NP-MRD: Showing NP-Card for 4-[12,16-dihydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoic acid (NP0186116)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 01:49:12 UTC

Updated at

2022-09-04 01:49:12 UTC

NP-MRD ID

NP0186116

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[12,16-dihydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoic acid

Description

4-[12,16-Dihydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]Docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoic acid belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system. 4-[12,16-dihydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoic acid is found in Garcinia hanburyi. 4-[12,16-Dihydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]Docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251505182D          

 42 47  0  0  0  0            999 V2000
    7.0462    3.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7909    2.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9838    2.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7122    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7472    0.5595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5420    0.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1311    0.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9258    0.6943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3307    1.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7931    0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1314   -0.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5423   -0.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7476   -0.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1585   -1.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4117   -1.8522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3638   -0.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8062   -1.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0780   -2.2816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0186   -1.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5872   -1.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5649   -2.7414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8270   -1.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0706   -0.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0436    0.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4451    0.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5841    1.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9962    1.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9039    0.1934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6018   -0.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9650    0.7477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7388    1.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7299    2.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0110    2.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4399    2.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4310    3.2757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1587    2.0460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1365   -1.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3545   -1.4059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5993   -0.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3212    0.1655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1581   -0.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3426    1.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  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
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 30  1  4  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 29 37  1  0  0  0  0
 22 37  1  0  0  0  0
 37 38  2  0  0  0  0
 29 39  1  0  0  0  0
 19 39  1  0  0  0  0
 24 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
  5 41  1  0  0  0  0
 16 41  2  0  0  0  0
  2 42  1  0  0  0  0
M  END

     RDKit          3D

 80 85  0  0  0  0  0  0  0  0999 V2000
   -2.5750    3.8338   -1.8764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2880    2.6402   -2.7129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609    2.6352   -4.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5837    1.6131   -2.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9601    1.4840   -0.9761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4553    0.2957   -0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7200    0.3193    0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1396   -0.8063    1.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3932   -1.9540    1.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7534   -3.0951    1.8065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1184   -1.9436    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6793   -0.8385   -0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5809   -0.8549   -0.7113 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5560   -1.8071   -0.4528 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0214   -3.1392   -0.0738 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2631   -3.1085    0.6394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6259   -4.0820    1.3254 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0455   -4.0185    0.6064 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9472   -3.9681    1.9746 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4069   -3.5362    0.1575 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3618   -3.2106   -1.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5032   -2.0147   -1.6345 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2731   -0.7020   -1.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6852   -0.8171   -1.9994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5530    0.2779   -2.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1223   -0.2185   -0.2561 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5442   -1.2100    0.5252 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8828   -0.5775    1.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8611    0.0045    2.6487 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0192    1.2413    2.9965 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1022    1.5822    3.9915 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2352    2.3324    2.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2999    2.2882    1.6693 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5058    3.6524    2.9588 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5990   -2.2003    0.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5516   -2.0014    1.5506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4551   -0.7539    1.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2061    0.3098    1.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8077    1.5297    0.8223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8022    2.6476    1.8796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8449    1.9352   -0.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5315    1.4226    0.2636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6848    4.6998   -2.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7357    4.1083   -1.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5300    3.7101   -1.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5882    1.7167   -4.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9505    2.7719   -3.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4632    3.5354   -4.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4269    0.7867   -3.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1432    1.3918   -1.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1596    2.3596   -0.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6271   -3.2003    2.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8036   -3.6723   -1.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9046   -5.0953    0.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3797   -4.6385    2.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2155   -4.2285    0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8721   -4.0976   -1.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3725   -3.1588   -1.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9620   -2.0692   -2.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3670   -1.0976   -1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9907    0.1985   -2.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7333   -1.4899   -2.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4221    1.2714   -1.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1271    0.4802   -3.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5268   -0.0706   -2.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1489    0.1337    1.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3072   -1.3242    2.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5714   -0.7081    3.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0015    1.9487    3.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3756    0.7197    4.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7117    2.3914    4.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2986    4.1295    2.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8000   -1.6482    2.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1900    0.2611    2.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1982    3.5052    1.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8421    2.9189    2.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3786    2.1680    2.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8198    1.5894    0.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6617    1.4850   -1.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7728    3.0310   -0.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 42  1  0
 42 39  1  0
 39 40  1  0
 39 41  1  0
 39 38  1  0
 38 37  2  0
 37  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 14 13  1  6
 14 22  1  0
 22 21  1  0
 21 20  1  0
 20 18  1  0
 18 19  1  0
 18 15  1  0
 15 16  1  0
 16 17  2  0
 20 35  1  0
 35 36  2  0
 35 27  1  0
 27 28  1  1
 28 29  1  0
 29 30  2  0
 30 31  1  0
 30 32  1  0
 32 34  1  0
 32 33  2  0
 27 26  1  0
 26 23  1  0
 23 24  1  0
 23 25  1  0
 12  6  2  0
 15 14  1  0
  8  7  2  0
 16 11  1  0
 27 14  1  0
 23 22  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  3 46  1  0
  3 47  1  0
  3 48  1  0
  4 49  1  0
  5 50  1  0
  5 51  1  0
 40 75  1  0
 40 76  1  0
 40 77  1  0
 41 78  1  0
 41 79  1  0
 41 80  1  0
 38 74  1  0
 37 73  1  0
 10 52  1  0
 22 59  1  6
 21 57  1  0
 21 58  1  0
 20 56  1  6
 18 54  1  6
 19 55  1  0
 15 53  1  6
 28 66  1  0
 28 67  1  0
 29 68  1  0
 31 69  1  0
 31 70  1  0
 31 71  1  0
 34 72  1  0
 24 60  1  0
 24 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 25 65  1  0
M  END


  Mrv1533004251505182D          

 42 47  0  0  0  0            999 V2000
    7.0462    3.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7909    2.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9838    2.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7122    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7472    0.5595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5420    0.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1311    0.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9258    0.6943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3307    1.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7931    0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1314   -0.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5423   -0.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7476   -0.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1585   -1.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4117   -1.8522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3638   -0.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8062   -1.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0780   -2.2816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0186   -1.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5872   -1.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5649   -2.7414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8270   -1.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0706   -0.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0436    0.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4451    0.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5841    1.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9962    1.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9039    0.1934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6018   -0.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9650    0.7477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7388    1.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7299    2.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0110    2.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4399    2.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4310    3.2757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1587    2.0460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1365   -1.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3545   -1.4059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5993   -0.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3212    0.1655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1581   -0.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3426    1.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  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
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 30  1  4  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 29 37  1  0  0  0  0
 22 37  1  0  0  0  0
 37 38  2  0  0  0  0
 29 39  1  0  0  0  0
 19 39  1  0  0  0  0
 24 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
  5 41  1  0  0  0  0
 16 41  2  0  0  0  0
  2 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0186116

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC13C4CC(C(O)C1C2=O)C(=O)C3(CC=C(C)C(O)=O)OC4(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C33H38O9/c1-15(2)8-9-18-26-17(11-12-30(4,5)40-26)23(34)21-25(36)22-24(35)19-14-20-31(6,7)42-32(28(19)37,13-10-16(3)29(38)39)33(20,22)41-27(18)21/h8,10-12,19-20,22,24,34-35H,9,13-14H2,1-7H3,(H,38,39)

> <INCHI_KEY>
GITYGECAVAWXHS-UHFFFAOYSA-N

> <FORMULA>
C33H38O9

> <MOLECULAR_WEIGHT>
578.658

> <EXACT_MASS>
578.251582804

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
60.6702696301993

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[12,16-dihydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoic acid

> <ALOGPS_LOGP>
3.80

> <JCHEM_LOGP>
5.120797836

> <ALOGPS_LOGS>
-4.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.36867105489333

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.73431069088793

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1383464684259756

> <JCHEM_POLAR_SURFACE_AREA>
139.59

> <JCHEM_REFRACTIVITY>
155.92160000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[12,16-dihydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      13.153   6.142   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.676   4.677   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.170   4.358   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.663   2.800   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.728   1.044   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.212   0.631   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.311   1.709   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      14.795   1.296   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.551   2.708   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.414   1.585   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.179  -0.195   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.079  -1.274   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.596  -0.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.496  -1.938   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.969  -3.457   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.012  -1.525   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.972  -2.699   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.479  -4.259   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.501  -2.102   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.696  -3.472   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.654  -5.117   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.277  -2.833   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.732  -1.320   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.681   0.411   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.564   1.541   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.957   2.239   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.593   3.046   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.554   0.361   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.857  -0.598   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.535   1.396   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.979   2.251   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.962   3.790   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.621   4.546   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.288   4.575   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.271   6.115   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       9.630   3.819   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.988  -1.962   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       2.528  -2.624   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       6.719  -0.626   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       8.066   0.309   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       9.629  -0.034   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      13.706   3.532   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   42                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   41                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    6   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   41                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   39                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   37                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   39                                                  
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29                                                       
CONECT   29   28   30   37   39                                             
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   29   22   38                                                  
CONECT   38   37                                                            
CONECT   39   29   19   24   40                                             
CONECT   40   39   41                                                       
CONECT   41   40    5   16                                                  
CONECT   42    2                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Value	Source
4-[12,16-Dihydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0,.0,.0,.0,]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoate	Generator
4-[12,16-Dihydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoate	Generator

Chemical Formula

C₃₃H₃₈O₉

Average Mass

578.6580 Da

Monoisotopic Mass

578.25158 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC13C4CC(C(O)C1C2=O)C(=O)C3(CC=C(C)C(O)=O)OC4(C)C

InChI Identifier

InChI=1S/C33H38O9/c1-15(2)8-9-18-26-17(11-12-30(4,5)40-26)23(34)21-25(36)22-24(35)19-14-20-31(6,7)42-32(28(19)37,13-10-16(3)29(38)39)33(20,22)41-27(18)21/h8,10-12,19-20,22,24,34-35H,9,13-14H2,1-7H3,(H,38,39)

InChI Key

GITYGECAVAWXHS-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
Garcinia hanburyi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranoxanthones

Alternative Parents

Substituents

Pyranoxanthone
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Aromatic monoterpenoid
Monoterpenoid
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Oxepane
Benzenoid
Tetrahydrofuran
Vinylogous acid
Cyclic alcohol
Secondary alcohol
Ketone
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.8	ALOGPS
logP	5.12	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	3.73	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.59 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	155.92 m³·mol⁻¹	ChemAxon
Polarizability	60.67 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[12,16-dihydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoic acid (NP0186116)

MOL for NP0186116 (4-[12,16-dihydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoic acid)

3D MOL for NP0186116 (4-[12,16-dihydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoic acid)

3D SDF for NP0186116 (4-[12,16-dihydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoic acid)

3D-SDF for NP0186116 (4-[12,16-dihydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoic acid)

PDB for NP0186116 (4-[12,16-dihydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoic acid)

3D PDB for NP0186116 (4-[12,16-dihydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoic acid)

SMILES for NP0186116 (4-[12,16-dihydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoic acid)

INCHI for NP0186116 (4-[12,16-dihydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoic acid)

Structure for NP0186116 (4-[12,16-dihydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoic acid)

3D Structure for NP0186116 (4-[12,16-dihydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoic acid)