NP-MRD: Showing NP-Card for 12'-acetyl-10'-hydroxy-6,9'-dimethyl-4'-methylidene-5-(3-oxobut-1-en-1-yl)-4,6',9-trioxaspiro[tricyclo[6.3.0.0³,⁵]undecane-11,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-5',10-dione (NP0150387)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 06:28:32 UTC

Updated at

2022-09-02 06:28:32 UTC

NP-MRD ID

NP0150387

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12'-acetyl-10'-hydroxy-6,9'-dimethyl-4'-methylidene-5-(3-oxobut-1-en-1-yl)-4,6',9-trioxaspiro[tricyclo[6.3.0.0³,⁵]undecane-11,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-5',10-dione

Description

12'-Acetyl-10'-hydroxy-6,9'-dimethyl-4'-methylidene-5-(3-oxobut-1-en-1-yl)-4,6',9-trioxaspiro[tricyclo[6.3.0.0³,⁵]Undecane-11,13'-tricyclo[8.4.0.0³,⁷]Tetradecan]-11'-ene-5',10-dione belongs to the class of organic compounds known as xanthanolides. These are sesquiterpenoids with a structure based on the xanthanolide skeleton consistsing of a cycloheptane ring usually attached to a four-carbon chain (at carbon 1 ) and a methyl group (at carbon 10), and fused to a five-member lactone ring (sharing carbons 7 and 8). The lactone ring can be conjugated with a methyl or methylene group at position 11. 12'-acetyl-10'-hydroxy-6,9'-dimethyl-4'-methylidene-5-(3-oxobut-1-en-1-yl)-4,6',9-trioxaspiro[tricyclo[6.3.0.0³,⁵]undecane-11,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-5',10-dione is found in Xanthium strumarium. 12'-Acetyl-10'-hydroxy-6,9'-dimethyl-4'-methylidene-5-(3-oxobut-1-en-1-yl)-4,6',9-trioxaspiro[tricyclo[6.3.0.0³,⁵]Undecane-11,13'-tricyclo[8.4.0.0³,⁷]Tetradecan]-11'-ene-5',10-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251511292D          

 38 43  0  0  0  0            999 V2000
    3.7569    1.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9124    0.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7099    0.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -0.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8549   -0.4860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9739   -1.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7043   -1.6860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2342   -1.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0951   -2.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6581   -1.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8479   -1.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2212   -0.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4928   -1.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7931   -0.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784   -1.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2970   -2.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560   -2.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3382   -3.6543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5862   -3.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3041   -4.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8345   -4.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6469   -4.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9290   -3.8036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1773   -5.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7920   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2462   -3.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4714   -2.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8659   -1.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4785   -0.8785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0516   -0.2850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6642    0.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8218    0.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5502    0.5653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2499    0.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2169    0.9525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1221    0.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1508    1.4395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3051    0.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 19  1  0  0  0  0
 20 19  1  4  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 14 30  1  0  0  0  0
 30 31  2  0  0  0  0
 14 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
 12 34  1  0  0  0  0
 34 35  1  0  0  0  0
 32 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
M  END

     RDKit          3D

 74 79  0  0  0  0  0  0  0  0999 V2000
   -3.7160   -0.4087   -3.7901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4419    0.1170   -2.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2155    1.3512   -2.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2872    2.0535   -4.0326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8324    1.5842   -1.7403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9949    0.9604   -0.7710 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8018    1.8726   -0.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0342    1.6726    0.6237 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6860    2.3317    0.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7952    0.1890    0.9175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0043   -0.3558    1.4346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8448    0.1455    2.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7654   -0.5586    2.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0684   -0.5320    3.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3248    0.3015    4.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1248   -1.1933    3.3268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3675   -1.4047    0.8996 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3188   -1.5278   -0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4335   -0.5350   -0.3168 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6990   -1.2086   -0.8524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6965   -0.3282   -1.4476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0387   -2.8009    1.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8093   -3.5581    2.0436 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2697   -3.1243    1.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5845   -2.3077   -0.0073 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9535   -2.2288   -0.4855 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8376   -1.1455    0.0313 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9523   -1.2845    1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287    0.2448   -0.3803 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7191    1.0651   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6350    2.3765   -0.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7717    3.2495   -0.9859 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0633    2.6600   -1.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6050    4.4922   -0.8995 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7183    0.9874    0.6217 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2957    0.6851   -0.7581 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0473   -0.1074   -0.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0047   -0.9871    0.4418 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1842   -1.3338   -3.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6332    0.0407   -4.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5724    0.8656    0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2294    1.8593   -1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2432    2.9150   -0.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5734    2.1067    1.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6943    3.3889    0.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8751    1.8203    1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3707    2.4033   -0.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2213    0.1546    2.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1105    0.7712    2.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4718    1.3610    4.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4338    0.3119    5.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2671   -0.0548    4.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7347   -1.5518   -1.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7981   -2.5465   -0.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1448    0.1881   -1.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1718   -1.8560   -0.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3283   -1.9265   -1.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6663   -0.8898   -1.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9332   -2.6587   -0.8634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4800   -3.2020   -0.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9954   -2.1631   -1.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8676   -1.4206   -0.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9722   -1.6265    1.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7885   -0.3266    2.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2738   -2.1059    1.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6644    0.6373   -1.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    2.8382   -0.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6989    3.5155   -1.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8821    2.0166   -2.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5711    2.1157   -0.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2016    1.6331   -1.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0526   -0.7096   -1.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1722    0.5642   -0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5462   -0.4998    1.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
 27 26  1  0
 26 25  1  0
 25 24  1  0
 24 22  1  0
 22 23  2  0
 17 22  1  1
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
 17 38  1  0
 38 37  1  0
 37 36  1  0
 36 35  1  0
 35 29  1  0
 29 30  1  6
 30 31  2  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 29 27  1  0
 38 25  1  0
 29 36  1  0
 13 17  1  0
 10 19  1  0
  2 21  1  0
 28 63  1  0
 28 64  1  0
 28 65  1  0
 27 62  1  6
 26 60  1  0
 26 61  1  0
 25 59  1  6
 18 53  1  0
 18 54  1  0
 19 55  1  6
 20 56  1  0
 20 57  1  0
 21 58  1  6
  6 41  1  1
  7 42  1  0
  7 43  1  0
  8 44  1  1
  9 45  1  0
  9 46  1  0
  9 47  1  0
 11 48  1  0
 12 49  1  0
 15 50  1  0
 15 51  1  0
 15 52  1  0
  1 39  1  0
  1 40  1  0
 38 74  1  1
 37 72  1  0
 37 73  1  0
 36 71  1  6
 30 66  1  0
 31 67  1  0
 33 68  1  0
 33 69  1  0
 33 70  1  0
M  END


  Mrv1533004251511292D          

 38 43  0  0  0  0            999 V2000
    3.7569    1.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9124    0.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7099    0.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -0.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8549   -0.4860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9739   -1.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7043   -1.6860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2342   -1.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0951   -2.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6581   -1.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8479   -1.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2212   -0.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4928   -1.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7931   -0.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784   -1.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2970   -2.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560   -2.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3382   -3.6543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5862   -3.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3041   -4.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8345   -4.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6469   -4.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9290   -3.8036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1773   -5.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7920   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2462   -3.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4714   -2.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8659   -1.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4785   -0.8785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0516   -0.2850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6642    0.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8218    0.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5502    0.5653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2499    0.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2169    0.9525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1221    0.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1508    1.4395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3051    0.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 19  1  0  0  0  0
 20 19  1  4  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 14 30  1  0  0  0  0
 30 31  2  0  0  0  0
 14 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
 12 34  1  0  0  0  0
 34 35  1  0  0  0  0
 32 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0150387

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2OC(=O)C3(CC4CC5C(CC(C)C4(O)C=C3C(C)=O)OC(=O)C5=C)C2CC2OC12C=CC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H36O8/c1-14-8-23-20(17(4)26(33)36-23)10-19-12-28(22(18(5)32)13-29(14,19)35)21-11-25-30(38-25,7-6-16(3)31)15(2)9-24(21)37-27(28)34/h6-7,13-15,19-21,23-25,35H,4,8-12H2,1-3,5H3

> <INCHI_KEY>
ZEZSJAFXKAFJOL-UHFFFAOYSA-N

> <FORMULA>
C30H36O8

> <MOLECULAR_WEIGHT>
524.61

> <EXACT_MASS>
524.241018119

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
56.03094595711394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12'-acetyl-10'-hydroxy-6,9'-dimethyl-4'-methylidene-5-(3-oxobut-1-en-1-yl)-4,6',9-trioxaspiro[tricyclo[6.3.0.0³,⁵]undecane-11,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-5',10-dione

> <ALOGPS_LOGP>
1.69

> <JCHEM_LOGP>
2.905946471666666

> <ALOGPS_LOGS>
-5.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.14826716399291

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.909666573155462

> <JCHEM_PKA_STRONGEST_BASIC>
-3.275710375840654

> <JCHEM_POLAR_SURFACE_AREA>
119.5

> <JCHEM_REFRACTIVITY>
137.09089999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.45e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12'-acetyl-10'-hydroxy-6,9'-dimethyl-4'-methylidene-5-(3-oxobut-1-en-1-yl)-4,6',9-trioxaspiro[tricyclo[6.3.0.0³,⁵]undecane-11,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-5',10-dione

> <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       7.013   2.669   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.303   1.157   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.792   0.762   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.411  -0.648   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.929  -0.907   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      11.151  -2.431   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.515  -3.147   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.771  -3.113   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.511  -4.631   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.695  -2.011   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.183  -2.301   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.013  -1.300   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.653  -2.023   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.347  -1.207   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.133  -2.732   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.288  -3.751   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.211  -5.289   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.365  -6.821   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.961  -6.188   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.434  -7.635   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.424  -8.815   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.941  -8.547   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.467  -7.100   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.931  -9.727   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.478  -5.771   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.460  -6.926   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.880  -4.352   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.616  -3.000   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.893  -1.640   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.963  -0.532   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.240   0.828   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.401   0.332   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.760   1.055   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.066   0.239   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.005   1.778   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.095   1.148   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.148   2.687   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.570   1.362   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   34                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   30   32                                             
CONECT   15   14   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   19                                                       
CONECT   19   18   17   20   25                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   19   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   15   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   14   31                                                  
CONECT   31   30                                                            
CONECT   32   14   33   36                                                  
CONECT   33   32   34                                                       
CONECT   34   33    2   12   35                                             
CONECT   35   34                                                            
CONECT   36   32   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₆O₈

Average Mass

524.6100 Da

Monoisotopic Mass

524.24102 Da

IUPAC Name

12'-acetyl-10'-hydroxy-6,9'-dimethyl-4'-methylidene-5-(3-oxobut-1-en-1-yl)-4,6',9-trioxaspiro[tricyclo[6.3.0.0³,⁵]undecane-11,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-5',10-dione

Traditional Name

12'-acetyl-10'-hydroxy-6,9'-dimethyl-4'-methylidene-5-(3-oxobut-1-en-1-yl)-4,6',9-trioxaspiro[tricyclo[6.3.0.0³,⁵]undecane-11,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-5',10-dione

CAS Registry Number

Not Available

SMILES

CC1CC2OC(=O)C3(CC4CC5C(CC(C)C4(O)C=C3C(C)=O)OC(=O)C5=C)C2CC2OC12C=CC(C)=O

InChI Identifier

InChI=1S/C30H36O8/c1-14-8-23-20(17(4)26(33)36-23)10-19-12-28(22(18(5)32)13-29(14,19)35)21-11-25-30(38-25,7-6-16(3)31)15(2)9-24(21)37-27(28)34/h6-7,13-15,19-21,23-25,35H,4,8-12H2,1-3,5H3

InChI Key

ZEZSJAFXKAFJOL-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
Xanthium strumarium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthanolides. These are sesquiterpenoids with a structure based on the xanthanolide skeleton consistsing of a cycloheptane ring usually attached to a four-carbon chain (at carbon 1 ) and a methyl group (at carbon 10), and fused to a five-member lactone ring (sharing carbons 7 and 8). The lactone ring can be conjugated with a methyl or methylene group at position 11.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Xanthanolides

Alternative Parents

Substituents

Xanthanolide-skeleton
Sesquiterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Acryloyl-group
Cyclic alcohol
Enone
Alpha,beta-unsaturated ketone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Ketone
Lactone
Organoheterocyclic compound
Ether
Oxirane
Oxacycle
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
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	1.69	ALOGPS
logP	2.91	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	13.91	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	119.5 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	137.09 m³·mol⁻¹	ChemAxon
Polarizability	56.03 Å³	ChemAxon
Number of Rings	6	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

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 12'-acetyl-10'-hydroxy-6,9'-dimethyl-4'-methylidene-5-(3-oxobut-1-en-1-yl)-4,6',9-trioxaspiro[tricyclo[6.3.0.0³,⁵]undecane-11,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-5',10-dione (NP0150387)

MOL for NP0150387 (12'-acetyl-10'-hydroxy-6,9'-dimethyl-4'-methylidene-5-(3-oxobut-1-en-1-yl)-4,6',9-trioxaspiro[tricyclo[6.3.0.0³,⁵]undecane-11,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-5',10-dione)

3D MOL for NP0150387 (12'-acetyl-10'-hydroxy-6,9'-dimethyl-4'-methylidene-5-(3-oxobut-1-en-1-yl)-4,6',9-trioxaspiro[tricyclo[6.3.0.0³,⁵]undecane-11,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-5',10-dione)

3D SDF for NP0150387 (12'-acetyl-10'-hydroxy-6,9'-dimethyl-4'-methylidene-5-(3-oxobut-1-en-1-yl)-4,6',9-trioxaspiro[tricyclo[6.3.0.0³,⁵]undecane-11,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-5',10-dione)

3D-SDF for NP0150387 (12'-acetyl-10'-hydroxy-6,9'-dimethyl-4'-methylidene-5-(3-oxobut-1-en-1-yl)-4,6',9-trioxaspiro[tricyclo[6.3.0.0³,⁵]undecane-11,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-5',10-dione)

PDB for NP0150387 (12'-acetyl-10'-hydroxy-6,9'-dimethyl-4'-methylidene-5-(3-oxobut-1-en-1-yl)-4,6',9-trioxaspiro[tricyclo[6.3.0.0³,⁵]undecane-11,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-5',10-dione)

3D PDB for NP0150387 (12'-acetyl-10'-hydroxy-6,9'-dimethyl-4'-methylidene-5-(3-oxobut-1-en-1-yl)-4,6',9-trioxaspiro[tricyclo[6.3.0.0³,⁵]undecane-11,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-5',10-dione)

SMILES for NP0150387 (12'-acetyl-10'-hydroxy-6,9'-dimethyl-4'-methylidene-5-(3-oxobut-1-en-1-yl)-4,6',9-trioxaspiro[tricyclo[6.3.0.0³,⁵]undecane-11,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-5',10-dione)

INCHI for NP0150387 (12'-acetyl-10'-hydroxy-6,9'-dimethyl-4'-methylidene-5-(3-oxobut-1-en-1-yl)-4,6',9-trioxaspiro[tricyclo[6.3.0.0³,⁵]undecane-11,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-5',10-dione)

Structure for NP0150387 (12'-acetyl-10'-hydroxy-6,9'-dimethyl-4'-methylidene-5-(3-oxobut-1-en-1-yl)-4,6',9-trioxaspiro[tricyclo[6.3.0.0³,⁵]undecane-11,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-5',10-dione)

3D Structure for NP0150387 (12'-acetyl-10'-hydroxy-6,9'-dimethyl-4'-methylidene-5-(3-oxobut-1-en-1-yl)-4,6',9-trioxaspiro[tricyclo[6.3.0.0³,⁵]undecane-11,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-5',10-dione)