NP-MRD: Showing NP-Card for (1s,2r,7r,8s,9r,10r)-4,4,7,8-tetramethyl-11-oxotricyclo[5.4.0.0²,⁹]undecan-10-yl (2s,3s,4s,5r,6s)-6-(3,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylate (NP0259089)

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Record Information

Version

2.0

Created at

2022-09-08 00:50:16 UTC

Updated at

2022-09-08 00:50:17 UTC

NP-MRD ID

NP0259089

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,7r,8s,9r,10r)-4,4,7,8-tetramethyl-11-oxotricyclo[5.4.0.0²,⁹]undecan-10-yl (2s,3s,4s,5r,6s)-6-(3,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylate

Description

(1S,2R,7R,8S,9R,10R)-4,4,7,8-tetramethyl-11-oxotricyclo[5.4.0.0²,⁹]Undecan-10-yl (2S,3S,4S,5R,6S)-6-(3,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylate belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. (1s,2r,7r,8s,9r,10r)-4,4,7,8-tetramethyl-11-oxotricyclo[5.4.0.0²,⁹]undecan-10-yl (2s,3s,4s,5r,6s)-6-(3,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylate is found in Citrus limon. Based on a literature review very few articles have been published on (1S,2R,7R,8S,9R,10R)-4,4,7,8-tetramethyl-11-oxotricyclo[5.4.0.0²,⁹]Undecan-10-yl (2S,3S,4S,5R,6S)-6-(3,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082202502D          

 37 41  0  0  1  0            999 V2000
    1.5303   -1.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 73 77  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309082202502D          

 37 41  0  0  1  0            999 V2000
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    2.7380   -0.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9743   -0.8986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5611   -0.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8665    0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1772    1.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4461    0.6406    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7646    1.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  6  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  1  6  0  0  0
  4 26  1  0  0  0  0
 26 27  2  0  0  0  0
 28 26  1  6  0  0  0
 28 29  1  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 28 36  1  0  0  0  0
  2 36  1  0  0  0  0
 36 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0259089

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2[C@H]3CC(C)(C)CC[C@@]1(C)[C@H]3C(=O)[C@@H]2OC(=O)[C@H]1O[C@@H](OC2=CC(O)=CC(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O10/c1-11-16-15-10-26(2,3)5-6-27(11,4)17(15)18(30)22(16)36-24(34)23-20(32)19(31)21(33)25(37-23)35-14-8-12(28)7-13(29)9-14/h7-9,11,15-17,19-23,25,28-29,31-33H,5-6,10H2,1-4H3/t11-,15+,16-,17+,19-,20-,21+,22+,23-,25+,27+/m0/s1

> <INCHI_KEY>
VNOKNARUVZBJAJ-IDDGQWBCSA-N

> <FORMULA>
C27H36O10

> <MOLECULAR_WEIGHT>
520.575

> <EXACT_MASS>
520.230847359

> <ALOGPS_LOGP>
2.56

> <ALOGPS_LOGS>
-3.04

> <ALOGPS_SOLUBILITY>
4.79e-01 g/l

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       2.857  -2.141   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.100  -0.799   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.720  -0.443   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.403   0.602   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.919   0.334   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.446  -1.113   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.963  -1.380   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.456  -2.292   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.060  -2.025   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.050  -3.205   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.567  -2.938   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.556  -4.117   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.073  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.063  -5.030   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.579  -4.763   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.536  -6.477   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.019  -6.744   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.493  -8.191   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.030  -5.564   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.523  -4.652   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.513  -5.832   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.993  -4.919   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.520  -6.366   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.983  -3.739   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.500  -4.007   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.291   1.962   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.365   3.355   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.743   1.640   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.365  -0.024   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.724  -0.983   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.111  -0.202   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.552  -1.677   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.647  -0.097   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.351   1.338   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.064   2.266   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.699   1.196   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.427   2.064   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4   29                                                  
CONECT    4    3    5   26                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   24                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12                                                       
CONECT   20   10   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    8   25                                                  
CONECT   25   24                                                            
CONECT   26    4   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   36                                                  
CONECT   29   28    3   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   28    2   37                                             
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,7R,8S,9R,10R)-4,4,7,8-Tetramethyl-11-oxotricyclo[5.4.0.0,]undecan-10-yl (2S,3S,4S,5R,6S)-6-(3,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	Generator

Chemical Formula

C₂₇H₃₆O₁₀

Average Mass

520.5750 Da

Monoisotopic Mass

520.23085 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2[C@H]3CC(C)(C)CC[C@@]1(C)[C@H]3C(=O)[C@@H]2OC(=O)[C@H]1O[C@@H](OC2=CC(O)=CC(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C27H36O10/c1-11-16-15-10-26(2,3)5-6-27(11,4)17(15)18(30)22(16)36-24(34)23-20(32)19(31)21(33)25(37-23)35-14-8-12(28)7-13(29)9-14/h7-9,11,15-17,19-23,25,28-29,31-33H,5-6,10H2,1-4H3/t11-,15+,16-,17+,19-,20-,21+,22+,23-,25+,27+/m0/s1

InChI Key

VNOKNARUVZBJAJ-IDDGQWBCSA-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
Citrus limon	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Norbornane monoterpenoid
Aromatic monoterpenoid
Monoterpenoid
Phenoxy compound
Phenol ether
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alpha-acyloxy ketone
Phenol
Beta-hydroxy acid
Oxane
Hydroxy acid
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Pyran
Carboxylic acid ester
Ketone
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Monocarboxylic acid or derivatives
Carbonyl group
Hydrocarbon derivative
Alcohol
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

162962870

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,7r,8s,9r,10r)-4,4,7,8-tetramethyl-11-oxotricyclo[5.4.0.0²,⁹]undecan-10-yl (2s,3s,4s,5r,6s)-6-(3,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylate (NP0259089)

MOL for NP0259089 ((1s,2r,7r,8s,9r,10r)-4,4,7,8-tetramethyl-11-oxotricyclo[5.4.0.0²,⁹]undecan-10-yl (2s,3s,4s,5r,6s)-6-(3,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylate)

3D MOL for NP0259089 ((1s,2r,7r,8s,9r,10r)-4,4,7,8-tetramethyl-11-oxotricyclo[5.4.0.0²,⁹]undecan-10-yl (2s,3s,4s,5r,6s)-6-(3,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylate)

3D SDF for NP0259089 ((1s,2r,7r,8s,9r,10r)-4,4,7,8-tetramethyl-11-oxotricyclo[5.4.0.0²,⁹]undecan-10-yl (2s,3s,4s,5r,6s)-6-(3,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylate)

3D-SDF for NP0259089 ((1s,2r,7r,8s,9r,10r)-4,4,7,8-tetramethyl-11-oxotricyclo[5.4.0.0²,⁹]undecan-10-yl (2s,3s,4s,5r,6s)-6-(3,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylate)

PDB for NP0259089 ((1s,2r,7r,8s,9r,10r)-4,4,7,8-tetramethyl-11-oxotricyclo[5.4.0.0²,⁹]undecan-10-yl (2s,3s,4s,5r,6s)-6-(3,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylate)

3D PDB for NP0259089 ((1s,2r,7r,8s,9r,10r)-4,4,7,8-tetramethyl-11-oxotricyclo[5.4.0.0²,⁹]undecan-10-yl (2s,3s,4s,5r,6s)-6-(3,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylate)

SMILES for NP0259089 ((1s,2r,7r,8s,9r,10r)-4,4,7,8-tetramethyl-11-oxotricyclo[5.4.0.0²,⁹]undecan-10-yl (2s,3s,4s,5r,6s)-6-(3,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylate)

INCHI for NP0259089 ((1s,2r,7r,8s,9r,10r)-4,4,7,8-tetramethyl-11-oxotricyclo[5.4.0.0²,⁹]undecan-10-yl (2s,3s,4s,5r,6s)-6-(3,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylate)

Structure for NP0259089 ((1s,2r,7r,8s,9r,10r)-4,4,7,8-tetramethyl-11-oxotricyclo[5.4.0.0²,⁹]undecan-10-yl (2s,3s,4s,5r,6s)-6-(3,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylate)

3D Structure for NP0259089 ((1s,2r,7r,8s,9r,10r)-4,4,7,8-tetramethyl-11-oxotricyclo[5.4.0.0²,⁹]undecan-10-yl (2s,3s,4s,5r,6s)-6-(3,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylate)