NP-MRD: Showing NP-Card for [(1r,4s,12s,13r,16r,17s)-17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-yl]methyl hexadecanoate (NP0228487)

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Record Information

Version

2.0

Created at

2022-09-06 08:10:10 UTC

Updated at

2022-09-06 08:10:10 UTC

NP-MRD ID

NP0228487

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,4s,12s,13r,16r,17s)-17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-yl]methyl hexadecanoate

Description

DTXSID401002186 belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. [(1r,4s,12s,13r,16r,17s)-17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-yl]methyl hexadecanoate is found in Coffea arabica. Based on a literature review very few articles have been published on DTXSID401002186.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062210102D          

 40 44  0  0  1  0            999 V2000
    9.9375    8.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6520    7.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.5099    7.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          2D

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M  END


  Mrv1652309062210102D          

 40 44  0  0  1  0            999 V2000
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   15.6533    8.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3678    7.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0822    8.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7967    7.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5112    8.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2256    7.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9401    8.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6546    7.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6546    6.7906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3690    8.0281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0835    7.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0835    6.7906    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.2631    6.8771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9482    6.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3475    6.0798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.0741    6.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8131    6.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8652    5.3095    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.6081    4.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3718    5.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9045    4.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4700    3.9314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6688    4.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9866    3.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2437    4.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1830    4.8455    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.5063    4.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4132    5.1953    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.6978    4.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9354    5.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9036    5.9464    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.6445    5.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  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
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 26 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 23 36  1  0  0  0  0
 36 37  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 20 39  1  0  0  0  0
 39 40  1  6  0  0  0
 23 40  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0228487

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCC(=O)OC[C@]1(O)C[C@@]23C[C@H]1CC[C@H]2[C@]1(C)CCC2=C(C=CO2)[C@H]1CC3

> <INCHI_IDENTIFIER>
InChI=1S/C36H58O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-33(37)40-27-36(38)26-35-23-19-30-29-21-24-39-31(29)20-22-34(30,2)32(35)18-17-28(36)25-35/h21,24,28,30,32,38H,3-20,22-23,25-27H2,1-2H3/t28-,30-,32+,34-,35-,36-/m1/s1

> <INCHI_KEY>
DGPMHJKMSANHDM-XCPWRNKKSA-N

> <FORMULA>
C36H58O4

> <MOLECULAR_WEIGHT>
554.856

> <EXACT_MASS>
554.433510348

> <ALOGPS_LOGP>
8.60

> <ALOGPS_LOGS>
-5.59

> <ALOGPS_SOLUBILITY>
1.41e-03 g/l

$$$$

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      18.550  14.986   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.884  14.216   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.217  14.986   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.551  14.216   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.885  14.986   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.218  14.216   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.552  14.986   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      27.886  14.216   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      29.219  14.986   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.553  14.216   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.887  14.986   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      33.220  14.216   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      34.554  14.986   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.888  14.216   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      37.222  14.986   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      38.555  14.216   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      38.555  12.676   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      39.889  14.986   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      41.223  14.216   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      41.223  12.676   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      39.691  12.837   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      42.837  12.846   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      43.582  11.349   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      44.938  12.150   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      46.318  11.459   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      46.415   9.911   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      47.802   9.241   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      49.227   9.824   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      50.222   8.648   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      49.411   7.339   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      47.915   7.705   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      46.642   6.839   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      45.255   7.509   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      45.142   9.045   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      43.879   8.164   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      43.705   9.698   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      42.369   8.743   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      40.946   9.487   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      40.887  11.100   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      42.270  11.117   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   39                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   36   40                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   34                                                  
CONECT   27   26   28   31                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   27   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   26   35   36                                             
CONECT   35   34                                                            
CONECT   36   34   23   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   20   40                                                  
CONECT   40   39   23                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₅₈O₄

Average Mass

554.8560 Da

Monoisotopic Mass

554.43351 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(=O)OC[C@]1(O)C[C@@]23C[C@H]1CC[C@H]2[C@]1(C)CCC2=C(C=CO2)[C@H]1CC3

InChI Identifier

InChI=1S/C36H58O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-33(37)40-27-36(38)26-35-23-19-30-29-21-24-39-31(29)20-22-34(30,2)32(35)18-17-28(36)25-35/h21,24,28,30,32,38H,3-20,22-23,25-27H2,1-2H3/t28-,30-,32+,34-,35-,36-/m1/s1

InChI Key

DGPMHJKMSANHDM-XCPWRNKKSA-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
Coffea arabica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four 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

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Benzofuran
Fatty acid ester
Fatty acyl
Heteroaromatic compound
Tertiary alcohol
Furan
Cyclic alcohol
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
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

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

117974

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

133758

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1r,4s,12s,13r,16r,17s)-17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-yl]methyl hexadecanoate (NP0228487)

MOL for NP0228487 ([(1r,4s,12s,13r,16r,17s)-17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-yl]methyl hexadecanoate)

3D MOL for NP0228487 ([(1r,4s,12s,13r,16r,17s)-17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-yl]methyl hexadecanoate)

3D SDF for NP0228487 ([(1r,4s,12s,13r,16r,17s)-17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-yl]methyl hexadecanoate)

3D-SDF for NP0228487 ([(1r,4s,12s,13r,16r,17s)-17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-yl]methyl hexadecanoate)

PDB for NP0228487 ([(1r,4s,12s,13r,16r,17s)-17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-yl]methyl hexadecanoate)

3D PDB for NP0228487 ([(1r,4s,12s,13r,16r,17s)-17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-yl]methyl hexadecanoate)

SMILES for NP0228487 ([(1r,4s,12s,13r,16r,17s)-17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-yl]methyl hexadecanoate)

INCHI for NP0228487 ([(1r,4s,12s,13r,16r,17s)-17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-yl]methyl hexadecanoate)

Structure for NP0228487 ([(1r,4s,12s,13r,16r,17s)-17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-yl]methyl hexadecanoate)

3D Structure for NP0228487 ([(1r,4s,12s,13r,16r,17s)-17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-yl]methyl hexadecanoate)