NP-MRD: Showing NP-Card for (1's,2r,2's,3'r,4'r,7'r,8's,12'r,13's,14's,16'r)-2',14',16'-tris(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate (NP0298072)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 08:59:59 UTC

Updated at

2022-09-10 08:59:59 UTC

NP-MRD ID

NP0298072

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,2r,2's,3'r,4'r,7'r,8's,12'r,13's,14's,16'r)-2',14',16'-tris(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate

Description

(1'S,2R,2'S,3'R,4'R,7'R,8'S,12'R,13'S,14'S,16'R)-12',14',16'-tris(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]Heptadecane]-2'-yl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Based on a literature review very few articles have been published on (1'S,2R,2'S,3'R,4'R,7'R,8'S,12'R,13'S,14'S,16'R)-12',14',16'-tris(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]Heptadecane]-2'-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102211002D          

 41 44  0  0  1  0            999 V2000
    3.2991    4.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3368    3.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0693    3.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7642    3.5507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4967    3.1712    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1917    3.6159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1541    4.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4215    4.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8490    4.8846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5343    2.3471    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2293    2.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2669    1.9676    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9618    2.4122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6943    2.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3893    2.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7319    1.2086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3045    1.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6096    0.6988    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6472   -0.1253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3797   -0.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0746   -0.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4173   -1.3290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8770    1.0783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4975    0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0529    1.0407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8394    1.9024    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1069    2.2820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3018    1.6302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6219    0.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8866    0.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8129    1.0173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4120    1.8373    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1008    1.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2774    1.0234    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8568    0.4361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4617    0.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0822    0.1673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    1.6374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6794    2.2168    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6418    3.0410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9093    3.4205    0.0000 Cl  0  0  0  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  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 25  1  1  0  0  0
 26 23  1  6  0  0  0
 10 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 39 38  1  1  0  0  0
 32 39  1  0  0  0  0
 39 40  1  0  0  0  0
  2 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  END

     RDKit          3D

 78 81  0  0  0  0  0  0  0  0999 V2000
    2.5830   -2.8097   -2.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4790   -2.6073   -1.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2986   -3.2361   -0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0414   -2.8010   -1.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9142   -2.0098   -0.5769 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6714   -2.3953    0.7620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5867   -3.1061    1.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2154   -3.4536    2.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6844   -3.4250    1.0066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7895   -0.5024   -0.6964 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4066   -0.2313   -2.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414    0.0042   -0.7195 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0747   -0.9309   -1.3534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8085   -0.7087   -2.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6380   -1.8206   -3.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7474    0.4251   -3.0227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8053    0.3607    0.5978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8613    1.4806    1.0817 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3984    2.2091    2.1275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4872    3.5920    2.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0456    4.4540    3.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0770    4.1560    0.9546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6707    0.6389    1.5585 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1317    0.9311    2.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9941   -0.1564    2.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0757    0.0573    0.3473 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2287    0.9626   -0.0480 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9581    1.5729   -1.2033 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6997    2.8815   -1.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4076    3.4697   -2.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422    3.5383   -0.4404 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5895    0.4165    0.2650 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4236   -0.4414    1.3499 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5438    1.4942    0.7359 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4367    1.9146    2.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8393    0.8409    0.4780 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8471    0.8463    1.1885 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6543    0.2245   -0.7442 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3230   -0.3255   -0.7666 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4923   -1.7979   -0.5911 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7309   -2.3477    1.0560 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.8925   -3.3759   -3.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4421   -2.3559   -3.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4896   -4.3483   -0.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2601   -3.0770    0.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3266   -2.3965   -2.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4799   -3.7751   -1.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9554   -2.3784   -0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1151   -3.4963    2.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5370   -2.6469    3.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6425   -4.4355    3.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8491    0.7295   -2.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0531   -0.9655   -2.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6240   -0.3965   -2.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3274    0.9411   -1.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3946   -2.1617   -2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0075   -2.7235   -3.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1275   -1.5759   -3.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8122    0.7418    0.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8018   -0.4815    1.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5552    2.1131    0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9490    3.9577    4.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5489    5.4330    3.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1239    4.6347    2.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6164    1.7445    3.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8205    0.6261    3.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6109   -0.8214    0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838    1.8107    0.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4736    3.0059   -3.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1471    4.5364   -2.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2999    3.4740   -3.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7949   -0.1729    2.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5039    2.4019    0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0149    1.2743    2.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0180    2.8898    2.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4443    2.1913    2.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8921   -0.2021   -1.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4606   -2.0835   -1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
 35 34  1  0
 34 36  1  0
 36 37  2  0
 36 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 40  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
  7  8  1  0
  7  9  2  0
  5 10  1  0
 10 11  1  6
 10 12  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 27 32  1  0
 32 33  1  1
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 32 34  1  0
 32 39  1  0
 26 10  1  0
 23 25  1  1
 35 74  1  0
 35 75  1  0
 35 76  1  0
 34 73  1  6
 39 77  1  6
 40 78  1  6
  1 42  1  0
  1 43  1  0
  3 44  1  0
  3 45  1  0
  4 46  1  0
  4 47  1  0
  5 48  1  6
  8 49  1  0
  8 50  1  0
  8 51  1  0
 11 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  6
 17 59  1  0
 17 60  1  0
 18 61  1  6
 21 62  1  0
 21 63  1  0
 21 64  1  0
 24 65  1  0
 24 66  1  0
 26 67  1  1
 27 68  1  1
 30 69  1  0
 30 70  1  0
 30 71  1  0
 33 72  1  0
 15 56  1  0
 15 57  1  0
 15 58  1  0
M  END


  Mrv1652309102211002D          

 41 44  0  0  1  0            999 V2000
    3.2991    4.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3368    3.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0693    3.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7642    3.5507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4967    3.1712    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1917    3.6159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1541    4.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4215    4.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8490    4.8846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5343    2.3471    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2293    2.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2669    1.9676    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9618    2.4122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6943    2.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3893    2.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7319    1.2086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3045    1.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6096    0.6988    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6472   -0.1253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3797   -0.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0746   -0.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4173   -1.3290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8770    1.0783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4975    0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0529    1.0407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8394    1.9024    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1069    2.2820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3018    1.6302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6219    0.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8866    0.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8129    1.0173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4120    1.8373    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1008    1.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2774    1.0234    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8568    0.4361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4617    0.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0822    0.1673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    1.6374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6794    2.2168    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6418    3.0410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9093    3.4205    0.0000 Cl  0  0  0  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  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 25  1  1  0  0  0
 26 23  1  6  0  0  0
 10 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 39 38  1  1  0  0  0
 32 39  1  0  0  0  0
 39 40  1  0  0  0  0
  2 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0298072

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)CC[C@@H](OC(C)=O)[C@@]3(C)[C@H](C[C@@H](OC(C)=O)[C@]4(CO4)[C@@H]3[C@H](OC(C)=O)[C@]12O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H37ClO12/c1-12-8-9-18(37-14(3)30)26(7)19(38-15(4)31)10-20(39-16(5)32)27(11-36-27)22(26)24(40-17(6)33)28(35)13(2)25(34)41-23(28)21(12)29/h13,18-24,35H,1,8-11H2,2-7H3/t13-,18+,19-,20+,21-,22+,23-,24-,26-,27+,28-/m0/s1

> <INCHI_KEY>
MDILJZNWKHVGLR-AEXLFXGESA-N

> <FORMULA>
C28H37ClO12

> <MOLECULAR_WEIGHT>
601.04

> <EXACT_MASS>
600.1973543

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
58.30961722091621

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
0.7131929030000002

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.3681218247394

> <JCHEM_PKA_STRONGEST_BASIC>
-3.949983513858986

> <JCHEM_POLAR_SURFACE_AREA>
164.26

> <JCHEM_REFRACTIVITY>
136.8355

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2R,2'S,3'R,4'R,7'R,8'S,12'R,13'S,14'S,16'R)-2',14',16'-tris(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0^{3,7}]heptadecane]-12'-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       6.158   8.045   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.229   6.506   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.596   5.798   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.893   6.628   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.261   5.920   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      11.558   6.750   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      11.488   8.288   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.120   8.996   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.785   9.118   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.331   4.381   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.628   5.211   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.698   3.673   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.995   4.503   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      14.363   3.794   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.660   4.624   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.433   2.256   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.768   2.134   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.471   1.304   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.541  -0.234   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      11.909  -0.942   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.206  -0.112   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.979  -2.481   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.104   2.013   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.395   0.645   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.565   1.943   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.034   3.551   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.666   4.260   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.030   3.043   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.761   1.598   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.255   0.139   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.251   1.899   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.369   3.430   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.655   2.582   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.118   1.910   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.199   0.814   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.595   1.680   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.887   0.312   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       3.905   3.056   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       5.002   4.138   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.931   5.676   0.000  0.00  0.00           C+0
HETATM   41 Cl   UNK     0       3.564   6.385   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   40                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   12   26                                             
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24   25   26                                             
CONECT   24   23   25                                                       
CONECT   25   24   23                                                       
CONECT   26   23   10   27                                                  
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   27   33   34   39                                             
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   32   40                                                  
CONECT   40   39    2   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₂₈H₃₇ClO₁₂

Average Mass

601.0400 Da

Monoisotopic Mass

600.19735 Da

IUPAC Name

(1'S,2R,2'S,3'R,4'R,7'R,8'S,12'R,13'S,14'S,16'R)-2',14',16'-tris(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0^{3,7}]heptadecane]-12'-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)CC[C@@H](OC(C)=O)[C@@]3(C)[C@H](C[C@@H](OC(C)=O)[C@]4(CO4)[C@@H]3[C@H](OC(C)=O)[C@]12O)OC(C)=O

InChI Identifier

InChI=1S/C28H37ClO12/c1-12-8-9-18(37-14(3)30)26(7)19(38-15(4)31)10-20(39-16(5)32)27(11-36-27)22(26)24(40-17(6)33)28(35)13(2)25(34)41-23(28)21(12)29/h13,18-24,35H,1,8-11H2,2-7H3/t13-,18+,19-,20+,21-,22+,23-,24-,26-,27+,28-/m0/s1

InChI Key

MDILJZNWKHVGLR-AEXLFXGESA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 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

Diterpene lactone
Diterpenoid
Briarane diterpenoid
Pentacarboxylic acid or derivatives
Gamma butyrolactone
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organohalogen compound
Carbonyl group
Alkyl halide
Alkyl chloride
Organochloride
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	0.71	ChemAxon
pKa (Strongest Acidic)	12.37	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	164.26 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	136.84 m³·mol⁻¹	ChemAxon
Polarizability	58.31 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

163060233

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1's,2r,2's,3'r,4'r,7'r,8's,12'r,13's,14's,16'r)-2',14',16'-tris(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate (NP0298072)

MOL for NP0298072 ((1's,2r,2's,3'r,4'r,7'r,8's,12'r,13's,14's,16'r)-2',14',16'-tris(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate)

3D MOL for NP0298072 ((1's,2r,2's,3'r,4'r,7'r,8's,12'r,13's,14's,16'r)-2',14',16'-tris(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate)

3D SDF for NP0298072 ((1's,2r,2's,3'r,4'r,7'r,8's,12'r,13's,14's,16'r)-2',14',16'-tris(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate)

3D-SDF for NP0298072 ((1's,2r,2's,3'r,4'r,7'r,8's,12'r,13's,14's,16'r)-2',14',16'-tris(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate)

PDB for NP0298072 ((1's,2r,2's,3'r,4'r,7'r,8's,12'r,13's,14's,16'r)-2',14',16'-tris(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate)

3D PDB for NP0298072 ((1's,2r,2's,3'r,4'r,7'r,8's,12'r,13's,14's,16'r)-2',14',16'-tris(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate)

SMILES for NP0298072 ((1's,2r,2's,3'r,4'r,7'r,8's,12'r,13's,14's,16'r)-2',14',16'-tris(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate)

INCHI for NP0298072 ((1's,2r,2's,3'r,4'r,7'r,8's,12'r,13's,14's,16'r)-2',14',16'-tris(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate)

Structure for NP0298072 ((1's,2r,2's,3'r,4'r,7'r,8's,12'r,13's,14's,16'r)-2',14',16'-tris(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate)

3D Structure for NP0298072 ((1's,2r,2's,3'r,4'r,7'r,8's,12'r,13's,14's,16'r)-2',14',16'-tris(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate)