NP-MRD: Showing NP-Card for (5s)-3-[(2r)-7-[(2r,5s)-5-[(1s,4r)-1,4-dihydroxy-4-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-hydroxyheptyl]-5-methyl-5h-furan-2-one (NP0314283)

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Record Information

Version

2.0

Created at

2022-09-11 12:18:10 UTC

Updated at

2022-09-11 12:18:10 UTC

NP-MRD ID

NP0314283

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5s)-3-[(2r)-7-[(2r,5s)-5-[(1s,4r)-1,4-dihydroxy-4-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-hydroxyheptyl]-5-methyl-5h-furan-2-one

Description

Gigantecin 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)-3-[(2r)-7-[(2r,5s)-5-[(1s,4r)-1,4-dihydroxy-4-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-hydroxyheptyl]-5-methyl-5h-furan-2-one is found in Annona coriacea and Goniothalamus giganteus. (5s)-3-[(2r)-7-[(2r,5s)-5-[(1s,4r)-1,4-dihydroxy-4-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-hydroxyheptyl]-5-methyl-5h-furan-2-one was first documented in 2004 (PMID: 15469270). Based on a literature review a small amount of articles have been published on Gigantecin (PMID: 20110904) (PMID: 26118710) (PMID: 16836411).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309112214182D          

 45 47  0  0  1  0            999 V2000
   11.4397  -13.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8452  -12.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0434  -12.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4489  -11.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6470  -10.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4397  -10.4790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0342  -11.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8268  -10.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4213  -11.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2139  -11.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8084  -11.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6010  -11.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1955  -12.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.9973  -12.8815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9881  -11.8519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.2689  -11.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0934  -11.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3223  -11.8961    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.0980  -12.1769    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.2427  -12.9891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7291  -11.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5843  -10.8332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2154  -10.3018    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.9911  -10.5826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0707   -9.4896    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.3285   -9.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4419   -8.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2541   -8.1674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.6144   -7.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4373   -7.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.6205   -6.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9809   -5.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8038   -5.7639    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.2663   -6.4470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1641   -5.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9870   -4.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4229   -4.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2238   -4.4605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.8548   -3.9290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2828   -5.2834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5184   -5.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3202   -6.3946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6427   -8.8951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6391  -12.3586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
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 39 41  1  0  0  0  0
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 37 42  1  0  0  0  0
 42 43  2  0  0  0  0
 28 44  1  0  0  0  0
 25 44  1  0  0  0  0
 18 45  1  0  0  0  0
 15 45  1  0  0  0  0
M  END


  Mrv1652309112214182D          

 45 47  0  0  1  0            999 V2000
   11.4397  -13.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8452  -12.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0434  -12.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4489  -11.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6470  -10.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4397  -10.4790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0342  -11.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8268  -10.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4213  -11.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2139  -11.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8084  -11.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6010  -11.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1955  -12.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.9973  -12.8815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9881  -11.8519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.2689  -11.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0934  -11.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3223  -11.8961    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.0980  -12.1769    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.2427  -12.9891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7291  -11.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5843  -10.8332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2154  -10.3018    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.9911  -10.5826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0707   -9.4896    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.3285   -9.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4419   -8.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2541   -8.1674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.6144   -7.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4373   -7.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7977   -6.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6205   -6.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9809   -5.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8038   -5.7639    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.2663   -6.4470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1641   -5.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9870   -4.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4229   -4.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2238   -4.4605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.8548   -3.9290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2828   -5.2834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5184   -5.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3202   -6.3946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6427   -8.8951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6391  -12.3586    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  1  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  1  0  0  0
 25 23  1  6  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  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  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
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  6  0  0  0
 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
 28 44  1  0  0  0  0
 25 44  1  0  0  0  0
 18 45  1  0  0  0  0
 15 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0314283

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCC[C@@H](O)[C@H]1CC[C@@H](O1)[C@H](O)CC[C@H](O)[C@@H]1CC[C@@H](CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C37H66O8/c1-3-4-5-6-7-8-9-10-11-15-18-31(39)35-23-24-36(45-35)33(41)21-20-32(40)34-22-19-30(44-34)17-14-12-13-16-29(38)26-28-25-27(2)43-37(28)42/h25,27,29-36,38-41H,3-24,26H2,1-2H3/t27-,29+,30+,31+,32-,33+,34-,35+,36+/m0/s1

> <INCHI_KEY>
MJCVLDFXXAHQOH-FWWMILIYSA-N

> <FORMULA>
C37H66O8

> <MOLECULAR_WEIGHT>
638.927

> <EXACT_MASS>
638.475769085

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
111

> <JCHEM_AVERAGE_POLARIZABILITY>
78.31870855836323

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-3-[(2R)-7-[(2R,5S)-5-[(1S,4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-hydroxyheptyl]-5-methyl-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
7.295473406333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.821468298057265

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.258257837838709

> <JCHEM_PKA_STRONGEST_BASIC>
-2.722022876858394

> <JCHEM_POLAR_SURFACE_AREA>
125.68

> <JCHEM_REFRACTIVITY>
178.06609999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-3-[(2R)-7-[(2R,5S)-5-[(1S,4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-hydroxyheptyl]-5-methyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      21.354 -25.113   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.244 -24.046   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.614 -22.551   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.505 -21.483   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.874 -19.988   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.354 -19.561   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.464 -20.629   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.943 -20.201   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.053 -21.269   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.533 -20.842   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      27.642 -21.910   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      29.122 -21.483   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      30.232 -22.551   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      29.862 -24.046   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      31.711 -22.123   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      32.235 -20.675   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      33.774 -20.726   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      34.202 -22.206   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      35.650 -22.730   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      35.920 -24.246   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      36.828 -21.738   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      36.557 -20.222   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      37.735 -19.230   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      39.183 -19.754   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      37.465 -17.714   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      36.080 -17.041   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      36.292 -15.516   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      37.808 -15.246   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      38.480 -13.860   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      40.016 -13.750   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      40.689 -12.365   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      42.225 -12.255   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      42.898 -10.869   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      44.434 -10.759   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      45.297 -12.034   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      45.106  -9.374   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      46.642  -9.264   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      47.456  -7.956   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      48.951  -8.326   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      50.129  -7.334   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      49.061  -9.862   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      47.634 -10.442   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      47.264 -11.937   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      38.533 -16.604   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      32.926 -23.069   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   45                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   45                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   44                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   44                                                  
CONECT   29   28   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   28   25                                                       
CONECT   45   18   15                                                       
MASTER        0    0    0    0    0    0    0    0   45    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₇H₆₆O₈

Average Mass

638.9270 Da

Monoisotopic Mass

638.47577 Da

IUPAC Name

(5S)-3-[(2R)-7-[(2R,5S)-5-[(1S,4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-hydroxyheptyl]-5-methyl-2,5-dihydrofuran-2-one

Traditional Name

(5S)-3-[(2R)-7-[(2R,5S)-5-[(1S,4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-hydroxyheptyl]-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)CC[C@H](O)[C@@H]1CC[C@@H](CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O1

InChI Identifier

InChI=1S/C37H66O8/c1-3-4-5-6-7-8-9-10-11-15-18-31(39)35-23-24-36(45-35)33(41)21-20-32(40)34-22-19-30(44-34)17-14-12-13-16-29(38)26-28-25-27(2)43-37(28)42/h25,27,29-36,38-41H,3-24,26H2,1-2H3/t27-,29+,30+,31+,32-,33+,34-,35+,36+/m0/s1

InChI Key

MJCVLDFXXAHQOH-FWWMILIYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Annona coriacea	LOTUS Database	35616633
Goniothalamus giganteus	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	7.3	ChemAxon
pKa (Strongest Acidic)	13.26	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	178.07 m³·mol⁻¹	ChemAxon
Polarizability	78.32 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00044061

Chemspider ID

8547370

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10371925

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Spurr IB, Brown RC: Total synthesis of annonaceous acetogenins belonging to the non-adjacent bis-THF and non-adjacent THF-THP sub-classes. Molecules. 2010 Jan 21;15(1):460-501. doi: 10.3390/molecules15010460. [PubMed:20110904 ]
Mangal M, Khan MI, Agarwal SM: Acetogenins as Potential Anticancer Agents. Anticancer Agents Med Chem. 2015;16(2):138-59. doi: 10.2174/1871520615666150629101827. [PubMed:26118710 ]
Hoye TR, Eklov BM, Jeon J, Khoroosi M: Sequencing of three-component olefin metatheses: total synthesis of either (+)-gigantecin or (+)-14-deoxy-9-oxygigantecin. Org Lett. 2006 Jul 20;8(15):3383-6. doi: 10.1021/ol061383u. [PubMed:16836411 ]
Crimmins MT, She J: Enantioselective total synthesis of (+)-gigantecin: exploiting the asymmetric glycolate aldol reaction. J Am Chem Soc. 2004 Oct 13;126(40):12790-1. doi: 10.1021/ja0455852. [PubMed:15469270 ]
LOTUS database [Link]

Showing NP-Card for (5s)-3-[(2r)-7-[(2r,5s)-5-[(1s,4r)-1,4-dihydroxy-4-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-hydroxyheptyl]-5-methyl-5h-furan-2-one (NP0314283)

MOL for NP0314283 ((5s)-3-[(2r)-7-[(2r,5s)-5-[(1s,4r)-1,4-dihydroxy-4-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-hydroxyheptyl]-5-methyl-5h-furan-2-one)

3D MOL for NP0314283 ((5s)-3-[(2r)-7-[(2r,5s)-5-[(1s,4r)-1,4-dihydroxy-4-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-hydroxyheptyl]-5-methyl-5h-furan-2-one)

3D SDF for NP0314283 ((5s)-3-[(2r)-7-[(2r,5s)-5-[(1s,4r)-1,4-dihydroxy-4-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-hydroxyheptyl]-5-methyl-5h-furan-2-one)

3D-SDF for NP0314283 ((5s)-3-[(2r)-7-[(2r,5s)-5-[(1s,4r)-1,4-dihydroxy-4-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-hydroxyheptyl]-5-methyl-5h-furan-2-one)

PDB for NP0314283 ((5s)-3-[(2r)-7-[(2r,5s)-5-[(1s,4r)-1,4-dihydroxy-4-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-hydroxyheptyl]-5-methyl-5h-furan-2-one)

3D PDB for NP0314283 ((5s)-3-[(2r)-7-[(2r,5s)-5-[(1s,4r)-1,4-dihydroxy-4-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-hydroxyheptyl]-5-methyl-5h-furan-2-one)

SMILES for NP0314283 ((5s)-3-[(2r)-7-[(2r,5s)-5-[(1s,4r)-1,4-dihydroxy-4-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-hydroxyheptyl]-5-methyl-5h-furan-2-one)

INCHI for NP0314283 ((5s)-3-[(2r)-7-[(2r,5s)-5-[(1s,4r)-1,4-dihydroxy-4-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-hydroxyheptyl]-5-methyl-5h-furan-2-one)

Structure for NP0314283 ((5s)-3-[(2r)-7-[(2r,5s)-5-[(1s,4r)-1,4-dihydroxy-4-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-hydroxyheptyl]-5-methyl-5h-furan-2-one)

3D Structure for NP0314283 ((5s)-3-[(2r)-7-[(2r,5s)-5-[(1s,4r)-1,4-dihydroxy-4-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-hydroxyheptyl]-5-methyl-5h-furan-2-one)