NP-MRD: Showing NP-Card for (+)-Dukunolide C (NP0074130)

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Record Information

Version

2.0

Created at

2022-04-28 19:18:06 UTC

Updated at

2022-04-28 19:18:07 UTC

NP-MRD ID

NP0074130

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Dukunolide C

Description

(2R,3R,6S,8R,11R,12R,17S,18S)-18-(furan-3-yl)-2,11-dihydroxy-3,9,9,17-tetramethyl-5,10,20-trioxo-4,7,19-trioxahexacyclo[11.7.1.0²,¹¹.0³,⁸.0⁶,⁸.0¹⁷,²¹]Henicosa-1(21),13-dien-12-yl acetate 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 C is found in Lansium domesticum and Lansium domesticum Corr. . Based on a literature review very few articles have been published on (2R,3R,6S,8R,11R,12R,17S,18S)-18-(furan-3-yl)-2,11-dihydroxy-3,9,9,17-tetramethyl-5,10,20-trioxo-4,7,19-trioxahexacyclo[11.7.1.0²,¹¹.0³,⁸.0⁶,⁸.0¹⁷,²¹]Henicosa-1(21),13-dien-12-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221182D          

 39 45  0  0  1  0            999 V2000
    2.2219   -0.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5649   -1.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8042   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4932    1.6429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2539    1.3235    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3575    0.5050    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1182    0.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0145    1.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9108    1.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7007    1.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1713    2.2619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6723    2.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  5 18  1  0  0  0  0
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 18 39  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282221182D          

 39 45  0  0  1  0            999 V2000
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  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
  1 11  1  0  0  0  0
 10 12  1  6  0  0  0
  9 13  1  6  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 13 17  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 18 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  6  0  0  0
 28 34  1  6  0  0  0
 29 35  1  1  0  0  0
 27 36  1  0  0  0  0
 27 37  1  0  0  0  0
 19 38  1  1  0  0  0
 18 39  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0074130

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C2=CCC[C@]3(C)[C@H](OC(=O)C(=C23)[C@]2(O)[C@@]3(C)OC(=O)[C@H]4O[C@@]34C(C)(C)C(=O)[C@@]12O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H28O11/c1-12(29)36-18-14-7-6-9-24(4)15(14)16(20(30)37-17(24)13-8-10-35-11-13)27(34)25(5)28(19(38-28)21(31)39-25)23(2,3)22(32)26(18,27)33/h7-8,10-11,17-19,33-34H,6,9H2,1-5H3/t17-,18-,19-,24+,25-,26+,27+,28+/m1/s1

> <INCHI_KEY>
HOJFTRARYIFTJU-QKIOGUQASA-N

> <FORMULA>
C28H28O11

> <MOLECULAR_WEIGHT>
540.521

> <EXACT_MASS>
540.163161722

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
52.002261060945415

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,6S,8R,11R,12R,17S,18S)-18-(furan-3-yl)-2,11-dihydroxy-3,9,9,17-tetramethyl-5,10,20-trioxo-4,7,19-trioxahexacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{6,8}.0^{17,21}]henicosa-1(21),13-dien-12-yl acetate

> <ALOGPS_LOGP>
2.11

> <JCHEM_LOGP>
1.4023111446666663

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.297598341165545

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.746708368113833

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8734448372808514

> <JCHEM_POLAR_SURFACE_AREA>
162.1

> <JCHEM_REFRACTIVITY>
127.49419999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,6S,8R,11R,12R,17S,18S)-18-(furan-3-yl)-2,11-dihydroxy-3,9,9,17-tetramethyl-5,10,20-trioxo-4,7,19-trioxahexacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{6,8}.0^{17,21}]henicosa-1(21),13-dien-12-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.147  -1.181   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.921  -2.113   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.501  -1.517   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.308   0.011   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.112   0.607   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.306   2.135   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.726   2.732   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.921   3.067   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.341   2.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.534   0.943   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.954   0.346   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.760   1.874   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.567   3.402   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.041   2.957   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.920   4.222   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.988   5.449   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.534   4.942   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.338  -0.324   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.145  -1.852   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.275  -2.448   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.468  -3.976   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.888  -4.572   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.115  -3.641   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.082  -6.100   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.371  -2.783   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.178  -4.311   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.791  -2.187   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.985  -0.659   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.758   0.272   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -3.265   1.726   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -4.805   1.694   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -5.736   2.920   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -5.250   0.219   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.378  -1.315   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.636   1.327   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.437  -3.585   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.311  -2.434   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -0.951  -3.380   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -1.050   1.189   0.000  0.00  0.00           O+0
CONECT    1    2   11                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6   18                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9    4   11   12                                             
CONECT   11   10    1                                                       
CONECT   12   10                                                            
CONECT   13    9   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13                                                       
CONECT   18    5   19   29   39                                             
CONECT   19   18   20   25   38                                             
CONECT   20   19    3   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   19   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   36   37                                             
CONECT   28   27   29   33   34                                             
CONECT   29   28   18   30   35                                             
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   28   34                                                  
CONECT   34   33   28                                                       
CONECT   35   29                                                            
CONECT   36   27                                                            
CONECT   37   27                                                            
CONECT   38   19                                                            
CONECT   39   18                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   90    0
END

View in JSmol

Synonyms

Value	Source
(2R,3R,6S,8R,11R,12R,17S,18S)-18-(Furan-3-yl)-2,11-dihydroxy-3,9,9,17-tetramethyl-5,10,20-trioxo-4,7,19-trioxahexacyclo[11.7.1.0,.0,.0,.0,]henicosa-1(21),13-dien-12-yl acetic acid	Generator

Chemical Formula

C₂₈H₂₈O₁₁

Average Mass

540.5210 Da

Monoisotopic Mass

540.16316 Da

IUPAC Name

(2R,3R,6S,8R,11R,12R,17S,18S)-18-(furan-3-yl)-2,11-dihydroxy-3,9,9,17-tetramethyl-5,10,20-trioxo-4,7,19-trioxahexacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{6,8}.0^{17,21}]henicosa-1(21),13-dien-12-yl acetate

Traditional Name

(2R,3R,6S,8R,11R,12R,17S,18S)-18-(furan-3-yl)-2,11-dihydroxy-3,9,9,17-tetramethyl-5,10,20-trioxo-4,7,19-trioxahexacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{6,8}.0^{17,21}]henicosa-1(21),13-dien-12-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C2=CCC[C@]3(C)[C@H](OC(=O)C(=C23)[C@]2(O)[C@@]3(C)OC(=O)[C@H]4O[C@@]34C(C)(C)C(=O)[C@@]12O)C1=COC=C1

InChI Identifier

InChI=1S/C28H28O11/c1-12(29)36-18-14-7-6-9-24(4)15(14)16(20(30)37-17(24)13-8-10-35-11-13)27(34)25(5)28(19(38-28)21(31)39-25)23(2,3)22(32)26(18,27)33/h7-8,10-11,17-19,33-34H,6,9H2,1-5H3/t17-,18-,19-,24+,25-,26+,27+,28+/m1/s1

InChI Key

HOJFTRARYIFTJU-QKIOGUQASA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Lansium domesticum Corr.	Plant	KNApSAcK

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
Tricarboxylic acid or derivatives
Dihydropyranone
Pyran
Gamma butyrolactone
Para-dioxane
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Furan
Cyclic alcohol
Lactone
Ketone
Carboxylic acid ester
1,2-diol
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	2.11	ALOGPS
logP	1.4	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	10.75	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	162.1 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	127.49 m³·mol⁻¹	ChemAxon
Polarizability	52 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

163067554

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Dukunolide C (NP0074130)

MOL for NP0074130 ((+)-Dukunolide C)

3D MOL for NP0074130 ((+)-Dukunolide C)

3D SDF for NP0074130 ((+)-Dukunolide C)

3D-SDF for NP0074130 ((+)-Dukunolide C)

PDB for NP0074130 ((+)-Dukunolide C)

3D PDB for NP0074130 ((+)-Dukunolide C)

SMILES for NP0074130 ((+)-Dukunolide C)

INCHI for NP0074130 ((+)-Dukunolide C)

Structure for NP0074130 ((+)-Dukunolide C)

3D Structure for NP0074130 ((+)-Dukunolide C)