NP-MRD: Showing NP-Card for (1s,4s,5s,6s,8r)-8-[(1r,3ar,8as)-1,4,4-trimethyl-8-methylidene-hexahydro-2h-azulen-1-yl]-4-(acetyloxy)-3-oxo-2,7-dioxabicyclo[3.2.1]octan-6-yl acetate (NP0264514)

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Record Information

Version

2.0

Created at

2022-09-08 08:04:19 UTC

Updated at

2022-09-08 08:04:19 UTC

NP-MRD ID

NP0264514

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4s,5s,6s,8r)-8-[(1r,3ar,8as)-1,4,4-trimethyl-8-methylidene-hexahydro-2h-azulen-1-yl]-4-(acetyloxy)-3-oxo-2,7-dioxabicyclo[3.2.1]octan-6-yl acetate

Description

Macfarlandin E belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (1s,4s,5s,6s,8r)-8-[(1r,3ar,8as)-1,4,4-trimethyl-8-methylidene-hexahydro-2h-azulen-1-yl]-4-(acetyloxy)-3-oxo-2,7-dioxabicyclo[3.2.1]octan-6-yl acetate is found in Felimida macfarlandi and Felimida norrisi. (1s,4s,5s,6s,8r)-8-[(1r,3ar,8as)-1,4,4-trimethyl-8-methylidene-hexahydro-2h-azulen-1-yl]-4-(acetyloxy)-3-oxo-2,7-dioxabicyclo[3.2.1]octan-6-yl acetate was first documented in 2010 (PMID: 20332207). Based on a literature review very few articles have been published on Macfarlandin E (PMID: 21988207).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082210042D          

 31 34  0  0  1  0            999 V2000
    3.8336    1.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8246   -1.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9946   -1.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1907    1.4238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2085    0.8744    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5444    0.1876    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0604    0.7488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    1.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8013    1.8838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6829    2.0362    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5601    2.9045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1143    3.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9669    3.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8969    4.3862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4713    1.7930    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7727    1.0250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6953    1.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3009    0.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3086   -0.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0988    0.0098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602    0.3106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  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
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  1  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24 14  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 25 30  1  0  0  0  0
 15 30  1  1  0  0  0
 12 31  1  0  0  0  0
 31  2  1  6  0  0  0
  9 31  1  0  0  0  0
M  END

     RDKit          3D

 65 68  0  0  0  0  0  0  0  0999 V2000
   -1.7276    1.0817   -2.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8817    1.0575   -1.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3770    2.3575   -0.7071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8551    2.1746   -0.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8007   -1.1116    1.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0812   -1.1503    1.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5995   -1.3819    1.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3138   -0.1802    0.3065 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2410    0.9822    1.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2074   -1.2407   -1.4603 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3944   -2.5401   -0.9492 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1984   -2.7098    0.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5807   -3.8632    0.4586 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6234   -1.5439    0.9375 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0641   -1.5664    0.8970 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8552   -1.6694    2.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3582   -1.6881    1.9093 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2776   -1.7488    3.1334 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2313   -0.2327    0.3143 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1349   -0.1569   -0.9437 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1086    1.2313   -1.3106 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2558    1.9973   -1.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2595    3.4356   -1.7278 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3445    1.4555   -1.0595 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861   -0.8456   -1.9298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5493   -0.2027   -0.5565 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.9572    1.9794   -3.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3330    3.1631   -1.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3604    2.0831   -1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2002    3.1409    0.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5110    1.2913    1.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1974    1.2701    0.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5637   -2.1710    1.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6091   -0.7353    2.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8688   -0.8784    0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2804   -1.5901   -1.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4281    0.1298   -1.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7428   -0.6908   -1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8138   -1.9525   -0.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4221   -2.1369    1.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2610   -0.4040    2.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -2.3326    0.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0109   -1.4210    2.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2763    1.8432    0.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5016    0.6804    2.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1431    1.2184    1.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941    0.7613   -1.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5517   -1.1875   -2.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3854   -1.6257    2.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5913   -2.5714    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8270   -1.7352    2.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6409   -0.7928    1.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1420   -0.4988   -0.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3884    3.7106   -2.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3411    4.0622   -0.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1700    3.6679   -2.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2250   -0.9111   -1.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
 27 29  2  0
 27 26  1  0
 26 25  1  0
 25 30  1  0
 30 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
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 14 12  1  0
 12 13  1  1
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9 31  1  0
 31  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
 24 25  1  0
 31 12  1  0
 14 15  1  0
  6  9  1  0
 28 62  1  0
 28 63  1  0
 28 64  1  0
 25 61  1  1
 15 55  1  6
 19 56  1  1
 22 57  1  0
 22 58  1  0
 22 59  1  0
 24 60  1  1
 14 54  1  6
 13 51  1  0
 13 52  1  0
 13 53  1  0
 11 49  1  0
 11 50  1  0
 10 47  1  0
 10 48  1  0
  9 46  1  6
 31 65  1  6
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  7 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  8 45  1  0
M  END


  Mrv1652309082210042D          

 31 34  0  0  1  0            999 V2000
    3.8336    1.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8246   -1.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9946   -1.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1907    1.4238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2085    0.8744    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5444    0.1876    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0604    0.7488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    1.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8013    1.8838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6829    2.0362    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5601    2.9045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1143    3.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9669    3.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8969    4.3862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4713    1.7930    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7727    1.0250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6953    1.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3009    0.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3086   -0.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0988    0.0098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602    0.3106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  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
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  6  0  0  0
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 15 16  1  0  0  0  0
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 17 18  2  0  0  0  0
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 25 30  1  0  0  0  0
 15 30  1  1  0  0  0
 12 31  1  0  0  0  0
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  9 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0264514

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1O[C@H]2OC(=O)[C@@H](OC(C)=O)[C@@H]1[C@@H]2[C@]1(C)CC[C@@H]2[C@H]1C(=C)CCCC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O7/c1-12-8-7-10-23(4,5)15-9-11-24(6,17(12)15)18-16-19(28-13(2)25)20(27)30-22(18)31-21(16)29-14(3)26/h15-19,21-22H,1,7-11H2,2-6H3/t15-,16+,17-,18+,19+,21-,22-,24-/m1/s1

> <INCHI_KEY>
BPRCBAVNJUVNFL-PNOPMVMRSA-N

> <FORMULA>
C24H34O7

> <MOLECULAR_WEIGHT>
434.529

> <EXACT_MASS>
434.230453435

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
45.558680737858495

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,5S,6S,8R)-8-[(1R,3aR,8aS)-1,4,4-trimethyl-8-methylidene-decahydroazulen-1-yl]-4-(acetyloxy)-3-oxo-2,7-dioxabicyclo[3.2.1]octan-6-yl acetate

> <JCHEM_LOGP>
3.7917093759999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.78693094131978

> <JCHEM_PKA_STRONGEST_BASIC>
-4.520985556063122

> <JCHEM_POLAR_SURFACE_AREA>
88.13000000000001

> <JCHEM_REFRACTIVITY>
109.34779999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5S,6S,8R)-8-[(1R,3aR,8aS)-1,4,4-trimethyl-8-methylidene-hexahydro-2H-azulen-1-yl]-4-(acetyloxy)-3-oxo-2,7-dioxabicyclo[3.2.1]octan-6-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       7.156   2.795   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   1.347   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.760   1.004   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.428  -0.384   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.760  -1.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258  -2.114   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.139  -3.570   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.590  -3.723   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.054  -1.154   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590  -1.629   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.684  -0.384   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590   0.862   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.089   2.658   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.256   1.632   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.016   0.350   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.113   1.398   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.002   2.933   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.496   3.516   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.275   3.801   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.046   5.422   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.080   6.659   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.672   6.686   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.674   8.188   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.746   3.347   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.309   1.913   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.031   1.869   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.162   0.353   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.176  -1.092   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.651   0.018   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.539   0.580   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.054   0.386   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10   31                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   31                                             
CONECT   13   12                                                            
CONECT   14   12   15   24                                                  
CONECT   15   14   16   30                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   14   25                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   15                                                       
CONECT   31   12    2    9                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₄O₇

Average Mass

434.5290 Da

Monoisotopic Mass

434.23045 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1O[C@H]2OC(=O)[C@@H](OC(C)=O)[C@@H]1[C@@H]2[C@]1(C)CC[C@@H]2[C@H]1C(=C)CCCC2(C)C

InChI Identifier

InChI=1S/C24H34O7/c1-12-8-7-10-23(4,5)15-9-11-24(6,17(12)15)18-16-19(28-13(2)25)20(27)30-22(18)31-21(16)29-14(3)26/h15-19,21-22H,1,7-11H2,2-6H3/t15-,16+,17-,18+,19+,21-,22-,24-/m1/s1

InChI Key

BPRCBAVNJUVNFL-PNOPMVMRSA-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
Felimida macfarlandi	LOTUS Database	35616633
Felimida norrisi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
11-noriridane monoterpenoid
Monoterpenoid
Tricarboxylic acid or derivatives
Delta valerolactone
1,3-dioxepane
Dioxepane
Delta_valerolactone
Oxane
Tetrahydrofuran
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Oxacycle
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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

17208678

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22832375

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Schnermann MJ, Beaudry CM, Genung NE, Canham SM, Untiedt NL, Karanikolas BD, Sutterlin C, Overman LE: Divergent synthesis and chemical reactivity of bicyclic lactone fragments of complex rearranged spongian diterpenes. J Am Chem Soc. 2011 Nov 2;133(43):17494-503. doi: 10.1021/ja207727h. Epub 2011 Oct 11. [PubMed:21988207 ]
Schnermann MJ, Beaudry CM, Egorova AV, Polishchuk RS, Sutterlin C, Overman LE: Golgi-modifying properties of macfarlandin E and the synthesis and evaluation of its 2,7-dioxabicyclo[3.2.1]octan-3-one core. Proc Natl Acad Sci U S A. 2010 Apr 6;107(14):6158-63. doi: 10.1073/pnas.1001421107. Epub 2010 Mar 23. [PubMed:20332207 ]
LOTUS database [Link]

Showing NP-Card for (1s,4s,5s,6s,8r)-8-[(1r,3ar,8as)-1,4,4-trimethyl-8-methylidene-hexahydro-2h-azulen-1-yl]-4-(acetyloxy)-3-oxo-2,7-dioxabicyclo[3.2.1]octan-6-yl acetate (NP0264514)

MOL for NP0264514 ((1s,4s,5s,6s,8r)-8-[(1r,3ar,8as)-1,4,4-trimethyl-8-methylidene-hexahydro-2h-azulen-1-yl]-4-(acetyloxy)-3-oxo-2,7-dioxabicyclo[3.2.1]octan-6-yl acetate)

3D MOL for NP0264514 ((1s,4s,5s,6s,8r)-8-[(1r,3ar,8as)-1,4,4-trimethyl-8-methylidene-hexahydro-2h-azulen-1-yl]-4-(acetyloxy)-3-oxo-2,7-dioxabicyclo[3.2.1]octan-6-yl acetate)

3D SDF for NP0264514 ((1s,4s,5s,6s,8r)-8-[(1r,3ar,8as)-1,4,4-trimethyl-8-methylidene-hexahydro-2h-azulen-1-yl]-4-(acetyloxy)-3-oxo-2,7-dioxabicyclo[3.2.1]octan-6-yl acetate)

3D-SDF for NP0264514 ((1s,4s,5s,6s,8r)-8-[(1r,3ar,8as)-1,4,4-trimethyl-8-methylidene-hexahydro-2h-azulen-1-yl]-4-(acetyloxy)-3-oxo-2,7-dioxabicyclo[3.2.1]octan-6-yl acetate)

PDB for NP0264514 ((1s,4s,5s,6s,8r)-8-[(1r,3ar,8as)-1,4,4-trimethyl-8-methylidene-hexahydro-2h-azulen-1-yl]-4-(acetyloxy)-3-oxo-2,7-dioxabicyclo[3.2.1]octan-6-yl acetate)

3D PDB for NP0264514 ((1s,4s,5s,6s,8r)-8-[(1r,3ar,8as)-1,4,4-trimethyl-8-methylidene-hexahydro-2h-azulen-1-yl]-4-(acetyloxy)-3-oxo-2,7-dioxabicyclo[3.2.1]octan-6-yl acetate)

SMILES for NP0264514 ((1s,4s,5s,6s,8r)-8-[(1r,3ar,8as)-1,4,4-trimethyl-8-methylidene-hexahydro-2h-azulen-1-yl]-4-(acetyloxy)-3-oxo-2,7-dioxabicyclo[3.2.1]octan-6-yl acetate)

INCHI for NP0264514 ((1s,4s,5s,6s,8r)-8-[(1r,3ar,8as)-1,4,4-trimethyl-8-methylidene-hexahydro-2h-azulen-1-yl]-4-(acetyloxy)-3-oxo-2,7-dioxabicyclo[3.2.1]octan-6-yl acetate)

Structure for NP0264514 ((1s,4s,5s,6s,8r)-8-[(1r,3ar,8as)-1,4,4-trimethyl-8-methylidene-hexahydro-2h-azulen-1-yl]-4-(acetyloxy)-3-oxo-2,7-dioxabicyclo[3.2.1]octan-6-yl acetate)

3D Structure for NP0264514 ((1s,4s,5s,6s,8r)-8-[(1r,3ar,8as)-1,4,4-trimethyl-8-methylidene-hexahydro-2h-azulen-1-yl]-4-(acetyloxy)-3-oxo-2,7-dioxabicyclo[3.2.1]octan-6-yl acetate)