NP-MRD: Showing NP-Card for (3e,5r,7r,18s)-5,6,7-trihydroxy-18-methyl-1-oxacyclooctadec-3-en-2-one (NP0193167)

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Record Information

Version

2.0

Created at

2022-09-04 10:32:38 UTC

Updated at

2022-09-04 10:32:38 UTC

NP-MRD ID

NP0193167

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3e,5r,7r,18s)-5,6,7-trihydroxy-18-methyl-1-oxacyclooctadec-3-en-2-one

Description

Aspicilin belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (3e,5r,7r,18s)-5,6,7-trihydroxy-18-methyl-1-oxacyclooctadec-3-en-2-one was first documented in 2006 (PMID: 17048862). Based on a literature review a small amount of articles have been published on Aspicilin (PMID: 33333421) (PMID: 30893410) (PMID: 28748700) (PMID: 25402822).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 55 55  0  0  0  0  0  0  0  0999 V2000
   -3.2615   -3.0943   -0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9533   -2.2932   -0.4883 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2830   -0.8928   -0.9445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1724    0.0545    0.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1545    1.2004    0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4394    2.4910   -0.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5178    2.9600    0.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4187    3.8391    0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5298    3.0798   -0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9317    3.0159   -0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3534    1.6206    0.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0665    0.6158   -0.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1003   -0.4551   -0.9460 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3694    0.1030   -0.8669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9442   -1.5664    0.0687 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4063   -1.0547    1.2908 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5029   -1.9848    0.1470 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9027   -1.2146    1.1361 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3450   -3.4488    0.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2884   -3.9404    1.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8383   -3.2001    1.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2434   -3.4241    2.7370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5622   -2.2403    0.8474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9256   -2.7145   -1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8039   -2.9855    0.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0531   -4.1499   -0.7749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1933   -2.7536   -1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5123   -0.5881   -1.6803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2933   -0.8363   -1.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1214    0.4525    0.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4013   -0.4174    1.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8298    0.9616   -0.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7462    1.3814    0.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2456    3.2594   -0.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9760    2.3564   -1.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1130    2.1648    1.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0976    3.6355    1.4808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1353    4.3338    1.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9478    4.6594   -0.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5901    3.6517   -1.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1575    2.0703   -0.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6951    3.3638   -0.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0759    3.6687    0.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8052    1.3820    1.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4232    1.6612    0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0497    0.2521   -0.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0553    1.1624   -1.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9863   -0.9270   -1.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3484    0.9385   -1.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6201   -2.3918   -0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5746   -1.7899    1.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9676   -1.7768   -0.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4337   -1.1003    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1716   -4.0618    0.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2746   -5.0331    1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23  2  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  6
 14 49  1  0
 15 50  1  6
 16 51  1  0
 17 52  1  6
 18 53  1  0
 19 54  1  0
 20 55  1  0
M  END


  Mrv1652309042212322D          

 23 23  0  0  1  0            999 V2000
    2.1728    2.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    1.5918    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9924    2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8119    2.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1398    1.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6480    0.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9758   -0.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4841   -0.6794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8119   -1.4365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3202   -2.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -2.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0089   -2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1894   -2.5721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6976   -3.2345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8615   -1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0420   -1.7204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3533   -1.1526    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1728   -1.2472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0255   -0.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5172    0.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1894    1.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3698    1.1186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6811    1.6864    0.0000 O   0  0  0  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
  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  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  2 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0193167

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CCCCCCCCCC[C@@H](O)C(O)[C@H](O)\C=C\C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O5/c1-14-10-8-6-4-2-3-5-7-9-11-15(19)18(22)16(20)12-13-17(21)23-14/h12-16,18-20,22H,2-11H2,1H3/b13-12+/t14-,15+,16+,18?/m0/s1

> <INCHI_KEY>
KECCBFYFEOTIBV-OSMSTNRISA-N

> <FORMULA>
C18H32O5

> <MOLECULAR_WEIGHT>
328.449

> <EXACT_MASS>
328.22497413

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
37.02941953901023

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E,5R,7R,18S)-5,6,7-trihydroxy-18-methyl-1-oxacyclooctadec-3-en-2-one

> <JCHEM_LOGP>
3.1960575173333337

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.378699992517276

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.0238914222031

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1851441138850287

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
89.87169999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3E,5R,7R,18S)-5,6,7-trihydroxy-18-methyl-1-oxacyclooctadec-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       4.056   4.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.668   2.971   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.586   4.208   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.116   4.031   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.728   2.618   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.810   1.382   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.422  -0.032   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.504  -1.268   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.116  -2.681   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.198  -3.918   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.668  -3.741   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.750  -4.978   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.220  -4.801   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.302  -6.038   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.608  -3.388   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.078  -3.211   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.526  -2.152   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.056  -2.328   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.914  -0.738   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.832   0.498   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.220   1.911   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.690   2.088   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.138   3.148   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
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   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    2                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₃₂O₅

Average Mass

328.4490 Da

Monoisotopic Mass

328.22497 Da

IUPAC Name

(3E,5R,7R,18S)-5,6,7-trihydroxy-18-methyl-1-oxacyclooctadec-3-en-2-one

Traditional Name

(3E,5R,7R,18S)-5,6,7-trihydroxy-18-methyl-1-oxacyclooctadec-3-en-2-one

CAS Registry Number

Not Available

SMILES

C[C@H]1CCCCCCCCCC[C@@H](O)C(O)[C@H](O)\C=C\C(=O)O1

InChI Identifier

InChI=1S/C18H32O5/c1-14-10-8-6-4-2-3-5-7-9-11-15(19)18(22)16(20)12-13-17(21)23-14/h12-16,18-20,22H,2-11H2,1H3/b13-12+/t14-,15+,16+,18?/m0/s1

InChI Key

KECCBFYFEOTIBV-OSMSTNRISA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	3.2	ChemAxon
pKa (Strongest Acidic)	13.02	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	89.87 m³·mol⁻¹	ChemAxon
Polarizability	37.03 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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

13854534

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pant R, Joshi A, Joshi T, Maiti P, Nand M, Joshi T, Pande V, Chandra S: Identification of potent Antigen 85C inhibitors of Mycobacterium tuberculosis via in-house lichen library and binding free energy studies Part-II. J Mol Graph Model. 2021 Mar;103:107822. doi: 10.1016/j.jmgm.2020.107822. Epub 2020 Dec 8. [PubMed:33333421 ]
Kinfe HH: Versatility of glycals in synthetic organic chemistry: coupling reactions, diversity oriented synthesis and natural product synthesis. Org Biomol Chem. 2019 Apr 24;17(17):4153-4182. doi: 10.1039/c9ob00343f. [PubMed:30893410 ]
Schmidt R, Ostermeier M, Schobert R: Wittig Cyclization of omega-Hydroxy Hemiacetals: Synthesis of (+)-Aspicilin. J Org Chem. 2017 Sep 1;82(17):9126-9132. doi: 10.1021/acs.joc.7b01702. Epub 2017 Aug 11. [PubMed:28748700 ]
Zhang H, Yu EC, Torker S, Schrock RR, Hoveyda AH: Preparation of macrocyclic Z-enoates and (E,Z)- or (Z,E)-dienoates through catalytic stereoselective ring-closing metathesis. J Am Chem Soc. 2014 Nov 26;136(47):16493-6. doi: 10.1021/ja510768c. Epub 2014 Nov 17. [PubMed:25402822 ]
Dubost C, Marko IE, Ryckmans T: A concise total synthesis of the lichen macrolide (+)-aspicilin. Org Lett. 2006 Oct 26;8(22):5137-40. doi: 10.1021/ol0620287. [PubMed:17048862 ]
LOTUS database [Link]

Showing NP-Card for (3e,5r,7r,18s)-5,6,7-trihydroxy-18-methyl-1-oxacyclooctadec-3-en-2-one (NP0193167)

MOL for NP0193167 ((3e,5r,7r,18s)-5,6,7-trihydroxy-18-methyl-1-oxacyclooctadec-3-en-2-one)

3D MOL for NP0193167 ((3e,5r,7r,18s)-5,6,7-trihydroxy-18-methyl-1-oxacyclooctadec-3-en-2-one)

3D SDF for NP0193167 ((3e,5r,7r,18s)-5,6,7-trihydroxy-18-methyl-1-oxacyclooctadec-3-en-2-one)

3D-SDF for NP0193167 ((3e,5r,7r,18s)-5,6,7-trihydroxy-18-methyl-1-oxacyclooctadec-3-en-2-one)

PDB for NP0193167 ((3e,5r,7r,18s)-5,6,7-trihydroxy-18-methyl-1-oxacyclooctadec-3-en-2-one)

3D PDB for NP0193167 ((3e,5r,7r,18s)-5,6,7-trihydroxy-18-methyl-1-oxacyclooctadec-3-en-2-one)

SMILES for NP0193167 ((3e,5r,7r,18s)-5,6,7-trihydroxy-18-methyl-1-oxacyclooctadec-3-en-2-one)

INCHI for NP0193167 ((3e,5r,7r,18s)-5,6,7-trihydroxy-18-methyl-1-oxacyclooctadec-3-en-2-one)

Structure for NP0193167 ((3e,5r,7r,18s)-5,6,7-trihydroxy-18-methyl-1-oxacyclooctadec-3-en-2-one)

3D Structure for NP0193167 ((3e,5r,7r,18s)-5,6,7-trihydroxy-18-methyl-1-oxacyclooctadec-3-en-2-one)