NP-MRD: Showing NP-Card for 6-Acetylfuranofukinol (NP0048082)

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Record Information

Version

2.0

Created at

2022-03-17 20:50:47 UTC

Updated at

2022-03-17 20:50:47 UTC

NP-MRD ID

NP0048082

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-Acetylfuranofukinol

Description

(3Beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate, also known as 6-acetylfuranofukinol, belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5 (3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate has been detected, but not quantified in, giant butterburs and green vegetables. 6-Acetylfuranofukinol is found in Petasites japonica. This could make (3beta,6beta)-furanoeremophilane-3,6-diol 6-acetate a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308082D          

 21 23  0  0  0  0            999 V2000
    4.6119   -2.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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
    0.7145   -1.2375    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  8  2  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 12  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  6  1  0  0  0  0
 13 10  1  0  0  0  0
 14  7  1  0  0  0  0
 15  9  1  0  0  0  0
 15 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17  4  1  0  0  0  0
 17 10  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
 18 11  2  0  0  0  0
 19 13  1  0  0  0  0
 20  8  1  0  0  0  0
 20 14  1  0  0  0  0
 21 11  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048082

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(O)CCC2CC3=C(C(OC(C)=O)C12C)C(C)=CO3

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O4/c1-9-8-20-14-7-12-5-6-13(19)10(2)17(12,4)16(15(9)14)21-11(3)18/h8,10,12-13,16,19H,5-7H2,1-4H3

> <INCHI_KEY>
CXZIQFLLAXJLDS-UHFFFAOYSA-N

> <FORMULA>
C17H24O4

> <MOLECULAR_WEIGHT>
292.3701

> <EXACT_MASS>
292.167459256

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
32.06966005775904

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-3,4a,5-trimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl acetate

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
2.487233438

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.93666711678976

> <JCHEM_PKA_STRONGEST_BASIC>
-2.077936546348572

> <JCHEM_POLAR_SURFACE_AREA>
59.67

> <JCHEM_REFRACTIVITY>
78.7525

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-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       8.609  -4.251   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   17                                                            
CONECT    5    6   12                                                       
CONECT    6    5   13                                                       
CONECT    7   12   14                                                       
CONECT    8    9   20                                                       
CONECT    9    1    8   15                                                  
CONECT   10    2   13   17                                                  
CONECT   11    3   18   21                                                  
CONECT   12    5    7   17                                                  
CONECT   13    6   10   19                                                  
CONECT   14    7   15   20                                                  
CONECT   15    9   14   16                                                  
CONECT   16   15   17   21                                                  
CONECT   17    4   10   12   16                                             
CONECT   18   11                                                            
CONECT   19   13                                                            
CONECT   20    8   14                                                       
CONECT   21   11   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
(3b,6b)-Furanoeremophilane-3,6-diol 6-acetate	Generator
(3b,6b)-Furanoeremophilane-3,6-diol 6-acetic acid	Generator
(3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetic acid	Generator
(3Β,6β)-furanoeremophilane-3,6-diol 6-acetate	Generator
(3Β,6β)-furanoeremophilane-3,6-diol 6-acetic acid	Generator
6-Acetylfuranofukinol	HMDB
6-Hydroxy-3,4a,5-trimethyl-4H,4ah,5H,6H,7H,8H,8ah,9H-naphtho[2,3-b]furan-4-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₄O₄

Average Mass

292.3701 Da

Monoisotopic Mass

292.16746 Da

IUPAC Name

6-hydroxy-3,4a,5-trimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl acetate

Traditional Name

6-hydroxy-3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl acetate

CAS Registry Number

34335-95-0

SMILES

CC1C(O)CCC2CC3=C(C(OC(C)=O)C12C)C(C)=CO3

InChI Identifier

InChI=1S/C17H24O4/c1-9-8-20-14-7-12-5-6-13(19)10(2)17(12,4)16(15(9)14)21-11(3)18/h8,10,12-13,16,19H,5-7H2,1-4H3

InChI Key

CXZIQFLLAXJLDS-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 eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Furoeremophilane sesquiterpenoid
Naphthofuran
Benzofuran
Cyclic alcohol
Heteroaromatic compound
Furan
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.73	ALOGPS
logP	2.49	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	14.94	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.75 m³·mol⁻¹	ChemAxon
Polarizability	32.07 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

HMDB0034930

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013520

KNApSAcK ID

C00017350

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

78384665

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 6-Acetylfuranofukinol (NP0048082)

MOL for NP0048082 (6-Acetylfuranofukinol)

3D MOL for NP0048082 (6-Acetylfuranofukinol)

3D SDF for NP0048082 (6-Acetylfuranofukinol)

3D-SDF for NP0048082 (6-Acetylfuranofukinol)

PDB for NP0048082 (6-Acetylfuranofukinol)

3D PDB for NP0048082 (6-Acetylfuranofukinol)

SMILES for NP0048082 (6-Acetylfuranofukinol)

INCHI for NP0048082 (6-Acetylfuranofukinol)

Structure for NP0048082 (6-Acetylfuranofukinol)

3D Structure for NP0048082 (6-Acetylfuranofukinol)