NP-MRD: Showing NP-Card for 17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione (NP0319183)

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Record Information

Version

2.0

Created at

2022-09-11 20:05:26 UTC

Updated at

2022-09-11 20:05:26 UTC

NP-MRD ID

NP0319183

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione

Description

Dukunolide D 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 D is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, dukunolide D has been detected, but not quantified in, fruits. 17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione is found in Lansium domesticum. This could make dukunolide D a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308412D          

 34 39  0  0  0  0            999 V2000
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   -0.9640   -0.3739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

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M  END


  Mrv0541 05061308412D          

 34 39  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0319183

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12OC(=O)CC1C(C)(C)C(=O)C1(O)CC3=CCCC4(C)C(OC(=O)C(=C34)C21O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O8/c1-22(2)15-10-16(27)34-24(15,4)26(31)18-17-13(11-25(26,30)21(22)29)6-5-8-23(17,3)19(33-20(18)28)14-7-9-32-12-14/h6-7,9,12,15,19,30-31H,5,8,10-11H2,1-4H3

> <INCHI_KEY>
WUQGZJQZKDLECQ-UHFFFAOYSA-N

> <FORMULA>
C26H28O8

> <MOLECULAR_WEIGHT>
468.4957

> <EXACT_MASS>
468.178417872

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
47.29238849266529

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
2.2031678846666667

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.732358605088574

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.383618793578309

> <JCHEM_PKA_STRONGEST_BASIC>
-3.192382242758883

> <JCHEM_POLAR_SURFACE_AREA>
123.27000000000001

> <JCHEM_REFRACTIVITY>
118.16399999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione

> <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       6.316  -2.185   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.854  -3.520   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.906   3.375   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.578  -0.556   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.838   0.439   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.799  -0.698   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.971   4.672   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.372   1.907   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.607   6.074   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.658   0.123   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.743  -1.505   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.130   6.352   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.295  -0.367   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.440   4.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.255  -0.513   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.486   1.653   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.170   1.101   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.675   1.431   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.402   3.706   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.140   2.899   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.285  -2.311   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.789  -1.981   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.868   2.238   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.217   0.624   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.247  -1.174   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.713   0.294   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.624   2.692   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       3.644   3.229   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.819  -3.779   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.781  -2.642   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       3.197   1.779   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.469   7.112   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       1.102   4.036   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.978   1.963   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   22                                                            
CONECT    3   23                                                            
CONECT    4   24                                                            
CONECT    5    6    8                                                       
CONECT    6    5   13                                                       
CONECT    7    9   14                                                       
CONECT    8    5   23                                                       
CONECT    9    7   32                                                       
CONECT   10   15   16                                                       
CONECT   11   13   25                                                       
CONECT   12   14   32                                                       
CONECT   13    6   11   17                                                  
CONECT   14    7   12   19                                                  
CONECT   15   10   22   24                                                  
CONECT   16   10   27   34                                                  
CONECT   17   13   18   23                                                  
CONECT   18   17   20   26                                                  
CONECT   19   14   23   33                                                  
CONECT   20   18   28   33                                                  
CONECT   21   22   25   29                                                  
CONECT   22    1    2   15   21                                             
CONECT   23    3    8   17   19                                             
CONECT   24    4   15   26   34                                             
CONECT   25   11   21   26   30                                             
CONECT   26   18   24   25   31                                             
CONECT   27   16                                                            
CONECT   28   20                                                            
CONECT   29   21                                                            
CONECT   30   25                                                            
CONECT   31   26                                                            
CONECT   32    9   12                                                       
CONECT   33   19   20                                                       
CONECT   34   16   24                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Value	Source
(+)-Dukunolide D	HMDB
1,1'-Dimethyl-2,2'-oxydiethyl dibenzoate	HMDB
Dipropylene glycol dibenzoate	HMDB
Oxydipropane-1,2-diyl dibenzoate	HMDB
Propanol, oxybis-, dibenzoate	HMDB

Chemical Formula

C₂₆H₂₈O₈

Average Mass

468.4957 Da

Monoisotopic Mass

468.17842 Da

IUPAC Name

17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione

Traditional Name

17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione

CAS Registry Number

Not Available

SMILES

CC12OC(=O)CC1C(C)(C)C(=O)C1(O)CC3=CCCC4(C)C(OC(=O)C(=C34)C21O)C1=COC=C1

InChI Identifier

InChI=1S/C26H28O8/c1-22(2)15-10-16(27)34-24(15,4)26(31)18-17-13(11-25(26,30)21(22)29)6-5-8-23(17,3)19(33-20(18)28)14-7-9-32-12-14/h6-7,9,12,15,19,30-31H,5,8,10-11H2,1-4H3

InChI Key

WUQGZJQZKDLECQ-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

Substituents

Naphthopyran
Naphthofuran
Naphthalene
Dihydropyranone
Dicarboxylic acid or derivatives
Gamma butyrolactone
Pyran
Cyclic alcohol
Furan
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Tetrahydrofuran
Lactone
Ketone
Carboxylic acid ester
1,2-diol
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Organic oxide
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	2.34	ALOGPS
logP	2.2	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	11.38	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	123.27 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	118.16 m³·mol⁻¹	ChemAxon
Polarizability	47.29 Å³	ChemAxon
Number of Rings	6	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

HMDB0035732

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014460

KNApSAcK ID

C00035090

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

13970419

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione (NP0319183)

MOL for NP0319183 (17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione)

3D MOL for NP0319183 (17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione)

3D SDF for NP0319183 (17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione)

3D-SDF for NP0319183 (17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione)

PDB for NP0319183 (17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione)

3D PDB for NP0319183 (17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione)

SMILES for NP0319183 (17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione)

INCHI for NP0319183 (17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione)

Structure for NP0319183 (17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione)

3D Structure for NP0319183 (17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione)