NP-MRD: Showing NP-Card for 15-(furan-3-yl)-3,11-dihydroxy-5,5,10,16-tetramethyl-9,14,20-trioxahexacyclo[10.8.1.0¹,¹⁹.0³,¹¹.0⁶,¹⁰.0¹⁶,²¹]henicos-12(21)-ene-4,8,13-trione (NP0214463)

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Record Information

Version

2.0

Created at

2022-09-05 13:46:04 UTC

Updated at

2022-09-05 13:46:04 UTC

NP-MRD ID

NP0214463

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-(furan-3-yl)-3,11-dihydroxy-5,5,10,16-tetramethyl-9,14,20-trioxahexacyclo[10.8.1.0¹,¹⁹.0³,¹¹.0⁶,¹⁰.0¹⁶,²¹]henicos-12(21)-ene-4,8,13-trione

Description

Dukunolide E 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. Dukunolide E is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, dukunolide e has been detected, but not quantified in, fruits. 15-(furan-3-yl)-3,11-dihydroxy-5,5,10,16-tetramethyl-9,14,20-trioxahexacyclo[10.8.1.0¹,¹⁹.0³,¹¹.0⁶,¹⁰.0¹⁶,²¹]henicos-12(21)-ene-4,8,13-trione is found in Lansium domesticum. This could make dukunolide e a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241207462D          

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M  END

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  Mrv0541 02241207462D          

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M  END
> <DATABASE_ID>
NP0214463

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12OC(=O)CC1C(C)(C)C(=O)C1(O)CC34OC3CCC3(C)C(OC(=O)C(=C43)C21O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O9/c1-21(2)13-9-15(27)35-23(13,4)26(31)16-17-22(3,18(33-19(16)28)12-6-8-32-10-12)7-5-14-24(17,34-14)11-25(26,30)20(21)29/h6,8,10,13-14,18,30-31H,5,7,9,11H2,1-4H3

> <INCHI_KEY>
HQKQACOUFFEUAD-UHFFFAOYSA-N

> <FORMULA>
C26H28O9

> <MOLECULAR_WEIGHT>
484.4951

> <EXACT_MASS>
484.173332494

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
47.59812171925538

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
15-(furan-3-yl)-3,11-dihydroxy-5,5,10,16-tetramethyl-9,14,20-trioxahexacyclo[10.8.1.0¹,¹⁹.0³,¹¹.0⁶,¹⁰.0¹⁶,²¹]henicos-12(21)-ene-4,8,13-trione

> <ALOGPS_LOGP>
1.67

> <JCHEM_LOGP>
1.4634535603333334

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.726997067633814

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.378846915686477

> <JCHEM_PKA_STRONGEST_BASIC>
-3.15666904105325

> <JCHEM_POLAR_SURFACE_AREA>
135.8

> <JCHEM_REFRACTIVITY>
116.64989999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-(furan-3-yl)-3,11-dihydroxy-5,5,10,16-tetramethyl-9,14,20-trioxahexacyclo[10.8.1.0¹,¹⁹.0³,¹¹.0⁶,¹⁰.0¹⁶,²¹]henicos-12(21)-ene-4,8,13-trione

> <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      -4.438   2.896   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.971   1.401   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.279   0.654   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -6.493   1.495   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -5.932   2.989   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.662   0.841   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.541   1.868   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.140   1.401   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.514   2.803   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.141  -3.830   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.354  -3.830   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.850  -3.456   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.129  -1.962   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.289  -0.653   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.784  -0.841   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.196  -3.737   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.289  -2.148   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.878  -2.429   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.344  -3.924   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.981  -2.896   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.420  -2.523   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.794  -1.121   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.327  -0.094   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.915  -0.653   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.261   0.560   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.438   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.372   1.214   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.532   2.429   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.999   3.924   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       3.036   2.056   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.036   0.467   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.289   1.868   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.493  -0.841   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.999  -1.401   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.120  -2.616   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    1    4                                                       
CONECT    6    2    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8                                                            
CONECT   10   11   21                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14    6   13   15   22                                             
CONECT   15   14                                                            
CONECT   16   17                                                            
CONECT   17   16   18   20   24                                             
CONECT   18   17   19   34                                                  
CONECT   19   18                                                            
CONECT   20   17   21                                                       
CONECT   21   10   11   20   22                                             
CONECT   22   14   21   23                                                  
CONECT   23    8   22   24                                                  
CONECT   24   17   23   25   31                                             
CONECT   25   24                                                            
CONECT   26   27   31   34                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   24   26   30   32                                             
CONECT   32   31                                                            
CONECT   33   34                                                            
CONECT   34   18   26   33   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₈O₉

Average Mass

484.4951 Da

Monoisotopic Mass

484.17333 Da

IUPAC Name

15-(furan-3-yl)-3,11-dihydroxy-5,5,10,16-tetramethyl-9,14,20-trioxahexacyclo[10.8.1.0¹,¹⁹.0³,¹¹.0⁶,¹⁰.0¹⁶,²¹]henicos-12(21)-ene-4,8,13-trione

Traditional Name

15-(furan-3-yl)-3,11-dihydroxy-5,5,10,16-tetramethyl-9,14,20-trioxahexacyclo[10.8.1.0¹,¹⁹.0³,¹¹.0⁶,¹⁰.0¹⁶,²¹]henicos-12(21)-ene-4,8,13-trione

CAS Registry Number

Not Available

SMILES

CC12OC(=O)CC1C(C)(C)C(=O)C1(O)CC34OC3CCC3(C)C(OC(=O)C(=C43)C21O)C1=COC=C1

InChI Identifier

InChI=1S/C26H28O9/c1-21(2)13-9-15(27)35-23(13,4)26(31)16-17-22(3,18(33-19(16)28)12-6-8-32-10-12)7-5-14-24(17,34-14)11-25(26,30)20(21)29/h6,8,10,13-14,18,30-31H,5,7,9,11H2,1-4H3

InChI Key

HQKQACOUFFEUAD-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
Lansium domesticum	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	1.67	ALOGPS
logP	1.46	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	11.38	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	135.8 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	116.65 m³·mol⁻¹	ChemAxon
Polarizability	47.6 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0035733

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014461

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

131751857

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 15-(furan-3-yl)-3,11-dihydroxy-5,5,10,16-tetramethyl-9,14,20-trioxahexacyclo[10.8.1.0¹,¹⁹.0³,¹¹.0⁶,¹⁰.0¹⁶,²¹]henicos-12(21)-ene-4,8,13-trione (NP0214463)

MOL for NP0214463 (15-(furan-3-yl)-3,11-dihydroxy-5,5,10,16-tetramethyl-9,14,20-trioxahexacyclo[10.8.1.0¹,¹⁹.0³,¹¹.0⁶,¹⁰.0¹⁶,²¹]henicos-12(21)-ene-4,8,13-trione)

3D MOL for NP0214463 (15-(furan-3-yl)-3,11-dihydroxy-5,5,10,16-tetramethyl-9,14,20-trioxahexacyclo[10.8.1.0¹,¹⁹.0³,¹¹.0⁶,¹⁰.0¹⁶,²¹]henicos-12(21)-ene-4,8,13-trione)

3D SDF for NP0214463 (15-(furan-3-yl)-3,11-dihydroxy-5,5,10,16-tetramethyl-9,14,20-trioxahexacyclo[10.8.1.0¹,¹⁹.0³,¹¹.0⁶,¹⁰.0¹⁶,²¹]henicos-12(21)-ene-4,8,13-trione)

3D-SDF for NP0214463 (15-(furan-3-yl)-3,11-dihydroxy-5,5,10,16-tetramethyl-9,14,20-trioxahexacyclo[10.8.1.0¹,¹⁹.0³,¹¹.0⁶,¹⁰.0¹⁶,²¹]henicos-12(21)-ene-4,8,13-trione)

PDB for NP0214463 (15-(furan-3-yl)-3,11-dihydroxy-5,5,10,16-tetramethyl-9,14,20-trioxahexacyclo[10.8.1.0¹,¹⁹.0³,¹¹.0⁶,¹⁰.0¹⁶,²¹]henicos-12(21)-ene-4,8,13-trione)

3D PDB for NP0214463 (15-(furan-3-yl)-3,11-dihydroxy-5,5,10,16-tetramethyl-9,14,20-trioxahexacyclo[10.8.1.0¹,¹⁹.0³,¹¹.0⁶,¹⁰.0¹⁶,²¹]henicos-12(21)-ene-4,8,13-trione)

SMILES for NP0214463 (15-(furan-3-yl)-3,11-dihydroxy-5,5,10,16-tetramethyl-9,14,20-trioxahexacyclo[10.8.1.0¹,¹⁹.0³,¹¹.0⁶,¹⁰.0¹⁶,²¹]henicos-12(21)-ene-4,8,13-trione)

INCHI for NP0214463 (15-(furan-3-yl)-3,11-dihydroxy-5,5,10,16-tetramethyl-9,14,20-trioxahexacyclo[10.8.1.0¹,¹⁹.0³,¹¹.0⁶,¹⁰.0¹⁶,²¹]henicos-12(21)-ene-4,8,13-trione)

Structure for NP0214463 (15-(furan-3-yl)-3,11-dihydroxy-5,5,10,16-tetramethyl-9,14,20-trioxahexacyclo[10.8.1.0¹,¹⁹.0³,¹¹.0⁶,¹⁰.0¹⁶,²¹]henicos-12(21)-ene-4,8,13-trione)

3D Structure for NP0214463 (15-(furan-3-yl)-3,11-dihydroxy-5,5,10,16-tetramethyl-9,14,20-trioxahexacyclo[10.8.1.0¹,¹⁹.0³,¹¹.0⁶,¹⁰.0¹⁶,²¹]henicos-12(21)-ene-4,8,13-trione)