NP-MRD: Showing NP-Card for lobocrasol (NP0038489)

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Record Information

Version

2.0

Created at

2021-06-20 21:09:50 UTC

Updated at

2021-06-30 00:11:18 UTC

NP-MRD ID

NP0038489

Secondary Accession Numbers

None

Natural Product Identification

Common Name

lobocrasol

Provided By

JEOL Database JEOL Logo

Description

(1R,2R,3S,8Z,12R,13R)-3,12-dihydroxy-1,4,8,12-tetramethyl-16-oxatricyclo[11.2.1.1²,⁵]Heptadeca-4,8-dien-17-one belongs to the class of organic compounds known as oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms. lobocrasol is found in Lobophytum crassum. lobocrasol was first documented in 2009 (Lin, S.-T., et al.). Based on a literature review very few articles have been published on (1R,2R,3S,8Z,12R,13R)-3,12-dihydroxy-1,4,8,12-tetramethyl-16-oxatricyclo[11.2.1.1²,⁵]Heptadeca-4,8-dien-17-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123093D          

 54 56  0  0  0  0            999 V2000
    1.8176   -3.1553   -0.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3889   -2.0385   -0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7486   -0.8267   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7691   -0.2248   -1.8879 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7341    0.8925   -2.1207 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2872    0.4466   -2.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204   -0.4792   -3.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5674    1.9910    3.5756 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8040    1.1115    3.5419 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2665   -0.2278    3.0006 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0087   -1.1622    4.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792    0.0611    2.4113 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1593   -0.9075    1.9406 C   0  0  2  0  0  0  0  0  0  0  0  0
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  3  4  1  0  0  0  0
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  2 23  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202123093D          

 54 56  0  0  0  0            999 V2000
    1.8176   -3.1553   -0.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3889   -2.0385   -0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0618    0.1430    0.9210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3468    1.3087    0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3521    3.9042    1.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9857    3.5671    2.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6584    3.7411    3.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0227    0.3213    3.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3782    1.8498    1.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072    3.0571    3.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9938    1.7910    4.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5528    1.5573    2.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2766    1.0248    4.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4264   -2.0454    3.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4128   -0.6556    4.9658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9480   -1.4903    4.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1686   -1.0647    2.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6254   -2.5041    1.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0832   -4.1051    1.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
 21  3  1  0  0  0  0
  5  6  1  0  0  0  0
  3  2  2  0  0  0  0
  6  8  2  0  0  0  0
  2 23  1  0  0  0  0
  6  7  1  0  0  0  0
 16 15  1  0  0  0  0
  8  9  1  0  0  0  0
 15 14  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  0  0  0  0
 14 19  1  0  0  0  0
 17 18  1  1  0  0  0
 19 17  1  0  0  0  0
 11 13  1  1  0  0  0
 17 20  1  0  0  0  0
  2  1  1  0  0  0  0
 23 20  1  0  0  0  0
 11 12  1  0  0  0  0
 14 11  1  0  0  0  0
 23 24  1  0  0  0  0
 17 16  1  0  0  0  0
 20 52  1  1  0  0  0
 21 22  2  0  0  0  0
 14 44  1  6  0  0  0
 23 53  1  1  0  0  0
 16 47  1  0  0  0  0
 16 48  1  0  0  0  0
 15 45  1  0  0  0  0
 15 46  1  0  0  0  0
  4 28  1  0  0  0  0
  4 29  1  0  0  0  0
  5 30  1  0  0  0  0
  5 31  1  0  0  0  0
  8 35  1  0  0  0  0
  7 32  1  0  0  0  0
  7 33  1  0  0  0  0
  7 34  1  0  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
 10 38  1  0  0  0  0
 10 39  1  0  0  0  0
 18 49  1  0  0  0  0
 18 50  1  0  0  0  0
 18 51  1  0  0  0  0
 13 43  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 12 40  1  0  0  0  0
 12 41  1  0  0  0  0
 12 42  1  0  0  0  0
 24 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038489

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C(=C2C(=O)[C@@]1([H])[C@@]1(O[C@]([H])(C([H])([H])C1([H])[H])[C@@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])\C([H])=C(C([H])([H])[H])/C([H])([H])C2([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O4/c1-12-6-5-10-19(3,23)15-9-11-20(4,24-15)16-17(21)13(2)14(8-7-12)18(16)22/h6,15-17,21,23H,5,7-11H2,1-4H3/b12-6-/t15-,16+,17-,19-,20-/m1/s1

> <INCHI_KEY>
QRTUGLKKOAKYGZ-VJOHQUJZSA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.456

> <EXACT_MASS>
334.214409446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.10180588570287

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,3S,8Z,12R,13R)-3,12-dihydroxy-1,4,8,12-tetramethyl-16-oxatricyclo[11.2.1.1^{2,5}]heptadeca-4,8-dien-17-one

> <ALOGPS_LOGP>
2.31

> <JCHEM_LOGP>
2.5976989270000006

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.32869052727023

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.72701617368336

> <JCHEM_PKA_STRONGEST_BASIC>
-3.21621296760084

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
94.633

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3S,8Z,12R,13R)-3,12-dihydroxy-1,4,8,12-tetramethyl-16-oxatricyclo[11.2.1.1^{2,5}]heptadeca-4,8-dien-17-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
    1.8176   -3.1553   -0.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3889   -2.0385   -0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7486   -0.8267   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7691   -0.2248   -1.8879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7341    0.8925   -2.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2872    0.4466   -2.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204   -0.4792   -3.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505    0.8747   -1.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7381    1.8568   -0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2510    1.2253    0.9165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6640    1.8449    2.2097 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9207    3.3488    2.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3623    1.2367    3.3117 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8358    1.5016    2.3411 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5674    1.9910    3.5756 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8040    1.1115    3.5419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2665   -0.2278    3.0006 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0087   -1.1622    4.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792    0.0611    2.4113 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1593   -0.9075    1.9406 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2774   -0.1094    0.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7639    1.0110    0.5673 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5754   -2.2232    1.3970 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5137   -3.2702    1.6192 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8284   -3.4291   -0.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7066   -2.8972   -1.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4641   -4.0368   -0.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7677    0.2024   -2.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6692   -0.9991   -2.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    1.6461   -1.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0082    1.4093   -3.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4655   -1.4618   -3.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0506   -0.6321   -3.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4401   -0.0618   -4.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7472    0.5010   -1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2507    2.2944   -0.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3938    2.6952   -0.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0618    0.1430    0.9210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3468    1.3087    0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3521    3.9042    1.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9857    3.5671    2.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6584    3.7411    3.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0227    0.3213    3.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3782    1.8498    1.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072    3.0571    3.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9938    1.7910    4.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5528    1.5573    2.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2766    1.0248    4.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4264   -2.0454    3.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4128   -0.6556    4.9658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9480   -1.4903    4.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1686   -1.0647    2.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6254   -2.5041    1.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0832   -4.1051    1.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0
  3  4  1  0
  4  5  1  0
 21  3  1  0
  5  6  1  0
  3  2  2  0
  6  8  2  0
  2 23  1  0
  6  7  1  0
 16 15  1  0
  8  9  1  0
 15 14  1  0
  9 10  1  0
 11 10  1  0
 14 19  1  0
 17 18  1  1
 19 17  1  0
 11 13  1  1
 17 20  1  0
  2  1  1  0
 23 20  1  0
 11 12  1  0
 14 11  1  0
 23 24  1  0
 17 16  1  0
 20 52  1  1
 21 22  2  0
 14 44  1  6
 23 53  1  1
 16 47  1  0
 16 48  1  0
 15 45  1  0
 15 46  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  8 35  1  0
  7 32  1  0
  7 33  1  0
  7 34  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 18 49  1  0
 18 50  1  0
 18 51  1  0
 13 43  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 12 40  1  0
 12 41  1  0
 12 42  1  0
 24 54  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       1.818  -3.155  -0.889  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.389  -2.038  -0.081  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.749  -0.827  -0.523  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.769  -0.225  -1.888  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.734   0.893  -2.121  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.287   0.447  -2.275  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.020  -0.479  -3.438  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.751   0.875  -1.524  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.738   1.857  -0.385  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.251   1.225   0.917  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.664   1.845   2.210  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.921   3.349   2.290  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.362   1.237   3.312  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.836   1.502   2.341  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.567   1.991   3.576  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.804   1.111   3.542  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.267  -0.228   3.001  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.009  -1.162   4.197  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.979   0.061   2.411  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.159  -0.908   1.941  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.277  -0.109   0.659  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.764   1.011   0.567  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.575  -2.223   1.397  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.514  -3.270   1.619  0.00  0.00           O+0
HETATM   25  H   UNK     0       0.828  -3.429  -0.508  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.707  -2.897  -1.944  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.464  -4.037  -0.839  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.768   0.202  -2.051  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.669  -0.999  -2.656  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.847   1.646  -1.337  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.008   1.409  -3.051  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.466  -1.462  -3.266  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.051  -0.632  -3.610  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.440  -0.062  -4.359  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.747   0.501  -1.763  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.251   2.294  -0.255  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.394   2.695  -0.652  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.062   0.143   0.921  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.347   1.309   0.943  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.352   3.904   1.538  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.986   3.567   2.150  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.658   3.741   3.279  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.023   0.321   3.357  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.378   1.850   1.456  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.807   3.057   3.539  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.994   1.791   4.487  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.553   1.557   2.882  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.277   1.025   4.526  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.426  -2.045   3.919  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.413  -0.656   4.966  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.948  -1.490   4.654  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.169  -1.065   2.341  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.625  -2.504   1.860  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.083  -4.105   1.369  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    3   23    1                                                  
CONECT    3    4   21    2                                                  
CONECT    4    3    5   28   29                                             
CONECT    5    4    6   30   31                                             
CONECT    6    5    8    7                                                  
CONECT    7    6   32   33   34                                             
CONECT    8    6    9   35                                                  
CONECT    9    8   10   36   37                                             
CONECT   10    9   11   38   39                                             
CONECT   11   10   13   12   14                                             
CONECT   12   11   40   41   42                                             
CONECT   13   11   43                                                       
CONECT   14   15   19   11   44                                             
CONECT   15   16   14   45   46                                             
CONECT   16   15   17   47   48                                             
CONECT   17   18   19   20   16                                             
CONECT   18   17   49   50   51                                             
CONECT   19   14   17                                                       
CONECT   20   21   17   23   52                                             
CONECT   21   20    3   22                                                  
CONECT   22   21                                                            
CONECT   23    2   20   24   53                                             
CONECT   24   23   54                                                       
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    4                                                            
CONECT   29    4                                                            
CONECT   30    5                                                            
CONECT   31    5                                                            
CONECT   32    7                                                            
CONECT   33    7                                                            
CONECT   34    7                                                            
CONECT   35    8                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   10                                                            
CONECT   40   12                                                            
CONECT   41   12                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   15                                                            
CONECT   46   15                                                            
CONECT   47   16                                                            
CONECT   48   16                                                            
CONECT   49   18                                                            
CONECT   50   18                                                            
CONECT   51   18                                                            
CONECT   52   20                                                            
CONECT   53   23                                                            
CONECT   54   24                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  112    0
END

RDKit          3D

54 56  0  0  0  0  0  0  0  0999 V2000
    1.8176   -3.1553   -0.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3889   -2.0385   -0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7486   -0.8267   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7691   -0.2248   -1.8879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7341    0.8925   -2.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2872    0.4466   -2.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204   -0.4792   -3.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505    0.8747   -1.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7381    1.8568   -0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2510    1.2253    0.9165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6640    1.8449    2.2097 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9207    3.3488    2.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3623    1.2367    3.3117 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8358    1.5016    2.3411 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5674    1.9910    3.5756 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8040    1.1115    3.5419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2665   -0.2278    3.0006 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0087   -1.1622    4.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792    0.0611    2.4113 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1593   -0.9075    1.9406 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2774   -0.1094    0.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7639    1.0110    0.5673 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5754   -2.2232    1.3970 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5137   -3.2702    1.6192 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8284   -3.4291   -0.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7066   -2.8972   -1.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4641   -4.0368   -0.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7677    0.2024   -2.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6692   -0.9991   -2.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    1.6461   -1.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0082    1.4093   -3.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4655   -1.4618   -3.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0506   -0.6321   -3.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4401   -0.0618   -4.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7472    0.5010   -1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2507    2.2944   -0.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3938    2.6952   -0.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0618    0.1430    0.9210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3468    1.3087    0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3521    3.9042    1.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9857    3.5671    2.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6584    3.7411    3.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0227    0.3213    3.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3782    1.8498    1.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072    3.0571    3.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9938    1.7910    4.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5528    1.5573    2.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2766    1.0248    4.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4264   -2.0454    3.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4128   -0.6556    4.9658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9480   -1.4903    4.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1686   -1.0647    2.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6254   -2.5041    1.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0832   -4.1051    1.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0
  3  4  1  0
  4  5  1  0
 21  3  1  0
  5  6  1  0
  3  2  2  0
  6  8  2  0
  2 23  1  0
  6  7  1  0
 16 15  1  0
  8  9  1  0
 15 14  1  0
  9 10  1  0
 11 10  1  0
 14 19  1  0
 17 18  1  1
 19 17  1  0
 11 13  1  1
 17 20  1  0
  2  1  1  0
 23 20  1  0
 11 12  1  0
 14 11  1  0
 23 24  1  0
 17 16  1  0
 20 52  1  1
 21 22  2  0
 14 44  1  6
 23 53  1  1
 16 47  1  0
 16 48  1  0
 15 45  1  0
 15 46  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  8 35  1  0
  7 32  1  0
  7 33  1  0
  7 34  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 18 49  1  0
 18 50  1  0
 18 51  1  0
 13 43  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 12 40  1  0
 12 41  1  0
 12 42  1  0
 24 54  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₄

Average Mass

334.4560 Da

Monoisotopic Mass

334.21441 Da

IUPAC Name

(1R,2R,3S,8Z,12R,13R)-3,12-dihydroxy-1,4,8,12-tetramethyl-16-oxatricyclo[11.2.1.1^{2,5}]heptadeca-4,8-dien-17-one

Traditional Name

(1R,2R,3S,8Z,12R,13R)-3,12-dihydroxy-1,4,8,12-tetramethyl-16-oxatricyclo[11.2.1.1^{2,5}]heptadeca-4,8-dien-17-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C(=C2C(=O)[C@@]1([H])[C@@]1(O[C@]([H])(C([H])([H])C1([H])[H])[C@@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])\C([H])=C(C([H])([H])[H])/C([H])([H])C2([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H30O4/c1-12-6-5-10-19(3,23)15-9-11-20(4,24-15)16-17(21)13(2)14(8-7-12)18(16)22/h6,15-17,21,23H,5,7-11H2,1-4H3/b12-6-/t15-,16+,17-,19-,20-/m1/s1

InChI Key

QRTUGLKKOAKYGZ-VJOHQUJZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lobophytum crassum	JEOL database	Lin, S.-T., et al, Org. Lett. 11, 3012 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxolanes

Sub Class

Not Available

Direct Parent

Oxolanes

Alternative Parents

Substituents

Tertiary alcohol
Oxolane
Secondary alcohol
Ketone
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	2.31	ALOGPS
logP	2.6	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	13.73	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	94.63 m³·mol⁻¹	ChemAxon
Polarizability	37.1 Å³	ChemAxon
Number of Rings	3	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

27024062

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44205585

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lin, S.-T., et al. (2009). Lin, S.-T., et al, Org. Lett. 11, 3012 (2009). Org. Lett..

Showing NP-Card for lobocrasol (NP0038489)

MOL for NP0038489 (lobocrasol)

3D MOL for NP0038489 (lobocrasol)

3D SDF for NP0038489 (lobocrasol)

3D-SDF for NP0038489 (lobocrasol)

PDB for NP0038489 (lobocrasol)

3D PDB for NP0038489 (lobocrasol)

SMILES for NP0038489 (lobocrasol)

INCHI for NP0038489 (lobocrasol)

Structure for NP0038489 (lobocrasol)

3D Structure for NP0038489 (lobocrasol)