Np mrd loader

Showing NP-Card for (5s)-5-methyl-3-{2,8,15-trihydroxy-15-[(2r,5s)-5-(1-hydroxytridecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one (NP0305538)

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Record Information
Version1.0
Created at2022-09-10 21:27:06 UTC
Updated at2022-09-10 21:27:07 UTC
NP-MRD IDNP0305538
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5s)-5-methyl-3-{2,8,15-trihydroxy-15-[(2r,5s)-5-(1-hydroxytridecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one
Description(5S)-5-methyl-3-{2,8,15-trihydroxy-15-[(2R,5S)-5-(1-hydroxytridecyl)oxolan-2-yl]pentadecyl}-2,5-dihydrofuran-2-one 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. (5s)-5-methyl-3-{2,8,15-trihydroxy-15-[(2r,5s)-5-(1-hydroxytridecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one is found in Asimina triloba. Based on a literature review very few articles have been published on (5S)-5-methyl-3-{2,8,15-trihydroxy-15-[(2R,5S)-5-(1-hydroxytridecyl)oxolan-2-yl]pentadecyl}-2,5-dihydrofuran-2-one.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0305538 ((5s)-5-methyl-3-{2,8,15-trihydroxy-15-[(2r,5s)-5-(1-hydroxytridecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one)


  Mrv1652309102223272D          

 44 45  0  0  1  0            999 V2000
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   -0.0710  -14.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7495  -14.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2176  -11.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5532  -10.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3737  -10.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7092   -9.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5297   -9.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 18 44  1  0  0  0  0
 15 44  1  0  0  0  0
M  END
Download

3D MOL for NP0305538 ((5s)-5-methyl-3-{2,8,15-trihydroxy-15-[(2r,5s)-5-(1-hydroxytridecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one)

Download
3D SDF for NP0305538 ((5s)-5-methyl-3-{2,8,15-trihydroxy-15-[(2r,5s)-5-(1-hydroxytridecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one)

  Mrv1652309102223272D          

 44 45  0  0  1  0            999 V2000
   -0.4065  -14.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0710  -14.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7495  -14.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9055  -13.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0616  -12.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3971  -11.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2176  -11.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5532  -10.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3737  -10.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7092   -9.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5297   -9.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0146  -10.5582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.4729   -6.9076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.6163   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.4742   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4742   -8.9701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1887   -7.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9032   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.3321   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.7611   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7611   -8.9701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   19.1900   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9437   -7.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4957   -8.4226    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.3162   -8.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0832   -9.1371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2762   -8.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6631   -9.5176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6722   -8.9656    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
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  6  7  1  0  0  0  0
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 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 37 42  1  0  0  0  0
 42 43  2  0  0  0  0
 18 44  1  0  0  0  0
 15 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0305538

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCC(O)[C@@H]1CC[C@@H](O1)C(O)CCCCCCC(O)CCCCCC(O)CC1=C[C@H](C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C37H68O7/c1-3-4-5-6-7-8-9-10-11-18-23-33(40)35-25-26-36(44-35)34(41)24-19-13-12-15-20-31(38)21-16-14-17-22-32(39)28-30-27-29(2)43-37(30)42/h27,29,31-36,38-41H,3-26,28H2,1-2H3/t29-,31?,32?,33?,34?,35-,36+/m0/s1

> <INCHI_KEY>
ALYPJDVVTYTPDW-NUTQLTLISA-N

> <FORMULA>
C37H68O7

> <MOLECULAR_WEIGHT>
624.944

> <EXACT_MASS>
624.49650453

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
112

> <JCHEM_AVERAGE_POLARIZABILITY>
78.2867215768223

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-5-methyl-3-{2,8,15-trihydroxy-15-[(2R,5S)-5-(1-hydroxytridecyl)oxolan-2-yl]pentadecyl}-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
8.595391968000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.972784243939977

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.312197120797506

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2743089189136105

> <JCHEM_POLAR_SURFACE_AREA>
116.45

> <JCHEM_REFRACTIVITY>
178.5452

> <JCHEM_ROTATABLE_BOND_COUNT>
28

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-5-methyl-3-{2,8,15-trihydroxy-15-[(2R,5S)-5-(1-hydroxytridecyl)oxolan-2-yl]pentadecyl}-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0305538 ((5s)-5-methyl-3-{2,8,15-trihydroxy-15-[(2r,5s)-5-(1-hydroxytridecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one)
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PDB for NP0305538 ((5s)-5-methyl-3-{2,8,15-trihydroxy-15-[(2r,5s)-5-(1-hydroxytridecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one)
HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.759 -27.870   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.132 -26.463   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.399 -26.302   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.025 -24.895   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.557 -24.734   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.183 -23.327   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.715 -23.166   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.341 -21.759   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.873 -21.598   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.499 -20.192   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.031 -20.031   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.657 -18.624   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.189 -18.463   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.094 -19.709   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.815 -17.056   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.045 -15.722   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.076 -14.578   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.482 -15.204   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.816 -14.434   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      15.816 -12.894   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      17.150 -15.204   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.484 -14.434   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.817 -15.204   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.151 -14.434   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      22.485 -15.204   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      23.818 -14.434   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      25.152 -15.204   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      25.152 -16.744   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      26.486 -14.434   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      27.819 -15.204   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      29.153 -14.434   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      30.487 -15.204   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      31.820 -14.434   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      33.154 -15.204   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      33.154 -16.744   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      34.488 -14.434   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      35.821 -15.204   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      37.228 -14.578   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      38.259 -15.722   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      39.790 -15.561   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      37.489 -17.056   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      35.982 -16.736   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      34.838 -17.766   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      14.321 -16.736   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   44                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   44                                                  
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   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   37   43                                                  
CONECT   43   42                                                            
CONECT   44   18   15                                                       
MASTER        0    0    0    0    0    0    0    0   44    0   90    0
END

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3D PDB for NP0305538 ((5s)-5-methyl-3-{2,8,15-trihydroxy-15-[(2r,5s)-5-(1-hydroxytridecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one)
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SMILES for NP0305538 ((5s)-5-methyl-3-{2,8,15-trihydroxy-15-[(2r,5s)-5-(1-hydroxytridecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one)
CCCCCCCCCCCCC(O)[C@@H]1CC[C@@H](O1)C(O)CCCCCCC(O)CCCCCC(O)CC1=C[C@H](C)OC1=O
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INCHI for NP0305538 ((5s)-5-methyl-3-{2,8,15-trihydroxy-15-[(2r,5s)-5-(1-hydroxytridecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one)
InChI=1S/C37H68O7/c1-3-4-5-6-7-8-9-10-11-18-23-33(40)35-25-26-36(44-35)34(41)24-19-13-12-15-20-31(38)21-16-14-17-22-32(39)28-30-27-29(2)43-37(30)42/h27,29,31-36,38-41H,3-26,28H2,1-2H3/t29-,31?,32?,33?,34?,35-,36+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC37H68O7
Average Mass624.9440 Da
Monoisotopic Mass624.49650 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCC(O)[C@@H]1CC[C@@H](O1)C(O)CCCCCCC(O)CCCCCC(O)CC1=C[C@H](C)OC1=O
InChI Identifier
InChI=1S/C37H68O7/c1-3-4-5-6-7-8-9-10-11-18-23-33(40)35-25-26-36(44-35)34(41)24-19-13-12-15-20-31(38)21-16-14-17-22-32(39)28-30-27-29(2)43-37(30)42/h27,29,31-36,38-41H,3-26,28H2,1-2H3/t29-,31?,32?,33?,34?,35-,36+/m0/s1
InChI KeyALYPJDVVTYTPDW-NUTQLTLISA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Asimina trilobaLOTUS Database
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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty alcohols  
Direct ParentAnnonaceous acetogenins  
Alternative Parents
Substituents
  • Annonaceae acetogenin skeleton
    • 

  • Long chain fatty alcohol
    • 

  • 2-furanone
    • 

  • Dihydrofuran
    • 

  • Oxolane
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Secondary alcohol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Carboxylic acid derivative
    • 

  • Organoheterocyclic compound
    • 

  • Polyol
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4478632  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5320586  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]