NP-MRD: Showing NP-Card for 8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione (NP0239813)

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Record Information

Version

2.0

Created at

2022-09-06 23:28:53 UTC

Updated at

2022-09-06 23:28:53 UTC

NP-MRD ID

NP0239813

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione

Description

Ginkgolide B, also known as BN52021 or gingko lactone, belongs to the class of organic compounds known as ginkgolides and bilobalides. These are diterpene lactones with a structure based either on the gingkolide or the bilobalide skeleton. The ginkgolide skeleton is a very rigid structure consisting of hexacyclic C20 trilactone. The cis-fused F/A/D/C ring junction forms an empty semi-ball hole, the D ring contains a cage form tetrahydrofuran ring which occupies the center of the empty hole, and the oxygen atoms of the D,C and F ring and 10-hydroxyl group consist of an analogous crown ether structure. Ginkgolides are biologically active terpenic lactones present in Ginkgo biloba. Ginkgolide B is an extremely weak basic (essentially neutral) compound (based on its pKa). Ginkgolide B is also used in treatment for cerebrovascular disease. Ginkgolide B is a bitter tasting compound. Outside of the human body, ginkgolide b has been detected, but not quantified in, fats and oils and ginkgo nuts. This could make ginkgolide b a potential biomarker for the consumption of these foods. The molecular formulas were determined by high resolution mass spectrometry, and the overall structures by IR and NMR spectroscopic analysis and extensive derivitization techniques (g) This newly formed abietatriene undergoes a 1,2-alkyl shift to break the 6-membered ring into (7) with a five-membered ring (more favorable). When coupled together, they form one molecule of geranylgeranyl diphosphate with geranylgeranyl diphosphate synthase. 8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione is found in Ginkgo biloba and Machilus wangchiana. Structural elucidation was accomplished in 1967 by Maruyama et al.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 09111222022D          

 30 35  0  0  0  0            999 V2000
   -2.2744   -0.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6066   -1.3507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9374   -0.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1942   -0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0192   -0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1124   -0.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401   -0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5305    0.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0623   -1.1189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5063    0.5905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8037    0.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5416    1.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2849    1.1865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3911   -0.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2093   -0.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4618   -0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6274    0.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8743    1.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2093    1.6640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8037   -0.1394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869    0.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869    1.6461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6595    1.4501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4552    0.4043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620   -0.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0623   -0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8470   -0.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620   -1.1189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1013   -1.6640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4080    0.7216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  9  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  4 30  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  6 29  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  7 14  1  0  0  0  0
  8 13  1  0  0  0  0
  8 21  1  0  0  0  0
 11 12  1  0  0  0  0
 11 16  1  0  0  0  0
 11 17  1  0  0  0  0
 12 13  1  0  0  0  0
 12 19  1  0  0  0  0
 14 15  1  0  0  0  0
 14 20  1  0  0  0  0
 15 16  1  0  0  0  0
 16 25  1  0  0  0  0
 17 18  1  0  0  0  0
 17 24  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
M  END

     RDKit          3D

 54 59  0  0  0  0  0  0  0  0999 V2000
    4.8468   -0.1706   -1.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5294   -0.8157   -0.7143 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7643   -2.1197   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7355   -2.8884   -0.2002 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7043   -2.3190    0.8402 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2012   -1.0720    1.1898 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6719   -0.9919    1.0306 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2195   -0.7363    2.2801 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3540   -0.2090   -0.1155 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0619   -0.8868   -1.3915 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4463   -0.8995   -1.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044    0.1783   -0.4098 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9693   -0.2638    0.5288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2268   -0.7069   -0.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5598    0.8777    1.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7286   -1.4776    1.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7037    0.8446   -0.1229 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1585    1.6819    0.8946 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8783    2.9232    0.7148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6069    2.7847   -0.4623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6974    3.1963   -0.8238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5868    1.9117   -1.2293 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3905    2.8050   -1.2554 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1791    1.7946    0.4078 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5543    0.6778   -0.2494 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7325    0.6351   -1.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6797    1.1059   -2.4248 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6661   -0.0349   -2.3023 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7571   -0.0225    0.3133 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6114    0.8616    0.9744 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8783    0.9086   -0.7749 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0294   -0.2671   -2.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9665   -1.0400   -1.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5171   -0.8168    2.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3674   -2.0682    0.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3091   -1.5190    2.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4791   -1.9111   -1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8255   -0.7804   -2.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7460   -1.9197   -1.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5701    0.8242   -1.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0135   -0.9015    0.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4869    0.0783   -1.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9106   -1.6385   -0.7820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1977    1.4912    0.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8207    1.4168    1.9344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2529    0.3960    2.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4379   -1.2622    2.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0206   -2.1996    0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6756   -2.0481    1.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1121    1.4606    1.9353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0952    1.6408   -2.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1191    3.6550   -1.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6352    0.5628    1.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 12 17  1  0
 17 22  1  0
 22 23  1  0
 22 20  1  0
 20 21  2  0
 20 19  1  0
 19 18  1  0
 18 24  1  0
 25 24  1  1
 25 26  1  0
 26 27  2  0
 26 28  1  0
 25 29  1  0
 29 30  1  1
 29  2  1  0
 29  6  1  0
 17  9  1  6
 18 17  1  0
  9 25  1  6
 28 10  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  6
  6 35  1  1
  7 36  1  6
  8 37  1  0
 10 38  1  1
 11 39  1  0
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 12 41  1  6
 14 42  1  0
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 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 16 50  1  0
 22 52  1  6
 23 53  1  0
 18 51  1  1
 30 54  1  0
M  END


  Mrv0541 09111222022D          

 30 35  0  0  0  0            999 V2000
   -2.2744   -0.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6066   -1.3507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9374   -0.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1942   -0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0192   -0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1124   -0.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401   -0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5305    0.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0623   -1.1189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5063    0.5905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8037    0.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5416    1.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2849    1.1865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3911   -0.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2093   -0.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4618   -0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6274    0.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8743    1.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2093    1.6640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8037   -0.1394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869    0.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869    1.6461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6595    1.4501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4552    0.4043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620   -0.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0623   -0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8470   -0.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620   -1.1189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1013   -1.6640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4080    0.7216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  9  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  4 30  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  6 29  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  7 14  1  0  0  0  0
  8 13  1  0  0  0  0
  8 21  1  0  0  0  0
 11 12  1  0  0  0  0
 11 16  1  0  0  0  0
 11 17  1  0  0  0  0
 12 13  1  0  0  0  0
 12 19  1  0  0  0  0
 14 15  1  0  0  0  0
 14 20  1  0  0  0  0
 15 16  1  0  0  0  0
 16 25  1  0  0  0  0
 17 18  1  0  0  0  0
 17 24  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0239813

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(=O)OC2C(O)C34C5CC(C(C)(C)C)C33C(O)C(=O)OC3OC4(C(=O)O5)C12O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O10/c1-6-12(23)28-11-9(21)18-8-5-7(16(2,3)4)17(18)10(22)13(24)29-15(17)30-20(18,14(25)27-8)19(6,11)26/h6-11,15,21-22,26H,5H2,1-4H3

> <INCHI_KEY>
SQOJOAFXDQDRGF-UHFFFAOYSA-N

> <FORMULA>
C20H24O10

> <MOLECULAR_WEIGHT>
424.3986

> <EXACT_MASS>
424.136946988

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
39.06608332714507

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione

> <ALOGPS_LOGP>
0.49

> <JCHEM_LOGP>
-0.5822125509999996

> <ALOGPS_LOGS>
-1.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.305421395496875

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.70994054475649

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4968247045047107

> <JCHEM_POLAR_SURFACE_AREA>
148.82

> <JCHEM_REFRACTIVITY>
91.38200000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-12         0                                  
HETATM    1  C   UNK     0      -4.246  -1.612   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.999  -2.521   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.750  -1.612   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.229  -0.147   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.769  -0.147   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.210  -1.612   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.262  -0.147   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.990   0.755   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.716  -2.089   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.678   1.102   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.500   0.755   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.011   2.215   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.532   2.215   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.730  -1.612   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.257  -1.612   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.729  -0.147   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.038   0.755   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.499   2.215   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.257   3.106   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.500  -0.260   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.349   1.527   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.349   3.073   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.964   2.707   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.583   0.755   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.222  -0.543   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.716  -0.147   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.314  -1.635   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.222  -2.089   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.189  -3.106   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -2.628   1.347   0.000  0.00  0.00           O+0
CONECT    1    2    5    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5    8   30                                             
CONECT    5    1    4   10                                                  
CONECT    6    3    7   29                                                  
CONECT    7    6    8   11   14                                             
CONECT    8    4    7   13   21                                             
CONECT    9    1                                                            
CONECT   10    5                                                            
CONECT   11    7   12   16   17                                             
CONECT   12   11   13   19                                                  
CONECT   13    8   12                                                       
CONECT   14    7   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   11   15   25                                                  
CONECT   17   11   18   24                                                  
CONECT   18   17   19   23                                                  
CONECT   19   12   18                                                       
CONECT   20   14   21                                                       
CONECT   21    8   20   22                                                  
CONECT   22   21                                                            
CONECT   23   18                                                            
CONECT   24   17                                                            
CONECT   25   16   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25                                                            
CONECT   29    6                                                            
CONECT   30    4                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

View in JSmol

Synonyms

Value	Source
1-Hydroxy-(1beta)-ginkgolide a	HMDB
BN52021	HMDB
Gingko lactone	HMDB
Ginkolide b	HMDB
Ginkgolide b, (1beta)-isomer	HMDB
Ginkgolide b	MeSH

Chemical Formula

C₂₀H₂₄O₁₀

Average Mass

424.3986 Da

Monoisotopic Mass

424.13695 Da

IUPAC Name

8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione

Traditional Name

8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione

CAS Registry Number

Not Available

SMILES

CC1C(=O)OC2C(O)C34C5CC(C(C)(C)C)C33C(O)C(=O)OC3OC4(C(=O)O5)C12O

InChI Identifier

InChI=1S/C20H24O10/c1-6-12(23)28-11-9(21)18-8-5-7(16(2,3)4)17(18)10(22)13(24)29-15(17)30-20(18,14(25)27-8)19(6,11)26/h6-11,15,21-22,26H,5H2,1-4H3

InChI Key

SQOJOAFXDQDRGF-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ginkgo biloba	LOTUS Database	35616633
Machilus wangchiana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ginkgolides and bilobalides. These are diterpene lactones with a structure based either on the gingkolide or the bilobalide skeleton. The ginkgolide skeleton is a very rigid structure consisting of hexacyclic C20 trilactone. The cis-fused F/A/D/C ring junction forms an empty semi-ball hole, the D ring contains a cage form tetrahydrofuran ring which occupies the center of the empty hole, and the oxygen atoms of the D,C and F ring and 10-hydroxyl group consist of an analogous crown ether structure.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Ginkgolides and bilobalides

Alternative Parents

Substituents

Ginkgolide-skeleton
Diterpenoid
Tricarboxylic acid or derivatives
Furofuran
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
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	0.49	ALOGPS
logP	-0.58	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	11.71	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	148.82 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	91.38 m³·mol⁻¹	ChemAxon
Polarizability	39.07 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0036861

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ginkgolide

METLIN ID

Not Available

PubChem Compound

65243

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione (NP0239813)

MOL for NP0239813 (8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione)

3D MOL for NP0239813 (8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione)

3D SDF for NP0239813 (8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione)

3D-SDF for NP0239813 (8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione)

PDB for NP0239813 (8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione)

3D PDB for NP0239813 (8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione)

SMILES for NP0239813 (8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione)

INCHI for NP0239813 (8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione)

Structure for NP0239813 (8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione)

3D Structure for NP0239813 (8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione)