NP-MRD: Showing NP-Card for 4,6-O-isopropylidene of (6S)-cis-hexahydro-isohumulone (NP0030317)

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Record Information

Version

2.0

Created at

2021-06-19 21:42:24 UTC

Updated at

2021-06-29 23:58:13 UTC

NP-MRD ID

NP0030317

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,6-O-isopropylidene of (6S)-cis-hexahydro-isohumulone

Provided By

JEOL Database JEOL Logo

Description

(4R,5S,6S)-9-hydroxy-2,2-dimethyl-8-(3-methylbutanoyl)-4,6-bis(3-methylbutyl)-1,3-dioxaspiro[4.4]Non-8-en-7-one belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. 4,6-O-isopropylidene of (6S)-cis-hexahydro-isohumulone is found in Humulus lupulus. 4,6-O-isopropylidene of (6S)-cis-hexahydro-isohumulone was first documented in 2003 (Nord, L. I., et al.). Based on a literature review very few articles have been published on (4R,5S,6S)-9-hydroxy-2,2-dimethyl-8-(3-methylbutanoyl)-4,6-bis(3-methylbutyl)-1,3-dioxaspiro[4.4]Non-8-en-7-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123423D          

 69 70  0  0  0  0            999 V2000
   -2.4006   -0.4813    5.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4737    0.0017    4.7458 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6864    1.2217    5.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5524   -1.1500    4.3017 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3841   -0.8532    3.1180 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2927   -0.4100    1.8179 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1118   -1.4951    1.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8607   -2.2723    1.7194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9946   -1.4407   -0.3157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7526   -2.1677   -1.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5443   -1.8849   -2.5326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7629   -3.2148   -0.9120 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3792   -4.0009   -2.0819 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3793   -4.9973   -2.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6297   -4.7468   -1.6110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0185   -0.5585   -0.5588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4227   -0.1859   -1.8098 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6663   -0.0053    0.6655 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9187   -0.7158    0.7858 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9406    0.2703    0.9671 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7655    0.3803   -0.3172 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8460   -0.1346    2.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3194    1.5216    1.2743 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0693    1.4761    0.5676 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1370    2.5524    1.1227 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1652    2.6894    0.3292 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0788    3.8153    0.8487 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5954    3.5381    2.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2623    4.0024   -0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8309   -0.7970    6.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0867    0.3151    6.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1109    0.3050    3.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0765    1.6452    4.4222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3650    2.0102    5.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1630   -2.0291    4.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0877   -0.0762    3.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9733   -1.7610    2.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0080    0.3904    2.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5573   -2.6832   -0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2759   -3.9123   -0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6816   -3.3039   -2.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4876   -4.4911   -3.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0567   -5.7294   -1.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8296   -5.5458   -3.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3915   -5.4590   -0.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0858   -5.3025   -2.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3792   -4.0464   -1.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1001   -0.6844   -2.4807 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5186    1.1710   -0.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2632   -0.5681   -0.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1379    0.6210   -1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2904   -1.1211    1.9546 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2871   -0.1906    3.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6454    0.5985    2.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991    1.7518   -0.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6692    3.5130    1.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0522    2.3657    2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7204    1.7452    0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9111    2.8934   -0.7190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5101    4.7535    0.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7807    3.5346    2.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3048    4.3120    2.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1057    2.5704    2.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9147    4.2421   -1.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9050    4.8239    0.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8737    3.0952   -0.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
 16  9  2  0  0  0  0
  2  3  1  0  0  0  0
  9 10  1  0  0  0  0
  9  7  1  0  0  0  0
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 26 27  1  0  0  0  0
  6 18  1  0  0  0  0
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  6 41  1  1  0  0  0
 27 29  1  0  0  0  0
 18 24  1  0  0  0  0
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  6  5  1  0  0  0  0
 12 13  1  0  0  0  0
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 13 14  1  0  0  0  0
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 13 15  1  0  0  0  0
 19 20  1  0  0  0  0
  4  2  1  0  0  0  0
 20 21  1  6  0  0  0
 16 17  1  0  0  0  0
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  5 39  1  0  0  0  0
  5 40  1  0  0  0  0
  4 37  1  0  0  0  0
  4 38  1  0  0  0  0
  2 33  1  6  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  3 34  1  0  0  0  0
  3 35  1  0  0  0  0
  3 36  1  0  0  0  0
 24 58  1  6  0  0  0
 25 59  1  0  0  0  0
 25 60  1  0  0  0  0
 26 61  1  0  0  0  0
 26 62  1  0  0  0  0
 27 63  1  1  0  0  0
 28 64  1  0  0  0  0
 28 65  1  0  0  0  0
 28 66  1  0  0  0  0
 29 67  1  0  0  0  0
 29 68  1  0  0  0  0
 29 69  1  0  0  0  0
 13 44  1  6  0  0  0
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 15 48  1  0  0  0  0
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 15 50  1  0  0  0  0
 21 52  1  0  0  0  0
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 21 54  1  0  0  0  0
 22 55  1  0  0  0  0
 22 56  1  0  0  0  0
 22 57  1  0  0  0  0
M  END

     RDKit          3D

 69 70  0  0  0  0  0  0  0  0999 V2000
   -2.4006   -0.4813    5.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4737    0.0017    4.7458 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6864    1.2217    5.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5524   -1.1500    4.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3841   -0.8532    3.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2927   -0.4100    1.8179 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1118   -1.4951    1.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8607   -2.2723    1.7194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9946   -1.4407   -0.3157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7526   -2.1677   -1.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5443   -1.8849   -2.5326 O   0  0  0  0  0  0  0  0  0  0  0  0
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 22 57  1  0
M  END


  Mrv1652306192123423D          

 69 70  0  0  0  0            999 V2000
   -2.4006   -0.4813    5.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4737    0.0017    4.7458 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6864    1.2217    5.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5524   -1.1500    4.3017 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3841   -0.8532    3.1180 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2927   -0.4100    1.8179 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1118   -1.4951    1.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8607   -2.2723    1.7194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9946   -1.4407   -0.3157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7526   -2.1677   -1.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5443   -1.8849   -2.5326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7629   -3.2148   -0.9120 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3792   -4.0009   -2.0819 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.6663   -0.0053    0.6655 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.9406    0.2703    0.9671 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.3194    1.5216    1.2743 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0693    1.4761    0.5676 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -4.3915   -5.4590   -0.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1001   -0.6844   -2.4807 H   0  0  0  0  0  0  0  0  0  0  0  0
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 22 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030317

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C(=O)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])C(=O)[C@@]([H])(C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])[C@@]11OC(O[C@]1([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H40O5/c1-14(2)9-11-17-21(26)20(18(25)13-16(5)6)22(27)24(17)19(12-10-15(3)4)28-23(7,8)29-24/h14-17,19,27H,9-13H2,1-8H3/t17-,19-,24+/m1/s1

> <INCHI_KEY>
YVIGYPPKXGTXME-YJLYGGOZSA-N

> <FORMULA>
C24H40O5

> <MOLECULAR_WEIGHT>
408.579

> <EXACT_MASS>
408.287574388

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
47.53058775415989

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,5S,6S)-9-hydroxy-2,2-dimethyl-8-(3-methylbutanoyl)-4,6-bis(3-methylbutyl)-1,3-dioxaspiro[4.4]non-8-en-7-one

> <ALOGPS_LOGP>
4.81

> <JCHEM_LOGP>
5.8597473356666665

> <ALOGPS_LOGS>
-5.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.426215372533356

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1340254044483444

> <JCHEM_PKA_STRONGEST_BASIC>
-4.108481193539747

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
115.4038

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.08e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,5S,6S)-9-hydroxy-2,2-dimethyl-8-(3-methylbutanoyl)-4,6-bis(3-methylbutyl)-1,3-dioxaspiro[4.4]non-8-en-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 69 70  0  0  0  0  0  0  0  0999 V2000
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   -1.4737    0.0017    4.7458 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6864    1.2217    5.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2927   -0.4100    1.8179 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1118   -1.4951    1.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8607   -2.2723    1.7194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9946   -1.4407   -0.3157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7526   -2.1677   -1.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5443   -1.8849   -2.5326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7629   -3.2148   -0.9120 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7655    0.3803   -0.3172 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3194    1.5216    1.2743 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8296   -5.5458   -3.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6692    3.5130    1.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8737    3.0952   -0.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
 16  9  2  0
  2  3  1  0
  9 10  1  0
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M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.401  -0.481   5.865  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.474   0.002   4.746  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.686   1.222   5.224  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.552  -1.150   4.302  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.384  -0.853   3.118  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.293  -0.410   1.818  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.112  -1.495   1.146  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.861  -2.272   1.719  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.995  -1.441  -0.316  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.753  -2.168  -1.349  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.544  -1.885  -2.533  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.763  -3.215  -0.912  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.379  -4.001  -2.082  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.379  -4.997  -2.675  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.630  -4.747  -1.611  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.019  -0.559  -0.559  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.423  -0.186  -1.810  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.666  -0.005   0.666  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.919  -0.716   0.786  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.941   0.270   0.967  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.765   0.380  -0.317  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.846  -0.135   2.124  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.319   1.522   1.274  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.069   1.476   0.568  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.137   2.552   1.123  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.165   2.689   0.329  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.079   3.815   0.849  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.595   3.538   2.262  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.262   4.002  -0.104  0.00  0.00           C+0
HETATM   30  H   UNK     0      -1.831  -0.797   6.746  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.006  -1.330   5.530  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.087   0.315   6.173  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.111   0.305   3.908  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.021   0.964   6.055  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.077   1.645   4.422  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.365   2.010   5.567  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.163  -2.029   4.067  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.074  -1.450   5.153  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.088  -0.076   3.432  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.973  -1.761   2.936  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.008   0.390   2.021  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.557  -2.683  -0.374  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.276  -3.912  -0.221  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.682  -3.304  -2.873  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.488  -4.491  -3.057  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.057  -5.729  -1.927  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.830  -5.546  -3.509  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.391  -5.459  -0.814  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.086  -5.303  -2.437  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.379  -4.046  -1.228  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.100  -0.684  -2.481  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.519   1.171  -0.236  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.263  -0.568  -0.547  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.138   0.621  -1.181  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.290  -1.121   1.955  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.287  -0.191   3.062  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.645   0.599   2.276  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.299   1.752  -0.470  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.669   3.513   1.102  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.052   2.366   2.183  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.720   1.745   0.335  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.911   2.893  -0.719  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.510   4.753   0.867  0.00  0.00           H+0
HETATM   64  H   UNK     0      -1.781   3.535   2.992  0.00  0.00           H+0
HETATM   65  H   UNK     0      -3.305   4.312   2.575  0.00  0.00           H+0
HETATM   66  H   UNK     0      -3.106   2.570   2.316  0.00  0.00           H+0
HETATM   67  H   UNK     0      -2.915   4.242  -1.115  0.00  0.00           H+0
HETATM   68  H   UNK     0      -3.905   4.824   0.230  0.00  0.00           H+0
HETATM   69  H   UNK     0      -3.874   3.095  -0.162  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3    4   33                                             
CONECT    3    2   34   35   36                                             
CONECT    4    5    2   37   38                                             
CONECT    5    6    4   39   40                                             
CONECT    6    7   18   41    5                                             
CONECT    7    9    6    8                                                  
CONECT    8    7                                                            
CONECT    9   16   10    7                                                  
CONECT   10    9   12   11                                                  
CONECT   11   10                                                            
CONECT   12   10   13   42   43                                             
CONECT   13   12   14   15   44                                             
CONECT   14   13   45   46   47                                             
CONECT   15   13   48   49   50                                             
CONECT   16    9   18   17                                                  
CONECT   17   16   51                                                       
CONECT   18    6   24   16   19                                             
CONECT   19   20   18                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20   52   53   54                                             
CONECT   22   20   55   56   57                                             
CONECT   23   20   24                                                       
CONECT   24   25   18   23   58                                             
CONECT   25   24   26   59   60                                             
CONECT   26   25   27   61   62                                             
CONECT   27   26   28   29   63                                             
CONECT   28   27   64   65   66                                             
CONECT   29   27   67   68   69                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    2                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    5                                                            
CONECT   41    6                                                            
CONECT   42   12                                                            
CONECT   43   12                                                            
CONECT   44   13                                                            
CONECT   45   14                                                            
CONECT   46   14                                                            
CONECT   47   14                                                            
CONECT   48   15                                                            
CONECT   49   15                                                            
CONECT   50   15                                                            
CONECT   51   17                                                            
CONECT   52   21                                                            
CONECT   53   21                                                            
CONECT   54   21                                                            
CONECT   55   22                                                            
CONECT   56   22                                                            
CONECT   57   22                                                            
CONECT   58   24                                                            
CONECT   59   25                                                            
CONECT   60   25                                                            
CONECT   61   26                                                            
CONECT   62   26                                                            
CONECT   63   27                                                            
CONECT   64   28                                                            
CONECT   65   28                                                            
CONECT   66   28                                                            
CONECT   67   29                                                            
CONECT   68   29                                                            
CONECT   69   29                                                            
MASTER        0    0    0    0    0    0    0    0   69    0  140    0
END

RDKit          3D

69 70  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₄₀O₅

Average Mass

408.5790 Da

Monoisotopic Mass

408.28757 Da

IUPAC Name

(4R,5S,6S)-9-hydroxy-2,2-dimethyl-8-(3-methylbutanoyl)-4,6-bis(3-methylbutyl)-1,3-dioxaspiro[4.4]non-8-en-7-one

Traditional Name

(4R,5S,6S)-9-hydroxy-2,2-dimethyl-8-(3-methylbutanoyl)-4,6-bis(3-methylbutyl)-1,3-dioxaspiro[4.4]non-8-en-7-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C(C(=O)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])C(=O)[C@@]([H])(C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])[C@@]11OC(O[C@]1([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C24H40O5/c1-14(2)9-11-17-21(26)20(18(25)13-16(5)6)22(27)24(17)19(12-10-15(3)4)28-23(7,8)29-24/h14-17,19,27H,9-13H2,1-8H3/t17-,19-,24+/m1/s1

InChI Key

YVIGYPPKXGTXME-YJLYGGOZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Humulus lupulus	JEOL database	Nord, L. I., et al, Magn. Reson. Chem. 41, 660 (2003)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
Vinylogous acid
Meta-dioxolane
Cyclic ketone
Ketone
Oxacycle
Organoheterocyclic compound
Enol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aldehyde
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	4.81	ALOGPS
logP	5.86	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	1.13	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	115.4 m³·mol⁻¹	ChemAxon
Polarizability	47.53 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

10356694

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23247782

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nord, L. I., et al. (2003). Nord, L. I., et al, Magn. Reson. Chem. 41, 660 (2003). Mag. Reson. Chem..

Showing NP-Card for 4,6-O-isopropylidene of (6S)-cis-hexahydro-isohumulone (NP0030317)

MOL for NP0030317 (4,6-O-isopropylidene of (6S)-cis-hexahydro-isohumulone )

3D MOL for NP0030317 (4,6-O-isopropylidene of (6S)-cis-hexahydro-isohumulone )

3D SDF for NP0030317 (4,6-O-isopropylidene of (6S)-cis-hexahydro-isohumulone )

3D-SDF for NP0030317 (4,6-O-isopropylidene of (6S)-cis-hexahydro-isohumulone )

PDB for NP0030317 (4,6-O-isopropylidene of (6S)-cis-hexahydro-isohumulone )

3D PDB for NP0030317 (4,6-O-isopropylidene of (6S)-cis-hexahydro-isohumulone )

SMILES for NP0030317 (4,6-O-isopropylidene of (6S)-cis-hexahydro-isohumulone )

INCHI for NP0030317 (4,6-O-isopropylidene of (6S)-cis-hexahydro-isohumulone )

Structure for NP0030317 (4,6-O-isopropylidene of (6S)-cis-hexahydro-isohumulone )

3D Structure for NP0030317 (4,6-O-isopropylidene of (6S)-cis-hexahydro-isohumulone )