 Å³	ChemAxon
Number of Rings	3	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

HMDB0034658

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013182

KNApSAcK ID

C00021352

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

78385431

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 9-Acetoxyfukinanolide (NP0048037)

MOL for NP0048037 (9-Acetoxyfukinanolide)

3D MOL for NP0048037 (9-Acetoxyfukinanolide)

3D SDF for NP0048037 (9-Acetoxyfukinanolide)

3D-SDF for NP0048037 (9-Acetoxyfukinanolide)

PDB for NP0048037 (9-Acetoxyfukinanolide)

3D PDB for NP0048037 (9-Acetoxyfukinanolide)

SMILES for NP0048037 (9-Acetoxyfukinanolide)

INCHI for NP0048037 (9-Acetoxyfukinanolide)

Structure for NP0048037 (9-Acetoxyfukinanolide)

3D Structure for NP0048037 (9-Acetoxyfukinanolide)