NP-MRD: Showing NP-Card for (1r,2s,5s,6r,10r,11s,12r,15r,19s)-6-(furan-3-yl)-1,5,10,15-tetramethyl-18-oxo-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-8,16-dien-11-yl benzoate (NP0234788)

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Record Information

Version

2.0

Created at

2022-09-06 17:02:56 UTC

Updated at

2022-09-06 17:02:56 UTC

NP-MRD ID

NP0234788

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,5s,6r,10r,11s,12r,15r,19s)-6-(furan-3-yl)-1,5,10,15-tetramethyl-18-oxo-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-8,16-dien-11-yl benzoate

Description

CHEMBL2335035 belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. (1r,2s,5s,6r,10r,11s,12r,15r,19s)-6-(furan-3-yl)-1,5,10,15-tetramethyl-18-oxo-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-8,16-dien-11-yl benzoate is found in Chisocheton ceramicus. Based on a literature review very few articles have been published on CHEMBL2335035.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062219022D          

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M  END

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M  END


  Mrv1652309062219022D          

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    0.8028    0.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9443    1.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7189    1.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8314    2.7754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5180    1.3820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7152    2.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2106    0.6164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  2  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
  5 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 38 27  1  1  0  0  0
 30 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0234788

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CO[C@@H]3[C@@H]1[C@@](C)([C@H]1CC[C@@]4(C)[C@@H](CC=C4[C@]1(C)[C@@H]3OC(=O)C1=CC=CC=C1)C1=COC=C1)C(=O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C33H36O5/c1-30-15-13-25(34)33(4)24-12-16-31(2)22(21-14-17-36-18-21)10-11-23(31)32(24,3)28(26(27(30)33)37-19-30)38-29(35)20-8-6-5-7-9-20/h5-9,11,13-15,17-18,22,24,26-28H,10,12,16,19H2,1-4H3/t22-,24-,26+,27-,28+,30-,31-,32-,33-/m0/s1

> <INCHI_KEY>
OINZOSRLDSTGHZ-JRDOKHADSA-N

> <FORMULA>
C33H36O5

> <MOLECULAR_WEIGHT>
512.646

> <EXACT_MASS>
512.256274259

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
56.226319669471316

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5S,6R,10R,11S,12R,15R,19S)-6-(furan-3-yl)-1,5,10,15-tetramethyl-18-oxo-13-oxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadeca-8,16-dien-11-yl benzoate

> <JCHEM_LOGP>
6.342900317999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7847128077726024

> <JCHEM_POLAR_SURFACE_AREA>
65.74000000000001

> <JCHEM_REFRACTIVITY>
145.62510000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5S,6R,10R,11S,12R,15R,19S)-6-(furan-3-yl)-1,5,10,15-tetramethyl-18-oxo-13-oxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadeca-8,16-dien-11-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       9.994   4.594   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.274   3.233   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.323   4.444   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.799   4.226   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.225   2.797   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.176   1.586   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.126   0.374   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.700   1.804   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.882   0.816   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.186   1.635   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.810   3.129   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.798   4.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.334   4.206   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.908   5.635   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.726   6.623   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.422   5.804   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.602   0.157   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.553  -1.055   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.979  -2.484   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.454  -2.701   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.929  -3.695   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.454  -3.478   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.405  -4.689   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.831  -6.118   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.306  -6.336   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.356  -5.124   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.077  -0.061   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.219  -1.339   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.738  -0.918   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.680   0.621   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.298  -0.057   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.499   1.608   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.763   3.125   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.209   3.655   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.419   5.181   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.700   2.580   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.068   4.075   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.126   1.151   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8   11                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   36                                                  
CONECT    6    5    7    8   17                                             
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    2   12                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17    6   18   27                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27   17   28   38                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32   38                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    5   37   38                                             
CONECT   37   36                                                            
CONECT   38   36   27   30                                                  
MASTER        0    0    0    0    0    0    0    0   38    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₃₆O₅

Average Mass

512.6460 Da

Monoisotopic Mass

512.25627 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@]12CO[C@@H]3[C@@H]1[C@@](C)([C@H]1CC[C@@]4(C)[C@@H](CC=C4[C@]1(C)[C@@H]3OC(=O)C1=CC=CC=C1)C1=COC=C1)C(=O)C=C2

InChI Identifier

InChI=1S/C33H36O5/c1-30-15-13-25(34)33(4)24-12-16-31(2)22(21-14-17-36-18-21)10-11-23(31)32(24,3)28(26(27(30)33)37-19-30)38-29(35)20-8-6-5-7-9-20/h5-9,11,13-15,17-18,22,24,26-28H,10,12,16,19H2,1-4H3/t22-,24-,26+,27-,28+,30-,31-,32-,33-/m0/s1

InChI Key

OINZOSRLDSTGHZ-JRDOKHADSA-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
Chisocheton ceramicus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
17-furanylsteroid skeleton
Steroid
Naphthofuran
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Cyclohexenone
Monocyclic benzene moiety
Benzenoid
Tetrahydrofuran
Heteroaromatic compound
Furan
Carboxylic acid ester
Ketone
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen 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

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

29415332

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71567281

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,5s,6r,10r,11s,12r,15r,19s)-6-(furan-3-yl)-1,5,10,15-tetramethyl-18-oxo-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-8,16-dien-11-yl benzoate (NP0234788)

MOL for NP0234788 ((1r,2s,5s,6r,10r,11s,12r,15r,19s)-6-(furan-3-yl)-1,5,10,15-tetramethyl-18-oxo-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-8,16-dien-11-yl benzoate)

3D MOL for NP0234788 ((1r,2s,5s,6r,10r,11s,12r,15r,19s)-6-(furan-3-yl)-1,5,10,15-tetramethyl-18-oxo-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-8,16-dien-11-yl benzoate)

3D SDF for NP0234788 ((1r,2s,5s,6r,10r,11s,12r,15r,19s)-6-(furan-3-yl)-1,5,10,15-tetramethyl-18-oxo-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-8,16-dien-11-yl benzoate)

3D-SDF for NP0234788 ((1r,2s,5s,6r,10r,11s,12r,15r,19s)-6-(furan-3-yl)-1,5,10,15-tetramethyl-18-oxo-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-8,16-dien-11-yl benzoate)

PDB for NP0234788 ((1r,2s,5s,6r,10r,11s,12r,15r,19s)-6-(furan-3-yl)-1,5,10,15-tetramethyl-18-oxo-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-8,16-dien-11-yl benzoate)

3D PDB for NP0234788 ((1r,2s,5s,6r,10r,11s,12r,15r,19s)-6-(furan-3-yl)-1,5,10,15-tetramethyl-18-oxo-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-8,16-dien-11-yl benzoate)

SMILES for NP0234788 ((1r,2s,5s,6r,10r,11s,12r,15r,19s)-6-(furan-3-yl)-1,5,10,15-tetramethyl-18-oxo-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-8,16-dien-11-yl benzoate)

INCHI for NP0234788 ((1r,2s,5s,6r,10r,11s,12r,15r,19s)-6-(furan-3-yl)-1,5,10,15-tetramethyl-18-oxo-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-8,16-dien-11-yl benzoate)

Structure for NP0234788 ((1r,2s,5s,6r,10r,11s,12r,15r,19s)-6-(furan-3-yl)-1,5,10,15-tetramethyl-18-oxo-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-8,16-dien-11-yl benzoate)

3D Structure for NP0234788 ((1r,2s,5s,6r,10r,11s,12r,15r,19s)-6-(furan-3-yl)-1,5,10,15-tetramethyl-18-oxo-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-8,16-dien-11-yl benzoate)