NP-MRD: Showing NP-Card for 15-acetoxyheliangin (NP0044051)

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Record Information

Version

1.0

Created at

2021-11-12 23:47:22 UTC

Updated at

2021-11-26 17:44:52 UTC

NP-MRD ID

NP0044051

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-acetoxyheliangin

Description

15-acetoxyheliangin is found in Eupatorium kiirunense. It was first documented in 2005 (PMID: 15921421).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100472D          

 33 35  0  0  1  0            999 V2000
    6.3105    1.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0913    0.7508    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8294   -0.1526    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0609    0.6393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5980   -0.9444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7965   -1.1400    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3826   -1.9361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2264   -0.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9589    0.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9952    0.2096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5285   -0.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4709   -0.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5387   -1.5245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4249   -0.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8549   -0.1427    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0863    0.6492    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8878    0.8447    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8704    1.7913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4213    2.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8264    3.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5699    4.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1266    4.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6471    3.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5178    2.5794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4579    0.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4047    1.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0598    1.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7520    0.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8878    0.7271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0302   -0.1673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2337    1.4609    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5419   -0.9061    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6020    0.1367    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  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
 11 13  2  0  0  0  0
  8 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 19 24  2  0  0  0  0
 17 25  1  0  0  0  0
  2 25  1  0  0  0  0
 16 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 15 30  1  0  0  0  0
 16 31  1  1  0  0  0
 15 32  1  6  0  0  0
  3 33  1  1  0  0  0
M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
   -2.0669   -2.3810    1.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0702   -1.9563    0.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3966   -2.6717   -0.5955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843   -3.5988   -1.3301 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8878   -2.1417   -0.6483 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8943   -0.8056   -0.1105 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9566   -0.7939    0.9337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8958    0.0912    1.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8694   -0.1172    2.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1955   -0.2161    1.7758 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6154   -1.1727    0.8897 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0588   -1.1472    0.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8069   -2.0209    0.4676 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1227    1.3179    0.3061 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0476    1.0568   -1.0650 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2644    2.4838    0.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8022    2.2463    0.5488 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0064    3.4034    0.1131 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3241    2.2225   -0.7291 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9724    2.7805   -1.9806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8110    1.2979   -1.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886    0.4686    0.1147 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5340   -0.1137   -0.3093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7470    0.1939    0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8176    1.0298    1.1551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9394   -0.4655   -0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8584   -1.4606   -1.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1293   -0.1871    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3422   -0.8682   -0.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4212   -0.6346    0.5782 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5031   -1.7531    1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5208   -3.3544    1.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0740   -0.1668   -0.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8884   -1.6717    1.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6531   -1.0235    2.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7976    0.8029    2.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4423   -0.1071    0.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2025   -1.6606   -0.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6107   -1.7001    1.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1840    1.6902    0.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9127    0.7139   -1.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5149    2.6857    1.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5734    3.3540    0.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2947    1.8145    1.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1196    2.0120   -2.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8391    3.4136   -1.7867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1935    3.4746   -2.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5528    0.7254   -1.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6815    1.9471   -1.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5821    1.1738    0.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4247   -1.1287   -2.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2330   -2.4563   -1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7822   -1.6166   -1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1667    0.5416    1.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3433   -0.8869   -1.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2268   -0.2754    0.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3991   -1.8959    0.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851   -0.4919    1.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  1  6
 19 17  1  0
 17 18  1  0
 17 16  1  0
 16 14  1  0
 14 15  1  0
 14  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  8  7  2  0
  7  6  1  0
  6 30  1  0
 30 22  1  0
 22 23  1  0
 23 24  1  0
 24 26  1  0
 26 28  2  0
 28 29  1  0
 26 27  1  0
 24 25  2  0
 22 21  1  0
 30  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
 18 19  1  0
 21 19  1  0
  5  6  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 17 44  1  1
 16 42  1  0
 16 43  1  0
 14 40  1  6
 15 41  1  0
  9 35  1  0
  9 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
  7 34  1  0
  6 33  1  6
 30 58  1  1
 22 50  1  1
 28 54  1  0
 29 55  1  0
 29 56  1  0
 29 57  1  0
 27 51  1  0
 27 52  1  0
 27 53  1  0
 21 48  1  0
 21 49  1  0
  1 31  1  0
  1 32  1  0
M  END


  Mrv1652311132100472D          

 33 35  0  0  1  0            999 V2000
    6.3105    1.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0913    0.7508    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8294   -0.1526    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0609    0.6393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5980   -0.9444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7965   -1.1400    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3826   -1.9361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2264   -0.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9589    0.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9952    0.2096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5285   -0.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4709   -0.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5387   -1.5245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4249   -0.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8549   -0.1427    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0863    0.6492    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8878    0.8447    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8704    1.7913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4213    2.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8264    3.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5699    4.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1266    4.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6471    3.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5178    2.5794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4579    0.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4047    1.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0598    1.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7520    0.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8878    0.7271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0302   -0.1673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2337    1.4609    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5419   -0.9061    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6020    0.1367    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  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
 11 13  2  0  0  0  0
  8 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 19 24  2  0  0  0  0
 17 25  1  0  0  0  0
  2 25  1  0  0  0  0
 16 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 15 30  1  0  0  0  0
 16 31  1  1  0  0  0
 15 32  1  6  0  0  0
  3 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0044051

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@H](O)\C(COC(C)=O)=C\[C@@]3([H])OC(=O)C(=C)[C@]3([H])[C@@H](C[C@@]1(C)O2)OC(=O)C(\C)=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O8/c1-6-11(2)20(25)29-17-9-22(5)18(30-22)8-15(24)14(10-27-13(4)23)7-16-19(17)12(3)21(26)28-16/h6-7,15-19,24H,3,8-10H2,1-2,4-5H3/b11-6+,14-7+/t15-,16+,17+,18+,19-,22+/m0/s1

> <INCHI_KEY>
IOURGKLXEVLPNY-YDTTVYSASA-N

> <FORMULA>
C22H28O8

> <MOLECULAR_WEIGHT>
420.458

> <EXACT_MASS>
420.178417862

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
42.614466776529284

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4R,6R,8S,9E,11R)-9-[(acetyloxy)methyl]-8-hydroxy-4-methyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-9-en-2-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
1.5671157476666666

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.451513565135592

> <JCHEM_PKA_STRONGEST_BASIC>
-3.038707966609686

> <JCHEM_POLAR_SURFACE_AREA>
111.65999999999998

> <JCHEM_REFRACTIVITY>
106.46189999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4R,6R,8S,9E,11R)-9-[(acetyloxy)methyl]-8-hydroxy-4-methyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-9-en-2-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0      11.780   3.060   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.370   1.401   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.748  -0.285   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      13.180   1.193   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      12.316  -1.763   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.820  -2.128   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.048  -3.614   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.756  -1.015   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.257   0.508   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.191   0.391   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.187  -0.982   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.946  -1.052   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.206  -2.846   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.260  -1.380   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.196  -0.266   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.628   1.212   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.124   1.577   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.091   3.344   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.253   4.793   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.009   6.262   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.530   7.775   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.570   8.912   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.541   6.919   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.567   4.815   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.188   0.463   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.355   2.079   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.712   3.634   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.137   1.138   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.524   1.357   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.656  -0.312   0.000  0.00  0.00           O+0
HETATM   31  H   UNK     0       7.903   2.727   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       6.612  -1.691   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      14.190   0.255   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4   25                                             
CONECT    3    2    4    5   33                                             
CONECT    4    3    2                                                       
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8   15                                                       
CONECT   15   14   16   30   32                                             
CONECT   16   15   17   26   31                                             
CONECT   17   16   18   25                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20                                                            
CONECT   24   19                                                            
CONECT   25   17    2                                                       
CONECT   26   16   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   15                                                       
CONECT   31   16                                                            
CONECT   32   15                                                            
CONECT   33    3                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₈O₈

Average Mass

420.4580 Da

Monoisotopic Mass

420.17842 Da

IUPAC Name

(1R,2R,4R,6R,8S,9E,11R)-9-[(acetyloxy)methyl]-8-hydroxy-4-methyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-9-en-2-yl (2E)-2-methylbut-2-enoate

Traditional Name

(1R,2R,4R,6R,8S,9E,11R)-9-[(acetyloxy)methyl]-8-hydroxy-4-methyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-9-en-2-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@H](O)\C(COC(C)=O)=C\[C@@]3([H])OC(=O)C(=C)[C@]3([H])[C@@H](C[C@@]1(C)O2)OC(=O)C(\C)=C\C

InChI Identifier

InChI=1S/C22H28O8/c1-6-11(2)20(25)29-17-9-22(5)18(30-22)8-15(24)14(10-27-13(4)23)7-16-19(17)12(3)21(26)28-16/h6-7,15-19,24H,3,8-10H2,1-2,4-5H3/b11-6+,14-7+/t15-,16+,17+,18+,19-,22+/m0/s1

InChI Key

IOURGKLXEVLPNY-YDTTVYSASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Eupatorium kiirunense	Plant	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	1.03	ALOGPS
logP	1.57	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	14.45	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	111.66 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	106.46 m³·mol⁻¹	ChemAxon
Polarizability	42.61 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

Not Available

References

General References

Shen YC, Lo KL, Kuo YH, Khalil AT: Cytotoxic sesquiterpene lactones from Eupatorium kiirunense, a coastal plant of Taiwan. J Nat Prod. 2005 May;68(5):745-50. doi: 10.1021/np040214k. [PubMed:15921421 ]

Showing NP-Card for 15-acetoxyheliangin (NP0044051)

MOL for NP0044051 (15-acetoxyheliangin)

3D MOL for NP0044051 (15-acetoxyheliangin)

3D SDF for NP0044051 (15-acetoxyheliangin)

3D-SDF for NP0044051 (15-acetoxyheliangin)

PDB for NP0044051 (15-acetoxyheliangin)

3D PDB for NP0044051 (15-acetoxyheliangin)

SMILES for NP0044051 (15-acetoxyheliangin)

INCHI for NP0044051 (15-acetoxyheliangin)

Structure for NP0044051 (15-acetoxyheliangin)

3D Structure for NP0044051 (15-acetoxyheliangin)