NP-MRD: Showing NP-Card for 14-hydroxy-2,7,17-trimethyl-11-methylidene-3,15-dioxapentacyclo[8.8.0.0²,⁴.0⁵,⁹.0¹⁴,¹⁸]octadeca-5(9),17-diene-8,16-dione (NP0197893)

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Record Information

Version

2.0

Created at

2022-09-04 16:14:54 UTC

Updated at

2022-09-04 16:14:55 UTC

NP-MRD ID

NP0197893

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-hydroxy-2,7,17-trimethyl-11-methylidene-3,15-dioxapentacyclo[8.8.0.0²,⁴.0⁵,⁹.0¹⁴,¹⁸]octadeca-5(9),17-diene-8,16-dione

Description

NSC329500 belongs to the class of organic compounds known as jatropholane and crotopholane diterpenoids. These are diterpenoids with a structure based either on the jatropholane or the crotopholane skeleton. Jatropholanes arise by 5,13- and 6,10-cyclisation of a casbane precursor. Subsequent cleavage of the 2,15-cyclopropane bond affords crotofolane. 14-hydroxy-2,7,17-trimethyl-11-methylidene-3,15-dioxapentacyclo[8.8.0.0²,⁴.0⁵,⁹.0¹⁴,¹⁸]octadeca-5(9),17-diene-8,16-dione is found in Croton corylifolius. NSC329500 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231520442D          

 25 29  0  0  0  0            999 V2000
   -1.1269   -2.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3313   -2.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0402   -1.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7839   -1.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0022   -2.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8003   -2.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3802   -1.8789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2005   -1.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7255   -1.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5191   -0.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4930   -1.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1889   -1.1894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4424   -2.4559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6436   -2.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2038   -3.2679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3758   -3.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -3.7197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8976   -3.2850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2017   -3.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1619   -1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9575   -0.8650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9436   -0.2877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3637   -0.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3129   -2.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2747   -3.5345    0.0000 O   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  2  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  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  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  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  2  0  0  0  0
  7 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
  4 23  1  0  0  0  0
 20 23  1  0  0  0  0
  5 24  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END

     RDKit          3D

 47 51  0  0  0  0  0  0  0  0999 V2000
   -0.7824    1.7970   -2.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5914    1.4532   -1.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1433    2.3438   -0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5666    1.9681    0.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7549    0.6521    0.9373 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4558    0.7680    2.2753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0622    0.2343    0.7076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0165   -0.9504    0.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0656   -1.5713   -0.3582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6358   -1.3330   -0.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2640   -2.5863   -0.8978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8784   -0.4127    0.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4136   -0.4598    0.3678 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1771    0.1771   -0.8997 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5919    0.4643   -0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1481   -0.1826    0.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2012    0.7465    1.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7798    1.2918   -0.2643 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6902    0.2497   -0.8294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5684    1.3919   -1.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3832    2.1097   -2.1294 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7027   -1.5452    0.8490 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1748   -2.3514   -0.1234 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2143   -1.7695    0.6553 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4407   -2.6519    1.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3337    2.7153   -2.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4058    1.1910   -3.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5197    2.2101    0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0676    3.4050   -0.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0807    1.9266   -0.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0838    2.7416    0.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5692    1.6900    2.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3879   -3.4919   -0.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2670   -2.5840   -1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9656   -2.6890   -1.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0603    0.2308    1.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0591   -0.4479   -1.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9513    0.1920    1.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7196    1.5733    1.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2697    2.2721   -0.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7299    0.4377   -0.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6500    0.2789   -1.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3758   -0.7709   -0.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1745   -2.0049    1.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2221   -2.7288    2.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4474   -2.3160    1.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5236   -3.6641    1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 10  2  0
 10 11  1  0
 10  8  1  0
  8  9  2  0
  8  7  1  0
  7  5  1  0
  5  6  1  1
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
 13 24  1  0
 24 25  1  1
 24 23  1  0
 23 22  1  0
 15 20  1  0
 20 21  2  0
 20 18  1  0
 22 16  1  0
  2 14  1  0
 22 24  1  0
  5 12  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 18 40  1  1
 17 38  1  0
 17 39  1  0
 14 37  1  6
 13 36  1  1
 11 33  1  0
 11 34  1  0
 11 35  1  0
  6 32  1  0
  4 30  1  0
  4 31  1  0
  3 28  1  0
  3 29  1  0
  1 26  1  0
  1 27  1  0
 25 45  1  0
 25 46  1  0
 25 47  1  0
 22 44  1  1
M  END


  Mrv1533004231520442D          

 25 29  0  0  0  0            999 V2000
   -1.1269   -2.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3313   -2.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0402   -1.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7839   -1.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0022   -2.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8003   -2.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3802   -1.8789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2005   -1.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7255   -1.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5191   -0.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4930   -1.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1889   -1.1894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4424   -2.4559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6436   -2.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2038   -3.2679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3758   -3.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -3.7197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8976   -3.2850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2017   -3.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1619   -1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9575   -0.8650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9436   -0.2877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3637   -0.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3129   -2.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2747   -3.5345    0.0000 O   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  2  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  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  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  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  2  0  0  0  0
  7 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
  4 23  1  0  0  0  0
 20 23  1  0  0  0  0
  5 24  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0197893

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2=C(C3C(C4=C(C)C(=O)OC4(O)CCC3=C)C3(C)OC23)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O5/c1-8-5-6-20(23)14(10(3)18(22)25-20)15-12(8)13-11(7-9(2)16(13)21)17-19(15,4)24-17/h9,12,15,17,23H,1,5-7H2,2-4H3

> <INCHI_KEY>
GALZHQYJPOPISQ-UHFFFAOYSA-N

> <FORMULA>
C20H22O5

> <MOLECULAR_WEIGHT>
342.391

> <EXACT_MASS>
342.146723808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
35.818067133056616

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-hydroxy-2,7,17-trimethyl-11-methylidene-3,15-dioxapentacyclo[8.8.0.0²,⁴.0⁵,⁹.0¹⁴,¹⁸]octadeca-5(9),17-diene-8,16-dione

> <ALOGPS_LOGP>
1.64

> <JCHEM_LOGP>
2.256339457

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.24494143154816

> <JCHEM_PKA_STRONGEST_BASIC>
-4.257886103373732

> <JCHEM_POLAR_SURFACE_AREA>
76.13

> <JCHEM_REFRACTIVITY>
90.3051

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-hydroxy-2,7,17-trimethyl-11-methylidene-3,15-dioxapentacyclo[8.8.0.0²,⁴.0⁵,⁹.0¹⁴,¹⁸]octadeca-5(9),17-diene-8,16-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -2.104  -4.505   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.618  -4.097   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.075  -2.656   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.463  -2.728   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.871  -4.213   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.361  -4.603   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.443  -3.507   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.974  -3.671   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.954  -2.482   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.569  -0.991   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.387  -3.047   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.686  -2.220   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       8.292  -4.584   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.801  -4.970   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.847  -6.100   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.301  -6.426   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.851  -6.943   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.542  -6.132   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.243  -6.959   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.036  -2.022   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.521  -1.615   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.628  -0.537   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.546  -1.632   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.584  -5.059   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.513  -6.598   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   23                                                  
CONECT    5    4    6   24                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8   20                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    6   19                                                  
CONECT   19   18                                                            
CONECT   20    7   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22    4   20                                                  
CONECT   24    5    2   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂O₅

Average Mass

342.3910 Da

Monoisotopic Mass

342.14672 Da

IUPAC Name

14-hydroxy-2,7,17-trimethyl-11-methylidene-3,15-dioxapentacyclo[8.8.0.0²,⁴.0⁵,⁹.0¹⁴,¹⁸]octadeca-5(9),17-diene-8,16-dione

Traditional Name

14-hydroxy-2,7,17-trimethyl-11-methylidene-3,15-dioxapentacyclo[8.8.0.0²,⁴.0⁵,⁹.0¹⁴,¹⁸]octadeca-5(9),17-diene-8,16-dione

CAS Registry Number

Not Available

SMILES

CC1CC2=C(C3C(C4=C(C)C(=O)OC4(O)CCC3=C)C3(C)OC23)C1=O

InChI Identifier

InChI=1S/C20H22O5/c1-8-5-6-20(23)14(10(3)18(22)25-20)15-12(8)13-11(7-9(2)16(13)21)17-19(15,4)24-17/h9,12,15,17,23H,1,5-7H2,2-4H3

InChI Key

GALZHQYJPOPISQ-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
Croton corylifolius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as jatropholane and crotopholane diterpenoids. These are diterpenoids with a structure based either on the jatropholane or the crotopholane skeleton. Jatropholanes arise by 5,13- and 6,10-cyclisation of a casbane precursor. Subsequent cleavage of the 2,15-cyclopropane bond affords crotofolane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Jatropholane and crotopholane diterpenoids

Alternative Parents

Substituents

Diterpene lactone
Jatropholane or crotopholane diterpenoid
2-furanone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Hemiacetal
Ketone
Lactone
Ether
Oxirane
Oxacycle
Dialkyl ether
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	1.64	ALOGPS
logP	2.26	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.24	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	90.31 m³·mol⁻¹	ChemAxon
Polarizability	35.82 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

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

433421

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 14-hydroxy-2,7,17-trimethyl-11-methylidene-3,15-dioxapentacyclo[8.8.0.0²,⁴.0⁵,⁹.0¹⁴,¹⁸]octadeca-5(9),17-diene-8,16-dione (NP0197893)

MOL for NP0197893 (14-hydroxy-2,7,17-trimethyl-11-methylidene-3,15-dioxapentacyclo[8.8.0.0²,⁴.0⁵,⁹.0¹⁴,¹⁸]octadeca-5(9),17-diene-8,16-dione)

3D MOL for NP0197893 (14-hydroxy-2,7,17-trimethyl-11-methylidene-3,15-dioxapentacyclo[8.8.0.0²,⁴.0⁵,⁹.0¹⁴,¹⁸]octadeca-5(9),17-diene-8,16-dione)

3D SDF for NP0197893 (14-hydroxy-2,7,17-trimethyl-11-methylidene-3,15-dioxapentacyclo[8.8.0.0²,⁴.0⁵,⁹.0¹⁴,¹⁸]octadeca-5(9),17-diene-8,16-dione)

3D-SDF for NP0197893 (14-hydroxy-2,7,17-trimethyl-11-methylidene-3,15-dioxapentacyclo[8.8.0.0²,⁴.0⁵,⁹.0¹⁴,¹⁸]octadeca-5(9),17-diene-8,16-dione)

PDB for NP0197893 (14-hydroxy-2,7,17-trimethyl-11-methylidene-3,15-dioxapentacyclo[8.8.0.0²,⁴.0⁵,⁹.0¹⁴,¹⁸]octadeca-5(9),17-diene-8,16-dione)

3D PDB for NP0197893 (14-hydroxy-2,7,17-trimethyl-11-methylidene-3,15-dioxapentacyclo[8.8.0.0²,⁴.0⁵,⁹.0¹⁴,¹⁸]octadeca-5(9),17-diene-8,16-dione)

SMILES for NP0197893 (14-hydroxy-2,7,17-trimethyl-11-methylidene-3,15-dioxapentacyclo[8.8.0.0²,⁴.0⁵,⁹.0¹⁴,¹⁸]octadeca-5(9),17-diene-8,16-dione)

INCHI for NP0197893 (14-hydroxy-2,7,17-trimethyl-11-methylidene-3,15-dioxapentacyclo[8.8.0.0²,⁴.0⁵,⁹.0¹⁴,¹⁸]octadeca-5(9),17-diene-8,16-dione)

Structure for NP0197893 (14-hydroxy-2,7,17-trimethyl-11-methylidene-3,15-dioxapentacyclo[8.8.0.0²,⁴.0⁵,⁹.0¹⁴,¹⁸]octadeca-5(9),17-diene-8,16-dione)

3D Structure for NP0197893 (14-hydroxy-2,7,17-trimethyl-11-methylidene-3,15-dioxapentacyclo[8.8.0.0²,⁴.0⁵,⁹.0¹⁴,¹⁸]octadeca-5(9),17-diene-8,16-dione)