NP-MRD: Showing NP-Card for (5s)-3-[(2r,11r)-2,11-dihydroxy-11-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]undecyl]-5-methyl-5h-furan-2-one (NP0245176)

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Record Information

Version

1.0

Created at

2022-09-07 06:09:26 UTC

Updated at

2022-09-07 06:09:26 UTC

NP-MRD ID

NP0245176

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5s)-3-[(2r,11r)-2,11-dihydroxy-11-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]undecyl]-5-methyl-5h-furan-2-one

Description

Montalicin a belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Thus, montalicin a is considered to be an annonaceae acetogenin. (5s)-3-[(2r,11r)-2,11-dihydroxy-11-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]undecyl]-5-methyl-5h-furan-2-one is found in Annona montana. It was first documented in 2022 (PMID: 36087713). Based on a literature review a significant number of articles have been published on Montalicin a (PMID: 36083970) (PMID: 36082849) (PMID: 36077915) (PMID: 36051722).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072208092D          

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M  END

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M  END


  Mrv1652309072208092D          

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   16.3429   -6.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0574   -5.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7718   -6.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4863   -5.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2008   -6.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9153   -5.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6297   -6.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3442   -5.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0587   -6.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7731   -5.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4876   -6.2636    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.4876   -7.0886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2021   -5.8511    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.2883   -5.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0953   -4.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5078   -5.5735    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.3283   -5.6598    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.8132   -4.9923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6638   -6.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4843   -6.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8199   -7.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6403   -7.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9759   -8.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7964   -8.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1319   -8.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9524   -9.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2880   -9.7731    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   30.8031  -10.4405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1085   -9.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4440  -10.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2510  -10.7845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3372  -11.6050    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   34.0517  -12.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5835  -11.9406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0315  -11.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2110  -11.4137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9558   -6.1866    0.0000 O   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  6  0  0  0
 15 13  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 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  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 32 37  1  0  0  0  0
 37 38  2  0  0  0  0
 18 39  1  0  0  0  0
 15 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245176

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCC[C@@H](O)[C@H]1CC[C@@H](O1)[C@H](O)CCCCCCCC[C@@H](O)CC1=C[C@H](C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C33H60O6/c1-3-4-5-6-7-8-9-10-14-17-20-29(35)31-22-23-32(39-31)30(36)21-18-15-12-11-13-16-19-28(34)25-27-24-26(2)38-33(27)37/h24,26,28-32,34-36H,3-23,25H2,1-2H3/t26-,28+,29+,30+,31+,32+/m0/s1

> <INCHI_KEY>
WODXWQIGOUMEHH-ONILFDQGSA-N

> <FORMULA>
C33H60O6

> <MOLECULAR_WEIGHT>
552.837

> <EXACT_MASS>
552.438989652

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
99

> <JCHEM_AVERAGE_POLARIZABILITY>
70.5414905323379

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-3-[(2R,11R)-2,11-dihydroxy-11-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]undecyl]-5-methyl-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
8.203835835

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.972784244576374

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.312197120980954

> <JCHEM_PKA_STRONGEST_BASIC>
-2.722022871174217

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
158.4717

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-3-[(2R,11R)-2,11-dihydroxy-11-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]undecyl]-5-methyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      27.839 -11.692   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.173 -10.922   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      30.507 -11.692   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.840 -10.922   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      33.174 -11.692   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      34.508 -10.922   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      35.841 -11.692   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      37.175 -10.922   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      38.509 -11.692   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      39.842 -10.922   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      41.176 -11.692   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      42.510 -10.922   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      43.844 -11.692   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      43.844 -13.232   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      45.177 -10.922   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      45.338  -9.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      46.845  -9.070   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      47.615 -10.404   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      49.146 -10.565   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      50.051  -9.319   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      49.772 -11.972   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      51.304 -12.133   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      51.930 -13.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      53.462 -13.701   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      54.088 -15.107   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      55.620 -15.268   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      56.246 -16.675   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      57.778 -16.836   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      58.404 -18.243   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      57.499 -19.489   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      59.936 -18.404   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      60.562 -19.811   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      62.069 -20.131   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      62.229 -21.663   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      63.563 -22.433   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      60.823 -22.289   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      59.792 -21.145   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      58.261 -21.306   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      46.584 -11.548   0.000  0.00  0.00           O+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   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   39                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   39                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   32   38                                                  
CONECT   38   37                                                            
CONECT   39   18   15                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₆₀O₆

Average Mass

552.8370 Da

Monoisotopic Mass

552.43899 Da

IUPAC Name

(5S)-3-[(2R,11R)-2,11-dihydroxy-11-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]undecyl]-5-methyl-2,5-dihydrofuran-2-one

Traditional Name

(5S)-3-[(2R,11R)-2,11-dihydroxy-11-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]undecyl]-5-methyl-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCC[C@@H](O)[C@H]1CC[C@@H](O1)[C@H](O)CCCCCCCC[C@@H](O)CC1=C[C@H](C)OC1=O

InChI Identifier

InChI=1S/C33H60O6/c1-3-4-5-6-7-8-9-10-14-17-20-29(35)31-22-23-32(39-31)30(36)21-18-15-12-11-13-16-19-28(34)25-27-24-26(2)38-33(27)37/h24,26,28-32,34-36H,3-23,25H2,1-2H3/t26-,28+,29+,30+,31+,32+/m0/s1

InChI Key

WODXWQIGOUMEHH-ONILFDQGSA-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
Annona montana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
Long chain fatty alcohol
2-furanone
Dihydrofuran
Oxolane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	8.2	ChemAxon
pKa (Strongest Acidic)	13.31	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	158.47 m³·mol⁻¹	ChemAxon
Polarizability	70.54 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	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

C00051630

Chemspider ID

28282241

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162943746

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

O'Byrne LJ, Bodunde EO, Maher GM, Khashan AS, Greene RM, Browne JP, Mccarthy FP: Patient reported outcome measures evaluating postpartum maternal health and wellbeing: a systematic review and evaluation of measurement properties. Am J Obstet Gynecol MFM. 2022 Sep 7:100743. doi: 10.1016/j.ajogmf.2022.100743. [PubMed:36087713 ]
Panchal N, Desai C, Ghosal R: Fecal glucocorticoid metabolite levels in captive Indian leopards (Panthera pardus fusca) housed under three different enrichment regimes. PLoS One. 2022 Sep 9;17(9):e0261796. doi: 10.1371/journal.pone.0261796. eCollection 2022. [PubMed:36083970 ]
Polishchuk V, Filatova M, Rusanov E, Shandura M: Trianionic 1,3,2-Dioxaborine-Containing Polymethines: Bright Near-Infrared Fluorophores. Chemistry. 2022 Sep 9. doi: 10.1002/chem.202202168. [PubMed:36082849 ]
Keum SH, Kim WS, Ghassemi Nejad J, Lee JS, Jo YH, Park KY, Kim YR, Jo JH, Lee HG: Evaluation of the Feed Nutritional Value of Noni (Morinda citrifolia) Meal for Holstein Dairy Cows. Animals (Basel). 2022 Aug 26;12(17). pii: ani12172196. doi: 10.3390/ani12172196. [PubMed:36077915 ]
Wako M, Kono H, Koyama K, Fujimaki T, Furuya N, Haro H: The Anatomical Position of Graf's Standard Plane and Its Relationship With Pelvic Morphology: A Computed Tomography-Based Study. Cureus. 2022 Jul 28;14(7):e27424. doi: 10.7759/cureus.27424. eCollection 2022 Jul. [PubMed:36051722 ]
LOTUS database [Link]

Showing NP-Card for (5s)-3-[(2r,11r)-2,11-dihydroxy-11-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]undecyl]-5-methyl-5h-furan-2-one (NP0245176)

MOL for NP0245176 ((5s)-3-[(2r,11r)-2,11-dihydroxy-11-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]undecyl]-5-methyl-5h-furan-2-one)

3D MOL for NP0245176 ((5s)-3-[(2r,11r)-2,11-dihydroxy-11-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]undecyl]-5-methyl-5h-furan-2-one)

3D SDF for NP0245176 ((5s)-3-[(2r,11r)-2,11-dihydroxy-11-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]undecyl]-5-methyl-5h-furan-2-one)

3D-SDF for NP0245176 ((5s)-3-[(2r,11r)-2,11-dihydroxy-11-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]undecyl]-5-methyl-5h-furan-2-one)

PDB for NP0245176 ((5s)-3-[(2r,11r)-2,11-dihydroxy-11-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]undecyl]-5-methyl-5h-furan-2-one)

3D PDB for NP0245176 ((5s)-3-[(2r,11r)-2,11-dihydroxy-11-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]undecyl]-5-methyl-5h-furan-2-one)

SMILES for NP0245176 ((5s)-3-[(2r,11r)-2,11-dihydroxy-11-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]undecyl]-5-methyl-5h-furan-2-one)

INCHI for NP0245176 ((5s)-3-[(2r,11r)-2,11-dihydroxy-11-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]undecyl]-5-methyl-5h-furan-2-one)

Structure for NP0245176 ((5s)-3-[(2r,11r)-2,11-dihydroxy-11-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]undecyl]-5-methyl-5h-furan-2-one)

3D Structure for NP0245176 ((5s)-3-[(2r,11r)-2,11-dihydroxy-11-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]undecyl]-5-methyl-5h-furan-2-one)