NP-MRD: Showing NP-Card for 6-(furan-3-yl)-5,12,16,16-tetramethyl-8,20-dioxo-7,10,17,21-tetraoxahexacyclo[16.3.1.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]docosan-13-yl acetate (NP0169273)

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Record Information

Version

2.0

Created at

2022-09-03 05:12:05 UTC

Updated at

2022-09-03 05:12:05 UTC

NP-MRD ID

NP0169273

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(furan-3-yl)-5,12,16,16-tetramethyl-8,20-dioxo-7,10,17,21-tetraoxahexacyclo[16.3.1.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]docosan-13-yl acetate

Description

(7Alpha,10beta)-1(10->19)-Abeo-7-acetoxyisoobacun-3,10-olide belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings (7alpha,10beta)-1(10->19)-Abeo-7-acetoxyisoobacun-3,10-olide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (7alpha,10beta)-1(10->19)-abeo-7-acetoxyisoobacun-3,10-olide has been detected, but not quantified in, citrus. 6-(furan-3-yl)-5,12,16,16-tetramethyl-8,20-dioxo-7,10,17,21-tetraoxahexacyclo[16.3.1.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]docosan-13-yl acetate is found in Citrus medica and Citrus paradisi. This could make (7alpha,10beta)-1(10->19)-abeo-7-acetoxyisoobacun-3,10-olide a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308132D          

 37 43  0  0  0  0            999 V2000
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M  END

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M  END


  Mrv0541 05061308132D          

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    1.7755    4.4030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9947    2.2756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6485    3.2218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 14  1  1  0  0  0  0
 15  7  1  0  0  0  0
 15 13  2  0  0  0  0
 16 10  1  0  0  0  0
 16 12  1  0  0  0  0
 17  6  1  0  0  0  0
 18 11  1  0  0  0  0
 19 11  1  0  0  0  0
 20 10  1  0  0  0  0
 21 15  1  0  0  0  0
 23 22  1  0  0  0  0
 24  2  1  0  0  0  0
 24  3  1  0  0  0  0
 24 18  1  0  0  0  0
 25  4  1  0  0  0  0
 25  8  1  0  0  0  0
 25 21  1  0  0  0  0
 26  5  1  0  0  0  0
 26 17  1  0  0  0  0
 26 19  1  0  0  0  0
 27 12  1  0  0  0  0
 27 17  1  0  0  0  0
 27 18  1  0  0  0  0
 28 22  1  0  0  0  0
 28 25  1  0  0  0  0
 28 26  1  0  0  0  0
 29 14  2  0  0  0  0
 30 20  2  0  0  0  0
 31 23  2  0  0  0  0
 32  9  1  0  0  0  0
 32 13  1  0  0  0  0
 33 14  1  0  0  0  0
 33 19  1  0  0  0  0
 34 21  1  0  0  0  0
 34 23  1  0  0  0  0
 35 16  1  0  0  0  0
 35 24  1  0  0  0  0
 36 20  1  0  0  0  0
 36 27  1  0  0  0  0
 37 22  1  0  0  0  0
 37 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0169273

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC2C(C)(C)OC3CC(=O)OC2(C3)C2CCC3(C)C(OC(=O)C4OC34C12C)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O9/c1-14(29)33-19-11-18-24(2,3)35-16-10-20(30)36-27(18,12-16)17-6-8-25(4)21(15-7-9-32-13-15)34-23(31)22-28(25,37-22)26(17,19)5/h7,9,13,16-19,21-22H,6,8,10-12H2,1-5H3

> <INCHI_KEY>
MZPMDBUZYDUIEJ-UHFFFAOYSA-N

> <FORMULA>
C28H34O9

> <MOLECULAR_WEIGHT>
514.5642

> <EXACT_MASS>
514.220282686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
52.61235514833423

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-(furan-3-yl)-5,12,16,16-tetramethyl-8,20-dioxo-7,10,17,21-tetraoxahexacyclo[16.3.1.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]docosan-13-yl acetate

> <ALOGPS_LOGP>
3.75

> <JCHEM_LOGP>
2.335683313333334

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1213311149521448

> <JCHEM_POLAR_SURFACE_AREA>
113.80000000000001

> <JCHEM_REFRACTIVITY>
124.66089999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(furan-3-yl)-5,12,16,16-tetramethyl-8,20-dioxo-7,10,17,21-tetraoxahexacyclo[16.3.1.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]docosan-13-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      -2.346  10.039   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.470   9.397   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.375  10.014   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.386   1.446   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.374   3.999   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.021   3.368   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.686  -0.596   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.183   2.407   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.996  -1.973   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.399   5.220   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.681   7.955   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.700   5.570   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.222  -0.223   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.548   9.075   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.589   0.485   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.778   6.692   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.210   4.890   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.747   7.376   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.879   6.994   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.449   3.947   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.820   2.008   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.281   5.053   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.484   4.092   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.783   8.592   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.616   2.969   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.643   5.452   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.124   5.764   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.847   4.492   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.983   9.634   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.008   2.512   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -6.918   4.654   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.474  -1.743   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -3.314   7.553   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -5.254   2.570   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       3.314   8.219   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       1.857   4.248   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -3.077   6.014   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   24                                                            
CONECT    3   24                                                            
CONECT    4   25                                                            
CONECT    5   26                                                            
CONECT    6    8   17                                                       
CONECT    7    9   15                                                       
CONECT    8    6   25                                                       
CONECT    9    7   32                                                       
CONECT   10   16   20                                                       
CONECT   11   18   19                                                       
CONECT   12   16   27                                                       
CONECT   13   15   32                                                       
CONECT   14    1   29   33                                                  
CONECT   15    7   13   21                                                  
CONECT   16   10   12   35                                                  
CONECT   17    6   26   27                                                  
CONECT   18   11   24   27                                                  
CONECT   19   11   26   33                                                  
CONECT   20   10   30   36                                                  
CONECT   21   15   25   34                                                  
CONECT   22   23   28   37                                                  
CONECT   23   22   31   34                                                  
CONECT   24    2    3   18   35                                             
CONECT   25    4    8   21   28                                             
CONECT   26    5   17   19   28                                             
CONECT   27   12   17   18   36                                             
CONECT   28   22   25   26   37                                             
CONECT   29   14                                                            
CONECT   30   20                                                            
CONECT   31   23                                                            
CONECT   32    9   13                                                       
CONECT   33   14   19                                                       
CONECT   34   21   23                                                       
CONECT   35   16   24                                                       
CONECT   36   20   27                                                       
CONECT   37   22   28                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   86    0
END

View in JSmol

Synonyms

Value	Source
(7a,10b)-1(10->19)-abeo-7-acetoxyisoobacun-3,10-olide	Generator
(7Α,10β)-1(10->19)-abeo-7-acetoxyisoobacun-3,10-olide	Generator
6-(Furan-3-yl)-5,12,16,16-tetramethyl-8,20-dioxo-7,10,17,21-tetraoxahexacyclo[16.3.1.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]docosan-13-yl acetic acid	Generator

Chemical Formula

C₂₈H₃₄O₉

Average Mass

514.5642 Da

Monoisotopic Mass

514.22028 Da

IUPAC Name

6-(furan-3-yl)-5,12,16,16-tetramethyl-8,20-dioxo-7,10,17,21-tetraoxahexacyclo[16.3.1.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]docosan-13-yl acetate

Traditional Name

6-(furan-3-yl)-5,12,16,16-tetramethyl-8,20-dioxo-7,10,17,21-tetraoxahexacyclo[16.3.1.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]docosan-13-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC2C(C)(C)OC3CC(=O)OC2(C3)C2CCC3(C)C(OC(=O)C4OC34C12C)C1=COC=C1

InChI Identifier

InChI=1S/C28H34O9/c1-14(29)33-19-11-18-24(2,3)35-16-10-20(30)36-27(18,12-16)17-6-8-25(4)21(15-7-9-32-13-15)34-23(31)22-28(25,37-22)26(17,19)5/h7,9,13,16-19,21-22H,6,8,10-12H2,1-5H3

InChI Key

MZPMDBUZYDUIEJ-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
Citrus medica	LOTUS Database	35616633
Citrus paradisi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Not Available

Substituents

Not Available

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	3.75	ALOGPS
logP	2.34	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	113.8 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	124.66 m³·mol⁻¹	ChemAxon
Polarizability	52.61 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0035079

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013703

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

131751661

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-(furan-3-yl)-5,12,16,16-tetramethyl-8,20-dioxo-7,10,17,21-tetraoxahexacyclo[16.3.1.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]docosan-13-yl acetate (NP0169273)

MOL for NP0169273 (6-(furan-3-yl)-5,12,16,16-tetramethyl-8,20-dioxo-7,10,17,21-tetraoxahexacyclo[16.3.1.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]docosan-13-yl acetate)

3D MOL for NP0169273 (6-(furan-3-yl)-5,12,16,16-tetramethyl-8,20-dioxo-7,10,17,21-tetraoxahexacyclo[16.3.1.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]docosan-13-yl acetate)

3D SDF for NP0169273 (6-(furan-3-yl)-5,12,16,16-tetramethyl-8,20-dioxo-7,10,17,21-tetraoxahexacyclo[16.3.1.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]docosan-13-yl acetate)

3D-SDF for NP0169273 (6-(furan-3-yl)-5,12,16,16-tetramethyl-8,20-dioxo-7,10,17,21-tetraoxahexacyclo[16.3.1.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]docosan-13-yl acetate)

PDB for NP0169273 (6-(furan-3-yl)-5,12,16,16-tetramethyl-8,20-dioxo-7,10,17,21-tetraoxahexacyclo[16.3.1.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]docosan-13-yl acetate)

3D PDB for NP0169273 (6-(furan-3-yl)-5,12,16,16-tetramethyl-8,20-dioxo-7,10,17,21-tetraoxahexacyclo[16.3.1.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]docosan-13-yl acetate)

SMILES for NP0169273 (6-(furan-3-yl)-5,12,16,16-tetramethyl-8,20-dioxo-7,10,17,21-tetraoxahexacyclo[16.3.1.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]docosan-13-yl acetate)

INCHI for NP0169273 (6-(furan-3-yl)-5,12,16,16-tetramethyl-8,20-dioxo-7,10,17,21-tetraoxahexacyclo[16.3.1.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]docosan-13-yl acetate)

Structure for NP0169273 (6-(furan-3-yl)-5,12,16,16-tetramethyl-8,20-dioxo-7,10,17,21-tetraoxahexacyclo[16.3.1.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]docosan-13-yl acetate)

3D Structure for NP0169273 (6-(furan-3-yl)-5,12,16,16-tetramethyl-8,20-dioxo-7,10,17,21-tetraoxahexacyclo[16.3.1.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]docosan-13-yl acetate)