NP-MRD: Showing NP-Card for (1'r,2r,2's,3'r,4'r,7's,8'e,10'e,12's,13's,14'r,15'r,16'r)-12',14',15',16'-tetrakis(acetyloxy)-3'-hydroxy-9'-(hydroxymethyl)-4',13'-dimethyl-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecane]-8',10'-dien-2'-yl acetate (NP0301139)

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Record Information

Version

2.0

Created at

2022-09-10 13:55:21 UTC

Updated at

2022-09-10 13:55:21 UTC

NP-MRD ID

NP0301139

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1'r,2r,2's,3'r,4'r,7's,8'e,10'e,12's,13's,14'r,15'r,16'r)-12',14',15',16'-tetrakis(acetyloxy)-3'-hydroxy-9'-(hydroxymethyl)-4',13'-dimethyl-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecane]-8',10'-dien-2'-yl acetate

Description

(1'R,2R,2'S,3'R,4'R,7'S,8'E,10'E,12'S,13'S,14'R,15'R,16'R)-12',14',15',16'-tetrakis(acetyloxy)-3'-hydroxy-9'-(hydroxymethyl)-4',13'-dimethyl-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]Heptadecane]-8',10'-dien-2'-yl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1'r,2r,2's,3'r,4'r,7's,8'e,10'e,12's,13's,14'r,15'r,16'r)-12',14',15',16'-tetrakis(acetyloxy)-3'-hydroxy-9'-(hydroxymethyl)-4',13'-dimethyl-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecane]-8',10'-dien-2'-yl acetate is found in Junceella juncea. Based on a literature review very few articles have been published on (1'R,2R,2'S,3'R,4'R,7'S,8'E,10'E,12'S,13'S,14'R,15'R,16'R)-12',14',15',16'-tetrakis(acetyloxy)-3'-hydroxy-9'-(hydroxymethyl)-4',13'-dimethyl-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]Heptadecane]-8',10'-dien-2'-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102215552D          

 45 48  0  0  1  0            999 V2000
    3.0450    4.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3083    4.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184    5.0257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2615    3.7497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9515    3.2973    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6882    3.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3781    3.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1148    3.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1616    4.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8983    4.7826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8047    3.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7580    2.3116    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3388    1.7257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9610    0.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3323    0.2555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3208    1.2802    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5608    0.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0212    1.9403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5698    1.3976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3313    2.3926    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2845    1.5690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9745    1.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7112    1.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9277    0.2929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5946    2.0213    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9047    2.4737    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2147    2.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1680    2.1024    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4780    2.5547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7413    2.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6945    1.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0514    2.6358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1212    1.2787    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3845    0.9074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5707   -0.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2606   -0.6298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6009   -0.2876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8111    0.8263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7643    0.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0276   -0.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9808   -1.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3377    0.0837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5478    1.1976    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3715    1.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9191    0.4609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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
  8 11  2  0  0  0  0
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  5 26  1  0  0  0  0
 26 27  1  1  0  0  0
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 29 30  1  0  0  0  0
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 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
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 35 37  2  0  0  0  0
 33 38  1  0  0  0  0
 38 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 38 43  1  0  0  0  0
 25 43  1  6  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 43 45  1  6  0  0  0
M  END

     RDKit          3D

 83 86  0  0  0  0  0  0  0  0999 V2000
    1.2381    5.1940    0.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3609    4.0241    0.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0894    3.7880    1.9805 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8171    1.9934    0.0115 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0922    2.4770   -0.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9731    2.1243   -1.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1582    1.0249   -2.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9582    1.2239   -3.7638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8683    2.2182   -4.1901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5112   -0.1878   -1.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1746   -1.7921    4.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5135   -0.5168   -0.4355 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0347    0.9189   -0.5585 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0974    1.2541   -2.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0990    1.4712    2.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0892    1.0611    3.8047 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7122    2.4749    1.9990 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5008    0.0970    0.0890 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7543    0.5543   -0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8505    0.3552    0.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2572   -3.3192    2.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
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 23 65  1  0
 19 61  1  0
M  END


  Mrv1652309102215552D          

 45 48  0  0  1  0            999 V2000
    3.0450    4.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3083    4.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184    5.0257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2615    3.7497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9515    3.2973    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6882    3.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3781    3.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1148    3.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1616    4.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8983    4.7826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8047    3.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7580    2.3116    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3388    1.7257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9610    0.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3323    0.2555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3208    1.2802    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5608    0.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0212    1.9403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5698    1.3976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3313    2.3926    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2845    1.5690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9745    1.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7112    1.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9277    0.2929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5946    2.0213    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9047    2.4737    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2147    2.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1680    2.1024    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4780    2.5547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7413    2.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6945    1.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0514    2.6358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1212    1.2787    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3845    0.9074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5707   -0.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2606   -0.6298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6009   -0.2876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8111    0.8263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7643    0.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0276   -0.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9808   -1.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3377    0.0837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5478    1.1976    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3715    1.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9191    0.4609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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
  8 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 33 38  1  0  0  0  0
 38 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 38 43  1  0  0  0  0
 25 43  1  6  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 43 45  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0301139

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C(=O)O[C@H]2\C=C(\CO)/C=C/[C@H](OC(C)=O)[C@@]3(C)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@]4(CO4)[C@H]3[C@H](OC(C)=O)[C@@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C30H38O15/c1-13-27(37)45-21-10-19(11-31)8-9-20(40-14(2)32)28(7)23(26(30(13,21)38)44-18(6)36)29(12-39-29)25(43-17(5)35)22(41-15(3)33)24(28)42-16(4)34/h8-10,13,20-26,31,38H,11-12H2,1-7H3/b9-8+,19-10+/t13-,20-,21-,22+,23-,24-,25+,26-,28+,29-,30+/m0/s1

> <INCHI_KEY>
YRIFCYVSONYKSX-MGVRKCKRSA-N

> <FORMULA>
C30H38O15

> <MOLECULAR_WEIGHT>
638.619

> <EXACT_MASS>
638.221070524

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
61.55338131549997

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,2R,2'S,3'R,4'R,7'S,8'E,10'E,12'S,13'S,14'R,15'R,16'R)-12',14',15',16'-tetrakis(acetyloxy)-3'-hydroxy-9'-(hydroxymethyl)-4',13'-dimethyl-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0^{3,7}]heptadecane]-8',10'-dien-2'-yl acetate

> <JCHEM_LOGP>
-1.3603836403333325

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.120847971497458

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.353879838519958

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7467573931762077

> <JCHEM_POLAR_SURFACE_AREA>
210.78999999999996

> <JCHEM_REFRACTIVITY>
146.48140000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2R,2'S,3'R,4'R,7'S,8'E,10'E,12'S,13'S,14'R,15'R,16'R)-12',14',15',16'-tetrakis(acetyloxy)-3'-hydroxy-9'-(hydroxymethyl)-4',13'-dimethyl-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0^{3,7}]heptadecane]-8',10'-dien-2'-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

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       5.684   9.230   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.309   8.537   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.021   9.381   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.222   6.999   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.509   6.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.885   6.848   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.172   6.004   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.548   6.697   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.635   8.234   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.010   8.928   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.836   5.852   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.748   4.315   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.832   3.221   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.127   1.852   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.820   0.477   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.932   2.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.514   1.016   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.373   3.622   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.530   2.609   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.085   4.466   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.998   2.929   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.286   2.084   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.661   2.777   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.198   0.547   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.710   3.773   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.422   4.618   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.134   5.462   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.047   3.924   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.759   4.769   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.384   4.076   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.296   2.538   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.096   4.920   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.960   2.387   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.584   1.694   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.932  -0.331   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.220  -1.176   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.122  -0.537   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.247   1.542   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       5.160   0.005   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       3.785  -0.688   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.697  -2.226   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.497   0.156   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       6.623   2.236   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       8.160   2.148   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       7.316   0.860   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   26   43                                                  
CONECT   26   25    5   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   33   39   43                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   38   25   44   45                                             
CONECT   44   43   45                                                       
CONECT   45   44   43                                                       
MASTER        0    0    0    0    0    0    0    0   45    0   96    0
END

View in JSmol

Synonyms

Value	Source
(1'r,2R,2's,3'r,4'r,7's,8'e,10'e,12's,13's,14'r,15'r,16'r)-12',14',15',16'-Tetrakis(acetyloxy)-3'-hydroxy-9'-(hydroxymethyl)-4',13'-dimethyl-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0,]heptadecane]-8',10'-dien-2'-yl acetic acid	Generator

Chemical Formula

C₃₀H₃₈O₁₅

Average Mass

638.6190 Da

Monoisotopic Mass

638.22107 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@H]1C(=O)O[C@H]2\C=C(\CO)/C=C/[C@H](OC(C)=O)[C@@]3(C)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@]4(CO4)[C@H]3[C@H](OC(C)=O)[C@@]12O

InChI Identifier

InChI=1S/C30H38O15/c1-13-27(37)45-21-10-19(11-31)8-9-20(40-14(2)32)28(7)23(26(30(13,21)38)44-18(6)36)29(12-39-29)25(43-17(5)35)22(41-15(3)33)24(28)42-16(4)34/h8-10,13,20-26,31,38H,11-12H2,1-7H3/b9-8+,19-10+/t13-,20-,21-,22+,23-,24-,25+,26-,28+,29-,30+/m0/s1

InChI Key

YRIFCYVSONYKSX-MGVRKCKRSA-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
Junceella juncea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Briarane diterpenoid
Hexacarboxylic acid or derivatives
Diterpenoid
Diterpene lactone
Gamma butyrolactone
Tetrahydrofuran
Tertiary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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
logP	-1.4	ChemAxon
pKa (Strongest Acidic)	12.35	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	210.79 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	146.48 m³·mol⁻¹	ChemAxon
Polarizability	61.55 Å³	ChemAxon
Number of Rings	4	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

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

163194860

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1'r,2r,2's,3'r,4'r,7's,8'e,10'e,12's,13's,14'r,15'r,16'r)-12',14',15',16'-tetrakis(acetyloxy)-3'-hydroxy-9'-(hydroxymethyl)-4',13'-dimethyl-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecane]-8',10'-dien-2'-yl acetate (NP0301139)

MOL for NP0301139 ((1'r,2r,2's,3'r,4'r,7's,8'e,10'e,12's,13's,14'r,15'r,16'r)-12',14',15',16'-tetrakis(acetyloxy)-3'-hydroxy-9'-(hydroxymethyl)-4',13'-dimethyl-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecane]-8',10'-dien-2'-yl acetate)

3D MOL for NP0301139 ((1'r,2r,2's,3'r,4'r,7's,8'e,10'e,12's,13's,14'r,15'r,16'r)-12',14',15',16'-tetrakis(acetyloxy)-3'-hydroxy-9'-(hydroxymethyl)-4',13'-dimethyl-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecane]-8',10'-dien-2'-yl acetate)

3D SDF for NP0301139 ((1'r,2r,2's,3'r,4'r,7's,8'e,10'e,12's,13's,14'r,15'r,16'r)-12',14',15',16'-tetrakis(acetyloxy)-3'-hydroxy-9'-(hydroxymethyl)-4',13'-dimethyl-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecane]-8',10'-dien-2'-yl acetate)

3D-SDF for NP0301139 ((1'r,2r,2's,3'r,4'r,7's,8'e,10'e,12's,13's,14'r,15'r,16'r)-12',14',15',16'-tetrakis(acetyloxy)-3'-hydroxy-9'-(hydroxymethyl)-4',13'-dimethyl-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecane]-8',10'-dien-2'-yl acetate)

PDB for NP0301139 ((1'r,2r,2's,3'r,4'r,7's,8'e,10'e,12's,13's,14'r,15'r,16'r)-12',14',15',16'-tetrakis(acetyloxy)-3'-hydroxy-9'-(hydroxymethyl)-4',13'-dimethyl-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecane]-8',10'-dien-2'-yl acetate)

3D PDB for NP0301139 ((1'r,2r,2's,3'r,4'r,7's,8'e,10'e,12's,13's,14'r,15'r,16'r)-12',14',15',16'-tetrakis(acetyloxy)-3'-hydroxy-9'-(hydroxymethyl)-4',13'-dimethyl-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecane]-8',10'-dien-2'-yl acetate)

SMILES for NP0301139 ((1'r,2r,2's,3'r,4'r,7's,8'e,10'e,12's,13's,14'r,15'r,16'r)-12',14',15',16'-tetrakis(acetyloxy)-3'-hydroxy-9'-(hydroxymethyl)-4',13'-dimethyl-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecane]-8',10'-dien-2'-yl acetate)

INCHI for NP0301139 ((1'r,2r,2's,3'r,4'r,7's,8'e,10'e,12's,13's,14'r,15'r,16'r)-12',14',15',16'-tetrakis(acetyloxy)-3'-hydroxy-9'-(hydroxymethyl)-4',13'-dimethyl-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecane]-8',10'-dien-2'-yl acetate)

Structure for NP0301139 ((1'r,2r,2's,3'r,4'r,7's,8'e,10'e,12's,13's,14'r,15'r,16'r)-12',14',15',16'-tetrakis(acetyloxy)-3'-hydroxy-9'-(hydroxymethyl)-4',13'-dimethyl-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecane]-8',10'-dien-2'-yl acetate)

3D Structure for NP0301139 ((1'r,2r,2's,3'r,4'r,7's,8'e,10'e,12's,13's,14'r,15'r,16'r)-12',14',15',16'-tetrakis(acetyloxy)-3'-hydroxy-9'-(hydroxymethyl)-4',13'-dimethyl-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecane]-8',10'-dien-2'-yl acetate)