NP-MRD: Showing NP-Card for (1's,2s,3ar,4'r,5'r,8'r,9'r,12'r)-4'-(furan-3-yl)-4,4,5',9',12'-pentamethyl-3,3a-dihydro-3',10',14'-trioxaspiro[furo[3,2-c]pyran-2,13'-tetracyclo[7.4.1.0¹,⁵.0⁸,¹²]tetradecane]-2',6,11'-trione (NP0300795)

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Record Information

Version

2.0

Created at

2022-09-10 13:23:28 UTC

Updated at

2022-09-10 13:23:29 UTC

NP-MRD ID

NP0300795

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,2s,3ar,4'r,5'r,8'r,9'r,12'r)-4'-(furan-3-yl)-4,4,5',9',12'-pentamethyl-3,3a-dihydro-3',10',14'-trioxaspiro[furo[3,2-c]pyran-2,13'-tetracyclo[7.4.1.0¹,⁵.0⁸,¹²]tetradecane]-2',6,11'-trione

Description

Brownin F belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. (1's,2s,3ar,4'r,5'r,8'r,9'r,12'r)-4'-(furan-3-yl)-4,4,5',9',12'-pentamethyl-3,3a-dihydro-3',10',14'-trioxaspiro[furo[3,2-c]pyran-2,13'-tetracyclo[7.4.1.0¹,⁵.0⁸,¹²]tetradecane]-2',6,11'-trione is found in Harrisonia brownii. (1's,2s,3ar,4'r,5'r,8'r,9'r,12'r)-4'-(furan-3-yl)-4,4,5',9',12'-pentamethyl-3,3a-dihydro-3',10',14'-trioxaspiro[furo[3,2-c]pyran-2,13'-tetracyclo[7.4.1.0¹,⁵.0⁸,¹²]tetradecane]-2',6,11'-trione was first documented in 2013 (PMID: 23677035). Based on a literature review very few articles have been published on Brownin F.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102215232D          

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M  END

     RDKit          2D

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M  END


  Mrv1652309102215232D          

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M  END
> <DATABASE_ID>
NP0300795

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12OC(=O)[C@]3(C)[C@H]1CC[C@]1(C)[C@H](OC(=O)[C@@]1(O2)[C@]31C[C@H]2C(O1)=CC(=O)OC2(C)C)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O9/c1-21(2)14-11-25(32-15(14)10-17(27)33-21)23(4)16-6-8-22(3)18(13-7-9-30-12-13)31-20(29)26(22,25)35-24(16,5)34-19(23)28/h7,9-10,12,14,16,18H,6,8,11H2,1-5H3/t14-,16+,18+,22+,23-,24-,25-,26-/m0/s1

> <INCHI_KEY>
NJSZMBLTXPDGED-BRMNPCCASA-N

> <FORMULA>
C26H28O9

> <MOLECULAR_WEIGHT>
484.501

> <EXACT_MASS>
484.173332482

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       4.601   4.834   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.139   3.365   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.773   4.075   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.666   3.165   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.257   1.743   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.784   1.543   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.320   0.521   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.793   0.720   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.623  -0.281   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.309   0.523   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.668   2.021   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.203   2.143   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.045  -1.017   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.320  -0.335   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.001   1.419   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.595   2.839   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.677   1.938   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.673   3.013   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.092   4.439   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.715   1.112   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.957   0.202   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.884   2.233   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.524   2.046   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.271   0.648   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.629  -0.799   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.168  -0.747   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.365  -2.197   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.890  -2.414   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.962  -1.308   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.345  -1.986   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.128  -3.510   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.611  -3.775   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.291  -3.312   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.903  -2.609   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.444  -3.357   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   12                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13   20                                             
CONECT   11   10   12                                                       
CONECT   12   11    8    2                                                  
CONECT   13   10   14   25   34                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   17   22                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   10   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   15   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   13   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   28   33                                                  
CONECT   28   27   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   28                                                       
CONECT   33   27   34                                                       
CONECT   34   33   13   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

484.5010 Da

Monoisotopic Mass

484.17333 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@]12OC(=O)[C@]3(C)[C@H]1CC[C@]1(C)[C@H](OC(=O)[C@@]1(O2)[C@]31C[C@H]2C(O1)=CC(=O)OC2(C)C)C1=COC=C1

InChI Identifier

InChI=1S/C26H28O9/c1-21(2)14-11-25(32-15(14)10-17(27)33-21)23(4)16-6-8-22(3)18(13-7-9-30-12-13)31-20(29)26(22,25)35-24(16,5)34-19(23)28/h7,9-10,12,14,16,18H,6,8,11H2,1-5H3/t14-,16+,18+,22+,23-,24-,25-,26-/m0/s1

InChI Key

NJSZMBLTXPDGED-BRMNPCCASA-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
Harrisonia brownii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
1,3-dioxepane
Ketal
Dihydropyranone
Dioxepane
Oxepane
Gamma butyrolactone
Oxane
Pyran
Furan
Heteroaromatic compound
Oxolane
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
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

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

102202714

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rodier F, Parrain JL, Chouraqui G, Commeiras L: First studies directed towards the diastereoselective synthesis of the BCD tricyclic core of brownin F. Org Biomol Chem. 2013 Jul 7;11(25):4178-85. doi: 10.1039/c3ob40363g. [PubMed:23677035 ]
LOTUS database [Link]

Showing NP-Card for (1's,2s,3ar,4'r,5'r,8'r,9'r,12'r)-4'-(furan-3-yl)-4,4,5',9',12'-pentamethyl-3,3a-dihydro-3',10',14'-trioxaspiro[furo[3,2-c]pyran-2,13'-tetracyclo[7.4.1.0¹,⁵.0⁸,¹²]tetradecane]-2',6,11'-trione (NP0300795)

MOL for NP0300795 ((1's,2s,3ar,4'r,5'r,8'r,9'r,12'r)-4'-(furan-3-yl)-4,4,5',9',12'-pentamethyl-3,3a-dihydro-3',10',14'-trioxaspiro[furo[3,2-c]pyran-2,13'-tetracyclo[7.4.1.0¹,⁵.0⁸,¹²]tetradecane]-2',6,11'-trione)

3D MOL for NP0300795 ((1's,2s,3ar,4'r,5'r,8'r,9'r,12'r)-4'-(furan-3-yl)-4,4,5',9',12'-pentamethyl-3,3a-dihydro-3',10',14'-trioxaspiro[furo[3,2-c]pyran-2,13'-tetracyclo[7.4.1.0¹,⁵.0⁸,¹²]tetradecane]-2',6,11'-trione)

3D SDF for NP0300795 ((1's,2s,3ar,4'r,5'r,8'r,9'r,12'r)-4'-(furan-3-yl)-4,4,5',9',12'-pentamethyl-3,3a-dihydro-3',10',14'-trioxaspiro[furo[3,2-c]pyran-2,13'-tetracyclo[7.4.1.0¹,⁵.0⁸,¹²]tetradecane]-2',6,11'-trione)

3D-SDF for NP0300795 ((1's,2s,3ar,4'r,5'r,8'r,9'r,12'r)-4'-(furan-3-yl)-4,4,5',9',12'-pentamethyl-3,3a-dihydro-3',10',14'-trioxaspiro[furo[3,2-c]pyran-2,13'-tetracyclo[7.4.1.0¹,⁵.0⁸,¹²]tetradecane]-2',6,11'-trione)

PDB for NP0300795 ((1's,2s,3ar,4'r,5'r,8'r,9'r,12'r)-4'-(furan-3-yl)-4,4,5',9',12'-pentamethyl-3,3a-dihydro-3',10',14'-trioxaspiro[furo[3,2-c]pyran-2,13'-tetracyclo[7.4.1.0¹,⁵.0⁸,¹²]tetradecane]-2',6,11'-trione)

3D PDB for NP0300795 ((1's,2s,3ar,4'r,5'r,8'r,9'r,12'r)-4'-(furan-3-yl)-4,4,5',9',12'-pentamethyl-3,3a-dihydro-3',10',14'-trioxaspiro[furo[3,2-c]pyran-2,13'-tetracyclo[7.4.1.0¹,⁵.0⁸,¹²]tetradecane]-2',6,11'-trione)

SMILES for NP0300795 ((1's,2s,3ar,4'r,5'r,8'r,9'r,12'r)-4'-(furan-3-yl)-4,4,5',9',12'-pentamethyl-3,3a-dihydro-3',10',14'-trioxaspiro[furo[3,2-c]pyran-2,13'-tetracyclo[7.4.1.0¹,⁵.0⁸,¹²]tetradecane]-2',6,11'-trione)

INCHI for NP0300795 ((1's,2s,3ar,4'r,5'r,8'r,9'r,12'r)-4'-(furan-3-yl)-4,4,5',9',12'-pentamethyl-3,3a-dihydro-3',10',14'-trioxaspiro[furo[3,2-c]pyran-2,13'-tetracyclo[7.4.1.0¹,⁵.0⁸,¹²]tetradecane]-2',6,11'-trione)

Structure for NP0300795 ((1's,2s,3ar,4'r,5'r,8'r,9'r,12'r)-4'-(furan-3-yl)-4,4,5',9',12'-pentamethyl-3,3a-dihydro-3',10',14'-trioxaspiro[furo[3,2-c]pyran-2,13'-tetracyclo[7.4.1.0¹,⁵.0⁸,¹²]tetradecane]-2',6,11'-trione)

3D Structure for NP0300795 ((1's,2s,3ar,4'r,5'r,8'r,9'r,12'r)-4'-(furan-3-yl)-4,4,5',9',12'-pentamethyl-3,3a-dihydro-3',10',14'-trioxaspiro[furo[3,2-c]pyran-2,13'-tetracyclo[7.4.1.0¹,⁵.0⁸,¹²]tetradecane]-2',6,11'-trione)