NP-MRD: Showing NP-Card for (+)-Cascarillin I (NP0080208)

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Record Information

Version

1.0

Created at

2022-04-29 01:15:52 UTC

Updated at

2022-04-29 01:15:52 UTC

NP-MRD ID

NP0080208

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Cascarillin I

Description

(1AS,1bR,2'R,3R,4S,5S,5'R,5aS,7aR)-3-(acetyloxy)-5'-(furan-3-yl)-1a,1b,4-trimethyl-octahydro-1aH-spiro[naphtho[1,2-b]oxirene-5,3'-oxolane]-2'-yl acetate belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. (+)-Cascarillin I is found in Croton eleuteria and Croton eluteria. Based on a literature review very few articles have been published on (1aS,1bR,2'R,3R,4S,5S,5'R,5aS,7aR)-3-(acetyloxy)-5'-(furan-3-yl)-1a,1b,4-trimethyl-octahydro-1aH-spiro[naphtho[1,2-b]oxirene-5,3'-oxolane]-2'-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203152D          

 31 35  0  0  1  0            999 V2000
    2.1650    1.4867    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9847    1.5799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3266    0.8290    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7181    0.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0002    0.6784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2135    0.9267    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6051    0.3695    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7834   -0.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5701   -0.6843    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1785   -0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9653   -0.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7484   -1.4898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1399   -2.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3182   -2.8525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3532   -1.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1817    0.6179    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3600    1.4234    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2485    1.9806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0352    1.7322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9684    0.8662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4300   -0.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034   -0.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1350    0.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7434    1.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4613    0.8150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2966    0.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4768   -0.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6078    2.0952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8562    2.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    3.4904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6617    3.0602    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
  5  4  1  1  0  0  0
  1  5  1  0  0  0  0
  5  6  1  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
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
  9 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  7 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
  6 19  1  6  0  0  0
 17 20  1  6  0  0  0
 16 20  1  0  0  0  0
 16 21  1  1  0  0  0
  7 22  1  6  0  0  0
  3 23  1  1  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 23 27  1  0  0  0  0
  1 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END

     RDKit          3D

 63 67  0  0  0  0  0  0  0  0999 V2000
   -2.6196    4.1675    2.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5670    3.4052    0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1818    3.8749   -0.0689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9038    2.2341    0.7274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8283    1.4763   -0.4674 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5327    0.1892   -0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6895   -0.9899    0.0956 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7171   -1.0416    1.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3339   -1.0126   -0.4983 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5107   -2.0801    0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1628   -3.4286    0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5327   -3.4348   -0.4115 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5604   -3.3029    0.5797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3726   -2.2951   -0.3290 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5116   -2.1845   -1.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3983    0.2753   -0.6324 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4245    0.0521   -1.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7800    0.1862   -1.1326 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8100   -0.5982   -1.7951 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0147   -0.9813   -1.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6903   -1.7192   -2.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9027   -1.7488   -3.2793 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7776   -1.1022   -3.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5207   -0.2284    0.1732 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3779    0.5887    0.4272 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0295    0.3919    1.7351 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2070    1.3385    2.6899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8058    1.0636    4.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7059    2.4553    2.4256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4350    1.4428   -1.0023 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2021    2.7974   -0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4330    3.7865    2.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7208    5.2516    1.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6407    3.9846    2.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4413    2.0950   -1.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3682    0.3198    0.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0718   -0.0947   -1.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6526   -0.0543    2.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0453   -1.8038    2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7603   -1.4017    1.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4913   -1.4020   -1.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8025   -1.8623    1.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184   -2.1863   -0.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2016   -3.8777    1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365   -4.2014   -0.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8264   -4.2622   -1.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1482   -1.8107   -2.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3752   -1.6380   -0.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8681   -3.2180   -1.5379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3119    0.8181   -2.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3394   -0.9253   -2.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0200    1.2726   -1.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4484   -0.8056   -0.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6674   -2.1769   -2.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0038   -1.0252   -3.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7849    1.6004    0.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1753    1.8660    4.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6840    0.9050    4.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1840    0.1310    4.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5402    1.4063   -2.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2362    2.8613   -1.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171    3.1247    0.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3538    3.5326   -1.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  6
  9 16  1  0
 16 17  1  6
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 18 24  1  0
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 19 23  2  0
 23 22  1  0
 22 21  1  0
 21 20  2  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
 16 30  1  0
 25 16  1  0
 20 19  1  0
 14  7  1  0
 14 12  1  0
 31 61  1  0
 31 62  1  0
 31 63  1  0
 30 60  1  6
  5 35  1  6
  6 36  1  0
  6 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  6
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  6
 15 47  1  0
 15 48  1  0
 15 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  1
 25 56  1  1
 28 57  1  0
 28 58  1  0
 28 59  1  0
 23 55  1  0
 21 54  1  0
 20 53  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
M  END


  Mrv1652304292203152D          

 31 35  0  0  1  0            999 V2000
    2.1650    1.4867    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9847    1.5799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3266    0.8290    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7181    0.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0002    0.6784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2135    0.9267    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6051    0.3695    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7834   -0.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5701   -0.6843    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1785   -0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9653   -0.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7484   -1.4898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1399   -2.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3182   -2.8525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3532   -1.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1817    0.6179    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3600    1.4234    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2485    1.9806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0352    1.7322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9684    0.8662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4300   -0.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034   -0.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1350    0.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7434    1.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4613    0.8150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2966    0.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4768   -0.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6078    2.0952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8562    2.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    3.4904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6617    3.0602    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
  5  4  1  1  0  0  0
  1  5  1  0  0  0  0
  5  6  1  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
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
  9 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  7 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
  6 19  1  6  0  0  0
 17 20  1  6  0  0  0
 16 20  1  0  0  0  0
 16 21  1  1  0  0  0
  7 22  1  6  0  0  0
  3 23  1  1  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 23 27  1  0  0  0  0
  1 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0080208

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@H](C[C@]2(C)[C@H](CC[C@H]3O[C@@]23C)[C@@]11C[C@@H](O[C@@H]1OC(C)=O)C1=COC=C1)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O7/c1-13-17(28-14(2)25)10-22(4)19(6-7-20-23(22,5)31-20)24(13)11-18(16-8-9-27-12-16)30-21(24)29-15(3)26/h8-9,12-13,17-21H,6-7,10-11H2,1-5H3/t13-,17-,18-,19+,20-,21+,22-,23-,24-/m1/s1

> <INCHI_KEY>
VUPLMTRSSLQGTH-JXHNDXCSSA-N

> <FORMULA>
C24H32O7

> <MOLECULAR_WEIGHT>
432.513

> <EXACT_MASS>
432.21480337

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
44.97206565488351

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1aS,1bR,2'R,3R,4S,5S,5'R,5aS,7aR)-3-(acetyloxy)-5'-(furan-3-yl)-1a,1b,4-trimethyl-octahydro-1aH-spiro[naphtho[1,2-b]oxirene-5,3'-oxolane]-2'-yl acetate

> <ALOGPS_LOGP>
3.63

> <JCHEM_LOGP>
3.000129862999999

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.855768030759668

> <JCHEM_POLAR_SURFACE_AREA>
87.5

> <JCHEM_REFRACTIVITY>
108.6714

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1aS,1bR,2'R,3R,4S,5S,5'R,5aS,7aR)-3-(acetyloxy)-5'-(furan-3-yl)-1a,1b,4-trimethyl-hexahydro-2H-spiro[naphtho[1,2-b]oxirene-5,3'-oxolane]-2'-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       4.041   2.775   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.571   2.949   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.210   1.548   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.074   0.507   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.734   1.266   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.265   1.730   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.129   0.690   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.462  -0.814   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.931  -1.277   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.067  -0.237   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.535  -0.701   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.264  -2.781   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.128  -3.821   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.461  -5.325   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.659  -3.357   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.339   1.153   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.672   2.657   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.464   3.697   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.932   3.233   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.808   1.617   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.803  -0.315   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.006  -0.350   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.719   1.240   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.854   2.280   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.194   1.521   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.887   0.012   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.357  -0.162   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.001   3.911   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.465   5.380   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.425   6.515   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.968   5.712   0.000  0.00  0.00           C+0
CONECT    1    2    5   28                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    1    6   10                                             
CONECT    6    5    7   19                                                  
CONECT    7    6    8   16   22                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    7   17   20   21                                             
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18    6                                                       
CONECT   20   17   16                                                       
CONECT   21   16                                                            
CONECT   22    7                                                            
CONECT   23    3   24   27                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   23                                                       
CONECT   28    1   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
(1AS,1BR,2'r,3R,4S,5S,5'r,5as,7ar)-3-(acetyloxy)-5'-(furan-3-yl)-1a,1b,4-trimethyl-octahydro-1ah-spiro[naphtho[1,2-b]oxirene-5,3'-oxolane]-2'-yl acetic acid	Generator

Chemical Formula

C₂₄H₃₂O₇

Average Mass

432.5130 Da

Monoisotopic Mass

432.21480 Da

IUPAC Name

(1aS,1bR,2'R,3R,4S,5S,5'R,5aS,7aR)-3-(acetyloxy)-5'-(furan-3-yl)-1a,1b,4-trimethyl-octahydro-1aH-spiro[naphtho[1,2-b]oxirene-5,3'-oxolane]-2'-yl acetate

Traditional Name

(1aS,1bR,2'R,3R,4S,5S,5'R,5aS,7aR)-3-(acetyloxy)-5'-(furan-3-yl)-1a,1b,4-trimethyl-hexahydro-2H-spiro[naphtho[1,2-b]oxirene-5,3'-oxolane]-2'-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H](C[C@]2(C)[C@H](CC[C@H]3O[C@@]23C)[C@@]11C[C@@H](O[C@@H]1OC(C)=O)C1=COC=C1)OC(C)=O

InChI Identifier

InChI=1S/C24H32O7/c1-13-17(28-14(2)25)10-22(4)19(6-7-20-23(22,5)31-20)24(13)11-18(16-8-9-27-12-16)30-21(24)29-15(3)26/h8-9,12-13,17-21H,6-7,10-11H2,1-5H3/t13-,17-,18-,19+,20-,21+,22-,23-,24-/m1/s1

InChI Key

VUPLMTRSSLQGTH-JXHNDXCSSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Croton eleuteria	Plant	KNApSAcK
Croton eluteria	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Oxepane
Dicarboxylic acid or derivatives
Furan
Heteroaromatic compound
Tetrahydrofuran
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic oxide
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	3.63	ALOGPS
logP	3	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	87.5 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	108.67 m³·mol⁻¹	ChemAxon
Polarizability	44.97 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9038245

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10862956

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Cascarillin I (NP0080208)

MOL for NP0080208 ((+)-Cascarillin I)

3D MOL for NP0080208 ((+)-Cascarillin I)

3D SDF for NP0080208 ((+)-Cascarillin I)

3D-SDF for NP0080208 ((+)-Cascarillin I)

PDB for NP0080208 ((+)-Cascarillin I)

3D PDB for NP0080208 ((+)-Cascarillin I)

SMILES for NP0080208 ((+)-Cascarillin I)

INCHI for NP0080208 ((+)-Cascarillin I)

Structure for NP0080208 ((+)-Cascarillin I)

3D Structure for NP0080208 ((+)-Cascarillin I)