NP-MRD: Showing NP-Card for isodonhenrin A (NP0040941)

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Record Information

Version

2.0

Created at

2021-06-20 22:58:34 UTC

Updated at

2021-06-30 00:15:10 UTC

NP-MRD ID

NP0040941

Secondary Accession Numbers

None

Natural Product Identification

Common Name

isodonhenrin A

Provided By

JEOL Database JEOL Logo

Description

(1S,2R,4S,6S,8S,9R,13S,16S,17R)-17-formyl-8-hydroxy-10,10-dimethyl-3-methylidene-15-oxo-7,14-dioxapentacyclo[7.6.2.1¹,⁴.0⁶,¹⁶.0¹³,¹⁷]Octadecan-2-yl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. isodonhenrin A is found in Isodon henryi and Isodon rubescens. isodonhenrin A was first documented in 2011 (Hu, Z., et al.). Based on a literature review very few articles have been published on (1S,2R,4S,6S,8S,9R,13S,16S,17R)-17-formyl-8-hydroxy-10,10-dimethyl-3-methylidene-15-oxo-7,14-dioxapentacyclo[7.6.2.1¹,⁴.0⁶,¹⁶.0¹³,¹⁷]Octadecan-2-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100583D          

 57 61  0  0  0  0            999 V2000
   -1.6895   -2.7547   -0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3929   -1.4706   -0.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1760   -0.4214   -1.3686 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2630   -0.4912   -1.9062 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2292    0.3897   -1.1009 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5709   -0.0320   -1.3628 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5898    0.5422   -0.5437 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0758   -0.4776    0.2992 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0819    1.7366    0.2808 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1155    2.6666    1.0048 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1619    3.1783   -0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9069    2.0152    2.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417    3.9084    1.5433 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0448    3.5844    2.2932 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1351    2.6296    1.5054 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0765    2.4297    2.2301 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9190    0.3627    0.4079 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8560    1.3280    1.1638 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2492    0.5502    2.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6383    0.6067    3.4929 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4305   -1.5817    1.9525 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0267    1.7680   -1.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
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 20 19  1  0  0  0  0
 15 22  1  0  0  0  0
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 10  9  1  0  0  0  0
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  9 38  1  6  0  0  0
 10 12  1  0  0  0  0
 14 13  1  0  0  0  0
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  7  8  1  0  0  0  0
  3  2  1  0  0  0  0
 21  5  1  0  0  0  0
 25 26  1  0  0  0  0
 21 52  1  1  0  0  0
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  2  1  2  3  0  0  0
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 17 18  2  0  0  0  0
  9  7  1  0  0  0  0
 26 27  1  0  0  0  0
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 27 28  1  0  0  0  0
  5  4  1  0  0  0  0
 27 29  2  0  0  0  0
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M  END

     RDKit          3D

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    4.1155    2.6666    1.0048 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306212100583D          

 57 61  0  0  0  0            999 V2000
   -1.6895   -2.7547   -0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3929   -1.4706   -0.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2555   -2.5170    2.9978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7774   -3.1337   -1.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8693   -3.4573    0.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9045   -0.5217   -2.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2764   -0.1408   -2.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6273   -1.5257   -1.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1258    1.4097   -1.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3997    0.8451   -1.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4530   -1.1396   -0.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737    2.4064   -0.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8265    2.3742   -0.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7930    3.9591    0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6808    3.6081   -0.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2951    1.8174    3.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3812    1.0809    1.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7105    2.6804    2.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0765    4.5568    0.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9913    4.5110    2.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5009    4.5158    2.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2732    3.1718    3.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8438    3.1475    0.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0267    1.7680   -1.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4558    1.0328   -0.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2205   -0.6518    0.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0772   -0.1675    2.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796   -0.6868    1.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5316   -3.5574    4.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5640   -2.1905    4.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -3.6331    3.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0  0  0  0
 15 22  1  0  0  0  0
 13 10  1  0  0  0  0
 22 23  1  1  0  0  0
 10  9  1  0  0  0  0
 10 11  1  6  0  0  0
 22  9  1  0  0  0  0
 15 16  1  0  0  0  0
 22 21  1  0  0  0  0
 21 19  1  0  0  0  0
 19 17  1  1  0  0  0
 17 16  1  0  0  0  0
  9 38  1  6  0  0  0
 10 12  1  0  0  0  0
 14 13  1  0  0  0  0
 19 25  1  0  0  0  0
  7  8  1  0  0  0  0
  3  2  1  0  0  0  0
 21  5  1  0  0  0  0
 25 26  1  0  0  0  0
 21 52  1  1  0  0  0
 25  2  1  0  0  0  0
  2  1  2  3  0  0  0
 14 15  1  0  0  0  0
 17 18  2  0  0  0  0
  9  7  1  0  0  0  0
 26 27  1  0  0  0  0
  7  6  1  0  0  0  0
 27 28  1  0  0  0  0
  5  4  1  0  0  0  0
 27 29  2  0  0  0  0
  4  3  1  0  0  0  0
 23 24  2  0  0  0  0
  3 20  1  0  0  0  0
 23 53  1  0  0  0  0
  5  6  1  0  0  0  0
 14 47  1  0  0  0  0
 14 48  1  0  0  0  0
 13 45  1  0  0  0  0
 13 46  1  0  0  0  0
  7 36  1  6  0  0  0
 11 39  1  0  0  0  0
 11 40  1  0  0  0  0
 11 41  1  0  0  0  0
  8 37  1  0  0  0  0
  5 35  1  6  0  0  0
  4 33  1  0  0  0  0
  4 34  1  0  0  0  0
  3 32  1  6  0  0  0
 20 50  1  0  0  0  0
 20 51  1  0  0  0  0
 15 49  1  6  0  0  0
 12 42  1  0  0  0  0
 12 43  1  0  0  0  0
 12 44  1  0  0  0  0
 25 54  1  1  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
 28 55  1  0  0  0  0
 28 56  1  0  0  0  0
 28 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040941

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])O[C@@]2([H])C([H])([H])[C@@]3([H])C(=C([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@]4(C(=O)O[C@@]5([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])[C@]1([H])[C@]5(C([H])=O)[C@]24[H])C3([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O7/c1-10-12-7-13-15-21(8-12,17(10)27-11(2)24)19(26)29-14-5-6-20(3,4)16(18(25)28-13)22(14,15)9-23/h9,12-18,25H,1,5-8H2,2-4H3/t12-,13+,14+,15-,16-,17-,18+,21+,22+/m1/s1

> <INCHI_KEY>
JXRIWSKKASMDPB-CAHSFIEJSA-N

> <FORMULA>
C22H28O7

> <MOLECULAR_WEIGHT>
404.459

> <EXACT_MASS>
404.183503242

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.08048103584293

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,4S,6S,8S,9R,13S,16S,17R)-17-formyl-8-hydroxy-10,10-dimethyl-3-methylidene-15-oxo-7,14-dioxapentacyclo[7.6.2.1^{1,4}.0^{6,16}.0^{13,17}]octadecan-2-yl acetate

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
1.1201540886666668

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.126647419980968

> <JCHEM_PKA_STRONGEST_BASIC>
-4.055604418500324

> <JCHEM_POLAR_SURFACE_AREA>
99.13

> <JCHEM_REFRACTIVITY>
99.5131

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4S,6S,8S,9R,13S,16S,17R)-17-formyl-8-hydroxy-10,10-dimethyl-3-methylidene-15-oxo-7,14-dioxapentacyclo[7.6.2.1^{1,4}.0^{6,16}.0^{13,17}]octadecan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 61  0  0  0  0  0  0  0  0999 V2000
   -1.6895   -2.7547   -0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3929   -1.4706   -0.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1760   -0.4214   -1.3686 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2630   -0.4912   -1.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2292    0.3897   -1.1009 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5709   -0.0320   -1.3628 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5898    0.5422   -0.5437 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0758   -0.4776    0.2992 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0819    1.7366    0.2808 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1155    2.6666    1.0048 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1619    3.1783   -0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9069    2.0152    2.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417    3.9084    1.5433 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0448    3.5844    2.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1351    2.6296    1.5054 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0765    2.4297    2.2301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9991    1.5411    1.8097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1374    1.5890    2.2684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6099    0.5464    0.7258 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3872    0.8692   -0.5706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9190    0.3627    0.4079 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8560    1.3280    1.1638 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2492    0.5502    2.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6383    0.6067    3.4929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2729   -0.8245    1.0795 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4305   -1.5817    1.9525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0507   -2.3424    2.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0267   -2.9690    3.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2555   -2.5170    2.9978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7774   -3.1337   -1.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8693   -3.4573    0.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9045   -0.5217   -2.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2764   -0.1408   -2.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6273   -1.5257   -1.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1258    1.4097   -1.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3997    0.8451   -1.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4530   -1.1396   -0.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737    2.4064   -0.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8265    2.3742   -0.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7930    3.9591    0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6808    3.6081   -0.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2951    1.8174    3.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3812    1.0809    1.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7105    2.6804    2.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0765    4.5568    0.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9913    4.5110    2.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5009    4.5158    2.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2732    3.1718    3.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8438    3.1475    0.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0267    1.7680   -1.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4558    1.0328   -0.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2205   -0.6518    0.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0772   -0.1675    2.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796   -0.6868    1.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5316   -3.5574    4.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5640   -2.1905    4.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -3.6331    3.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 15 22  1  0
 13 10  1  0
 22 23  1  1
 10  9  1  0
 10 11  1  6
 22  9  1  0
 15 16  1  0
 22 21  1  0
 21 19  1  0
 19 17  1  1
 17 16  1  0
  9 38  1  6
 10 12  1  0
 14 13  1  0
 19 25  1  0
  7  8  1  0
  3  2  1  0
 21  5  1  0
 25 26  1  0
 21 52  1  1
 25  2  1  0
  2  1  2  3
 14 15  1  0
 17 18  2  0
  9  7  1  0
 26 27  1  0
  7  6  1  0
 27 28  1  0
  5  4  1  0
 27 29  2  0
  4  3  1  0
 23 24  2  0
  3 20  1  0
 23 53  1  0
  5  6  1  0
 14 47  1  0
 14 48  1  0
 13 45  1  0
 13 46  1  0
  7 36  1  6
 11 39  1  0
 11 40  1  0
 11 41  1  0
  8 37  1  0
  5 35  1  6
  4 33  1  0
  4 34  1  0
  3 32  1  6
 20 50  1  0
 20 51  1  0
 15 49  1  6
 12 42  1  0
 12 43  1  0
 12 44  1  0
 25 54  1  1
  1 30  1  0
  1 31  1  0
 28 55  1  0
 28 56  1  0
 28 57  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.690  -2.755  -0.536  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.393  -1.471  -0.292  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.176  -0.421  -1.369  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.263  -0.491  -1.906  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.229   0.390  -1.101  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.571  -0.032  -1.363  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.590   0.542  -0.544  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.076  -0.478   0.299  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.082   1.737   0.281  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.115   2.667   1.005  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.162   3.178  -0.015  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.907   2.015   2.152  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.342   3.908   1.543  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.045   3.584   2.293  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.135   2.630   1.505  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.077   2.430   2.230  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.999   1.541   1.810  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.137   1.589   2.268  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.610   0.546   0.726  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.387   0.869  -0.571  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.919   0.363   0.408  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.856   1.328   1.164  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.249   0.550   2.429  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.638   0.607   3.493  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.273  -0.825   1.079  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.431  -1.582   1.952  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.051  -2.342   2.893  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.027  -2.969   3.789  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.256  -2.517   2.998  0.00  0.00           O+0
HETATM   30  H   UNK     0      -1.777  -3.134  -1.550  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.869  -3.457   0.273  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.905  -0.522  -2.180  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.276  -0.141  -2.947  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.627  -1.526  -1.950  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.126   1.410  -1.493  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.400   0.845  -1.213  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.453  -1.140  -0.307  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.674   2.406  -0.495  0.00  0.00           H+0
HETATM   39  H   UNK     0       5.827   2.374  -0.348  0.00  0.00           H+0
HETATM   40  H   UNK     0       5.793   3.959   0.426  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.681   3.608  -0.901  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.295   1.817   3.034  0.00  0.00           H+0
HETATM   43  H   UNK     0       5.381   1.081   1.839  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.710   2.680   2.493  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.076   4.557   0.697  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.991   4.511   2.191  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.501   4.516   2.496  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.273   3.172   3.283  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.844   3.147   0.580  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.027   1.768  -1.082  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.456   1.033  -0.372  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.220  -0.652   0.704  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.077  -0.168   2.334  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.280  -0.687   1.495  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.532  -3.557   4.561  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.564  -2.191   4.279  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.618  -3.633   3.208  0.00  0.00           H+0
CONECT    1    2   30   31                                                  
CONECT    2    3   25    1                                                  
CONECT    3    2    4   20   32                                             
CONECT    4    5    3   33   34                                             
CONECT    5   21    4    6   35                                             
CONECT    6    7    5                                                       
CONECT    7    8    9    6   36                                             
CONECT    8    7   37                                                       
CONECT    9   10   22   38    7                                             
CONECT   10   13    9   11   12                                             
CONECT   11   10   39   40   41                                             
CONECT   12   10   42   43   44                                             
CONECT   13   10   14   45   46                                             
CONECT   14   13   15   47   48                                             
CONECT   15   22   16   14   49                                             
CONECT   16   15   17                                                       
CONECT   17   19   16   18                                                  
CONECT   18   17                                                            
CONECT   19   20   21   17   25                                             
CONECT   20   19    3   50   51                                             
CONECT   21   22   19    5   52                                             
CONECT   22   15   23    9   21                                             
CONECT   23   22   24   53                                                  
CONECT   24   23                                                            
CONECT   25   19   26    2   54                                             
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27   55   56   57                                             
CONECT   29   27                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    3                                                            
CONECT   33    4                                                            
CONECT   34    4                                                            
CONECT   35    5                                                            
CONECT   36    7                                                            
CONECT   37    8                                                            
CONECT   38    9                                                            
CONECT   39   11                                                            
CONECT   40   11                                                            
CONECT   41   11                                                            
CONECT   42   12                                                            
CONECT   43   12                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   13                                                            
CONECT   47   14                                                            
CONECT   48   14                                                            
CONECT   49   15                                                            
CONECT   50   20                                                            
CONECT   51   20                                                            
CONECT   52   21                                                            
CONECT   53   23                                                            
CONECT   54   25                                                            
CONECT   55   28                                                            
CONECT   56   28                                                            
CONECT   57   28                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  122    0
END

RDKit          3D

57 61  0  0  0  0  0  0  0  0999 V2000
   -1.6895   -2.7547   -0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3929   -1.4706   -0.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1760   -0.4214   -1.3686 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2630   -0.4912   -1.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2292    0.3897   -1.1009 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5709   -0.0320   -1.3628 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5898    0.5422   -0.5437 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0758   -0.4776    0.2992 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0819    1.7366    0.2808 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1155    2.6666    1.0048 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1619    3.1783   -0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9069    2.0152    2.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417    3.9084    1.5433 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0448    3.5844    2.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1351    2.6296    1.5054 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0765    2.4297    2.2301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9991    1.5411    1.8097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1374    1.5890    2.2684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6099    0.5464    0.7258 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3872    0.8692   -0.5706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9190    0.3627    0.4079 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8560    1.3280    1.1638 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2492    0.5502    2.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6383    0.6067    3.4929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2729   -0.8245    1.0795 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4305   -1.5817    1.9525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0507   -2.3424    2.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0267   -2.9690    3.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2555   -2.5170    2.9978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7774   -3.1337   -1.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8693   -3.4573    0.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9045   -0.5217   -2.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2764   -0.1408   -2.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6273   -1.5257   -1.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1258    1.4097   -1.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3997    0.8451   -1.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4530   -1.1396   -0.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737    2.4064   -0.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8265    2.3742   -0.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7930    3.9591    0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6808    3.6081   -0.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2951    1.8174    3.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3812    1.0809    1.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7105    2.6804    2.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0765    4.5568    0.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9913    4.5110    2.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5009    4.5158    2.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2732    3.1718    3.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8438    3.1475    0.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0267    1.7680   -1.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4558    1.0328   -0.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2205   -0.6518    0.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0772   -0.1675    2.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796   -0.6868    1.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5316   -3.5574    4.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5640   -2.1905    4.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -3.6331    3.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 15 22  1  0
 13 10  1  0
 22 23  1  1
 10  9  1  0
 10 11  1  6
 22  9  1  0
 15 16  1  0
 22 21  1  0
 21 19  1  0
 19 17  1  1
 17 16  1  0
  9 38  1  6
 10 12  1  0
 14 13  1  0
 19 25  1  0
  7  8  1  0
  3  2  1  0
 21  5  1  0
 25 26  1  0
 21 52  1  1
 25  2  1  0
  2  1  2  3
 14 15  1  0
 17 18  2  0
  9  7  1  0
 26 27  1  0
  7  6  1  0
 27 28  1  0
  5  4  1  0
 27 29  2  0
  4  3  1  0
 23 24  2  0
  3 20  1  0
 23 53  1  0
  5  6  1  0
 14 47  1  0
 14 48  1  0
 13 45  1  0
 13 46  1  0
  7 36  1  6
 11 39  1  0
 11 40  1  0
 11 41  1  0
  8 37  1  0
  5 35  1  6
  4 33  1  0
  4 34  1  0
  3 32  1  6
 20 50  1  0
 20 51  1  0
 15 49  1  6
 12 42  1  0
 12 43  1  0
 12 44  1  0
 25 54  1  1
  1 30  1  0
  1 31  1  0
 28 55  1  0
 28 56  1  0
 28 57  1  0
M  END

View in JSmol

Synonyms

Value	Source
(1S,2R,4S,6S,8S,9R,13S,16S,17R)-17-Formyl-8-hydroxy-10,10-dimethyl-3-methylidene-15-oxo-7,14-dioxapentacyclo[7.6.2.1,.0,.0,]octadecan-2-yl acetic acid	Generator

Chemical Formula

C₂₂H₂₈O₇

Average Mass

404.4590 Da

Monoisotopic Mass

404.18350 Da

IUPAC Name

(1S,2R,4S,6S,8S,9R,13S,16S,17R)-17-formyl-8-hydroxy-10,10-dimethyl-3-methylidene-15-oxo-7,14-dioxapentacyclo[7.6.2.1^{1,4}.0^{6,16}.0^{13,17}]octadecan-2-yl acetate

Traditional Name

(1S,2R,4S,6S,8S,9R,13S,16S,17R)-17-formyl-8-hydroxy-10,10-dimethyl-3-methylidene-15-oxo-7,14-dioxapentacyclo[7.6.2.1^{1,4}.0^{6,16}.0^{13,17}]octadecan-2-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])O[C@@]2([H])C([H])([H])[C@@]3([H])C(=C([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@]4(C(=O)O[C@@]5([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])[C@]1([H])[C@]5(C([H])=O)[C@]24[H])C3([H])[H]

InChI Identifier

InChI=1S/C22H28O7/c1-10-12-7-13-15-21(8-12,17(10)27-11(2)24)19(26)29-14-5-6-20(3,4)16(18(25)28-13)22(14,15)9-23/h9,12-18,25H,1,5-8H2,2-4H3/t12-,13+,14+,15-,16-,17-,18+,21+,22+/m1/s1

InChI Key

JXRIWSKKASMDPB-CAHSFIEJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, 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
Isodon henryi	JEOL database	Hu, Z., et al, Chem. Pharm. Bull. 59, 1562 (2011)
Isodon rubescens	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

Diterpene lactone
Diterpenoid
Kaurane diterpenoid
Delta valerolactone
Delta_valerolactone
Oxane
Dicarboxylic acid or derivatives
Lactone
Hemiacetal
Carboxylic acid ester
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aldehyde
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
logP	1.22	ALOGPS
logP	1.12	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.13	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	99.51 m³·mol⁻¹	ChemAxon
Polarizability	41.08 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

56834737

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hu, Z., et al. (2011). Hu, Z., et al, Chem. Pharm. Bull. 59, 1562 (2011). Chem. Pharm. Bull..

Showing NP-Card for isodonhenrin A (NP0040941)

MOL for NP0040941 (isodonhenrin A)

3D MOL for NP0040941 (isodonhenrin A)

3D SDF for NP0040941 (isodonhenrin A)

3D-SDF for NP0040941 (isodonhenrin A)

PDB for NP0040941 (isodonhenrin A)

3D PDB for NP0040941 (isodonhenrin A)

SMILES for NP0040941 (isodonhenrin A)

INCHI for NP0040941 (isodonhenrin A)

Structure for NP0040941 (isodonhenrin A)

3D Structure for NP0040941 (isodonhenrin A)